Stories about Software


Freelance Software Development: Speaking to Your Buyers

I believe that at two, you have to call it a streak.  And so I’d like to celebrate my illustrious streak of reader question Fridays successfully delivered.  Today’s topic?  Freelance software development.

This actually follows pretty naturally from last Friday’s post.  Toward the end of that post, I pleaded with software developers to stop worrying about impressing one another.  I did this because software developers are not your buyers — they’re your peers.  Just as you don’t see Target’s CEO calling Walmart’s to show him what great deals Target has this week, you shouldn’t market toward your peers.  Instead, you should direct your marketing efforts (blog included) at your buyers.

Doesn’t This Make You a Hypocrite, Erik?

If you dig through the archives of this blog, you will find an awful lot of posts directed at software developers.  So I’ll just head off the inevitable comment about my hypocrisy with a caveat heading.

First, I treated my blog as half journal, half catharsis for a lot of years.  That is, I didn’t set out to speak to my buyers because I didn’t have any when I started, prospective or otherwise.  I wouldn’t go off on my own until I’d already been blogging for years and, at that point, I had my own pipeline pretty well stocked.  Due to preparation through other means, I never relied on this blog to keep work rolling in.  I do get inquiries and business through the site, but usually about developer training and the assumption that I can teach/setup anything I blog about.

The other thing that I’ll say in defense of me speaking to developers through the blog is that developers now are my buyers.  You can buy my recent book if you don’t believe me, or check out my other developer-oriented offerings.  Over years and years of blogging, I learned that it makes sense to offer your audience things it might value monetarily.  (I encourage you prospective bloggers to be less obtuse than me and have this figured out from day one.)

So, yes, I speak to software developers on this blog and always have.  But I don’t do it in the hopes that someone will notice it and hire me to do custom app dev.

Onto the Reader Question(s)

Now that we have that out of the way, let’s move on to the reader question(s) that pertain to freelance software development.  Usually, I try to do a FIFO scheme, but I actually received more than one variant of the same question after last week’s post.  I figure that bumps it to the top of the list.  So here’s a composite of that question.

Do you have any tips on how to write for buyers, rather than fellow developers?  My interests (and my prospective freelancing) run heavily technical, and that’s what I know how to talk about.  So how do you recommend that I speak to buyers through the blog?

Short answer is, sure, I absolutely have tips for that.  And I’ll get to topic ideas in a bit.  But first, let’s get both a little blunt and a little philosophical, so that you understand what you’re up against.

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Turning Tech Hobbies into Side Hustle

I just dug up a tweet I made about 6 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.


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.

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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.


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