My 2020 Year in Review: Riding it out

I want to resist the urge to start this post talking about the pandemic but, since I write these posts for posterity, I think I have to start there. It was a weird year that affected my business life much more than my personal life, but the pandemic’s effects were felt throughout the year.

My business actually grew by about 15% in 2020, but that’s a deceptive summary. The underlying components of the business experienced some big and interesting swings in revenue even though the top line looked pretty steady. I almost said I was lucky but … there’s a little more to it than that. A combination of luck and conscious decision making have made the business more resilient (or maybe it’s more accurate to say “anti-fragile”) just in time to weather a big economic storm.

Personally, I had a great year that confirmed something I’ve been noticing for a while now: My family and community are the most important things I have. If my relationships with those are strong, everything else is much more consistent.

For both business and personal things, past investments have led to a stable year in the midst of substantial global upheaval.

2020 Goal review

Increase revenue by 50% again

This was a pretty big miss since the business grew by “only” 15%, but I also didn’t factor in a global economic catastrophe when I set this goal, so I’m giving myself a pass. If I had incorporated that into my projection, I think I would’ve said, “Gosh, if that’s going to happen in 2020, then I guess breaking even would be a very good year.” So the fact that my business grew at all feels like a huge win.

Sub-7:00 pace 5k

Miss, but just barely. I almost hit this one in a training run very early in the year—I had a 7:03 pace 5k on the Hawthorne trail—and if I had just had a different view of the real-time stats on my Apple Watch during my run, I would’ve gotten it.

Then I ran a race in February and ended up at a 7:06 pace, but that’s deceptive because it was 45 degrees out that morning and very windy. In fact, I was pretty much on track to hit this goal until I turned into a super strong headwind that slowed me way down for the final mile.

So I think I would’ve gotten this one but for some bad luck (wrong real-time stats on my Watch followed by non-conducive weather in the race). As misses go, this feels like a hit.

My overall time from the 5k I ran I 2020 was 21:54 and 7:06 per mile

Sub-60-second 400m

I didn’t even try this one. In fact, I’m not even sure I did a single track workout this year. Maybe I’ll hit this one in 2021 (but probably not).

Travel more

Again, this is relative thanks to the pandemic. I got the normal ski trip in just under the wire in February (actually, I extended the trip by a few days this year), and I went on a week-long RV trip with some friends in June. I would say this is actually a win.

Be more generous

This is a win—I think I succeeded here. Could I have succeeded more? Sure, but that will always be true. I was intentional about finding opportunities to be generous and to be generous in meaningful, specific ways that would really be useful.

I’m not sure how to write more about this without seeming braggy, but I do think I might be able to share some more thoughts on this in a tactful way that could be helpful to others, so I’ll try to do that either later in this post or in a separate post entirely.

2020 Year in Review – Business

The business grew about 15% this year. What’s strange is that when I drill down one or two layers into individual stats, things could look very different depending on which stats I choose to focus on.

COVID-19

Before unpacking that intro, I should address the elephant in the room: COVID-19. It very clearly had a huge impact on my business this year, especially on the product side. Organic search traffic took a big hit in January with a Google algorithm update—that’s not unusual. But then it mostly recovered until the second week in March when it fell off a cliff and basically never recovered.

That drop in traffic shifted my email list growth from “steady” to “zero”—my email list has been treading water all year. Search traffic leads to email list growth, which leads to product sales. So with fewer new email subscribers came fewer direct product sales.

Meanwhile, a few pages on my site that are specifically to help folks navigate negotiations with big tech companies actually had a material increase in traffic this year. The traffic to those pages does not generally lead to product sales, but does lead to coaching clients. So traffic to the coaching side of the business was up this year.

All that nets out to more coaching revenue, less product revenue, and modest growth for the business this year.

That’s what things looked like from my side of my business. But clearly this reflects much more substantial issues for folks who were either job seeking in 2020 or would have been job seeking in 2020. It sure looks like companies slowed or stopped hiring altogether and people probably didn’t look for new opportunities as aggressively as they normally would’ve because of the substantial economic uncertainty as we navigated a global pandemic all year.

So I’m thankful that my business grew, and I know that what I described above reflects a lot of economic turmoil for a lot of people.

I’m leading with this because it colors everything else I’ll say in my business recap. There’s just no way to talk about the business without accounting for COVID-19.

Stats

I normally end with stats, but I’m leading with them this year because of COVID-19.

Visits to FearlessSalaryNegotiation.com: About 660,000 (down from 1.2M)
Unique page views: About 940,000 (down from 1.7M)
Total email subscribers at the end of the year: About 40,000 (down from about 46,000 after an early-2020 pruning)
Product sales through the site: About 300 (down from about 800; about 20% of the 2019 product sales were a single partner promotion, so this is still a huge drop, but not as huge as it seems)
Coaching applications: 87 (up from 63)
Coaching clients: 16 (down from about 30)

Conversion rates are more or less the same as last year.

The one thing I’ll point out now and unpack later is that the drop in coaching clients was intentional. To help unpack this, I added a new stat this year: Coaching applications. That number went up by almost 40%, but the number of clients I actually worked with dropped by almost 50%.

Why?

I was focused on working with more senior engineers and executives, looking for opportunities where my service would add the most value possible. I wanted to be sure I had maximum time available to give the best service possible to the clients I did work with because I knew that each client would probably need more of my attention given the complexity of their negotiations.

Coaching revenue

The overall growth was driven mostly by growth in coaching revenue. But even there, digging down selectively would make things look quite a bit different. As I mentioned above, I actually worked with fewer coaching clients this year than I did last year—that seems bad. But my average revenue per client is up quite a bit—that’s obviously good.

This is one of the strange parts about running a business and making changes with an eye on the future: Even though the coaching results this year were more or less exactly what I was hoping for when I changed my fee structure and positioning, it still feels bad to see that I worked with fewer clients. This was by design and yet a declining stat feels bad.

One fun fact from 2020: A single coaching engagement generated more revenue than my business generated for the entire year of 2016 (the first full year I operated the business).

Product revenue

Product revenue was even weirder. It’s basically flat for the year, but a lot more of my sales came through partnerships than in previous years. Overall website traffic was way down due to combination of Google algorithm changes and the pandemic, but partner revenue was up thanks to connections and relationships I’ve built over the past several years.

Again, drilling into specific stats could lead me to say “Oh no! That’s bad!” Or “Wow, that’s great!” But the net result is flat product revenue for the year.

Given the pandemic, I’m very happy with this.

Strategy paying off

Last year, I made two explicit changes that drove significant growth in the coaching business and helped that part of the business to continue to grow through 2020.

First, I changed to a two-fee model: service fee up front; result fee based on the result we negotiate. Second, I continued to position my coaching further up market to work with more-senior software engineers, managers, and executives.

Either one of those changes in a vacuum would’ve netted an increase in revenue, but combined they drove a significant increase in revenue while reducing the number of clients I worked with. This is one of the few times where the outcome of a change I made pretty much exactly matched the intent behind the change.

By moving up market, I am positioning my service for clients where my expertise will generate more nominal value. What I mean by “nominal value” is “real dollars created as opposed to percent increases (marginal value)”. For some of my clients, both the nominal and marginal value are greater than for clients I’ve worked with in the past, which has an additive effect on the monetary result.

By moving to a fee structure that includes a result fee, I also capture more of the value I create and align my incentives with my clients.

So I’m creating more nominal value and capturing more of the value that I create, which has a sort double-bounce effect: I work with fewer clients but generate more revenue. That’s exactly what I was hoping for when I made those two changes, and it’s satisfying to see them work as I hoped they would.

As I mentioned above, I’m also fighting against the tendency to hone in on specific stats (eg, “number of clients booked this year”) which make me less happy. I designed the business to allow me to work with fewer clients, and yet it feels weird to work with fewer clients. Everything is fine, but it feels weird.

Last year, I shared my lifetime career earnings trajectory, and I’ve updated it to include 2020. You can see that this year looked a lot like last year.

Monthly income for my entire career to date

Investing in the business

This year, I also began make substantial investments to improve the business over time. I’m working on a rebrand and site redesign, and I’m investing in training to get better at selling courses to help more people. Just those things will cost about 10% of my 2020 revenue.

I haven’t begun rolling out the new branding yet (and won’t for a while), but here’s what it looks like:

On one hand, this is sort of scary because I don’t know whether and how this work will pay off. That’s the uncomfortable part of being a solo entrepreneur: the buck stops with me. Not only do I have to decide where and how to invest, but I alone absorb the consequences of those investments. So far, the cumulative investments I’ve made in my business have resulted in continuous growth. But there’s no guarantee that trend will continue.

The upside to a growing business is that I have more revenue to reinvest, so each successive investment can be larger. That means a potentially larger nominal return, but also means a potentially larger nominal loss. Since my personal and business finances are a hair’s breadth apart, this can be pretty scary.

But that’s the deal I made with myself when I quit my day job, and if I could make big investments when I was slowly going broke, I can certainly do it when business is better than ever. I just hope the investments I’m making now continue the trend of positive returns.

2020 Year in Review – Personal

This was a good year for me. I almost didn’t write that because I know this has not been a good year for a lot of people. But I feel I can acknowledge two seemingly conflicting things at once: I had a good year; many people did not.

COVID-19

Just like with my business review, it makes sense to start here for my personal review.

And I don’t want to bury the lede: I had COVID-19 right in the middle of the year. My experience was very mild and I only really felt symptoms for about 24 hours. I also know many people who have had COVID and all of them are fine. I feel very fortunate that this has been my experience.

My birthday was in March, and I planned a pretty big party for March 15. One week earlier and I wouldn’t have even considered COVID when planning it. One week later and I almost certainly would not have gone through with it. But on the 15th, things were still very much up in the air and after talking with everyone involved, we decided to go ahead with the party.

After that, everything changed. While my year was more confined than usual, I live in Florida where the response to the pandemic has been different than it has in a lot of other places. This has undoubtedly affected my experience in myriad ways.

I have a small, close-knit group of friends who I navigated the pandemic with. Many of them are medical professionals, so I was able to keep up to date with all the latest information, and I had good, real-time insight into how things were going here.

