Stories about Software


Employment Teaches You How Not to be a Free Agent: You Have Stuff to Unlearn

Recently, I was doing something that occupies a surprising amount of my time these days: using LinkedIn for lead gen.  This involves researching companies, connecting with people, and, occasionally, consuming LinkedIn.

It was in that latter capacity that I stumbled across this post, from Jonathan Stark.  I nearly spit out my coffee.

It’s funny, right?  But the thing is, it’s also true.

Seriously.  I could probably write an entire post about why telling prospects that you’re “passionate” is a bad idea, both from a positioning and a realpolitik perspective.  But that’s not what I want to talk about today.  At least, not entirely.

When I read this, an idea for a blog post snapped home in my mind.  It had been kind of rolling around, not fully formed.  But then I read this and the basic thesis struck me.

Learning to be a good employee is tantamount to learning to suck at being freelancer/business owner.

Of course, this isn’t exhaustively true.  Very basic qualities like competence, diligence, and “EQ” will serve you well anywhere you go.  But in many important ways, the instincts you develop while advancing as a corporate employee serve you absolutely terribly if you decide to go off on your own.

Let’s Start with Passion: A Good Trait for Employees

I might as well start with the subject that made the thesis click into place: passion.  As Jonathan (or, I guess, Blair Enns) points out, if you want to consult on your own paper, telling prospective clients that you’re “passionate” is… vaguely icky.

I’ll back away from the sexual overtones here, and talk instead about how I’d see this from as a business buyer.  A lot of folks talk to me about writing paid blog posts for my content agency.  So I’m imagining someone explaining that they want to write for Hit Subscribe, and saying “I’m passionate!”

There are certain things that I value in authors as the owner of this business.  They include reliability, promptness, ability to speak to a variety of personas, versatility in topics, and, above all, ability to deliver work the clients like.  Why do I value these things?  Well, all of them help the business run more smoothly.

Do you know what I don’t value?  Passion.  And, do you know why?  I mean, I’m happy for you and all, if you get excited while you do your work.  But passion is really about your feels and not my results.  And it’s also only valuable to me, as a business owner, if it drives you to do more work for the same rate.

Now, in our case at Hit Subscribe, this isn’t really a factor.  We pay per post and not based on time, so whether you burn the midnight oil or not is irrelevant to me.  But if I were an employer, your passion would be great.  It’d make you more likely to come in early and stay late for no extra money.  But when you go free agent, that’s just a race to the bottom.

Employees Optimize for Serial Employability, Which Is Actually Kinda Unrequited Codependency

Switching gears a bit, I’d like to relate a brief personal anecdote that makes me smile ruefully today.  At the time, however, it was deadly serious.

A Brief Tale of My Ruined Career

I graduated with a CS degree from Carnegie Mellon University, but right into the teeth of the dot com bubble bursting.  In 2000, companies were begging us to work for them when we graduated.  Fast forward to 2002, and I ran out of money while looking for work, and took a temporary gig at Radioshack.

By 2003, I found work as a software engineer, abruptly ending my professional crisis.  But, during the whole year of 2002, I was convinced that my career was over before it started.  It was all over.  I’d spend the rest of my life hawking cell phones to people who would crinkle their noses ever so slightly at the subtle smell of my professional failure.

Why was I so beside myself?

Because I was worried about being unemployable.  Specifically, I graduated in 2002 (actually, technically, winter of 2001) and, a year later, I had no serious job.  I had the dreaded gap in my resume.  How would I ever manage to explain this to an employer?  Why should anyone hire me when my resume showed, plain as day, that other employers had passed on me for a year straight?

There Is No Entrepreneurial Equivalent of Employability

If you’re a career employee, you know exactly what I’m talking about.  Should you ever quit your job without another job lined up, people look at you as if you’re insane.  And when you’re laid off, the first month is “funemployment,” but go too much longer than that and people start to pity you.  Whether you have money issues or not, the pressure mounts to land the next job.

This is all about the soft concept of employability.  If you were going to create an employability equation, it would probably vary inversely with the square of the time you spent not employed.  It’s almost as though all employers in the economy form a cabal of sorts and freeze you out if you don’t stay almost eternally in their collective good grace.

There is nothing like this in the entrepreneurial world.

Take a look at my LinkedIn profile, if you’d like.  I left a CIO gig and, following that, I hustled under the umbrella of DaedTech, my consulting brand.  (Hit Subscribe would follow much later.)  Do you know how many of my consulting clients ever asked me, “so, how long has it been since your last gig?”  None.

Whether explicitly or by convention, employers look at your employability — your faithfulness to the wage world — as a risk indicator.  Long periods of dormancy might indicate laziness or, contrarily, they might indicate a willingness to bail as soon as your hustle takes off.  So people looking for wage employees intuitively search for those most freaked out by the prospect of employment gaps.

Mimicking Employability Leads to Bad Entrepreneurial Decisions

The upshot here is that free agents who are newly minted from the ranks of the employed do something unfortunate.  They panic and take any clients that show up flashing money.

