Lessons learned from being self-employed, 12 months in

This months marks one year of working for myself, and undoubtedly I feel mixed about it. I’ve made a number of mistakes that I can’t help feeling dumb about. In retrospect, I probably wasted three months learning these lessons the hard way. And yet, it’s a lot like a hot stove. People can tell you it’s hot, but until you touch it you won’t quite grasp it. Here is what I’ve learned from a year of self-employment

What I learned

Don’t force your job into your dream job

When I quit my job, I had ambitions of doing all the things that give me life. I was going to attend more conferences. I was going to study all of the time. I was going to write more. I would work whatever hours I wanted, whenever I wanted. These were all things I imagined I would do once I quit my job.

And while I did many of these things, I was putting the cart before the horse. What I learned is that I needed to get the fundamentals in place first. I had to learn how work from home. I had to learn how to rebuild the boundaries and structure of a normal job. I had to learn how to create a new routine.

And as a result, I probably spent the first two months a bit unfocused. I also made a number of commitments that I am finally coming out the other side of. While I’m proud of all the presenting and speaking I’ve done this year, I wish that I had put first things first.

Respect your human fragility

I underestimated just how human I am and how hard this would be. Often it was dumb stuff, like needing to set office hours. I’m used to just being productive, just getting things done. But in reality, there was so much invisible scaffolding that had been supporting me, that I had interpreted as my own strength.

When you have a day job, you often have set working hours. You have coworkers and expectations. Consequences are often direct and measurable. Most people work in a different environment than they live in, so our brains have context clues.

All of this goes out the window when you work for yourself and work from home. Consequences are both diffuse and existential. No one will yell at you if you put off marketing or sales, and yet your whole life depends on it. There’s a vagueness there that is unsettling. The temptation is to just work harder, to push harder if things aren’t working. But without some structure to push off against, it is exhausting.

Find a way to rebuild that structure

Through trial and error, I found a way to rebuild the structure I had given up. I set office hours of 9AM-6PM, with an hour lunch. I peppered exercise through the day. I worked on breaking things into concrete tasks. I started building a python app to track personal todos and basic things like checking my blood sugar.

I feel like I’m starting to get the hang of it, but I’m not quite there. I find mixing consulting work with creative work to be a challenge. It reminds me of Paul Graham’s essay on Manager’s schedules versus Maker’s schedules.

The contrast of urgency and distant deadlines, of deep work and quick meetings, can be quite jarring. In theory I’d like to have dedicated days for creative work, but it never seems to quite work.

Join a peer group

One of the smartest things I did during this process was a lucky accident. I was friends with a wonderful peer in the Pluralsight space. He lived near me and was a full time author. And when I quit, he invited me to join his mastermind group. We have a Slack chat and we have a Skype call every other week.

Working for yourself is incredibly and brutally lonely, and alienating. You are making all of these decisions and going through new experiences. Having someone to bounce ideas off of is critical. It is so relieving to have a group of peers going through the same thing.

Take a vacation

Schedule a vacation. Make it happen. It took me 8 months but I had a real vacation. By planning it far in advance, I could warn clients and build it into my schedule.

When you work for yourself, there is a creeping sense of opportunity cost. Let’s say your billable rate is $100. That means every movie is $200 you could be earning. That board game is $100 you could have made. And that vacation is $2,000 you didn’t bill someone.

And that is why you need set office hours. That’s why your need strong boundaries. And that’s why you need to schedule a  vacation. Because otherwise there is a temptation to work yourself into the ground.

Was it worth it?

So, was it worth it? Would I do it again? Let’s look at it financially first.

Financial benefits

At my prior job, I made about $65,000. This year I made $85,000 in gross revenue. So, big improvement right? Well…

So, when you work for yourself you have to pay all of your own health insurance, 401k and vacation. You also have to pay both halves of the payroll taxes. Realistically, it turns out to be a bit of a wash, when you factor in all of these costs. Overall, it has been a modest improvement, at the cost of monthly consistency.

If I really wanted to make more money, I could have taken a job with “Senior” in the title and gotten paid $80-$100k AND benefits. At the same time, It probably would involve being on call or quite a bit of stress.

Personal benefits

The personal benefits are huge, and I will probably not take a regular job for the next ten years. When you work for yourself, you decide what you want to focus on and specialize in. You do set your own hours and eventually you can fire your worst clients. There really is something soothing in knowing you have control over your career.

But beyond that, working for myself has allowed me to be a caretaker for my mother. I’m able to visit her 3 days a week and take her in to a Medicare replacement program. I’ve been able to see a marked improvement in her quality of life as a result.

So yes, it was worth it and I would do it again. I just wish I had a time machine so I could do the first year the easy way, haha.

3 thoughts on “Lessons learned from being self-employed, 12 months in

  1. Honest writing. I’ve often wondered if I would have the discipline to work for myself. You summed up one of my concerns: “But without some structure to push off against, it is exhausting.” I appreciate that you shared your perspective after a year of doing it. Best of luck to you as you keep on keeping on.

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