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Moonlighting as a Software Developer: Getting Started

I think I’m now on enough of a roll to stop lavishing praise on myself for sticking to reader question Fridays.  So I’ll just get right to business.  Today’s question is about moonlighting as a software developer.  It’s short but sweet.

Any tips for finding moonlighting opportunities?

Sure!  Let’s do that.

Defining Moonlighting

First, though, I want to make it very clear what we’re talking about here.  Moonlighting isn’t a synonym for freelancing or contracting.  Instead, it has a very specific connotation.  You can look to the dictionary for the technical specifics.  Emphasis mine.

Paid work that you do in addition to your normal job, especially without telling your employer.

To unpack, we have a core component and a second, common one.  You do work in addition to a salaried job, and usually without informing your primary employer.

For the rest of this post, I’m going to assume that you don’t want your primary employer to know that you’re doing this.  I’m also going to assume that we’re talking about moonlighting related to your software development work and not you getting a cashier’s job at the local bodega.  You make a living as a techie and want to earn some additional cash, also as a techie.

A programmer moonlighting... literally.

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Starting a Software Company from Scratch

When I reflect back on my free agent career, it strikes me that I more or less did everything wrong.  I mean, I don’t actually believe that when I look at it analytically.  But it does feel that way, knowing what I know now.  Starting a software company from scratch invites plenty of missteps.

In the lead into last Friday’s reader question post, I talked about starting this blog as a journal of sorts.  That’s a good example of what I’m talking about.

In the end, I built an audience, established a brand, and wound up in a good place.  But if I could go back in time 7 years and give myself advice, my path would have been more direct.

It goes beyond blogging, of course.

That was one example, but it applies generally to my entire approach to starting my software development/consulting company.  I did things that worked out, but it hardly seems optimized in retrospect.

You’re probably thinking that this applies to everyone.  Hindsight is 20/20 and all that.

And you’re right, which is exactly my point.  I dove in with severely imperfect knowledge, made a lot of mistakes, and it still worked out pretty well.

If you pursue the free agent life, you’ll flail, make mistakes, and have some false starts.  But you’ll recover, figure it out, and do fine, even if it sometimes seems like you’re drowning in the moment.

Flat Squirrels and Driving Directions

Perhaps you’ve heard an expression.

“Be decisive. The road of life is paved with flat squirrels who couldn’t make a decision.”

Don’t blame me for the macabre nature —  I didn’t make it up.

I like part of the sentiment, but I think it misses the mark slightly.

If you picture a terrified squirrel in the road, its biggest problem is thousands of tons of steel and plastic death bearing down on it.  It starts left, then moves right, then freezes and then… well, you get it.

Indecision costs it dearly, but only once it has a large problem already.

When starting a software company from scratch, indecision won't flatten you, but it will impede your progress.

This probably doesn’t describe you in most situations that call for more decisiveness.  We face paralysis by analysis, rather than paralysis by mortal terror.

Have you ever sat in your car, debating whether to take the highway or side roads during rush hour?  Have you ever sat there debating this for so long that you get to your destination later than if you had simply picked either option and started immediately?  (Come on, I bet you have.)

This makes for a better analogy for our lives, especially when it comes to starting something new.  We put off action out of fear of taking a sub-optimal path.

But, at some point, even a sub-optimal path beats sitting in your car fretting.

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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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How to Freelance: The Low-Risk Path from Software Developer

Ah, the eternal opportunistic question: how to freelance?  You work as a software developer, making $100K per year or something.  This is a great wage, and so you have a great life, sitting pretty high up atop Maslow’s famed hierarchy.  But then you figure out that Steve in your group is actually a contractor, and a little later, you figure out that they pay Steve $70 per hour.  A quick google search for “work hours per year” and fast math tell you that Steve makes $145,600 per year (so you think, anyway).  Suddenly, you feel less like a prosperous citizen and more like a sucker.

How to Freelance like Steve and make big money

How can I get some of that Steve money?

Not far behind that thought comes another.  I should become a contractor!  And then, finally, we get back to the titular concern: how to freelance?

The Reader Question and Some Housekeeping

As regular readers may have deduced, I’m doing a reader question today.  And, as regular readers may have noticed, I haven’t done reader questions (or DaedTech-only posts) in a while.  Please forgive me on that count.  I spent a lot of writing energy on my recent book launch and then even more on starting a tech company blogging business.  With all of that writing, I’ve had trouble mustering spare writing cycles the last few weeks.

But I’m turning a corner on that and launching the first of what will be a series: “reader question Fridays.”  I’m making the vision of this site more and more oriented around the Developer Hegemony vision (software developers becoming the bosses of software development), so please fire away with questions.  I take all comers, but I’ll prioritize questions that speak to the subject of software developer agency.

Anyway, I’ll paraphrase the reader question.

I currently work as a salaried software developer.  I think I’d like to figure out the freelance thing, but I’m not sure.  It’d mean a lot of risk to quit my job and hang out my shingle, so I’m wondering what you advise to make this a less risky transition.

I actually wrote about a related topic recently.  But that question more concerned my personal background and how to become a consultant.  Freelance software development is not, in my opinion, consulting.  I refer to people who do that as software pros.  Firms pay consultants for their opinions and they pay software pros for their labor.  I draw the distinction here because software pros need to worry a lot less about specializing and niching — at least at first.

But forget about the taxonomy and let’s look at how to become a freelance software developer with a low risk playbook.

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The Opportunist’s Guide to Start Consulting (Abridged)

Given the recent launch of Developer Hegemony, I decided to address a reader question.  This question hits near and dear to my heart and to the subject matter of the book. I’m going to paraphrase for the sake of anonymity.  But, either way, it amounts to a question about how to start consulting.

But First, Some Housekeeping

Before I dive into that, though, I’d like to make offer some links.  If you want to hear and read more from me, I offer you the chance.  Check these out.

And now, back to your regularly scheduled post.

The Reader Question

Without additional preamble, I’ll offer up the (paraphrased) reader question.

I’m currently a developer, and want to transition to freelance consulting. But I’m not quite sure where to start.. Do you have any advice on that? How did you manage to start a consultancy business?

First of all, understand the dichotomy here.  He asks for my advice and he also asks how I did it.  I ask everyone reading to understand that these aren’t necessarily the same thing.  In other words, I can tell you exactly what I did, but that doesn’t mean I think you should do it in exactly that way.

Oh, don’t get me wrong.  I don’t think I made any horrible mistakes or anything like that.  But I kind of wandered my way through the experience, not entirely sure at the time what I wanted.  Unlike the reader asking the question, I never explicitly decided to become a freelance consultant.  In fact, I just had some free time and wanted some extra money.

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