My family lives nearby, but I wasn’t able to see them as much as I normally would because of COVID. In fact, we took some family photos on March 14—again, right on the timeline tipping point—and I didn’t see them again for a while after that.

Overall, my personal life was affected much less than my business life. I’m extremely thankful for this. My friends, family, and community are all far more important than my business.

Ski trip

I made some big strides in Breck this year. Not only was I totally healthy this year, but I was able to build on everything I’ve learned the past few years to make some big leaps forward.

I did a lot of black diamond runs, and generally felt more comfortable on skis than I have before. It took me a while, but I think I’m a decent skier now.

We managed to get this trip in just under the wire—about two weeks after our trip, things started shutting down. During the trip, we talked about COVID-19, but it was more of a “What’s that all about? Should we be worried?” type of atmosphere.

2020 Ski Trip Crew

Birthday bash, just under the wire

In March, I had a really fun birthday party where I hired a private chef to prepare a nice meal in a house I borrowed for the evening. I didn’t know it at the time, but this was simultaneously a commemoration of my birthday and a last hurrah before everything shut down.

I had been planning to do something big for my birthday, and I decided to go with the most “Josh” thing I could: A nice meal, friends, and conversation. As for the meal itself, the apps and desserts were all fantastic. The entrees were good, but not amazing. But what I was really after was the experience and that delivered in spades.

2020 Birthday Dinner

Survivor Fantasy League goes International

My friends and I have a Survivor Fantasy League, which I realize sounds ridiculous, but which is also basically the most fun we have every week. Unfortunately, we didn’t get any new Survivor this year, so we did some digging and discovered that several other countries also have Survivor, and some of those countries have had epic seasons.

So we went and found one of the best seasons of Australian Survivor and we’ve been watching that all year. And I mean literally all year—we started in June and we didn’t finish until January 2021. We’ve pared things down a bit—no weekly challenges, no draft—but we still watch all the episodes and find ways to make it interesting. I actually won a free meal at Outback Steakhouse (heh) since I won our Survivor Survivor this season.

On one hand, it’s absurd that this season of Australian Survivor has like 30 episodes. On the other hand, I think we’re all really happy we found something to help us fill all the time when everything (especially sports) was paused this year.

An epic RV trip

In June, a friend of mine turned 30 and wanted to celebrate in a big way. The initial plan was some sort of international weekend trip, but COVD-19 shut that down, so we stayed stateside. A group of us rented a big RV and drove around the southeast for a week, doing as many cool hikes as we could.

The entire week went off without a hitch and we had a blast. I hiked about 45 miles that week, visiting some of the coolest overlooks and seeing some of the most beautiful sunsets I’ve ever seen.

Sunset on Black Balsam Knob in North Carolina

One thing that was, um, interesting about the trip was driving a 38-foot RV on winding mountain roads. We eventually learned to bungee the fridge and cabinet doors shut to avoid everything dumping out onto the floor during a sharp turn. And something that felt very 21st Century was that a few of us brought our consoles and tethered to our phones to play video games to pass the time. Even in the mountains, our connections were all pretty good and it was weird to think that we were playing games online against people all over the world while we drove along the Blue Ridge Parkway.

A big highlight of our trip was actually a Pizza Hut experience. We had been hiking all day (this was one of our longest days and we did at least three hikes that day) and got off the mountain so late that we had to race the sun to get off a three-mile trail before it got too dark to see.

We were famished, so we started looking for open-late dinner options only to be supremely disappointed pretty much everywhere we went. We tried a few different places and they had all closed for the night. Finally, we found a Pizza Hut that seemed to be open late enough for us to race over before they closed.

Unfortunately, they had closed early, so we sat in the parking lot trying to figure out what to do. One of the guys suggested we just go through the drive through to see if they were open, and most of us laughed and joked about how Pizza Huts don’t have drive throughs. Finally, another guy decided to just walk up and knock on the door. Someone came out, they talked for a while, and he came back to the van and said, “They’ll take us. Just go around to the drive through.”

Apparently Pizza Huts do have drive throughs, and this particular Pizza Hut with a drive through was run by manager who said, “I’m not gonna turn down money. Come on around.”

We ordered over $120 worth of stuff from Pizza Hut, raced back to the RV (we were in a van for the day) and ate like kings.

Another food highlight was a quick stop for Taco Bell as we raced between RV parks. We were super tight on time, so we drove the RV unreasonably fast down winding roads to hit Taco Bell and get to the camp in time to check in. I ended up spending $20 on Taco Bell and I ate every bite. That may not sound like much, but take a look at the Taco Bell menu next time you’re there and ask yourself how much food you can get for $20. Hiking burns a lot of calories.

Weird football season

This is one of the strangest football seasons I can remember. For the first time in over a decade, the Gators had a dynamic offense with one of the best college quarterbacks to ever play the game (this may seem a bit like hyperbole now, but I think it’s really likely Kyle Trask will be very good in the NFL and would’ve been one of a kind in college if he got to play more than a couple seasons). Unfortunately, we also had one of the worst defenses Florida has ever put on the field, so we totally wasted a generational offense.

Meanwhile, we were in the middle of a global pandemic, which made the schedule weird, and the in-stadium experience even weirder. And yet I went to more games this year than I have in a very long time. (I’m pretty sure I went to five games, but I honestly can’t remember.)

The stadium atmosphere was very strange. Quarter-full stadiums feel empty and there’s no energy, so most of the games felt more like a scrimmage than a real game. Texas A&M had lots of fans and it actually got pretty rowdy, and the Florida vs. Georgia game in Jacksonville ended up being pretty crazy (although that might just be how I remember it since we won). But in general, it was really eerie watching a football game when my nearest neighbors were six feet away and masked up.

Florida vs Texas A&M Football, 2020

My main takeaway from the season was that it was really fun to watch Kyle Trask, Kyle Pitts, and a bunch of other dynamic Gator players run beautiful offense, and I’m glad I got to see them do their thing in several games this year. This team will have some guys playing in the NFL for many years.

Five years since I quit my day job

September 18 2020 marked five years since I quit my day job. I’ll eventually add that story to my blog, but for now here’s a link to the twitter thread for posterity: 5 years since I quit my day job

The cool thing is that I’ve also been tracking each year in these yearly reviews, so I’ve got a much more detailed version here on the blog. It’s so strange to look back, especially at the early summaries, because I had no idea what I was getting into. But I managed to find my way to a growing, successful business doing something unique and valuable that also affords me the chance to set my own priorities and totally control my schedule.

My first disc golf tournament

Although I’ve been playing disc golf for most of my life, I had never played a tourney until this year. There’s a pretty active disc golf community called the Chain Hawks here in Gainesville, and they have an annual tournament called the Chain Hawks Open where they play the two best courses in Gainesville (which also happen to be the two courses I’ve played the most).

This year, a friend and I decided to play and see how we did. We both signed up for the “Advanced” division, which was one level below the open division where all the pros played. I actually played pretty well, shooting even par on Day 1, +4 on Day 2, and +4 on Day 3 for a total of +8 to finish middle of the pack.

Overall, I was really happy with my play, especially on Day 1. It was really windy and I made most of my putts. Days 2 and 3 were both much tougher because of pin placements, and I was frustrated to leave several strokes on the course by missing putts on Day 3 (I literally missed five very makable putts off the metal, including three consecutive birdie misses on the final three holes). But the overall result was pretty good considering it was my first tourney, and I was really fortunate to play with good guys in every group.

First tee of my first disc golf tourney

2021 Goals

This year’s goals are simple. I’m not making any new running goals because I’ve changed my workouts to facilitate recovery from leg workouts over progress in running times. I would like to hit some of those goals from years past, but that’s not a priority.

Increase business revenue by 50%

I almost balked on this one, but this is what I had in mind before the year started. I say “almost balked” because I’m still writing this in February and January was my worst month in about two and a half years. So this goal seems kind of crazy.

But! I’m making some substantial investments in the business, and if those investments pay off then this goal is achievable. Namely, I’m doing the first rebrand and site redesign since I started the business over five years ago. I’m also updating my product offerings to be more streamlined and more valuable (and hence, more expensive).

I think all of these things stacked together could have a multiplicative effect, but it will still be at least a few months before those changes are in place. So I would say best case scenario for the year is a slow Q1, the new changes start to take effect in Q2, and both Q3 and Q4 are off the charts. As always, it’s basically impossible to predict what will actually happen, but this scenario isn’t totally implausible. We shall see.

Be more generous

Same goal as last year. My business is still doing well overall, and my life is pretty simple. There’s a lot of room for me to be generous, and I enjoy it. So I will do more of it this year.

Here’s to a better 2021!

Big Strides in Breck

Last day on the slopes in Breck

2020 brought another amazing ski trip and it went much better than I hoped. Yes, it’s been nearly two months since I actually got back and I’ve been trying to finish this writeup the whole time, but things have been…strange since then thanks a little thing called COVID-19.

It’s weird to look back on the last week in February knowing what I know now. I remember being aware of COVID-19, and even slightly concerned that it could become a big deal in the States. But we were still on a ski trip and nothing was materially different about this year’s trip compared to the last couple of years.

But within two weeks of our trip, the resorts starting shutting down. And within three weeks of our trip, Stay at Home orders began rolling out across the country. I didn’t know it at the time, but this was a sort of last hurrah before the shutdown.

And now, as of the last week in April, everything is still more or less shut down. We’re talking about reopening things soon, but that hasn’t really happened yet. I think that’s why it has taken me so long to write this: I can live vicariously through Past Josh, slowly reliving a fun trip with a group of friends who had no idea what was coming.

This was an amazing trip. And the fact that we got it in under the shutdown wire makes it even more special.

And now, on to the recap…

Two years ago was essentially my first time skiing and it was verrrrrryyy slow going. Technically, I skied a few times in high school, but those were all east coast trips where I was on fake snow and nobody ever taught me anything at all about skiing. I literally just put on skis and started going down icy runs with no idea what I was doing and no way to stop on purpose.

So two years ago, when I actually took lessons and skied on real snow, was the beginning of my skiing journey, as far as I’m concerned.

ANYWAY, it was slow going at first.

