It’s been five years since I quit my day job

This is the story of the first five years of the Fearless Salary Negotiation business. I initially shared this as a Twitter thread, and I’m publishing it here because it’s a personally significant document and it might be interesting to other folks as well. This is exactly as I wrote it in that Twitter thread, but I’ve corrected a few typos and added section headings to make it easier to skim.

Today marks 5 years since I quit my day job. I’ve been thinking about that this morning and my thoughts are surprisingly sort of scattered. I thought, “Why not share some of those thoughts?” So here we go…

Setting the stage

I didn’t quit my job on a lark; I had been working in that direction for about five years before I actually made the jump. I did a trial run after I finished my MBA in 2011: I quit my job to take about eight months and just do stuff I found interesting. That sabbatical was very useful because I learned something important about myself: I did not need a job—fixed schedule, clear responsibilities, steady paycheck, co-workers—to be productive. In that eight months, I was probably more productive than I had ever been. I did some traveling (Las Vegas, Seattle, Vancouver), played in the World Series of Poker Main Event (and a lot of other poker), started writing Heads-Up Tournament Poker, learned Ruby on Rails, built my first web app, and lived on savings the entire time.

To set the sabbatical up, I had saved most of my income for the previous 15 months. So I had essentially run a test and written my own playbook for the next time I would quit my day job and try to make it permanent: Save as much money as possible, pay down debt, have a plan.

Making a plan

By early 2012, I had rejoined the full-time employee world and I had a plan to quit my day job again, but permanently this time. I described my multi-year plan to friends during a round of disc golf, so I vividly remember when I realized, "I’m actually going to try to do this.?" The plan was as follows:

  • Pay down all debt (mostly student loans) except my mortgage, which I refinanced to a super low rate.
  • Save enough money for a 15–18 month runway.
  • Learn to write useful software.
  • Build a software business.
  • Make the jump when the time was right.

For those of you who know me as "the salary negotiation guy", you might be thinking, "Wait. Build a software business? What am I missing here?" But that was the plan! First I shipped ShareAppeal—a proof of concept social sharing app that was very cool. Then I started TaskBook. TaskBook was a B2b (small business) app for managing recurring tasks on teams. At first it was for small retail shops. Then I began focusing on agencies and consultancies (project management applications). It was ALSO a cool app. By the end of 2014 I had some paying customers.

Starting to write Fearless Salary Negotiation

Meanwhile, I had been noodling on the idea of writing a career management book, which I formally started writing in late 2014. I had made some really unorthodox career decisions and people asked me about career stuff all the time, so I thought, "Why not write about this?"

Maybe you noticed I said "career management" and not "salary negotiation". At first it was a much bigger project, more like a textbook. I called it "Take Control of Your Career: A Career Management Guide" and I totally understand if you nodded off while reading that boring title.

By Spring of 2015 I had a good amount written, but the outline had MANY more topics to cover. I went to MicroConf in Vegas and lucked out to end up eating pizza with Josh Kaufman and Tim Grahl. I cannot overstate how important this one conversation was. It changed everything. In about an hour, Josh suggested I narrow the focus of the book and gave me the title "Fearless Salary Negotiation: A step-by-step guide to getting paid what you’re worth", they talked me into launching on Amazon, and showed me which categories to target.

Quitting my day job

So now I’m working a full-time job, writing a book, and running a B2b SaaS while saving up money as quickly as possible. At this point, the book was more a labor of love and a chance to try self-publishing for the first time. I was still ultimately planning to focus on TaskBook. As my runway approached 15–18 months and I moved into the final stages of Fearless Salary Negotiation, I started to think about when it would be right to quit my day job. I got more and more antsy while also wearing down a bit from doing so much (I was working seven days a week). I decided on September 18, 2015. Here was my plan:

  • Publish FSN by end of 2015.
  • Ship FSN courses so I would have an info-product tiered offering as soon as possible.
  • Make enough monthly income from FSN to survive while pushing TaskBook up the Long, Slow, SaaS Ramp of Death.

In October, I self-published Mastering Business Email, which was a big part of FSN that I removed when I narrowed the scope to salary negotiation. MBE was a self-publishing test run so I could learn the process before launching FSN in December. MBE did surprisingly well! October was also my first full month self-employed and my net revenue for the month was $103.01. November net revenue was $1.72. I felt the full weight of burning large chunks of cash from my runway every month. I realized that runway would go FAST, so I absolutely had to focus.

I spent the rest of the year prepping and launching Fearless Salary Negotiation. I did literally everything except the cover design (which was done by the excellent Pete Garceau, who of course was recommended by Josh Kaufman at that fateful MicroConf pizza dinner).

Publishing Fearless Salary Negotiation

I launched Fearless Salary Negotiation in December. It hit #1 in two categories on Amazon and sold about 220 copies that month. At the time, my mailing list was about 600 people. I made $602.04 that month, putting me at $706.77 net revenue for 2015 (since I quit my day job).

I don’t usually mention specific revenue numbers, but I think that’s important here. It’s now January 2016, four months after I quit my day job to begin burning through my savings. I had been working relentlessly for four months, made $700, and reduced my runway to 14 months.

I was, shall we say, starting to get a little nervous.?

Sunsetting TaskBook

The plan was "Make enough monthly income from FSN to survive while pushing TaskBook up the Long, Slow, SaaS Ramp of Death." I began to see how hard that would be, realizing I was trying to build TWO businesses at once. I had to choose between building a SaaS and building an info-product business. This was not a choice I anticipated when I quit my day job, but here I was at a crossroads only about four months into my journey.

