Bootstrapper to 9-5er

I got my start in tech almost two decades ago. Back then the landscape was much different, but I feel in love, and made it my career choice.

I found a friend, started selling software and doing custom development. Back then no one used the fancy term bootstrapper and I was just a partner in a small business, like thousands of others.

Flash forward a lot of years and I found myself getting a full time job. Something I hadn’t done in such a long time that it was a shock. I went from setting my own hours, working a few minutes away, and wearing many hats. To having to drive an hour each day, a set schedule, limited vacation, someone else making decisions, and having to focus on just code.

On one hand it was easier. Being an owner, all these questions stayed in the back of my mind, and at all hours:

  • Are we making enough money this month?
  • Did we put back enough for taxes?
  • Can I afford health insurance for the family?
  • Is the company growing?
  • Is our marketing working?
  • and on and on and on.

If you notice almost everything in my list was around money. Being a bootstrapper without a large net worth is stressful. A few bad months without proper savings can hurt you in a bad way. I had a hard time with the income being unstable from month to month. This stress compounded when I had kids.

Going to a full time job took away most of that. I could depend on a paycheck, had insurance coverage, and taxes would be handled like the rest of the population.

That doesn’t mean it wasn’t without issues. Mostly driving into an office. I took a job in the next city over, on a good day about 30 minutes one way, but that hour a day really adds up.

My kids go to bed between 7 and 8 which meant I would only get to see them for an hour or two and I didn’t like that at all. Especially in the toddler stage when they are doing all the good stuff for the first time.

I was able to eliminate the drive by getting a job working remote. Which also included the side benefit of being home for lunch and to be a big part of my kids lives.

Working from home is not without challenges. For me it’s mostly training the kids that during work hours they are to not be to loud and keep interruptions to a minimum. I would say that works 90% of the time but I do make an exception after school. Having them hold in their excitement until after work is impossible.

The other thing I’ve heard about working from home is isolation. This hasn’t affected me and I assume it’s because of my personality. I prefer not to talk and chatting with friends via online messaging is just as well with me. You could say this is my introversion showing it’s true colors.

All in all I’m happy with my experiences on both sides. One benefit is now as an employee I have a pretty good understanding of the business side, and how when you work for a bootstrapper you are an integral part of the company.

0 thoughts on “Bootstrapper to 9-5er”

  1. The one and only thing I don’t like working from home is isolation. Not from people, but from other developers. Working at a development company, we could pod-storm (have all occupancy of a cubicle pod turn their chairs to the center and brainstorm). This was a huge learning opportunity to get feedback from dev with different experiences. I was able to learn a lot more in less time in that kind of environment.

    Working from home, I find myself challenged by learning from books or online tutorials. There is an element of feedback that is sorely missing. I guess this isn’t as prevalent if you’re not a lone developer working for yourself, but part of a team, where you can get on a call and share ideas or get feedback.

    Thanks for sharing your experiences. 🙂 Always interesting to see what others have been through as well.

    1. You comment is interesting to me because of my history. I’ve never worked in a company with other developers so my entire career has been in developer isolation even in the office.

      I can see how that could be beneficial.

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