Then last year I had a busted adductor that held me back and slowed me down even more. Nevertheless, I improved a bit and even skied down my first black run (although everyone knows Duke’s isn’t a real black run).

Last year was particularly frustrating because not only was my time on the mountain limited by my injury, but it dumped snow the last couple days I was there. Unfortunately, I couldn’t appreciate all that powder because I wasn’t very good and had already worn myself out.

This year was different. I extended my trip by a few days so that I could get more skiing in while also pacing myself and building in some rest days. We also got a lot of snow early in the trip, so I was able to appreciate skiing in powder this time.

I skied three mountains—Beaver Creek, Vail, and Breckenridge—so I’ll go through each of those in turn.

Beaver Creek

We headed west at 6 AM on Saturday morning, February 22—it was a long day. When we finally got to Beaver Creek, we grabbed some dinner and then I crashed early back at our Airbnb. We had seven people in a one-bedroom apartment that night, but I still slept great. The crowd thinned over the next few days as people headed back to work in Denver.

My first ski day was on Sunday and I took it easy on greens and blues. Beaver Creek is known for being beginner-friendly, so their greens and blues are easier than a lot of other places. That was good for me because I just wanted to get my skis under me and work on some technique.

That first day, I did two separate runs with very experienced skiers who showed me a couple of really useful techniques that immediately made me feel more comfortable on my skis.

Staying forward and poling around turns

When I start to pick up speed, I tend to lean back to brake—I think it is pretty typical for beginners. Paradoxically, leaning back can both increase speed and reduce control, so it’s a real bad idea.

I immediately felt better by making sure my weight was forward (poling around turns helps with this). I could go faster when I wanted, but I generally had more control and my speed was more consistent.

Letting my edges do the work

Leaning back also makes it harder to turn because it flattens out the skis. And, as I mentioned before, leaning back also makes it harder to control speed.

Until this trip, I was basically getting down the mountain by traversing for a bit, slide-stopping to regain control, turning abruptly, then picking up speed by traversing the other way, slide-stopping, etc. I was taking very jagged lines and had little control while also burning out my quads and hip flexors. Not good.

Now I was leaning forward more, and since my skis’ edges weren’t flatted out as much, I was also able to use the edges of my skis to help me turn. The skis will do pretty much all the work on turns if you just let them.

So by staying forward, poling around turns, and using my edges, I could actually control my descent and I was far less tired after each run. Those two quick lessons flipped a switch that paid dividends all week so I was no longer gassed after every run. Later in the week, I could do tricky black runs and still feel fresh at the bottom. Skiing feels totally different now.

By the end of the day at Beaver Creek, I felt great and started looking forward to trickier runs and big improvements during the rest of the trip.

Looking up from the base at Beaver Creek

My first full-on spa experience

Although I was staying down the mountain at an Airbnb, I was able to take advantage of the ameneties offered by a friend’s resort up the mountain in Beaver Creek. That meant ski in/ski out access, which saved a lot of time, which meant I had some time to hit the spa after I hit the slopes.

I think it would’ve been good anyway, but after several hours skiing with mediocre technique, a suana, jacuzzi, and some time to relax on a heated tiled chair was pretty great.

Vail (semi-fail)

Our next step was Vail—my first time back since the infamous Vail Fail in 2018. The good news is that we didn’t accidentally do any black runs. The bad news is the weather was not ideal. I take that back: for the experts in the group, the weather was great because they got to lap their favorite runs with fresh powder and very little traffic. For less-ambitious folks like myself, it was pretty gross. It was very cold (20s), windy, overcast and snowy. Visibility would spontaneously drop to almost zero.

But despite all that, it was pretty fun! I really only skied for about three hours, and we just lapped some easy greens and blues the whole time. We started out on Swingsville and Cappuccino (technically my first tree run), then did a few laps of Ramshorn.

My big takeaway was that I had improved significantly since the Vail Fail two years ago. I remember even the easiest greens being pretty tough my first time out, and they were easy this time. Even some of the blues weren’t bad (Vail is a little more challenging that Beaver Creek or Breck in general). I also got some time to work on my technique, and I felt like I was ready to start tackling more difficult runs when we moved over to Breck.

We ended up cutting things a little short because of the weather, and because our group dominoed itself down from four to three to two to one to zero people who wanted to go back out after lunch. We ended up getting a good lunch and doing some shopping in Vail Village for a while. It was a great day.

Moving day

Part of my plan this year was to extend my trip so I could get more ski days in and more rest days. I decided to take a rest day on Tuesday since we would be relocating from Beaver Creek to Breckenridge by the end of the day.

I spent the morning reading, catching up on email, and generally relaxing. Then I headed up the mountain to hang out and do some shopping before finally getting to try the famous Beaver Creek cookies. I ate … three? four? They were fantastic.

Beaver Creek Chocolate Chip Cookies

After one last trip to the hottub, we sped (very literally) from Beaver Creek over to Breck to make our dinner reservation at the Canteen, a delicious restaurant known for its brisket, mac n cheese, and giant cocktails among other things. We also played Body, Body, Body and I was not mafia per the usual.

It was a good day.

Back at Breck

Now we’re getting into the normal ski trip I’ve been on the past couple years. Everyone assembles in Breck, we have 15 or so people in a giant house, and we move into our normal routine:

  • Wake up around 8 or 9
  • Get some breakfast
  • Make snacks to eat on the slopes
  • Head out either in one big group or smaller groups
  • Ski, ski, ski
  • Head back once the lifts start closing
  • Hot tub time
  • Dinner
  • Crepes
  • Body, Body, Body
  • Sleep

There are variations on this schedule, but this is our baseline. The strangest thing about it is that it always feels like I’ve put in a full day by the time we’re done skiing, but then we have another 8 hours before we go to sleep. Every day feels like two days.

Wednesday

This is what we woke up to on Wednesday morning:

Our view from the porch in Breck

It would be beautiful like this all week.

My plan for this trip was to use the first part in Beaver Creek to remember how to ski and work on my fundamentals so I could jump right into tougher runs immediate once we got to Breck. So that’s what I did.

We started our first Breck day on a couple green and blue runs, and I quickly found my first black run of the year: Spruce.

Before I go on, I should say that most of the single-diamond black runs in at Breck are basically difficult blues. Spruce used to be labeled blue until several years ago when they moved it to black. But for me, the point is to slowly try harder runs so I’m always making progress. That’s how I approach pretty much everything I learn and skiing is no different.

I wanted to tackle Spruce first because I’ve been eyeing it for the past couple years as I rode the Colorado Super Chair lift over it. I remember thinking, “Whoa. That looks tough.” But our first time up the Colorado this year, I looked at Spruce and thought, “That actually looks…pretty easy?” I wanted to capitalize on that confidence so I went for it right away.

I ended up making two runs and the second was much easier. Sure enough, my skiing has improved. Last year, I did Duke’s run (the bluest of black runs) as my final run of the trip. This year, one of my first runs in Breck was Spruce—a more difficult black run, which felt pretty easy.

After a few laps on the Colorado, our group assembled for our annual group photo featuring our 80s gear. I remember it was very cold and windy, so just hanging out while everyone found their way to us was tough.

2020 80s Day in Breck

I spent the rest of the day doing blue runs and mostly taking it easy and having fun. I think I might’ve run Duke’s once, but I don’t remember for sure. That’s a good thing! What was a highlight last year became an unmemorable afterthought this year. That’s progress.

Thursday

By now, I had a crew to run with and we decided to head over to Peak 6. This was another step forward for me because I skipped Peak 6 day last year to ski solo and work on technique all day. I felt like I had enough to work on without some of the trickier stuff over at Peak 6.

But this year, I was ready to give it a shot and I’m glad I did. We ended up lapping Kensho Chair several times, starting with a few laps of Bliss, which is basically a steep blue bowl that I found harder than most of the black runs, and we finished up on Reverie.

I had a pretty big epiphany on my second run down Bliss: I was leaning back when I turned left, trying to slow down and gain more control. Ironically, the result was more speed and less control, which meant I would turn left and then go straight across the slope bouncing over tracks that were already there. Once I realized what I was doing, I started leaning forward more, using the tracks as a guide, and all my runs for the rest of the day were much easier.

This was probably the most progress I’ve made in a single day so far.

We had to head back to Peak 8, so we finished up with a run down Spruce before hitting the 4 O’clock home.

2020 Thursday in Breck

Friday (rest day)

I had planned for two rest days, and I took my second one on Friday after two consecutive ski days. A friend and I decided to head to downtown Breck and see what there was to see and this was a great choice.

We ate gelato for lunch and chased it with pecan praeleans from a local chocolate shop. Then we visited a bunch of other little local shops and just sort of killed the afternoon walking around.

It was a really relaxing day and I was glad I took the time to recuperate so I can make the most out of my last day on the slopes on Saturday.

Downtown Breck

Saturday

Our final ski day started with a pretty big group going after some tougher runs. We made our way over to Peak 10 via Frosty’s Freeway, which was a fun little black run connecting the peaks. I almost got into some trouble in the moguls at the bottom of this one because I was following a friend’s line, but I made it down ok. I also almost got taken out by two of my snowboarder friends, but we managed to narrowly avert catastrophe.

Cimarron at Breck

Over on Peak 10, we lapped Cimarron a few times and it was a lot of fun. I think the flat, steep runs are my favorite—I don’t like bumps very much. That could change as I get better, but for now this is the kind of stuff I’m after.The big group disbanded and I went back over to Peak 8 with a smaller crew. We started off doing a couple black runs over there—Duke’s and maybe Rounders—before heading over to lap Northstar a few times.

Our crew for the Luge

On the way to Northstar, I asked the more experienced snowboarder in our crew to show us where the Luge is. The Luge is an unofficial tree run off of Columbine, and a lot of Breck veterans talk about it as a staple. Although I planned to do the Luge eventually, I just wanted to get a look at it this time. The pla was to head to Northstar.

But my clever snowboarder friend decided to show us where the Luge was by dropping into the Luge and stopping. “It’s right here. See? Not so bad. This is actually the steepest part. It flattens out right away and you just have to watch the trees.”