My original plan was not tenable; I was making a new plan on the fly. This choice was nuanced and I won’t go into every factor here. But it was really a choice between pursuing a moonshot in an area where I had little genuine interest, or building a lifestyle business in an area I REALLY enjoyed.

I chose the lifestyle business, going all-in on FSN. I told the few TaskBook customers that I was sunsetting the product, worked out a plan with them, and turned my full-time focus to turning FSN into a revenue-generating business as soon as possible.

Building the Fearless Salary Negotiation Business

My first order of business was to ship the FSN courses as quickly as I could. Turns out that learning to write and produce video courses is difficult. Who knew?! I had no idea what I was in for and fortunately Justin Jackson and the MegaMaker community were super helpful while Caleb Wojcik helped me figure out the on-camera part. It was a grueling process.

I’m generally very risk-averse and had planned and saved meticulously for this move to give myself the best chance possible of never going back to a day job. But my runway continued to burn, I had already significantly modified my plan, and I started to see how risky this was. I was making steady progress, working seven days a week, but I was worried I had made a mistake and set myself up for failure.

One or two days a week, I felt down—I called them "blue days". Those days didn’t affect my productivity, but I felt tremendous pressure and isolation. I was fortunate to be part of a close-knit community, near family and friends who encouraged me. I also had lots of entrepreneurial friends who had experienced similar things, and they helped me keep the right perspective and keep moving forward. I just had to keep moving.

May of 2016 I went to my second Bacon Biz Conf. The timing couldn’t have been better. I had been in 2014, but mostly to network—I met Josh Kaufman there; it was very info-product focused and I had been building a SaaS. By 2016 I was in full-on info-product mode and ready to learn.

Easing into salary negotiation coaching

Just before Bacon Biz Conf, a couple of people asked me if I would help them negotiate their job offers. I had worked with a friend to negotiate his job offer when I was writing FSN, and now his wife asked if I would work with her one-on-one to negotiate a job she was considering. I said I would be happy to help. She asked, "What’s your rate?" I hadn’t ever considered that, and she was freelancing at the time, so I said, "Whatever your hourly rate is, that’s my hourly rate." We got to work, she got a good result, and I had my first coaching success story.

After we’d wrapped up, I asked her, "You already have my book—I gave you and your husband each a copy of it. Why did you hire me when you could’ve just read the book?" She said, "I just wanted someone to do it for me."???

A few weeks later, a friend from middle school (you read that right) reached out and asked if I would help negotiate a job offer. I told her I’d be happy to, and quoted a rate about 50% more than my first client. "Sounds good!" She also got a good result—my second success story.

Coincidentally, I was visiting my friends Rick and Tina when that second coaching client reached out and agreed to my new rate. Tina said, "This coaching thing seems like it could be big. Maybe you should focus on that?" Until then, I was only pursuing info-products.

And that brings us back to Bacon Biz Conf in 2016. (You didn’t think I forgot about that, did you?) I pulled Josh Kaufman and Sean Fioritto aside to talk about my info-product business and how I could grow it. I happened to mention coaching and Josh immediately honed in on that. Instead of talking info-products, Josh, Sean, and I talked exclusively about coaching and how to structure it so it made sense. "No more hourly billing—fixed-fee instead. Charge $1,500 and share some of the best success stories to demonstrate what a good investment it is."

I went home, set up a Salary negotiation coaching landing page, and a slow trickle of people began to find me and occasionally hire me. One coaching client could easily bring in more revenue than all product sales for that month. I was on to something.

By the Fall of 2016, two things had happened:

  1. My runway was burning more slowly. I was bringing in non-trivial revenue most months. Not enough to cover my expenses, but I was occasionally getting CLOSE.
  2. I noticed that my best coaching results were for software developers.

I finally had some breathing room, and I mostly just kept my head down and focused on building the business for the rest of 2016. That mainly meant growing my newsletter, working on SEO, and writing new articles on the FSN site. It was a grind.

Focusing on helping Software Developers

I had still been occasionally coaching people across all industries. But Software Developers continued to get the best results. I mentioned this to Philip Morgan, who (of course) suggested I re-position my coaching offering to be FOR Software Developers. That made me nervous. I had the usual objections to niching down: "What if I’m missing out on tons of other coaching clients in other industries? What if I can’t find enough Software Devs to work with?"

"I’ll bet you a steak dinner you have at least one non-dev ask to hire you in the first 60 days." He persuaded me and I rewrote the landing page and all of my marketing material to say that I was "A salary negotiation coach for software developers". And of course he was right: More devs hired me AND I still got a non-dev client soon afterward.

Business slowly picked up. But it’s important to emphasize that I was still primarily focused on info-product sales. That sweet, sweet promise of "passive income"—if I could build a good enough marketing machine, I might make a good living without constantly grinding or trading my time for revenue.

Meanwhile, my runway was still slowly shrinking—it was under 6 months. My revenue was consistently better than it was a year earlier, but still wasn’t enough to cover my monthly expenses. I was getting nervous that it would eventually run out and I’d have to go get a day job.

Saving the business by focusing on salary negotiation coaching

In May of 2017, I was at a friend’s house and we talked for several hours about my business and my shrinking runway. "Why are you so focused on selling books when you can make so much more on each coaching client? You should be focused on coaching, not books." He was right.

The next day, I changed my positioning from "Author who also does coaching" to "Salary negotiation coach for software developers (who also sells books)". Another inflection point that cannot be overstated: This change saved my business and turned everything around.

That June I had my best month ever—almost triple my May revenue. Looking backward at my best month before this change, each of the next 16 months was better than that. My revenue in May 2018 was almost 10x my revenue from May 2017. I had pulled out of the nosedive just in time.

