Working Man's Lament

There is a bit of “grass is always greener” going on in today’s post, I’ll warn you.  Of course, for someone who believes in balance and paradox, this is perhaps not surprising.  In any given situation where you’re trying to decide “which one is better?”, the answer is almost always: both.  Everything in life has both advantages and disadvantages, so any given binary choice is going to have you weighing pros and cons.  If you’re lucky, it’s easy to see which side outweighs the other.  Generally, you’re not lucky.

For instance, I went to college in two different spurts, with a gap of about 3 years in between.  What I usually tell people by way of explanation of this is that I dropped out of college, because college sucked, and went to work in the real world.  Then I went back to college because the real world sucked even more.  But of course the truth is that both sucked.  And both were awesome.  Just differently, and in different ways, and at different times.  The first time I went to college, I wasn’t prepared to appreciate how cool college can be.  Having to hold down a real job certainly made me appreciate that a lot more.  On the other hand, the first time I had to hold down a real job, I definitely wasn’t prepared to appreciate the freedom in it, the satisfaction that comes with responsibility.  After 3 more years of college, I was much better prepared.

Now I’m going to back to full-time work after a six week sabbatical.  I’ll be honest: I’m having a bit of trouble adjusting.  I’ve been working full-time for a lot of years now—decades, in fact—and I never thought that I’d be interested in retirement.  I always figured I’d be that guy that worked so long he was retired forcibly.  Now, though ... now I think I see the attraction.

My working life has had its interruptions too.  I spent 3 years in between college and college (as I mention above) working on jobs from furnace cleaer up to C programmer.  Then, while I was in school (the second time), I went back to part-time work, but eventually fell in with some guys who made me a business partner.  Which worked for a while, until it didn’t.

After I graduated, I felt ready to take the step of starting my own business.  I wasn’t too keen on lots of aspects of it (I had seen first-hand the effects of the stress on my partners), but I was also ready to be in charge of my own business fate for a change.  I ran my own company for 14 years, with anywhere from zero to 15 employees (or subcontractors), most of whom were (naturally enough) other programmers, but also project managers, bookkeepers, graphics artists, sys admins, salesmen, and office handymen.  I met The Mother while running my own business.  I hired nearly every one of my friends at one point or other (including The Mother, who was our bookkeeper and office manager for many moons), or at least put them on the Board of Directors.  Our biggest sales year was three-quarters of a million dollars, which doesn’t seem like much to many of the business folks I know, but, for a company that never accepted a dime of venture capital, it was plenty impressive to us.

Then I went back to working for other folks.  My current job is the second I’ve had since those days.  And, right now, I won’t lie: I’m starting to miss the freedom I had when I ran my own shop.  Constantly working for someone else can sometimes make you feel like you’re working hard to make other people rich.  Plus it’s twice as frustrating when they won’t even listen to you on how to get rich.

But of course being the boss was no picnic either.  Feeling that responsibility for everyone’s livelihood is pretty scary.  There’s the simultaneous pressure to do things yourself to make sure they get done right, and the pressure to teach other people how to do things so there’s a backup, and the pressure to learn how to delegate simply to keep your sanity intact.  There’s never anyone to go to to ask what to do next: everyone comes to you and expects you to have that answer.  You work harder than everyone else, you put in longer hours, and you often pay yourself less (at least I did).  Moreover, you expect more from yourself than you do from everyone else, and everyone else returns the favor by expecting more from you too.  It can be very stressful, which impacts not only your mental health but your physical health as well.

And, then again, there are certainly a lot of upsides.  I don’t mind failing.  What I can’t stand is being forced to fail.  When you work for someone else, particularly in the world of publicly-owned corporations, you end up doing a lot of things you know are not going to work.  You tell people they’re not going to work.  You send emails and hold meetings and write reports explaining that they’re not going to work.  Then your boss makes you do them anyway.^*  Then they don’t work.  And what satisfaction is it to say “I told you so” when the answer is “yep, you were right; now go clean up the mess.”  At least when you work for yourself, your mistakes are honest, your own, and you can do your damnedest to make sure you only ever make them once.  Not that you always succeed at that, of course.  But then, if you fail, you have only yourself to blame.  And I’ve always felt that that was cleaner, somehow.  I personally never got hung up blaming myself.  I give myself permission to make mistakes.  But when I have to blame someone else because there was nothing I could do about it, that feeling of helplessness makes me a little crazy.

So neither position—being the boss or being the worker bee—is perfect.  They both have their good days and bad days.  Perhaps one day I’ll go back to running my own business.  And perhaps, after that, I’ll go back to working for someone else again.  No reason I have to stick with only one or the other the rest of my life.  I suppose I’ll probably complain either way, some days.  But I also try to look at the bright side, whenever I can.  Right now, I’m working for a company owned by a company owned by another company.  I have five levels of bosses from three different companies, and that’s just counting the ones who are in the same building as I am.  There’s more floating around in other buildings, in other cities.  But, you know what?  They’re in charge.  All the responsibility and all the stress is on them.  And I’m happy enough with that.

For now.


* This is not to imply anything negative about my boss, who is an awesome guy and generally doesn’t do that sort of thing to me.  But sometimes these types of things just come down from above.