DaedTech

Stories about Software

By

Turning Tech Hobbies into Side Hustle

I just dug up a tweet I made about 4 years ago.  I did this because I remembered saying it, and because it perfectly illustrates a distinction I’m going to make today.  Specifically, I’ll talk about the distinction between technical hobbies and side hustle.  And, I’ll then advocate for side hustle.  But first, the tweet.

Quick and to the point.  The year was 2013, and, during the course of yet another oppressive Chicago winter, I wanted to learn F#.  At the time, I ran an IT department as the CIO for a company, and I had come to miss writing code.  So, I took to Twitter and threatened to teach myself yet another programming language.

I’m embarrassed about this tweet, in a sense.  You might think the fact that I never wound up learning F# embarrasses me.  But no, I’ll get over that.  Rather, the undirected, goalless nature of the sentiment embarrasses me.  It does in the context of career, anyway.

Programming Hobbies

Before I go any further, I want to talk about the idea of hobbies and career.  At times, I’ve enjoyed hobbies, such as guitar playing, cooking, and home improvement, among others.  Given that I’ve historically earned my living in software development, nobody would confuse these hobbies with career plays.

The line blurs a bit with certain other considerations, however.  For instance, I could have regarded writing as a hobby for a good bit of my career.  These days, however, people explicitly pay me to write in various capacities.  This kind of knocks writing out of the realm of pure hobby for me.  And then there’s time you spend outside of work doing what you do for a living.  Let’s say, going home to learn F#.  It doesn’t pay your bills, but you can file it under the heading of “sharpening the saw.”  Sure, my job may not call for F#, but it makes me a better programmer (and, a better CIO, I guess).  So it counts as career-something.  Right?

Actually, I would now argue that no, it does not.  Had I gone home to learn F#, for the sake of learning F#, I would have engaged in a hobby rather than a career play.  You can’t just blindly count something tangentially related to stuff you do for a wage as career improvement.  And yet, we do that.  A lot.

Read More

By

The Aspiring Free Agent Survival Guide

It often feels as though I have no idea what I’m talking about.  I don’t say this in an attempt to garner sympathy and I’m not really suffering from impostor syndrome (at least not in this domain).  It’s more that running my own show, business-wise, has demanded of me a form of trial-by-fire, just-in-time learning.  It’s as though I moved to a small village in Germany, in spite of the fact that I don’t speak a lick of the language.

But in muddling my way through all of the details, large and small, I’ve actually managed to pick up a fair bit.  What I’d like to offer today is a preparedness guide of sorts.  The free agent’s life is an attractive one in a lot of ways, and I definitely recommend at least considering it.

I have no regrets, myself.  But I do acknowledge that it can seem like a pretty daunting leap, particularly if you’re well established in life and have responsibilities.  People telling you to take the plunge probably seem like friends swimming in an chilly lake, already used to the water, telling you that it’s fine.   I’m not that used to the water yet, though, so I can still appreciate your position.  It’s cold, but it’s refreshing.  And I’d like to offer some thoughts before I get too acclimated to the temperature.

ColdSwimming

So here are those thoughts.  These are things to be aware of if you contemplate, however idly, the free agent life. Read More