As I worked with more coaching clients, I slowly raised my rate to help manage demand and because the service was so valuable. But I was slow to raise rates because of a common fear with the Charge More™? (obligatory hat tip to @patio11) tactic: "What if my business dries up?"

In March of 2018, I had a long chat with Mark Butler. He explained why my current pricing was way too low and not sustainable. He helped me see all the hidden costs of the work I was doing, and emphasized the value I was adding for my clients.

I decided to make a big change.

Raising my rates

I significantly increased my rates and moved to a three-tiered pricing structure that was based on the "Total Offer Value" of the offers I helped clients negotiate. It was a clumsy attempt at value-based pricing, but it was effective and revenue kept going up.

By the end of 2018, I had completely transitioned from "just try to survive" to "how do I make this grow?" For the year, I made almost the same as I had made in my last year at a day job. I could finally breathe and now my focus was on optimizing my business to be sustainable.

I began to run into a problem I hadn’t anticipated: Consumer psychology was making it difficult to continue raising prices. The issue wasn’t the value I offered, but the fact that people just weren’t comfortable paying above a certain amount to hire a stranger on the internet. My top pricing tier was $9k. I rarely got clients in that tier, but I did get them occasionally. The next obvious move to Charge More™? was to go to $10k, but people just weren’t going to pay that kind of money to a stranger on the internet for a fixed-fee, paid-up-front service. I had already gotten some resistance at the $9k point, so I knew $10k wouldn’t work. But since all my tiers were sort of tied together, I had to raise the top tier to raise the lower tiers (where most of my business was). I would need to get creative to raise prices this time.

Changing my salary negotiation coaching fee structure to include a result fee

This brought me back to an idea I had considered early in the business, and which lots of people had suggested: Why not charge a fee based on clients’ results? Maybe a percentage of the improvement we negotiated? I don’t think it would’ve worked early on, but it might work now.

But I had a pretty good thing going! Revenue was up, clients were finding and hiring me, everyone was happy. Why mess with that? I felt that if the business was going to keep growing, and I was going to start actually doing value-based pricing, I had to consider a result fee. This was an even more drastic change that repositioning to focus on coaching (which was already working for me), or niching down to work with software developers (who were already hiring me). This was a wholesale pricing model change on a business that was doing pretty well.

But part of the fun of running my own business and working for myself is testing things and optimizing the business. I had to know if a result fee would work now that I was established. I hadn’t tried it earlier because I could see several pitfalls with result fee-only pricing. The main issue was that I wanted to work with clients who were fully bought into my methodology. Negotiating is scary and I need people to be totally on board for us to get the best result. If I only charged a result fee, they wouldn’t have any skin in the game.

I decided on a service-plus-result fee model: A service fee to work with me and benefit from my expertise, and then a result fee based on the actual improvement we negotiated. I started with a $3k service fee—the lowest tier from my old structure—and a 10% result fee. This is truly value-based pricing and since I had negotiated huge results for past clients (more than a million dollars paid out over four years), I knew it enabled me to charge an amount closer to the value I add to salary negotiations. I moved to this model in April 2019.

It turns out, clients LOVE this model. It reduces their up-front investment and they only pay a result fee when they get an improvement. Bigger result fees mean bigger improvements, of which they keep 90%. They’re happier, I’m happier, my business is happier and more sustainable.

Breaking even on my previous day job salary

2019 was the first year I earned more than I had at my day job. 2020 is on track to be even better. But my five-year path to this point was a bumpy one. I thought I was going to build a SaaS and I ended up building a bespoke services business. I almost went broke 18 months in. I had to turn my business upside down, change my target market and risk alienating a lot of potential customers, change my pricing model drastically multiple times, and take other big risks.

There’s still a lot of work to do

And there are still challenges that don’t have easy solutions.The pandemic killed my product sales and organic search traffic. That part of the business is basically dead. I think it can be revived, but it’s not going to be easy. And that’s why I still love running my little lifestyle business after 5 years. I always need a new challenge.

A couple of weeks ago, I reached out to a fellow entrepreneur who I’ve partnered with to help his audience negotiate their job offers. I love his business and just wanted to know more about how he started. It seemed like he came out of nowhere and found success earlier this year. "So take me through this. How did you get started? It seems like you hit a home run right away." "Well, I actually started about five years ago…"

I should’ve known better. Most successful businesses start with that grind. His story was a lot like mine. Building a business is hard and it takes time. I had to survive long enough to find the thing that works. And along the way, I tried lots of things that just didn’t work. I probably offered 5 different coaching offerings before I found the one that took off. That’s the process. Now I try to make my business as anti-fragile as possible (hat tip to Nassim Nicholas Taleb). I try things because I know they will fail and I want to know how they will fail so I can make my business stronger with that information.

My business is a lab where I always try new things. Five years in, that’s what keeps me interested, engaged, energized. I love trying new things, finding new ways to help people, and learning about myself and other people. It’s been a lot of fun and a wild ride so far. I can’t wait to see what the next five years bring.

I scream, you scream, we all scream for…a 15-minute drive to get ice cream?

I bet this precise conversation happened 1,522 times here in Gainesville this summer:

“Have you seen the new Avengers movie yet? It’s great!”

“Nah, I just haven’t gotten around to it yet, but I plan to.”

“When you see it, make sure you go to the new theatre – it’s awesome!”

“Oh yeah? Ok, I’ll check it out!”

Other than a slowly degrading mall, we’ve never had much shopping in Gainesville. There have been rumors of a new Town Center circulating for years, but they’ve finally started building it and the buzz is building.

We all thought a Town Center was a good idea, but we weren’t sure where they would build it.