By now it was clear that the other two of us would either have to leave him there and meet up with him later, or join him and run the Luge. We both reluctantly dropped in and I immediately hit a tree. I thought I might be in trouble, but the rest of the run actually wasn’t too bad. It was difficult because I don’t know how to ski moguls or make tight turns, but I made it down pretty quickly without any falls. Next time, I’ll try to do fewer three-point turns (my go-to maneuver in the tight channels, apparently).

Once we all made it down the Luge, we headed into Rip’s Ravine, which is a fun little path through the woods. I hadn’t seen this before, but it’s a lot of fun to string together with Northstar. You can get a ton of speed up at the bottom of Northstar, then shoot into Rip’s Ravine and just cruise for a few minutes looking at the scenic path they’ve laid out.

Northstar is a great marker for progress becuase I remember the first time I did it back in 2018: it seemed really steep at the top and the whole run was sort of intimidating. This year, it was our fun run to unwind after a day of black runs capped off with a Luge run. I think we lapped it three times to end our day, and the whole game was “Get as much speed as possible without endangering any children so you can speed through Rip’s Ravine at the bottom”.

This was easily my best day of skiing so far and it left me wanting more.

Odds and ends

In hindsight, last year’s trip was less about progress and more about managing my adductor injury while still having some amount of fun. At the time, I felt a little bad about taking it so easy but it’s clear that I did the right thing. If anything, the fact that I made some progress last year was impressive.

Ramping up to five ski days this year was also the right thing and I think I struck the right balance between maximizing the ski time on this trip and enjoying my vacation. It was cool to ski three mountains and I made huge amounts of progress this year.

I did not have a single fall during a run this year, but I fell probably 10 times otherwise. Sitting next to a snowboarder on the ski lift is apparently dangerous for me, and that accounts for at least three or four falls. I also tumped over a couple times learning how to use my edges just before a run. And my best fall of the week was just before my first Spruce run when I inexplicably fell over between the lift and the top of the run.

Next year, I might get more aggressive so that I have a few more falls during runs. “No falls on a run” sounds kind of neat, but it almost certainly means I’m not challenging myself enough. I’m reminded of a useful poker axoim: “If you never get caught bluffing, then you’re not bluffing enough.”

We had a great crew of people this year. Although big groups of people isn’t generally something I crave, our big ski trip is undoubtedly an asset. We have so many people that everyone can find a few people at their skill level to spend a day with. That makes it a lot easier to learn in a comfortable environment where you’re not holding anyone else back, but you’re also not holding back too much for less experienced skiers.

Next year, I want to hit some harder stuff and maybe even get good enough to hang with the expert-level crew for half a day or so. I’d like to hit Imperial Bowl, Peak 7 Bowl, and Whale’s Tail before the end of the trip next year. And of course I’d like to put in a better performance on the Luge as well.

It took a couple years, but I think I’m finally decent at skiing and it’s fun to have a new winter hobby.

Surviving Breckpocalypse 2019 (another awesome ski trip in the books)

Our group in 80s gear

I’m back from our annual ski trip and I had a blast. This year was an interesting mix of firsts and caution, and I made a ton of progress. (Last year was great too, read about it here.)

80s day was a hit

This year, we added an 80s day, which got us a ton of attention and made our first day on the slopes a lot of fun. There were two types of outfits:

  1. Authentic retro 80s attire. Maybe half the group went this route, wearing headbands, sweaters, jackets, and pants that were either actually from the 80s or could’ve been.
  2. Caricature 80s attire. And about half the group wore stuff that I describe as “What people today think people wore in the 80s.” I was in the camp, wearing a super loud 80s onesie.

Me in my 80s Day onesie

We picked the perfect day to do this since it was relatively warm, the sun was out, and the sky was blue all day. The groups pics we got at the top of Peak 8 made the whole thing worthwhile (the rest of the day was gravy).

Our group in 80s gear

Our group playing our air instruments

Slow and steady progress as a skier

This was basically my second time skiing. Technically, I skied a few times in high school, but I don’t count those because we were on east coast ice, and no one ever actually showed me how to ski. So I was terrible and I hated it.

Last year was the first time I skied on anything resembling powder and I also took lessons, so I immediately felt better about it and made progress quickly.

This year was interesting because I was the worst skier in our group, so I was the one holding things up most of the week. But I wanted to take my time and work on some things to make sure I was actually improving as a skier and not just ramping up the difficulty.

First day on the slopes

Our first day on the slopes, I felt pretty uncomfortable on my skis. Skiing is not like riding a bike—and I felt like it was my first time out. But after a few runs, things started coming back and I felt a bit better.

By the end of our first day, I felt like I was pretty much back to where I left off last year. I could comfortably cruise down most of the blues, occasionally feeling like I wasn’t quite in control. This was a super long day because we went out early-ish and came home late-ish. We did a bunch of runs and those runs were challenging for me since my form was so rusty. I was totally spent at the end of the day.

Second day on the slopes

I decided to take our second day and just focus on technique—specifically turning and maintaining my speed while staying in control. My friends would frequently say, “Wow, you really flew down that one! You’re getting a lot better!” And I would say, “Well, that’s because I only have two speeds—Stop and Go. Once I’m in Go-mode, I’m just trying to stay upright until I can slow down.”

I wanted to feel in control most of the time instead of feeling like I was just trying to stay upright and avoid wipeouts. So I stuck to blues and slowly improved.

Although I didn’t move up to more difficult runs as quickly as I did last year, I made a lot more progress in my first couple of days on this trip. By the end of the second day, I actually felt more like I had control, I could slow down when I wanted to, and I was able to choose my lines rather than just taking wide S turns and hoping for the best.

My turns got much tighter and I was intentionally hitting spots that seemed easier to navigate. I actually went in about an hour ahead of most of my peers because I was still beat from the first day, and I felt I had accomplished what I wanted for the second day.

Third day on the slopes

I asked a couple of friends where I could find the easiest black run at Breck. The answer came back: “Dukes.” It was a relatively short run that used to be a blue, but they turned it black so intermediate skiers wouldn’t get spooked. So it was technically a black, but only just.

My goal for the entire day was to get more comfortable and eventually do at least one black run, so I pretty much mapped out the day to slowly move toward that goal.

Powder, powder everywhere

Even before I started going on this trip last year, there was much lamenting that fresh snow never arrived. It was almost like this specific trip had some sort of jinx on it so that it was always warm and sunny with no new snow during the trip.

That all changed this year, and we made up for lost time. In our last two days at Breck, I think there was over a foot of snow and it just kept coming.

So I swapped out my regular skis for “powder” skis to start the third day. At first, this was kind of frustrating because I had to re-learn a lot of what I had worked on the previous day. Turning was harder, stopping was harder, maintaining control was harder. Everything was harder.

But once I got used to the new skis, they were much better and easier to control.

A solo run for my first black

After several good blue runs, it was time to make my way to Dukes, the easy black my friends recommended. I actually scoped it out during my first run of the day since it starts from a common catwalk that we use to move between peaks.

I was going to run it with a friend, but he ended up stopping early, so I was on my own. But before we parted ways, I asked if he had any suggestions—he had three:

  1. Stay to the right, away from the moguls.
  2. Wait for a big opening so I could do “my run” without traffic around me.
  3. If I felt like I needed to slow down to regain control, turn slightly back up the mountain to regroup.

And off I went.

The lift dropped me about 100 yards from the top of Dukes, so there wasn’t too much time to think about it once I was off the lift. I initially planned to get to the top of the run and give myself a minute or two to gather my courage, but it turned out I didn’t need that kind of time.

I got to the top of Dukes, looked at it and thought, “Meh, that doesn’t seem so bad. Let’s go.” And I was off. Overall, it was a pretty good run and I used all three of my friend’s tips.

I actually made it down the steepest part without any issues, but I relaxed too early because I didn’t realize there was a second steep part that was also icy and bumpy. All of a sudden, I realized, “Uh oh, I’m going too fast and this is all bumpy ice. Need to slow down… or need to at least try to maintain control until I can slow down.”

I didn’t quite succeed, but I didn’t quite fail either. I basically ended up spinning out so that I didn’t technically “fall”, but came as close as I could’ve. After a few very ungraceful flailing spins, I found myself stopped, skis splayed, hands on the ground in front of me, holding me up. I regained my composure and it was easy from there on out.

I remember getting to the bottom and thinking, “Huh. That wasn’t so bad.” I almost talked myself into doing it one more time, but I thought better of it and made my way back to our house.

Right after my black run on Dukes

Fourth day on the slopes – or not

I finished my third day on a real high. I finally felt comfortable on my skis, I felt more in control than I had at any other time this year or last, and I did my first black.

But I also felt like I had been pretty lucky so far. I had been really tired a few times during the week, but had managed to get good runs in despite the fatigue. I also had a strained right adductor to watch out for.

Before I went skiing, my doctor said, “Sure, you can ski. But don’t do anything crazy and stay off the tougher blacks.” Remember the spinout I mentioned on Dukes? It was exactly the kind of awkward motion that could’ve reinsured the adductor. I’d been rehabbing that stupid thing for 5 weeks, and hadn’t run in almost 10 weeks because of it, and I wasn’t looking to re-injure it if I didn’t have to.

So I had a really tough time deciding whether to go back out for our fourth ski day, or if I should just take it easy.

I ultimately decided to take an actual vacation day and just hang around the house, and there were a few factors at play there:

  • I felt like I had been pretty lucky that I didn’t re-injure my adductor despite some close calls.
  • I accomplished my primary goal for the trip—do a black run.
  • The conditions were very powdery, but I wasn’t good enough to really take advantage of that. And powdery also meant cold, snowy, low-visibility.
  • It was the Saturday beginning Spring Break, and I knew the lift lines would be long (so I’d be waiting around a lot, and wouldn’t do much skiing for the time I would be out there).
  • I hadn’t taken a real vacation day—a full day off to just relax—in…I can’t remember the last time I did that, but it was years ago.

It was basically a coin flip that came down to, “I’ve checked all the boxes for this trip and I didn’t re-injure my adductor. I finished on a high and I am anxious to get better and ski more when I’m healthy. Maybe I should just quit while I’m ahead.”

