The best things about being self-employed

One of the great benefits of being self-employed is having a flexible schedule. I sometimes think about what my plan B would be if for some reason I needed to go back and get a “regular” job.

It’s one of those thoughts that can be a little depressing, but I had a realization recently—many of the recent improvements to my schedule and life really are things that don’t actually require that I’m self-employed at all.

Wanted to share some of these thoughts—if you’re working a full time job and looking forward to the day when you could be self-employed and not have to deal with all the things you hate about work, maybe this can help you to have a little bit of a different filter on your work.

I think there are many ways you can make your day job more enjoyable and more aligned with your true interests than you would realize.


I’ve been taking about three 45 minute walks per day—one in the morning with my dog, one around 11am when I take a call, and one at 4pm when I take my dog for another walk. It’s something that I’ve really started to look forward to - grounds me, gets my brain firing on all cylinders, and I really enjoy the calls that I do while I’m walking. Sure, I might need to tweak the timing on it a little bit if I had a 9-5, but it wouldn’t be too hard to squeeze it in.


I’ve been doing yoga about 6 days a wek for the past month or so now. It’s fantastic—not only is it relaxing but I feel myself getting stronger, improving my balance, more flexible, better posture. It’s absolutely wonderful. Could still do that during a lunch break.


One of the things that’s great about being self-employed is that I don’t have to take a lot of meetings. As a typical developer, I’ve generally thought that I hated meetings, and once my businesses got to a point where cashflow-wise I didn’t need to take many meetings, I pretty much stopped almost entirely or down to a bare minimum.

But it turns out that I actually like meetings—I’ve started to schedule 2 of them per day for about 45 minutes each—it’s just that I do them while I’m on a walk.

Now sure these are meetings that I want to take and they’re not always directly related to work goals, but the point is that I just put some parameters in place in order to make them more enjoyable and effective. Could probably do that even with a full time job.


I’ve enjoyed podcasting for a number of years now and I’ve been starting to do some more of that in a little bit of a different form. Of course, when I started Magetalk it was on the side to my day job, so that’s obviously something I could still do. Or perhaps even something that could be done within work.


I try to carve out an hour each day to do some long-form writing. It’s been a great way to get ideas out of my head and onto paper, and it’s also just a good intellectual challenge for me to have some deep work that I have to do every day.

This is of course something that can be done in the context of a full time job.


One of the most recent things I’m looking forward to eliminating or greatly minimizing from my day is email handling by hiring an assistant. This very much feels like something you have to be your own boss in order to do, but I realized there’s really nothing stopping you from doing this even in a full time job, as long as you handle everything you need to handle.

Whether you could hire someone to be your assistant at work or just use your own money to do it.

Family time

Not work-related but one of the things that’s been giving me great satisfaction is starting to carve out time with my family more—longer breakfasts and dinners together.

Interesting thing is that this is all still mostly pre-work and post-work time that I’m spending with them. While it’s true that I do have more time available now than if I had a full time job, I could still be getting in the same amount of quality time with them even with a full time job.


This is covered by the walking and yoga bullet points a bit, but just generally focusing on getting in better health is something that’s been huge for me the last several months—and is certainly something that anyone with a full time job can do.


What’s interesting about all of these things is that I didn’t mention money at all. Sure, some of these things cost money—but really none of them are things that I couldn’t afford on a regular salaried job. Money doesn’t make you happy.