All the options seemed pretty bad because there just wasn’t space for a big development anywhere in the city. They would have to build somewhere on the outskirts of town, so people would have to drive a bit to get to it.

This is sort of a Catch-22: How do you build a big shopping center over several years if nobody is willing to drive that far to shop?

For starters, you would build at least one or two things worth driving to and use those things as anchors while the other things get built.

What would you build first?

In Gainesville, the answer was a fancy new movie theatre: a 10-screen Regal RPX theatre with comfy reclining chairs, huge screens, and great audio. It’s the first new theatre here in over 20 years and it’s lightyears ahead of our other theaters.

It didn’t take very long for all of my friends to find it and recommend it—now it’s our go-to theatre because it’s so much better than the others.

I’ve been out to “Celebration Pointe” (with a silent ‘e’ so you know it’s fancy!) several times to see new movies, but there was no way I would’ve gone out there to buy clothes or eat dinner.

But now they’re starting to open other shops around the theatre and I’m already acclimated to driving out to Celebration Pointe so it’s no big deal to drive out to shop or just hang out in the common areas.

Last week, some friends and I drove 15 minutes to get ice cream at Kilwins and then hung out and talked in a pergola for a couple hours. We never would’ve done that if they hadn’t been so intentional by opening the movie theatre first.

The big picture and overall vision matter, but so do the individual steps you take to implement your plan.

An amazing 4th of July

This 4th of July was the opposite of last 4th of July in almost every way. I won’t recap all of last year, but it was a harrowing experience.

This year, everything went swimmingly.

Getting down to Sarasota

We went down a little later this year and arrived at dinner time on the 3rd. We ate at a place called Pop’s Sunset Grill and it wasn’t bad. It was nice catching up with some friends I hadn’t seen in a while.

The view from Pop's Sunset Grill

After we dropped our stuff off at the house, we made a run to Kilwins. This is a nice tradition, but it’s not quite as special now that we finally got a Kilwins in Gainesville a few months ago.

That being said, I ended up with the largest single scoop I’ve ever had (I described it as “a pint on a waffle cone”) and it was delicious.

We wrapped things up by playing Pictionary (my team got destroyed) and then Taboo (my team won easily). Word games are my bailiwick, but I’m terrible with drawing and visual stuff.

The 4th

We took our time getting started on the 4th, hanging out and drinking coffee until 11 AM or so. We had a big group this year, so we split into two and decided to do shifts on the wakesurfer.

My group was on the beach first, and we played some bocce (my team barely won) and goofed off in the water while the first wakesurfing crew had fun in the Gulf.

After a couple hours, we did a pretty quick shift change and had to change locations because the Gulf got too choppy. We made our way to the water sports area and got to work.


The thing about water sports is I have never done them and I don’t particularly like water. I mean, I went tubing a couple times as a kid, and would occasionally find myself on a lake, but that’s about it. So I’m terrible at them and it takes me a bit to get the hang of them.

And so it is with wakesurfing. I tried for quite a while last year and could never even get up on the board, so I had a pretty clear goal for this year: Get up on the stupid wakesurfing board at least once.

I almost got up on my first try, and then failed probably eight times in a row. I was getting pretty close to just calling it quits when everything fell into place and I got it. I quickly got up four times in a row and got that monkey off my back.

Me, wakesurfing

That’s the good news. The bad news is I never really had a good run, so I still haven’t really experienced the fun part of wakesurfing. But I guess that’s a goal for next year.

The festivities

When our shift ended, we headed back to the house for a traditional 4th of July cookout. There’s something comforting about grilling burgers and hotdogs on the 4th. And the desserts this year were phenomenal—some kind of frozen lemon pie and a delicious blueberry cobbler.

The skies looked pretty good before we got on the boat to head out into the Gulf, but they looked ok last year too. I think we were all a little nervous that we’d get caught in another lightning monsoon even though all signs pointed to good weather.

It was cool and breezy the whole time and we got to see an amazing sunset.

Sunset on the Gulf

The beach and Gulf were significantly less full than last year, and there was hardly anyone on the water for the fireworks.

I think part of it was that the 4th fell on a Wednesday, and part of it was people shying away from another run-in with a lightning monsoon. The end result was basically a private fireworks display for our crew and it was amazing.

Fireworks on the Gulf

Fireworks on a boat

We didn’t make it back early enough to get Kilwins so we just jumped straight to games instead. This time, we played Mad Gab first. We only got through about half a game before we quit because it was too easy and our scores were basically identical. We audibled over to Taboo and my team pulled out the win.

Everyone turned in surprisingly early this time, probably because we were all pretty tired from the day’s festivities.

Heading home

Our return trip was pretty uneventful. We rolled out around 10 and just headed straight home. It was nice to have a super easy day after a pretty busy couple of days in Sarasota.

A great week in Boston

A couple buddies and I went to Boston and it was a ton of fun. We did exactly the right amount of stuff so we had a great time without feeling burnt out.

Day 1: Travel and dinner at Carmelina’s

Our travel there was pretty uneventful, which is always great. We got lucky in Orlando when they pulled us out of the regular back-check line and moved us to the fast lane since we were likely to miss our flight if we stayed the course in the regular line.

By the time we actually got to our apartment in Beacon Hill, it was around 5:00.

We were already hungry, so we decided to head to the North End with a hope and a dream that we could get a table at Carmelina’s. A couple of us had heard that it’s a great place to eat, but it’s typically booked out.

I actually tried calling ahead to try to get a last-minute reservation, but they were basically booked solid for the next few days. I made sure to tell the host that my buddies and I were in town for a few days and were hoping to try Carmelina’s while in Boston so he would remember us and have pity on us if we talked to him later.