I decided to just take the day off. If my adductor had been healthy, I would’ve gone out. But I knew that if I went out, I would want to try tougher blacks, and that would make re-injury more likely.

Even in hindsight, I’m not quite sure if this was the right thing to do.

A great trip with friends

The coolest part of the ski trip is that each day essentially has two major events: Skiing and hanging out.

Skiing is typically over around 4:00 at the latest, and that means we have another eight hours before we go to sleep. We typically try to squeeze in all four of these things after skiing:

  1. Hot tub time
  2. Dinner
  3. Crepes a la Carte—an amazing crepe place in Breck
  4. Games (usually Body, Body, Body, but not always)

We checked all those boxes a couple times and hit three of four every night (I think).

We had some amazing food—The Canteen, Michael’s, Giampietro, Empire Burger (the sides and sauces are amazing)—but I didn’t document any of it because I was too busy eating it.

And I was finally mafia in Body, Body, Body and got the win. So now I’m one-for-one as mafia, but still only like one-for-fifteen being mafia. The law of averages will eventually catch up and I’ll go on a mafia spree (or maybe I’ll just cheat—ahem, GP—and make it happen on my own)

Surviving the Breckpocalypse

About half way through our trip, it began to snow. And snow and snow and snow and snow. There was a lot of snow.

This made my final ski day a lot of fun, and I’m sure it made Dukes (at least the top part) much easier. My friends said it was the best snow day they had ever seen, and some of them even extended their trip to get more time in the powder.

Here’s a short video of the view off of the balcony…

Short video of our balcony view

Of course, the snow giveth and the snow taketh away… the ability to travel. We had a few rental cars with varying numbers of passengers, and some of the cars had trouble either explicitly getting through the snow, or in driving from Breck back to Denver. My car was pretty lucky because we left early. It took us almost three hours to get to Denver (normally two hours), and we had to stop to manually de-gunk the windshield a couple times, but we made it. There was also an avalanche about 20 miles west of us on I-70, so I’m obviously glad we missed that.

Some other folks either missed their flights after a long (five hours!) drive to Denver, or simply got stuck in the snow in Breck and had to wait it out (this may or may not have been related to an ill-advised decision to rent a 2WD truck despite a steep driveway and a snow-heavy forecast).

When we finally go to Denver, it was 3 degrees outside—the lowest March temperature in like 140 years. Apparently it got as low as -6, so we got there when it was nice and toasty outside.

All in all, this was another amazing ski trip and I can’t wait to get back out there and hit some real blacks next year.

My 2018 Year In Review: Finally making a good living

It’s been three years since I quit my day job to build the Fearless Salary Negotiation business. It’s finally paying off.

I didn’t think this year would go so well for my business, especially considering that I was almost out of runway only 18 months ago. But my 2018 income is very close to what it was when I quit my day job in 2015, and now I have the freedom, flexibility, and personal satisfaction that comes with making a living from something I built from scratch.

The decision to double down on salary negotiation coaching in 2017 continues to pay dividends as I work with more clients and raise my rates to capture more of the value I create with my work.

That’s the business side of things.

Personally, things are great. I’m fortunate to have a very close group of friends. I’ve gotten better at running, and I’m pretty good at making omelettes. Of course there are things I would like to work on for 2019, but 2018 was amazing!

Here’s a Table of Contents so you can jump to wherever you want…

2018 Goal Review

So how did I do this year? Let’s take a look at my 2018 Goals.

Make a good living

The goal was I want to make $10,000 per month in net revenue in 2018. More specifically, I would like to do that by selling $5k in products and booking $5k in coaching per month for the year.

I missed this goal, but not by very much. And each $5k sub-goal is pretty close to what I actually did.

The difference between hitting and missing this goal comes down to a consulting retainer that ended in September after about a year. If that kept going, I would’ve made it.

I also could’ve made it if October wasn’t so horrible revenue-wise.

To be honest, this is bonkers to me. I didn’t actually think I might hit this goal—I just wanted to make sure I set an ambitious-but-achievable goal to maximize my earning potential in 2018.

I did hit a secondary goal, which was to double revenue year-over-year from 2017 to 2018. I did that from 2016 to 2017, and it seems like “do twice what I did last year” is a reasonable goal that can be achieved through good planning, execution, and moderate growth.

More traffic

The goal was I would like to build my organic search traffic to 100,000 unique visitors a month.

This one is interesting. I did hit this goal, but then traffic fell off and settled in around 80,000 visitors a month.

2018 Organic Traffic

The good news is that with more traffic came more revenue, so there was a direct benefit to this goal.

Improve at Sales

Here’s that goal: My goal is that 2% of email subscribers become paying customers within the first 30 days.

This was a huge miss. HUGE miss.

That’s the bad news.

The good news is I did build one funnel—the one that gets the most traffic—that pretty consistently converts 1% of subscribers to customers for a $47 product.

So there’s a lot to build on there.

Help other businesses get more search traffic and email opt-ins

Ehhh, I did some of this but not very much. I worked with a few clients to tweak their SEO, and I worked with some clients on their content strategy. But I just didn’t feel motivated to push this part of the business.

I think there are still things to focus on in my core business and I didn’t want to get too distracted.

Running goals

  • 10k – Sub-8:00 pace Hit it with a week to go in 2017
  • 5k – Sub-7:00 pace (currently 7:14)
  • Mile – Sub-6:00 pace (currently 6:08) Ran a 5:54 mile in August
  • 400m – Sub-60s pace (currently ~64s~ 62.75s)

I’ll write about this later, but I also ran a PR for 15k and finished my first Half Marathon.

A detailed 2018 Year In Review – Business

At the beginning of this year, I felt like the trajectory was in the right direction, but I still had some concerns. I started the year in a bit of a cash crunch as I was still digging out from the financial hole I dug to get through 2017.

To free up cash for 2017 taxes, I had parked some expenses on a 0% credit card. It looked like I would be able to pay it off before the interest rate jumped in August, but it would be close. I also decided all 2018 taxes would be taken off the top and held in a dedicated account so I wouldn’t have to scramble to pay taxes this year.

Saving ahead for 2018 taxes plus paying down that 0% card meant 2018 could be sort of a financial grind. I knew that was likely when I made those decisions in 2017, and now it was time to pay the piper.

January was mediocre, but then things took off: February was my best month ever, and March, April, and May were all consecutively better.

By June, I was out of the woods and starting to replenish my savings. It was almost exactly one year from “Uh oh, I might have to get a day job.” to “This seems to be working and I have some room to breathe again.”

With the exception of a horrible October, the second half of the year was great (but not quite as strong as Q2). I may be doing enough business that I’m able to spot some seasonality, but I’ll have to wait and see.

For now, things are good with the business and I finally feel like I can relax a little and enjoy what I’ve worked to build over the past few years.

Salary negotiation coaching

In June of 2017, I repositioned myself as a salary negotiation coach for experienced software developers. Before that, I was basically positioned as an author who also did some coaching.

That shift in focus is what saved my business.

I kept pulling on that thread in 2018 and it continues to pay off in a few ways.

First, I’ve gotten more and more reps negotiating job offers with big tech firms, so I know their playbooks. This has made me more confident and gives me the tools to pitch my coaching offering more effectively.

Second, I’ve been able to raise my prices so I earn more for my work by reaching a more experienced market where my work has more value. Basically, I’ve enabled more and more experienced software developers and senior managers to find me when they have job offers, and their job offers are usually very substantial, which means their improvements are often substantial.

The combination of those two things is what has really enabled my coaching business to take off.

I also really like what I do. It’s fun to help people who’ve worked so hard to build a valuable skill set actually capture more of the value of the skill set they’ve built.

Product sales

Selling digital products is at once a boon to my business and an enigma. Traffic and sales were up this year, but I continue to suspect that I’m selling far less than I should given my traffic levels, and the quality and value of my products.

This has to be a focus for me in 2019. With over a million visitors to my site in 2018, I should be selling a lot of products.

Email list growth

I hit some pretty big milestones this year. I was this close to hitting 35,000 email subscribers before I pruned almost 10,000 subscribers. Since I started building my list in January 2015, I’ve had more than 60,000 people join my list. About 20,000 of those unsubscribed over time, and I pruned another 12,000 or so.

The churn is normal. The pruning is sort of controversial among my peers. But the bottom line is I had a ton of people on my list who were not opening or interacting with any of my emails, and I don’t think it’s good for anyone if I keep emailing those folks.

So I’ll end 2018 just shy of 30,000 active email subscribers. That’s crazy to me. I had 600 subscribers after my first full year doing this. Now I get more than that in a typical business week.

Now I just need to get better at aligning my product offerings to my email subscribers’ needs.

Consulting retainer

I also had a fun opportunity to consult with a very successful business. It was an unusual arrangement without any real parameters: Just come hang out, observe what we’re doing, and make suggestions to help us improve.

It worked really well for a while and it was a ton of fun, but the business itself eventually became so active that I found myself lost in the shuffle. I would love to do more of this sort of thing, and it’s good to have this experience so I can help define the desired outcomes—for myself and for the business—of this sort of engagement better in the future.

Essential Salary Negotiation Email Pack

Last year, I made a small product called The 15-Minute Counter Offer. I was trying to learn more about how I could help folks finding FearlessSalaryNegotiation.com when they needed help negotiating a job offer.

What I found was that most of those people were in a real hurry—they had just a few hours from the time they found myself site until they had negotiated their offer.

So I built The Essential Salary Negotiation Email Pack to help with their specific needs in a very short timeframe. That product, plus The Salary Negotiation Crash Course—a more in-depth-but-still-streamlined, end-to-end job offer negotiation course, offered as an upsell to the email pack—made almost $12,000 in 2018 and I didn’t start selling it until April.

This is by far my most successful new product and I hope to create a similarly successful offering for folks who aren’t sure how to ask for a raise in 2019.

Overall stats

Here are some high-level stats for 2018 (all as of December 26):

Traffic

There were 1.023 million New Users on FearlessSalaryNegotiation.com, and 90% of those were from organic search traffic.

