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Reader Question Roundup: Working at Google, Remote Freelancing, and Side Projects

I’m doing reader question Monday on a Tuesday once again.  But this time it’s not my fault.  You can thank organized labor for interrupting your reader question Monday with their US holiday yesterday.

I did this once before, and I’m going to dust it off and do it again.  You folks send me far more questions than I can answer at a pace of once per week.  And thanks for that!  It’s awesome.

The result is an ever-growing backlog of questions.  And, while I may start doing something ala John Sonmez with his youtube channel, where he answers a lot of reader questions as videos, for now, I’ll try to catch up a little bit by answering several in a single post.

On the docket today, an eclectic mix that hopefully you find interesting.  I’ve picked questions likely to be relevant to a decent cross section of folks.

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Scale Your Freelancing: Hiring Others

Last week, I answered a composite reader question about everyone’s favorite subject: taxes.  This week, I’ll build on that with another composite question.  This time about how to scale freelancing work that you might do.

I’ve gotten a few different questions about this over the last several months.  I’ll try to cover everything you all have asked by answer this composite question.

Freelancing is going well enough, but now I’ve got a spike in work that will be more than I can probably do on my own.  I’ll need to hire someone, somehow, to do something.  How does that work?

It’s understandable to wonder this.  Speaking from my own experience and what I’ve heard from many others, you’ll probably have your own freelancing practice or side hustle for a long time before this comes up.  Or, it might never come up, and you still have a rich happy professional life.

But when it does come up, it’ll probably happen quickly.  And, you’ll be swamped when it does, since, by definition, you’re looking to hire due to too much work for yourself.  So it’s good to at least have a concept of how this works ahead of time.

Caveats Again

As I mentioned in the last post, I am neither lawyer nor accountant.  I’ve hired subs and done a lot of business this way, but I am not a professional advisor.  What you’re getting here is my best understanding and things that have worked for me in the past.

Use the advice here to orient yourself and get a feel for how this works.  But before you actually go execute this stuff, you should contact your lawyer and accountant to verify that it’s right and that it makes sense for your situation.

And, once again, a lot of this may be US specific, but I hope non-US readers can get something out of it as well.

Can I just pay someone, the way I pay the neighbor kid to shovel my driveway?

This is the first thing that might occur to you.  You’ve got to deliver 4 modules by the end of the week, and you can only possibly deliver two of them.  Can’t you just offer a fellow developer $1,000 or whatever in exchange for her doing the other two?  Seems simple, and it should be simple, you think.  That’s what I thought.  And it would actually be simple if not for the tax man.

Think of the kid you give $10 to shovel your driveway.  Seems innocent enough and like pure commerce in action, right?  Wrong.  In the first place, you’re probably technically violating some kind child labor law and possibly running afoul of minimum wage laws.  But, even if that little scamp were 18 and of legal working age, this would still represent an illegal transaction because he’s almost certainly not making a note of that $10 of income so that he can report it on his tax return.

So now, you can’t “just pay someone.”

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Becoming a Freelance Developer and Taxes

It’s been a while since my last reader question post.  That was the one where I confusingly announced on a Tuesday that I’d be doing reader question Mondays.  Well, today I start a new streak of doing reader question posts on Mondays.  My apologies for dropping the ball on that, but I took on a full time consulting gig for a few weeks while also running my content business evenings and weekends.  It was a busy run.

Anyway, let’s get down to business.  Both in the Developer Hegemony Facebook group and through other media, people have asked about some nuts and bolts freelancer/entrepreneur type things.  And, after recent videos about creating an EIN and filing for an LLC, the pace of those questions has increased.  So, apologies to those who come to this blog looking for rants about the perils of global state or unit testing.  Today, we talk taxes.

If I’m thinking of going off on my own, how do taxes work?

Nobody has asked me the question in these exact words.  Rather, this is a composite of what various people have asked.  So, without further ado, let’s dive right into the least interesting subject on the planet.  I’ll do what I can to make it fun.

Obligatory Disclaimers

Mercifully, I am neither a lawyer nor an accountant.  Nothing against either profession, per se — they’re just not for me.  I mention that here so that you understand the context of this advice.

I am going to describe what I have, myself, done, along with my understanding of how it works and various other options that I might have.  I’m pretty confident that I have a relatively complete understanding for a layman in those fields.  But there may be finer points that you’d need an accountant or lawyer to illuminate.