Sure enough, we walked over and managed to get a table on the sidewalk because they had a no-show. It was a good meal and a great way to ease into Boston.

Our view from Carmelina'sCarmelina's meatball appetizerAll of us standing in front of Carmelina's

We all split a meatball starter and a few entrees—the carbonara was the best one.

Afterward, we walked across the street to Mike’s Pastry, which we’d heard was a must-visit place. It did not disappoint. I got a caramel pecan cannoli, and my friends had to sort of lure me out of the place because it was chalk full of delicious-looking treats.

Mike's Pastry box of treatsMy caramel pecan cannoli

We took our cannolis to a table at The Greenway to watch the sun set and enjoy the Boston weather. It was like mid-70s all week, which was a nice change of pace from the Gainesville summer.

Rick looking at something on the Greenway
We were already pretty tired and full of carbs, so we headed back to settle into our flat and call it a night.

Day 2: A whale of a time

We heard that whale watching tours are fantastic in Boston this time of year, so we got on a boat to go see the whales.

I spent the first 45 minutes feeling progressively worse until we finally got to the viewing area. Although I felt terrible, I was determined to see at least a couple whales for my trouble, so I forced myself to stand, posted up on the rail and waited for a couple whales to pop up.

Technically, I saw some whales.

Once I saw them, I sat back in my seat and didn’t move for the next two hours or so trying to keep it together until we could get back on land. I’ve never been seasick before, and I do not recommend it.

Seasick on a whale-watching boat

I don’t think I really got right again until a couple days later.

Once back on land, we made a beeline for a local market where a couple of us got lobster rolls for lunch. They were tasty.

Boston Harbor from the boat

Then we headed back to the flat to recover and get ready for the highlight of our trip…


My buddy Rick is a lifelong Red Sox fan, but he didn’t attend his first game at Fenway until this trip. We saw a satisfying route of the Angels, including several home runs and some great defensive plays.

Fenway Park entranceRed Sox game at dusk

Aside from a random business guy loudly talking about his business behind us (we all wonder what will become of his COO Gary, who he mentioned several times), it was a fantastic game and a great time.

We did it right, dropping some coin on concessions for dinner and Rick even got a new hat to replace his old well-worn hat that probably should’ve been retired a couple years ago.

Classic Allen face

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

And of course we got the full experience with "Take Me Out to the Ball Game" and "Sweet Caroline".

After the game, we walked back to Beacon Hill. This was probably our best walk of the trip, clocking in at nearly an hour and taking us through several great neighborhoods.

We got back pretty late, so we turned in to make sure we were ready for a big hiking day on Wednesday.

Day 3: The Freedom Trail and un-split lobster tails

The main event for Wednesday was the Freedom Trail. But before we got started, we spent some time at Boston Common and the Public Garden.

It took some searching around the Frog Pond , but we eventually found the bench from Good Will Hunting. It was surprisingly hard to find—we all expected some sort of memorial for Robin Williams or something—but it was just a bench by a pond.

Good Will Hunting Bench at the Frog PondThe Freedom Trail

Then we set off for The Freedom Trail.

This was the hike that everyone told us we had to do. We found a podcast that had little two-minute blurbs about several of the stops on the Trail, but I was jealous of the tourists with guides telling them all about each stop.

The Freedom Trail

If I did it again, I would get a tour guide or an audio tour or something to make sure I learned a lot along the way. Visiting the sites was great and seeing so much of Boston was fantastic, but I didn’t learn as much about the history as I would’ve liked.

Paul Revere

Still, it was a fantastic hike that took us all over Boston and lasted about five hours. There’s something really cool about standing in spots that are well-known pieces of American history while looking around to see the hustle and bustle of the modern world—a fun juxtaposition.

The USS Constitution

After we finished the Freedom Trail, we walked over to the USS Constitution, which is the world’s oldest commissioned naval vessel that’s still afloat.

The USS Constitution (and a random dude)

Although it’s called Old Ironsides, its hull is entirely made of wood, which makes it a really beautiful boat. Some of the crew told us about its history and pointed out some of the unique characteristics of the ship while we bobbed and weaved between the low-slung beams and around the columns below deck.

It was really neat to actually walk around and feel what it was like to be below deck surrounded by cannons in such a tight space.

Below deck on the USS Constitution

We were all pretty much exhausted by this point (we had been walking for six hours or so), and we headed back to the flat to recover before heading out to dinner.


For dinner, we made our way to Yankee Lobster in South Boston. Rick and I got the twin lobster and it was really good. This was my first time breaking down a whole lobster and it was quite an experience.

They didn’t split the tails for us, so we had to do some work to get to the good stuff. I prefer to work as little as possible when I eat my food, but all the work was worth it in this case.

Lobsters from Yankee Lobster

As an added bonus, Joan Jett, Styx and Tesla did a show right next door while we ate. So we got to eat delicious lobster and take in a free show to boot. (I’m pretty sure we also helped some people sneak in through a back gate near our table.)


After lobsters, we walked to Drink, which is a small bar where the bartenders make you whatever they think you’ll like. It was a great place to relax and catch up since we hadn’t all hung out in a long time.

Back to the flat!

Day 4: A small excursion

By Thursday, we were all starting to get a little tired. We had been walking everywhere pand I still hadn’t quite recovered from being seasick, so I was happy to take it easy all day.

Night Shift Brewing

We got a late start and headed to Night Shift Brewing out in Everett. We each got a flight and then just hung out talking for several hours.

It was a really cool space and surprisingly cozy for such an industrial building.

Although this his probably the easiest possible tourist activity, I struggled to stay awake and was pretty happy when we decided to head straight back to the flat and chill until dinner.