My email list

Here’s an updated list of end-of-year email subscribers:

December 2015: ~700
December 2016: ~2,500
December 2017: ~11,500
December 2018: ~28,500

In 2018, I had 24,300 new email subscribers, but since I pruned about 12,000 recently, active email subscribers is “only” 28,500.

Here’s a graph of my email list growth in 2018:

2018 Email List Growth

No hockey stick this year—just consistent growth.

Conversion rates

They’re basically the same as they were last year—about .4% of email subscribers purchase something from me in the first 30 days. The consistency is a little deceptive as I did significantly increase conversions for one funnel, and I also significantly increased opt-ins for all other funnels.

Last year, I said, “If I hit [5% opt-ins and 2% conversions] by the end of 2018, I should be able to hit my revenue goals.”

On one hand, it’s really frustrating to see such a huge miss. On the other hand, I almost hit my revenue goals anyway, so if I actually find a way to get those sorts of conversion rates I’ll be doing very well.

A detailed 2018 Year In Review – Personal

Two things stand out when I think back on this year: traveling and running.

Travel

2012 was the beginning of a years-long plan to build a business and stop working for other people. That’s vague, but it’s about as specific a plan as I had in mind.

I started by getting a good-paying day job to leverage my prior career experience and newly-acquired MBA. I used that income to start paying down debt as aggressively as I could, and I began slowly acquiring the basic skills I would need to (eventually) build a successful business.

For the next few years, I was either paying down debt or saving up a runway while basically working seven days a week on my day job and side projects.

In 2015, debt free and comfortable with my runway, I quit my day job to focus full-time on building a business. For a little over two years, I worked really, really hard seven days a week. I think that sort of work was necessary to build the basic infrastructure of my business, but it was also very taxing.

In 2017, I decided the seven-days-a-week schedule needed to end, so I sort of re-entered normal society and focused on community. Either the foundation I had built would facilitate a real business or it wouldn’t—it was time to find out.

So I stopped working so much, but I still wasn’t earning enough to take non-business trips or anything like that. I had to pass on a number of super fun trips to avoid burning too much of my savings.

That changed in 2018 as my business actually started to take off.

Ski trip

I went skiing for the first time since high school and I loved it. My friends go on a ski trip every year, and I was always a little jealous I couldn’t make it. But I also remembered absolutely hating skiing, so it didn’t sting too badly to miss that part.

I figured I would give it a shot this year, mostly so I could say, “See! I went skiing and it’s still awful!” But it turns out I really liked it, and that getting ski lessons is actually very useful. Who knew?

I had a blast and I can’t wait to get back out there in 2019.

Our group at Vail

Boston

I also went to Boston with a couple college buddies in June. It was amazing. I hadn’t taken a trip like that in a very long time, and it was everything I hoped for.

Classic Allen face

I have a lot of “Allen makes this face at a sporting event” photos

Running stuff

At the end of 2017, I asked “Am I a runner now?” In hindsight, that question was pretty naive. The answer is vey clearly no.

Runners run a lot more than I do. But I am a hobbyist and I made progress on my hobby this year.

My first 15k

In January, I ran my first 15k and it did not go well. Turns out that running a 15k with the flu just isn’t a great idea. But I finished and my time wasn’t terrible (for a guy with the flu).

My first 15k

Sub-6:00 mile

One of my original running goals was to run a sub-6:00 mile. It took me a few tries and about 18 months, but I smashed that goal with a 5:54 in August.

My six-minute mile time with 400m splits

This may have been my most satisfying PR yet because it as almost exclusively mental. I had to try and fail a few times to understand exactly how to run a fast mile, but once I understood it I was able to knock it out.

15k PR on a training run

I was prepping for a Half Marathon and I ran an 8:00-flat pace 15k. This wasn’t even on my list of goals, but it felt pretty good. When I started running at the beginning of 2017, I set a goal of running this pace for 10k. So it’s cool to run that time for a longer distance.

15k training run - 8:00 pace

My first Half Marathon

I was planning to run a Half Marathon earlier in the year, but the aforementioned flu ruined my training and I bailed. Plus, the Half I was going to run would be during the winter and the weather was going to be awful.

A wise friend told me, “Do you really want your first Half Marathon to be a miserable experience? Why not just wait for a better one?” So I did.

I ended up running a Half in sunny, 60º weather and it was a pretty good experience. The one hitch was that the course was only 12.1 miles, so I literally had to go the extra mile to finish.

At least we got cupcakes at the end.

My first Half Marathon (with cupcakes!)

I ended up with a pretty good pace of 8:24. I was very happy with my race strategy as I felt I did the best I could, and I’m certain I could go quite a bit faster with better training.

That said, I doubt I’ll run too many more Halfs. I’m glad I did it, but it really took a toll for like two weeks after the race.

2019 Goals

I’m going to keep things pretty simple this year.

Double revenue again

I have no idea if this is possible or how I will do it, but I don’t think it’s a crazy goal.

Can I double product revenue? I think I can, although I don’t quite know how. I have the traffic and products to do it. There are also a lot of sub-goals that I won’t write about here, but which I think will help with this high-level goal.

Can I double coaching revenue? Yes, by more consistently booking clients and continuing to raise my rates.

This year, I earned pretty much what I earned in my last year of full-time employment. That feels amazing. But I didn’t quit my day job to make the same money I made before. I quit my day job to earn multiples of what I was earning before (among other things). So I want to continue pursuing that as long as it doesn’t require me to return to being a hermit.

Sub-7:00-pace 5k

I’ve been chasing this one for a while, and I probably should’ve tried to knock this out when I ran the sub-6:00 mile earlier this year. Unfortunately, I was battling some injuries and decided to slow down before I really hurt myself. I would like to check this one off the list.

Sub-60-second 400m

I’m honestly not sure if I can do this or not. For one thing, I’ve got nagging injuries that basically prevent me from sprinting. But if I can get healthy, I think I’ve learned enough about proper running that I can do this.

This wasn’t one of my original running goals (I wasn’t sure I’d ever break 70s), but I think it’s still an achievable stretch goal. Or maybe it’s not. I dunno.

More trips

I travel to relax, and I’d like to do that more this year.

I’d like to take another trip with the Boston crew this summer. That trip was a lot of fun and I think the three of us are pretty much an ideal traveling group.

A trip to Europe would also be great—I miss Italy—but I don’t have anything specific in mind yet.

My first ski trip since high school was awesome

The Monte Carlo at Breck

I lay on my back, staring up at the blue sky. I assume it was beautiful, although I can’t really remember because I was desperately trying to catch my breath at 11,000 feet above sea level.

I looked past my feet, up the mountain to find my ski. My friend had already found it and was bringing it down to me.

“I. Don’t think. I’ve. Ever. Been. This tired.” was all I could say.

Our group had just accidentally gone down a Blue run, which we later found out was basically a Black, and it had not gone well. I tried my best to maintain control, but I had gone down the un-groomed part of the run, which meant I was basically skiing down a black on ice.

This moment was one of many that we would later call the #VailFail, and it was definitely a low point. But around this low point was a week of high points and a lot of fun.

Skiing for the first time in a long time

Last week, I went skiing for the first time since high school. All of my previous skiing experiences were terrible, so I wasn’t expecting to have much fun.

Fortunately, my friends insisted I try skiing on real mountains with real snow, so I went to Breck to give it a shot.

I had an amazing week and really enjoyed skiing. It was a lot easier than I expected and I picked it up faster than I thought I would.

So this will be more of an old-school day-by-day recap of my trip, mostly for posterity.

Day 1: Traveling there

A few of us rented a car and drove from Gainesville to Orlando, where we flew Southwest directly to Denver. Then we rented cars and drove from Denver to Breck. Everything was entirely uneventful, which is how I prefer to travel.

Once in Breck, I immediately felt the altitude and got winded just walking up stairs and doing other simple things. I also got a low-level headache that persisted for a couple of days despite all the water I drank.

We rented a ridiculous three-story house that slept 13 people. “The bunk room”, which I shared with three other guys, was crowded but fun.

That first night, we got our ski gear, settled in, and went out for our first crepes of the trip.

A picture of a giant crepe

These crepes are delicious and enormous.

Day 2: Lessons and getting settled

Everyone I talked to said, “You should definitely take lessons on your first day. It’s the best way to learn the basics.” This was great advice, which I think they learned to give after other training methods failed.

For example, I think they used to teach newbies how to ski using a sort of Scared Straight methodology (“This is a blue run. You will fall a lot, but by the time you make it to the bottom, you’ll be ok at skiing.”), which probably isn’t the best way to learn.

So several of us split into groups for snowboarding and skiing lessons. There were only two of us skiers, and our instructor was Dave. There were two other folks in our group, which meant Dave only had to work with four students—that was great for us.

My first ski lesson

We gradually worked through the basics, and I felt pretty good right away. Skiing was already less awful than I remembered. By lunch time, my friend and I had progressed past our two fellow students and were quite a bit more comfortable with the green runs we were doing.

Just before lunch, Dave took my friend and I on a couple runs while the other two members of our cohort took a breather (they were very tired and frustrated, and I think Dave correctly assumed the best thing was for them to rest so they didn’t get hurt). We did our first blue and it went pretty well—we could see that we were making real progress already.

After lunch, we did a few more runs, worked on some more advanced (for us) techniques, and officially graduated to “Level 4” (of 5?), which felt pretty good.

We finished the day by meeting up with most of our other friends to ride up and do the 4 O’Clock Home run (which is mostly green with a little blue up top).

One of the nice things about the awesome house we rented was that we could almost ski in and ski out. It was super convenient to walk for three or four minutes, put our skis on, and hit the lift. And it was even more convenient to ski down the 4 O’Clock, pop our skis off, and get home in about 5 minutes.

Our only in-house group dinner

After we finished skiing, some of us headed off-site for some hot-tub time while others went shopping to get supplies for our only in-house group meal of the week. I sautéed asparagus for everyone, which meant I got to hang in the kitchen and meet new people as they passed through to see what we were up to.

This was probably my favorite meal of the week and I’m hoping we do at least two of these next year.

Body Body Body

After dinner, we played Body Body Body, which is like a live-action version of a game called Mafia. I’ve always liked Mafia and I like Body Body Body even more.