Now, don’t get me wrong.  For a lot of new freelancers/independents, finance plays a major factor here.  If you’re new to freelancing and burning through your savings, you’ll take on a bad client to pay the mortgage.  And, no judgment at all.  Do what you gotta do.

But this instinct survives the desperation phase, and it makes you take on work you shouldn’t.  You’ve learned a lesson from the wage world:

  1. Continuous work is best.
  2. Try to make your next gig ideal, or at least better.
  3. But if that doesn’t work after a few weeks, you’d best settle and sit down in this game of musical chairs.

So you take on a bad client.  You have a prospect call that makes you cringe, or you receive an inquiry from someone about work that isn’t really in your wheelhouse.  And you say “yes” if you have any bandwidth.  The employability concept runs deep.

Seasoned free agents learn to pass on this sort of thing, even if it creates a temporary cash flow issue.  They come to understand that taking on bad clients is very locally maximizing, occupying the time and head space that they should spend pursuing better clients.  And this tendency comes precisely from the concept of employability, where you’d never drag things out with the idea that something better is out there.  The person seeking employability would settle, take the job, and keep looking.

That goes terribly as a consultant or freelancer.

Generalizing Makes You a Great Employee and a Terrible Free Agent

Speaking of things going terribly, let’s talk about being a generalist.  I’ve talked about this subject before, so regular readers know my feelings.  Heck I’ve written two posts with “recovering generalist” in the title.

Generalizing makes you a great employee (and commodity).  But it’s generally bad business, particularly when you’re a free agent.

Think about it this way.  Let’s say you hire on with a company into a role where your initial responsibility will involve chipping away at modernizing some legacy app.  Well, sooner or later, you’ll finish modernizing that app.

What then?  Unemployment?  Well, no, of course not.  The company will figure out something else for you to do.  The more general and adaptable your skill set, the easier this figuring.

The essential proposition with employment is “you’ll work here forever, and we’ll eternally figure out more things you can help with.”  But as a free agent, this is a nonsensical proposition.  So when you carry your generalist tendencies into the world of running your own business, it goes… not great.

Employment conditions into us an utter terror of specializing and niching.  Specialists can’t possibly last at a company.  But generalists can’t easily last on their own.

Performance Evaluation: Employees Seek Good Marks, Entrepreneurs Seek Assets

I’ll offer one last point here in support of my thesis.  Specifically, let’s talk about how these two different sets of people evaluate performance.

In an employment context, the amount of value you that you add to a business is often strictly unknowable.  (With perhaps an exception for staff augmentation agencies selling things like app dev.)  Evaluation thus commonly takes on a more abstract form, borrowed heavily from our collective youth.  Bosses act as professors and grade the employee-students.

The result is that employment teaches you to optimize for good marks, so to speak.  Oh, don’t get me wrong — I understand that those good marks are vaguely tied in with money on a long enough timeline.  But you’re not thinking, “let me send out a ton of emails with my boss CCed because … profit!”  You’re thinking “let me send out a ton of emails with my boss CCed because my boss recently said that I need to improve in the ‘customer focus’ and ‘over-communicate’ categories.”

If you’re consulting or building a business, there’s obviously nothing like this.  I don’t think anyone would struggle with that point.

But where this become insidious is the employee’s instincts for how to manufacture this sort of validation.  It comes in the form of seeking platitudinal feedback from buyers or customers.  “Am I doing a good job” or “would you buy this thing I’m thinking of building?”

These questions can start interesting conversation and they can help with goodwill.  But they don’t tell you the kinds of things you really need to know. Asking someone whether they’d pay for something isn’t the same thing as sending them a bill and seeing what they do.  Doing a “good job” isn’t a guarantee of future business or even payment.

The best way I can summarize this for free agents and business owners is that you need to stop worrying about what stakeholders think, except inasmuch as that translates into actual actions that they take.  Actions matter.  Opinions?  Not so much.

Get Ready to Unlearn

I’ve covered a good bit of ground here.  And I can see the cynic reading this and saying, “wow, Erik, thanks for the newsflash that being an entrepreneur or consultant isn’t like being a wage employee.”

But the point isn’t that they’re different.  The point is how they’re different.  And, more specifically, the point is how one actively teaches you bad habits for the other.  (For fans of my takes on the corporate hierarchy and of Developer Hegemony, this cuts to the essential point of how opportunists differ from the other archetypes — opportunists are entrepreneurs that happen to be operating inside of a company.)

So if you’re eyeballing free agency, or in the process of starting it, take note.  There are landmines in your way, and they include things like calling yourself a “specializing generalist” or, as in the lead-in, declaring that you’re “passionate.”  Understand that your learning curve in this world might be more steep than you’d imagined.

Being a free agent isn’t just a question of who signs your checks and when.  It’s a fundamentally different mindset and it requires a fundamentally different set of skills.

But don’t worry.  You’ll get there.  Just make sure you’re acting like the CEO of your own little company instead of its sole employee.  And, if you don’t know how to do that yet, at least you know what you need to be learning to do.