Trattoria Il Panino

For our final dinner in Boston, we found our way to Trattoria Il Panino, which was amazing. This was my favorite meal in Boston by far.

We started with a charcuterie board (who doesn’t love a good charcuterie board?) and again split a few entrees. All three entrees were fantastic: Veal Saltimbocca (veal medallions), Ziti alla Amatriciana, and Ravioli con Aragosta (lobster ravioli in crab sauce).

Charcuterie board

Entrees at Trattoria Il PaninoThis would’ve been the ideal time for a final stop at Mike’s, but we were all so full we couldn’t drag ourselves over there. I regret this now.

It was starting to get late and we all needed to pack up for our travel day on Friday, so we walked back to the flat.

Day 5: Heading home

Our flight wasn’t until around 3:00, so we had time to see a little more of Boston before we took off. One of my favorite parts of this trip was that we were in Beacon Hill, a beautiful neighborhood where everything is very walkable.

Beacon Hill

The view from Starbucks

We decided to head back to Boston Common and split up for a couple hours so we could each do our own thing.

I found a shaded bench by the Frog Pond and spent a couple hours reading and listening to music to decompress and take it easy after a good week.

Reading by the Frog Pond

Our travel home was pretty uneventful except that the Chick-Fil-A we built our homeward route around ended up being closed for renovations. This was easily the saddest moment of our trip. But we all managed to overcome the adversity on the field by enduring a trip to a futuristic Wendy’s run by giant iPads.

Our drive back to Gainesville from Orlando went by quickly as we listened to NBA podcasts and talked basketball most of the time.

All in all, this was an amazing trip with great friends and I think we did it right.

Where was this video BEFORE my first time skiing?

I couldn’t see through all the snow spraying me in the face, so I just closed my eyes and waited for impact. Another skier was trying to stop before he ran me over, and he barely missed me. I had fallen – again – and couldn’t get up.

This was my first ski lesson. It was not going well.

Even better, the skier trying to avoid me was my good friend and instructor, Scott. He was much better than I was and he didn’t have much patience for teaching a newbie how to ski.

I would just sort of point myself down the mountain and try to maintain some control while zipping down in a straight line. When I eventually got to the bottom, I would either coast to a stop or intentionally wipe out to avoid hitting anyone.

It was awful, and I was content to never ski again.

Then my friends convinced me to give it one more shot, on powder this time. So I’m heading to Colorado next week to try again. They insist it’ll be a lot more fun than I remember.

We’ll see!

It’s a big investment—time and money—for something that could turn out to be really un-fun. So I put on my “learn a new thing, even if it might be unpleasant” hat and started doing some research.

I found this fantastic video on YouTube—it’s exactly what I needed:

How to ski | 10 beginner lessons for the first day of skiing

What impressed me most is how the instructor anticipates almost every fear that I have about skiing. “How do I turn?” “What if I fall?” “What if I accidentally end up on a slope that’s uncomfortably steep?”

He’s been teaching for so long that he’s heard all of those concerns before. His list of “10 beginner lessons” probably came directly from hundreds of terrified students who have said, “What if I fall? How do I get up again?!” as they pictured themselves stuck on the side of a mountain, people zipping by as they struggle to stand up, for hours and hours and hours.

After watching that short video, I have enough confidence to give it a shot. I’m still going to take lessons the first day, but I’m a lot less worried about embarrassing myself than I was before.

Most people feel the same way about getting a raise. Maybe they tried it once before, but it didn’t go very well. So they gave up and decided to just wait for their next raise to come along whenever it happens to come along.

Sometimes, they don’t even get that far—the idea of asking for a raise and having to defend their request may be so daunting that they never even try.

Does that sound familiar?

Now it’s February again and most companies are gearing up for performance evaluation season.

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My current business challenge: Providing the right solution at exactly the right time

It’s Thanksgiving, so this post will be a little different. I’m going to tell you all about what I’ve been up to with my business. If you’re curious about how I do things behind the scenes, this is for you 🙂

How my business works

My income comes from two primary sources: Salary Negotiation Coaching and product sales (Fearless Salary Negotiation books and courses). The coaching business is doing well—I’m happy with both the volume and quality of clients I get to work with.

The product business has been doing alright, but I would like to grow that side of the business.

Obviously, selling more products means more revenue. That’s important since this is how I make my living.

But selling more products also means providing a valuable solution to an expensive problem ("How do I negotiate my salary without leaving anything on the table?" or "How do I get more job offers?") at the right time. I like helping people, and it’s frustrating that lots of people get some of the help I have to offer while never knowing about other ways I can help from 1-on-1 coaching to a full-on step-by-step DIY guide to negotiating a job offer.

Slow and steady progress

My newsletter will cross 10,000 subscribers by the end of the week. I can hardly believe I just wrote that number. It seems crazy to me, especially considering my newsletter had only about 2,400 subscribers at the beginning of 2017.

The business-y way to describe that is, "My marketing efforts have been effective." I mostly focus on content marketing—writing long, detailed articles designed to teach people how to do difficult things by following a process. Most of my newsletter subscribers found me through an article I wrote.

That’s the thing I’m best at, so that’s where I focus.

Where I need to get better is at articulating the value of salary negotiation and giving folks the the opportunity to buy products and services to help them negotiate higher salaries and get more job offers.

The business-y way to describe that is, "I need to get better at Sales." On one hand, I feel a little uncomfortable saying that. On the other hand, "Sales" is a key part of any business.

The timing problem

My primary Sales challenge is that most of the people who find me are looking for a specific tool to negotiate their salary and they are on a very tight timeline to respond to a job offer.