There were about 10 townspeople and 3 mafia members. Once the mafia members have identified each other, we turn the lights out, crank up spooky music, and wander around the mansion in the dark. Mafia members kill townspeople by mock-slashing their throats. Once a townsperson has been killed, they stop walking and drop to the floor. The game continues until someone finds the “body” and shouts “Body body body!” so that everyone can turn the lights on and run to see who died.

Then the game moves to the more typical “Mafia”-style game where everyone talks things through and nominates a couple people they think might be in the mafia. Eventually someone is voted out and the game resumes unless the mafia have all been discovered. The game ends when either the mafia are all voted out or there are equal numbers of townspeople and mafia remaining.

The game is a lot of fun and we played pretty much every night. My only regret is that despite playing 10+ games, I was never mafia (which is the most fun part of the game) thanks to a series of unfortunate events that culminated in our narrator tilting and skipping one game, causing some logistical snafus that caused us to redraw for spots the one time I actually drew a “Mafia” card.

C’iest la vie.

Day 3: First normal ski day

Lessons were physically and mentally exhausting, plus I was still feeling the altitude, so I was admittedly not super stoked to hit the slopes again.

Fortunately, a couple of experienced friends, who arrived later than the rest of us, were heading out for their first day on the slopes and offered to take me along and help me slowly work up from Greens to Blues. (Shout out to James and Jen for being awesome teachers.)

By lunch, we were doing Blue runs and I felt pretty comfortable. They were a little fast for me, and I didn’t quite have the control I wanted, but I was able to move down them pretty quickly, mostly maintaining control, and without falling. All in all, a pretty big win.

By the end of the day, I felt comfortable on Blues, which was pretty remarkable considering I had taken beginner lessons the previous morning. Some of the group took a short Black to finish the day, but I skipped it. I was super tired and just didn’t want to risk hurting myself with two days left to ski.

Mi Casa

We went to a local Mexican restaurant for dinner, and it was pretty good. Although… my stomach didn’t take too kindly to it. Normally, this would be no big deal, but an upset stomach plus altitude meant Day 4 at Vail would be challenging.

Assume there was hot-tubbing, Body Body Body, and probably crepes

The evening routine was pretty consistent. Here was our view from the hot-tub:

Hot Tub View

Day 4: #VailFail

This brings us full circle to the beginning of this post. We decided to make a day trip to Vail, which is about 45 minutes from Breck. At first, it was a smaller group, then it expanded to be almost everyone. In theory, the skiing is better at Vail, plus we could get an awesome group picture at a famously beautiful spot on the mountain.

But, all the best laid plans…

We arrived at Vail and easily got onto the mountain thanks to some great planning by the more experienced members of our crew. Our first order of business was to rendezvous at the top of Lift 37 for the infamous picture, and then we could all split off into groups based on experience level.

Our plan was to take a long catwalk to another catwalk that would drop us at Lift 37. But a Vail employee convinced one of our crew that there was a better way: We could cut out a lot of catwalking by taking an easy Blue after the first catwalk.

“We have a lot of beginners. Is that Blue going to be ok for beginners?”
“Definitely!”

We knew we were in trouble pretty much right away. The entrance to the first catwalk gave a lot of folks serious problems. I made it down to the catwalk without falling, but it was a dicey run.

Once we eventually got across the first catwalk, we stopped to regroup before heading to the beginner-friendly Blue we had been promised. But first, we had to wait out a pretty serious windstorm that made me thankful I brought my balaclava since the wind-driven snow felt like a sandblaster to the face.

Another ominous sign.

At last, we all get around to the entrance of the beginner-friendly Blue and we realized… this was not beginner-friendly. It was super steep and icy—not good for beginners. I tried my best to take shallow angles and control my speed, but I just wasn’t good enough to manage it. I fell over a few times—nothing serious—before heading to a part that another skier said was probably a less-steep way to get down.

Turns out I was heading for the most steep part of the run, and a more experienced skier in our group later told me, “I saw you heading over there and thought, ‘He needs to turn back the other way or this could get really ugly.'” I did not turn back the other way. Things got pretty ugly.

This is the part where I wound up sliding head-first down the mountain on my back, losing one of my skis in the process. Ironically, this may have been the best outcome for me once I chose this particular path.

We later found out from another Vail employee—a friend of the group—that this was basically a Black run and that beginners had no business being on it. There was a groomed section, which they considered a Blue, but most of us had not taken the groomed section. (This might be my only regret of the trip—if I had known about the groomed section, I may have gotten down with little trouble.)

Exhausted from accidentally attempting a Black run, I caught my breath and chugged half a bottle of blue Gatorade, then made my way down to the second catwalk. As I worked my way across the catwalk, the wind picked back up—it was getting worse.

Most of us met up at a natural stopping point before heading down to Lift 37. Bad news was waiting for us there: Lift 37 had been closed because of the wind; only Lift 36 was open; there was no way to ski down.

A few of us had made it onto Lift 37 before it closed. Some of us were stuck waiting for Lift 36. And others had been so far behind that they were blocked from the catwalk and could not even make it Lift 36. We were now scattered all over the mountain.

The lift line at Vail

They had also been slow to close the catwalk, so people continued pouring in as the line backed up. We waited there for over an hour, totally exhausted and dehydrated.

By the time we got off Lift 36, it was after 1:00 PM. We had been on the mountain for over three hours and had almost nothing to show for it. We finally made it down to our next rendezvous spot where we were able to regroup and get a less-spectacular version of the picture we had been chasing for the past several hours:

Our group at Vail

And here is where we coined #VailFail. We had been on the mountain for about four hours and had almost nothing to show for it. The back side of the mountain had been closed, we had done like 1.5 runs, we didn’t get the picture we were chasing, and several of our crew were wiped out from the initial “Blue” that we descended.

We split up by experience level and managed to get a few runs in before calling it quits and meeting up at The George for an early dinner. Even the Greens at Vail were pretty steep and challenging—some of them harder than the Blues I had done at Breck.

After the high of making such quick progress the day before, this was a pretty serious low for almost everyone. I was glad the day was over and that we would be back at Breck for the rest of our trip.

Day 5: Redemption

This would be our final ski day, and I was really happy to be back at Breck. I spent most of the day doing Blue runs, which all felt really easy after the runs we did at Vail.

We all met for lunch on Peak 7, where there was a food court with a fantastic view of the mountain.

The last real run I did was Monte Carlo, which is a really long, fun Blue. A friend got some photos and video of the run so I have a record of where I was skill-wise after my first real ski trip. I felt much more comfortable than I expected, but can also see that I have a lot of work to do.

The Monte Carlo at Breck

I finished the day paying it forward: A less-experienced skier in our group and I did a couple of super-slow Blue runs to get down off the mountain. This gave me a chance to help someone the same way I was helped on Day 3, and also gave me a chance to really enjoy the views and reflect on how much I had learned in just a few days.

On Wednesday, I had no idea what I was doing and felt accomplished for scooting down the bunny slope without falling over. On Saturday, I was helping another skier get down Blues to get off the mountain.

Day 6: Traveling back

After a long week, I was ready to get home. But first we had to drive back to Denver, fly east for a few hours, rent a car in Orlando, grab dinner and drive back to Gainesville. We would be lucky to get home by 11 PM.

But on our way to dinner, we passed Andretti Karting and our crew couldn’t resist. Actually, I could totally resist—I was about 5 hours past my “have fun while traveling” limit—but the other four in our little group were all about it.

So after about seven hours of traveling, we stopped off for some kart racing. My only options were to just sit around and watch them race, or to join them and hope I could compete despite how tired I was. We warmed up by playing a reaction-time game and two quick-shot basketball games (I won two of three of the games I played) while waiting for our track to be ready.

The race was really fun except we were surrounded by terrible drivers who kept puttering around the middle of the track. All of us would’ve gone much faster if we hadn’t had to work around the slower drivers. I tied for 2nd overall, and I felt pretty good about that.

Our Andretti Racing crew

Then we finally started our drive home from Orlando, talking about the Oscars most of the way.

I finally got home around 1:00 AM and immediately crashed.

Planning for next year

Before this trip, I had decided I hated skiing. Now I’m looking forward to heading back out next year. My friends were right: I hadn’t really skied before, and skiing out west is much more fun.

Hopefully I’ll be shredding Black runs by the end of our next trip.

Dodgin’ storms in the U.S.A.

Two Sets of Fireworks

As we finished the last of the vanilla ice cream and blueberry cobbler, it began to rain. And not just a light drizzle – a pretty serious summer downpour, even by Florida standards.

We hadn’t seen this one coming on the radar and then it was right on top of us, soaking everything only 30 minutes before we were supposed to take the boat out to the Gulf to watch the fireworks.

What we had here was a classic Florida pop-up shower, which is usually a quick-hitter sort of thing. You don’t see them coming, then you get drenched for a few minutes, then they’re gone.

We had a decision to make: Go out on the boat as planned, or watch the fireworks from the porch? Although there was a pretty dark group of clouds behind us on the horizon, we decided to head out and chance it. Even if we got hit by a couple small pop-up showers, at least we’d get a great view of the fireworks.

As you can see behind my friend Jenn and me, the sky wasn’t too bad as we made our way out. We barely made it out to the Gulf before they blocked the channel, and we went to our spot where we would watch the show that would begin in about 45 minutes.

But then, that dark gray storm began drifting in from the west. And we noticed another storm to the north. We started getting a little nervous: Those weren’t little pop-up storms; they looked pretty nasty.

But our intrepid captain had a plan: “I’ll shoot the gaps!” He told us how he would hop around to avoid this storm, then that one, then pop down to this other gap, then back over and we would be fine.

And then the rain started.

No problem! We would just “shoot the gaps!” So we punched it and got to the first gap. Nice! The sky was actually pretty blue and the rain stopped for a minute.

But then it started up again, so we had to try to find another gap. This time, instead of following the coast, we headed seaward. But the gap we were heading for closed, the rain got heavier and colder, and the sky got darker.

Uh oh. In hindsight, playing Boat Frogger with thunderstorms probably wasn’t the best idea. Hindsight is 20/20, of course.

