Lessons learned from being self-employed, 3 years in

This month marks my 3 year anniversary of working for myself. I think it was undoubtedly the right decision, but it doesn’t quite feel firm and real. Here are some lessons learned as I enter my third year.

Learn how to work, or fail

I think the hardest lesson for me is that the biggest challenge has not been the technical piece. I know how to do that, and I’d like to think I do it well. I even have somewhat of a grasp on the sales and marketing piece. The hardest part is the daily art of working.

I’ve said it many times before, but there is so much scaffolding that comes from having a workplace, co-workers, and a boss telling you what to do. You expect to just be able to get stuff done when you work for yourself, and that’s just not the case. It’s frustratingly difficult.

In reality, there is a whole suite of skills that need to be learned to work for yourself, to work from home, etc. for example:

  1. Switching between strategy and execution
  2. Setting boundaries at home
  3. Scheduling work
  4. Identifying what’s profitable and drives the business forward
  5. Tolerating financial and career uncertainty

My biggest regret has been not focusing on these things from day one. My biggest struggle right now is the art of daily working and daily success.

Invest in your environment

Related to that, in the last 5 months, my royalties have been at an all time high. That this feels real and stable, and has caused me to reinvest in my environment. I think that is also something I wish I had done earlier.

When I first started, I was using the same laptop for both leisure and work, and this quickly lead to a poor work-life balance and everything feeling like a blur. For the longest time I used a $100 desk from Staples.

More recently, I purchased a standing desk and it has been wonderful. I bought three 27″ monitors. I bought a streamdeck and use it for time tracking launching applications. I purchased $400 headphones, which feels utterly decadent. But I’m realizing it’s all worth it.

Ultimately, not investing in my environment for so long is a kind of stubbornness. I keep expecting to just be able to work, but this depends on some reservoir of willpower and focus, which is always more limited that I expect. Too often I indulge in “should” thinking.

How much money do you need?

One thing that has been a point of frustration is that my top line revenue for the past 3 years has been fairly flat. And sometimes I wonder if I’ve made a mistake. But just looking at top line revenue doesn’t tell the whole story.

First, if you look at where that revenue came from, there’s been a huge shift over time. That first year, 80% of my income was consulting and 20% was royalties. And much of that consulting was work I didn’t want to do, but did to pay the bills. By year three, that ratio has flipped. Covid tanked a lot of consulting but doubled my viewership.

One big benefit of that is now my income, while not higher, has become more stable and predictable. Not once during the pandemic did we have to worry about paying the mortgage. In contrast, I know a couple consultant friends who had to go back to getting a job.

Another benefit has been supreme flexibility. It comes with frustrations, as mentioned above, but I’ve been able to just take a day off, whenever I want. I can take my mom to a bird fair, and it’s fine. I think a lot about folks who get promoted, make an extra $20k but are working 50 hours per week and are miserable. I try to remind myself that I’ve take the reverse choice.

So what’s next?

I plan to continue doing consulting on Power BI and the Azure data platform. I think it’s essential as an instructor to stay grounded and relevant. And I enjoy it! But I’m accepting that my main job is to be a perpetual newbie, having to constantly learn technology and package it up for others. This means focusing on instructional design and, more importantly, how to get work done on a daily basis.

In the short term, I’m working on 3 Power BI courses for Q4 and then hopefully taking the last 6 weeks off for 2021!

2 thoughts on “Lessons learned from being self-employed, 3 years in

  1. Hi,

    Congratulations on making the shift and surviving to tell the tale. I work in a school ( not made the jump) where school results have been largely flat oer a few years now. This is simply because the school is not taking a risk to change it’s ways or chaning the way of doing things.

    You will see different outcomes ONLY if you make changes to way you operate. I only wish I had the courage you have.

    That’s all I can say and wish you well.

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