I call this "The timing problem" because there’s such a small window between "job offer in hand" and "compensation package finalized". For a long time, the challenge was simply enabling those people to find me when they need help. Over the past year or so, I’ve gotten pretty good at that part as I write better articles on salary negotiation and related topics (this is how I know my Marketing efforts are paying off).

The issue is that the folks who find my articles and other tools are in such a hurry to respond to their job offer that most of my advice gets to them after they’ve already finished negotiating. They may not even know that they could have purchased products or services to help with all other aspects of their negotiation and done even better (this is how I know I need to work on Sales).

My current focus

So once a new person finds Fearless Salary Negotiation by searching for help on a specific topic, I need to find a way to make it crystal clear that there’s a lot more help available, and I have to convey that message very quickly (in 24-48 hours or less).

I haven’t worked out the details, but I need to move faster and communicate more when new people find me. This is tough for me because I don’t want to bother people—I want to help them. I realize this sounds cheesy, but it’s true: If I were just trying to make money, I never would’ve quit my day job two years ago.

Instead of saying, "Here is a free thing to help a little bit, good luck!" and then waiting a day and saying, "Here’s a tip to help negotiate your salary" and then another day and "Here’s another tip!", I need to do something more like:

Here is a free tool to help negotiate your salary – we’re going to move quickly because you probably have an offer in hand and there’s a lot I need to share with you. If you want help right now, here’s where to get it and here’s the monetary value of that help.

These are the key things to consider when negotiating your salary. I’m going to share insight into each of those things over the next few days. We’re going to move fast, so buckle up!

If I can figure this out, I’ll be able to help a lot more people get paid what they’re worth and my business will grow. This is the kind of challenge I love, and it’s why I do what I do.

So that’s where I’m at with my business. Now I’m off to bake a couple of pecan pies for Thanksgiving 🙂

UPDATE: My first attempt at solving this problem is The Salary Negotiation Crash Course. It’s a focused course to help folks respond to a job offer in less than 90 minutes. My intuition is that this could be exactly what people are looking for and it could be a turning point for my business. Only time will tell.

I bought this painting

My friend Rick is a an artist who I met in Charleston earlier this year when I went up there to run a 10k race. I was running the race with Rick’s son, so we all stayed at his house in Charleston while we were in town.

While we were staying at Rick’s house, I saw a painting that I really liked. I didn’t say much at the time because I wasn’t sure if it was ok to ask about buying art from an artists’ house.

But then Rick brought several of his pieces down to Gainesville for an art show, and that piece was among them. It was for sale, so I made an offer, which eventually turned into an agreement. I’m now the proud owner of this original piece:

Here’s the weird thing: It’s a mystery why I like this piece. Rick had lots of great pieces at the show, but this particular piece really speaks to me.

Why? Who knows!

All I know is that I saw it, liked it, and eventually bought it.

I used to think hiring managers felt this way about job candidates. They had a job to fill, they posted a job opening online, they got a stack of resumes, they talked to a few candidates, and one of the candidates just seemed like the right fit.

It seemed mysterious, almost magical.

But then I spent a year building a team of 25 Support Engineers, which meant reviewing scores of resumes and interviewing lots and lots of candidates.

The team we built was very good at what they did, and I learned there’s a very concrete, tactical side to interviewing, which is unlike evaluating a piece of art.

Let’s go back to something I said earlier:

“They had a job to fill, they posted a job description online, they got a stack of resumes…”

Did you catch that?

The hiring manager isn’t hoping for a mysterious connection with a piece of art. They’re hoping to find a candidate with attributes clearly articulated in their job description. They want a candidate who can help the company or team meet its goals and overcome challenges they’re experiencing.

With a job description and a little research, you can position yourself as the candidate for a specific job. It’s almost like you can peer into their mind to figure out what sort of art they’ll like so you can present it right back to them.

Interviewing can be intimidating, but it isn’t mysterious. Your goal in your interviews is to make sure they know that you are that person they’re looking for.

My comprehensive guide to answering interview questions shows you how to position yourself as the candidate they want to hire. Even if you’re not interviewing right now, you should bookmark this for later. And if you know someone who has job interviews coming up, do them a favor and send them this link:

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Take advantage of the Summer lull

I live in Gainesville, FL, which is a college town featuring the University of Florida. And I would be remiss if I didn’t include this to celebrate our first College World Series National Championship: Go Gators!

But enough about how great it is to be a Florida Gator. Let me tell you about my #SummerOfFun.

Gainesville is a strange place because more than half of the city disappears every summer as students head home for summer break. All of a sudden the traffic dissipates, restaurant wait times collapse, and we locals have free reign for a few months.

This also means that most organized activities stop during the summer, and we’re left to our own devices when it comes to leisure time.

Fortunately, a few of my friends have pretty serious FOMO, which means we do something pretty much every night. Here are a few of the things we’ve done so far this summer:

  • Watched the NBA finals
  • Watched the NHL finals
  • Played Spades (we only got through like half a game before we…)
  • Played King of Tokyo, which is extremely fun and you should play it although I can’t ever seem to win (UPDATE: Winnar!)
  • Watched John Wick 2 (exactly what you’d expect)
  • Played Scattergories (Winnar!)
  • Played Cranium (Two-time Winnar!)

It’s a lot of fun. And that’s just a partial list from the past couple weeks—we’re only about half way home.

I realize your summer probably doesn’t quite look like my #SummerOfFun. But I do have a point!

Summers are different

There’s a distinct shift in tone and energy during the summer. Personally, this means #SummerOfFun ramps up for me. Professionally, I’ve noticed a similar lull as things just move more slowly.

