Did I Go Back to a Full-Time Job? 🧐

Life is full of uncertainty.

This fact used to be a point of anxiety for me. For a lot of my twenties, I moved through the world thinking that anything could go wrong at any point. I still think that idea is true. However, I realized that worrying about every possible risk was making me miserable. So in the past few years, I've tried to do my best to protect against catastrophe and not concern myself with the rest. I work to cap the downside and then do my best to live in joy and peace.

So, when a few large, unexpected bills/financial risks came up in the past few weeks, I felt I handled things with relative calm. They were:

  1. A $4,000 tax bill. My fault for screwing up my paycheck withholding in 2021.
  2. A $6,500 hospital bill from my trip to the ER. The actual bill will likely be less – my wife's insurance hadn't fully processed me in their system, so they assumed I didn't have coverage and passed the full cost on to me. I'm still working this out with all of the various parties.
  3. Getting sued due to a three-year-old fender bender. My insurance told us to expect the suit, and the case will likely settle under the policy limits. But there's a small chance that it won't, and it's hard to know exactly what to expect if the case goes to court. (I've since gotten an umbrella policy, speaking of capping the downside.)

The question is, what do these things mean for my self-employment? The answer has been: they lit a fire under me to secure billable work a bit faster than I intended to. For the past few weeks, I've been talking to recruiters, interviewing, weighing offers, and starting full-time work. I just finished the first week of a three-month contract. It was harder than I thought to find an opportunity that matched my preferences (15-20 hours/week), so I ended up deciding to be less picky.

At this point, you may be questioning my strategy. I made such a big deal about leaving traditional employment – aren't I simply back where I started?

In a way, yes. That said, I think there are some key differences between typical 9-to-5 work and my current setup:


It's a little bit hard to do an apples to apples comparison, but with my current rate I've effectively doubled my most recent annual salary. This is due to a variety of factors (1099 work generally pays higher, strong demand for engineers, well-funded startups, etc.), but even I am a little surprised at the result.


I've written in the past about wanting to include more seasonality in my working life. I always find it easier to work hard when there's a light at the end of the tunnel, and I enjoy periods of sprinting followed by times of rest, similar to a semester in college. Due to the market rates for engineers, I think there's a viable way to pursue a 6 months on/6 months off pattern (at minimum). Since my ultimate goal is to have a high degree of time autonomy, this contract is a step towards sustainably deciding how to structure my days.


The mindset shift may be the most important piece of the new arrangement, and is the biggest reason why I think this new contract is distinct from standard employment. Something interesting happens when you take a W-2 job in America; there's a lot of written and unwritten rules that come with full-time jobs: you get a manager, the company gives you healthcare and retirement, the company invests in you, and in return the implicit expectation is that you should make the company a priority (if not the priority) in your life and care on a personal level about what the organization is trying to achieve.

With contracting, a lot of those preconceived ideas are taken away. I'm hired to do a job and provide value. In exchange, I get paid. If it's not working out, either side can walk away. That's really all employment has ever been, or ever will be. It's just that this form of work makes obvious what tends to be obscured by our cultural narratives. There are no romantic notions with a contract, just the tasks that need to be done.


To conclude, even if things look the same, I feel I've taken my work more into my own hands. And since increasing autonomy has always been the goal, I think I'm on the right track.

Pete's Picks

  1. What I'm Watching: The last few episodes (ever!) of Ozark. A genuinely great show at a time when Netflix is churning out some questionable stuff.
  2. What I'm Listening To: Joseph Henrich on Armchair Expert. AE has become one of my favorite podcasts in the past year. High recommend.

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