The ponchos and towels came out, albeit a little late. I was wearing cotton shorts and a t-shirt. There were not enough ponchos. Did I mention the rain was cold?

We spotted another gap and headed that way. This time, we arrived in what felt like a sort of clearing. It was dusk, so the sky above us was dark blue and calm with a few whispy clouds. But this was little solace because we were now surrounded by storms on all sides—there were no more gaps to shoot and it seemed like our present gap was closing even as we arrived.

Justin, who was huddled in a sort of parka fort on the floor of the boat, got out his iPhone 7—they’re water resistant now!—to take a look at the radar and see where our gaps went.

Sure enough, we were in a teenie-tiny gap which was literally surrounded by red storms. This was not good. Red basically means “THIS IS VERY HEAVY RAIN AND WIND! YOU DO NOT WANT TO BE OUT IN THIS STUFF!” But we were out in this stuff. On a boat. In the Gulf. At dusk.

Suddenly, there was a lot of lightning and things went from bad to worse.

I grew up in Florida. Heavy rainstorms happen here all the time. In the summer, they happen pretty much daily. So being stuck in a rainstorm in a boat on the Gulf isn’t like FANTASTIC or anything, but it’s not too far away from what a typical Floridian experiences once every year or so as they make an afternoon run to Publix.

Of course, as a Floridian who grew up with frequent intense rainstorms and hurricanes, I also learned to have a healthy respect for lightning because it will kill you. This lightning was probably 5–10 miles away, which meant we were in striking distance.

Where do I go from “Uh oh.”?

Things got nastier still.

“I think we should go south!”, Justin shouted from his parka fort as he stared at the ever-updating radar. Then he showed us the radar, which showed that things were about to get considerably worse. But maybe there was a gap down south, so we headed south.

As we were heading to our new southern destination, Justin showed us the latest radar. The area we had just evacuated was now PURPLE. This is worse than red. According to Weather Underground, we were experiencing the second-most-intense level of rain they measure. On a boat. In the gulf. At dusk. Plus there was lightning everywhere.

The rain was steady, though less intense than it had been earlier in our ordeal. But now we were literally surrounded on all by sides by dark skies and lightning.

Here’s a video of one of the bigger, more surprising strikes. You can hear our intrepid captain’s concern excitement as he and his dad marvel at Mother Nature’s fireworks as she tried to kill us.

This meant that although we were hopefully headed for a gap, we first had to head directly into a lightning storm. Still, the floorboard-parka-fort command center said to go south, so we went south.

After 10 or 15 minutes of heading into a lightning storm at full throttle, we found the gap the radar had foretold. It was near the shore, which happened to be one of the only stretches of uncolonized beach in the area. It was beautiful and eerie. The clouds had dissipated overhead, so we were in a sort of void, surrounded by lightning storms, next to an empty beach as the sky got darker.

We waited and watched the radar, hoping that no more storms would pop up and that the storm we had escaped would continue moving westward into the Gulf.

After 20 minutes or so, a few small fireworks popped just inland of us—a good sign. The gap we were in began to grow so that we could see several miles up the shore to the original position we had abandoned earlier.

We could see that the people who had stuck it out were getting absolutely hammered by an enormous storm. The sky above them was black, constantly lit by lightning strikes. As bad as our situation had been, theirs may have been worse.

More fireworks began dotting the shoreline to our north, and we consulted the radar to confirm the worst had passed. The red was all to our west, so we began creeping northward along the sleepy shore, dodging the beach’s outstretched piers as they reached for us.

Things still looked pretty bad by the channel where we naively began our journey—dark skies, lightning and rain—but then we saw some bigger fireworks that seemed like they would be part of the big show. Our technicolor lighthouse showed the way, so we pushed the throttle, heading back to our starting point.

When we finally cut the engine a few hundred yards short of the police boats and buoys that cordoned off the splash zone, we got to see not one, but two spectacular fireworks shows: In the foreground, the man-made one we had come to see; in the background, the lightning that had chased us from gap to gap, into the Gulf, then south, and finally back to the shore we followed home.

Two Sets of Fireworks

Why I cut my 2014 WSOP trip short

NOTE: I wrote the first draft of this on Sunday morning, July 6.

I’m in Atlanta, waiting on my 8:00 AM connecting flight back to Gainesville. It’s been a while since I took a redeye, but this is the real deal. I took this flight because I didn’t have many other options when I decided to cut my annual WSOP trip to Vegas short.

Why did I do that? To be honest, I’m really not sure, and I’m processing that question as I write this. I was really excited to head out this year, and I’d been looking forward to it since I returned from last summer’s trip. So I packed my bags, flew to Vegas, and immediately just felt… off. Instead of looking forward to playing tournaments, I sort of dreaded it. I was there for three days before I played my first tournament (the $1,500 Monster Stack, where I hung out for 10 hours and busted at the end of Day 1). It was another four days before I played my second tournament (a $300 tourney at the Wynn, where I busted on a bad beat after about four hours).

After playing only two tournaments in a week, I thought the remaining 11 days of my vacation could be better spent than puttering around Vegas, playing a tournament every few days. I decided I would rather spend my final week off in Gainesville, where I can relax and work on TaskBook. So here I am.

But I can’t help but wonder if there’s a little more to it. I’ve been playing poker for 11 years, and I was really, really fascinated by it when I began playing in little home games in college. I was the guy who went out and bought books and started reading poker forums to get better in my five-dollar home game. When I graduated from college, moved to Dallas, and started working full-time, I also started playing a lot of poker online at night after work.

I played a lot and read a lot, but I never went all-in the way some online pros and grinders did. I just didn’t have the will or desire to grind eight to 10 hours a day online. That didn’t sound fun to me.

I continued playing a lot of poker online for the next several years, and started visiting Vegas for the WSOP beginning in 2009. A couple months after my WSOP trip in 2009, I was let go from my job and started playing a lot more online poker. I still enjoyed playing, but not nearly as much as I had when I began, and playing online started feeling like more and more of a grind. I think that’s when I began to burn out.

My poker reserves began running low late in 2009, then my online time tapered a bit through 2010 and had all but disappeared by the time Black Friday hit online poker in April of 2011. From then on, I would play the occasional cash game in Florida, but mostly just played during the summers in Vegas.

Late in 2011, I began writing Heads-Up Tournament Poker and building my first web application (ShareAppeal). Pretty much all of my poker energy went into the book, and the remainder of my creative and intellectual energy went into learning Ruby on Rails. I never really saw poker as a way to create a dependable income, but I felt differently about web applications – I felt there could really be something there for meaningful future income. I began shifting my energy and interest from poker to app development and stopped playing poker entirely except during the summers in Vegas.

My 2012 trip was a month long, but I was working full time for the entire month, so I didn’t play much poker. I almost didn’t make the trip in 2013, but was persuaded by a friend to make the trip (and I’m glad I did – that was a fun two weeks). I think my 2013 trip emptied the tank, although I didn’t realize it at the time. I didn’t play a single hand of poker between the WSOP 2013 and my trip this summer, or maybe I would’ve realized sooner that I had used up most of my interest in poker for now.

I’m not saying I’ve quit poker, or that I’m over it. I just wasn’t feeling it this summer. I’ve been working hard on TaskBook, and that takes a lot of energy and can be sort of distracting when playing poker. I see TaskBook in particular, and app development in general, as a way to generate real income on the side, and it’s still very interesting to me. Unfortunately for poker, app development uses a lot of the same creative energy as poker does, so there’s just not enough room for a deep interest in both.

I hope that I can replenish my poker-energy reserves over time. I may play some cash games around town, or jump into some Florida tournament series this fall, or I may not. But for now, I’m just not as interested in poker as I used to be, and I’m more and more interested in app development. So my guess is my energy will be focused there for a while, and poker could be on the back burner indefinitely.

Off to Vegas for the 2012 WSOP and lots of work

I’m writing this post from a plane somewhere over New Mexico, and I’m on my iPad, so this may not be the best-written or -formatted post I’ve ever written.

Anyway, I’m heading to Vegas for my annual trip to the World Series of Poker. This is the first year I’m staying in a condo instead of hotel hopping like I usually do. My typical routine is to hop back and forth from the luxurious Gold Coast to the Rio (where the WSOP happens) since they’re right across the street from each other. I will usually stay at the GC on the weekends (when it’s significantly cheaper than the Rio), and at the Rio during the week.

This year, I have a job, so I need a place where I can work without the sounds of slot machines and depression in the background, so I decided to rent a condo. I managed to talk Luckbox Larry into splitting it with me, so I’ll even have a roommate. The bottom line is we’ll probably both feel like we’re living in the lap of luxury since we’ll have our own rooms and, you know, the creature comforts like a fridge and oven. My guess is it’ll cost 30-50% more at the condo than it usually does I’m the hotels. But it’s hard to compare because we’ll have much better accommodations, WiFi, laundry, a gym and that sort of thing. All in all, I think it’s a good value.

Originally, I booked this trip so I could be here to promote the heads-up book, which we were trying to release before the WSOP Main Event, but that ain’t happening so I’m just here to work and pay poker this summer. When I say “work”, I really mean several things: my “day job”, of course; ShareAppeal, which is really getting rolling; writing a new book about my career so far (I’ve already written about 2,000 words since we took off); and editing the heads-up book so it’s ready to release later this year. I’m keeping pretty busy, as always.

But of course there’s poker too, right? I hope so. I don’t know how much I’ll be able to play with all the other stuff I have going on, but I’m going to at least try to play a few WSOP events and some side tournaments. I would like to play the Main Event again, but I have no idea if that’ll actually happen. Last year, I didn’t decide to play until about three hours before the beginning of Day 1 D (scroll down to Day 18), some still have about three weeks to figure out a way to play again this year.

We’re starting our descent, so I’m going to sign off. I don’t know if I’ll do a daily diary this year, but I’ll be sure to keep everyone up to date one what’s going on.

Oh! But I would like to give people a better sense of what the WSOP is like, and what it’s like for me every summer I Vegas. So, if you want to know more about that sort of thing, leave some comments with suggestions on what you want to know or see. I’ll do my best to create some content to give a sense of what it’s like out here at the WSOP.