People go on vacation. Deadlines become malleable. The office gets quieter.

It’s the perfect time to slow down and recuperate, and it’s a great time think about your plan for the rest of the year.

It’s hard to stop and take time to think about your career and what you’ll accomplish next. But the summer lull makes it a little easier to step back and make a plan.

Take advantage of the summer lull

This summer, take some time to do a little market research to see if your salary is in line for your industry. Maybe it’s time to start planning to ask for your next raise. Or consider the next move on your career path. Maybe it’s time to start planning for a promotion.

Take advantage of the summer lull to recuperate and make a plan as you head into the into the second half of 2017.

Not sure where to start when it comes to asking for a raise or promotion? Fearless Salary Negotiation will show you how to estimate your market value, and has a step-by-step process you can use to get your next raise or promotion.

3D Printing will change everything

The tech world is buzzing about “3D printing” (for some examples, see the links at the bottom of this piece.). I first heard about it a few years ago in the context of printing replacement organs (kidneys, hearts, etc.) for people. More recently, there’s talk about how it could upend the manufacturing world, offer “personal manufacturing”, and shrink the costs associating with prototyping new devices. All these things are true, but the whole way people talk about 3D printing seems short-sighted to me.

The bigger picture is that 3D printing will not only upend manufacturing, but also packaging and distribution. It’ll change how we consume things by drastically increasing the scope of what’s available for consumption 1, and removing almost all of the friction between the creator and the consumer of those things.

Amidst these developments, an interesting domain where the implications of 3D printing are also evident is the realm of anime and game merchandise. Platforms like are poised to leverage 3D printing’s potential, allowing enthusiasts to materialize their favorite characters and items with unprecedented ease and customization. Imagine being able to craft your treasured anime figurines or collectibles in the comfort of your home, thanks to this technology. This not only brings fandom closer to the creative process but also aligns perfectly with the democratizing spirit of 3D printing.

In essence, while the discussions surrounding 3D printing often center on its impact on manufacturing and accessibility, its far-reaching influence is reshaping entire landscapes. Whether it’s the way we shop, the goods we consume, or the unique items we hold dear from the worlds of anime and gaming, the undercurrent of change driven by 3D printing is undeniable.

There are obviously many potential applications for 3D printing, but the game changer is how 3D printers will impact regular old consumers. I think the best way to illustrate this is with a simple story:

Little Tommy is getting ready for his first day of second grade. The family just finished dinner, and it’s time to start getting ready for bed. But first, mom and dad let him know they need to get all his things together for his first day of school. He needs his uniform (a polo shirt with his school’s logo on it, a pair of kakis, a brown belt, brown shoes), a ruler, some pencils and pens, paper, a notebook, and a messenger bag to carry all of his gear. So they all head to the living room to use the biggest screen (suitable for family-style shopping). They spend some time picking out the stuff he’ll need on (surprisingly agile and still-profitable) Amazon, choosing the “Buy now with 1-Click” option for everything.

Tommy heads off to brush his teeth while they wait on all his new school equipment to be delivered. Once he finishes brushing his teeth, he heads back to the living room, where all his new gear is sitting next to the family’s 3D printer. He puts the ruler, pencils, pens, paper and notebook in his new messenger bag and leaves it by the front door. He doesn’t need to try on his clothes because they were printed to his current specifications 2, so he takes those in his room and drops them on the floor next to his bed.

The next morning, Tommy wakes up, ready for his big day. But his mom won’t let him leave without a healthy breakfast. She tells the house to make Tommy a couple scrambled eggs with cheddar cheese on them, and a piece of wheat toast with strawberry jelly. A few minutes later, Tommy’s breakfast is ready and waiting under the hood of the family’s food printer. Tommy eats up, and then heads off for his big day at school.

This example raises a lot of questions, so I’ll finish this post off with a sort of self-Q&A.

  • Why is Tommy using paper and pencil at school? Shouldn’t he be using tablets or something? He should definitely be using a tablet, or a “smart desk” or something, but I had to come up with stuff for Tommy to take to school and I didn’t want to spend a lot of time thinking about it.
  • Ah, but where’d the materials used in the printers come from?! Well, at first I think 3D printers will be stocked similarly to 2D printers–we’ll buy buckets of a few basic materials and load them into the printer. Eventually, maybe that stuff will be piped into our homes so we don’t have to go get it. And ultimately, the printers will be materials-free like tele porters in StarTrek. I have no idea how this would work, but it seems like this is an application for a mature understanding of quantum entanglement or home-sized particle accelerators or something.
  • How is the stuff “delivered” from Amazon? Digitally, just like pictures, music and movies are delivered online today. Amazon would just send a digital file (“TommysMessengerBag.3DP”) to the printer, and the printer takes it from there. The product is a one-time-use, DRM-protected digital file, which is created by Amazon or another vendor. This will be true for almost everything – companies (brands) will sell digital downloads of their products. In this story, the pencils Tommy bought would be Paper Mate pencils.
  • Why wouldn’t Tommy just design his own pants and print them off? The same reason I don’t grow my own strawberries. But the bigger reason is that brands and styles will still exist, and Tommy has better things to do than try to ape those brands and styles with his own homemade version. This is sort of like asking why I buy Levi’s 514s when I could just make my own at home. I have better things to do.

I’m curious what other questions people might have about this, and I think it’s fun to think about. This is not sci-fi, it will happen. The question is really how long it will take before the story above is totally plausible. I have no idea, but I’m thinking something like 2030. How fast this happens really depends on how well Moore’s law will apply to 3D printing. My guess is it will apply pretty well, so things should start ramping up here in the next decade.

Links to cool stuff about 3D printing