In the context of the software world, think of me as a the equivalent of a guy with 3 years of .NET experience teaching newbies.  I’ll get enough right to help them a lot, but I might not nail some of the more arcane language points or sophisticated design strategies.  Caveat emptor.

Non-US readers, this is also entirely US-centric.  I hope some of it helps, though.  I’ve had people from other countries tell me in the past that some of my videos/posts along these lines are helpful.

Taxes in the Wage Labor World

For the sake of easy math, let’s say that you take a job for $120,000 per year.  Let’s also say that the employer pays you monthly, at a nice, round $10,000 per month.  That should make it easy to figure out how much you’ll pay in taxes, right?

Wrong!  There’s no figure round enough to make it easy to figure that out in the US.  You go to a calculator like this, expecting to type in $10,000 per month and seeing that you owe something like $2,200 per month in taxes.  Instead, it wants to know whether you’re single, how many “dependents” you have, and something about “exemptions.”  And that’s a simple one.  Some probably ask you about your mortgage, whether you live in a flood plain, and how many blind uncles named Dwayne you put in rest homes last year.

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From Employable Generalist to Successful Efficiencer

For regular followers, I bet you thought I forgot about reader question Fridays last week.  I didn’t.  Friday is a relatively low traffic day for bloggers, so I’ve decided to switch over to reader question Monday.  But, on Sunday night, I did forget about the post draft, so the first reader question Monday is actually Tuesday’s post.  I know.  I’m a little disoriented too.  But we’ll figure it out.

About a year ago, I wrote a post about niching down.  I asked readers to imagine if, instead of listing the services that they provided, housing contractors described the number of years they’d spent using their tools.  “I have 6 years of hammer, 3 years of reciprocating saw, etc.”  From that, they left it up to you to figure out if you could translate those skill into something useful, like fixing your garage door.  That’s us, in the software development world.  “Here are my experience tuples, and now I just need some kind of manager to figure out how to turn me into a useful resource.”

Given my tone, you can probably infer that I advise against this approach.  In fact, I frequently suggest specializing and figuring out how to solve business problems.  But as a few people have now pointed out via reader questions, I’ve not offered a lot in the way of advice to bridge the gap.   A reader in the Developer Hegemony Facebook group put it quite succinctly, in the parlance of my old post.

How do you translate 3 years C#, 6 years C++, etc… into “I can fix your garage”?

It’s a good question.

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Weaponized Mastery, Autonomy, And Purpose

Years ago, I published a post called How to Keep Your Best Programmers.  In it, I discussed what drives programmers out of jobs and what keeps them happy.  This discussion touched heavily on the concepts of mastery, autonomy, and purpose as important motivators for knowledge workers.  If you want to keep skilled programmers, you can’t just throw money and bonuses at them — you need to appeal to these other forms of motivation.

This post became quite popular and has remained so over the years.  I think the popularity results from the resonant idea of wanting our lives and careers to mean more than just a paycheck.  We want to be proud of what we do.

Since my own discovery of it years ago, I’ve seen frequent reference to these motivators and to Daniel Pink’s talk about them.  People use it to explain the difference between work that pays the bills and work that deeply satisfies.  More and more, we exhort our employers to appeal to mastery, autonomy, and purpose.  And more and more, they seem to do it, to our benefit and that of the industry at large.

But with this trend, I’ve noticed an interesting and unanticipated side effect.  People can appeal to autonomy, mastery, and purpose to enrich our lives, but they can also do so to manipulate us.

Mastery, autonomy, purpose -- they make us happy, but they can mesmerize us.

Mastery, Autonomy, and Purpose as Vices

To understand how that works, consider our desires in a different light.  Consider what happens when you take them to extremes.

We enjoy getting better at things (mastery), but that can lead to obsessive behavior.  I think most of us can relate, at some point in our life or another, to playing way too much of some kind of stupid video game.  We know it wastes our time and that we should probably delete it, but… just… one… more level.  Mastering the game drives us even when we know it wastes our time.

We also enjoy autonomy, but chasing that can lead to problems as well.  Have you ever known someone serially unemployed because they bristled at the thought of anyone telling them what to do?  Some people with that demeanor become entrepreneurs, but some become angry criminals.

And purpose as a vice can be, perhaps, the scariest of all.  Think about the phrase, “the ends justify the means.”  What is this if not a statement that purpose trumps all?  As long as you’re chasing a lofty enough goal, it doesn’t matter who you step on to get there.

We can chase mastery, autonomy, and purpose into problematic territory.  But other people can also use them to chase us there.

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