I am getting old and theoretically that means I’ve gained a little wisdom along the way.  (I think sometimes I’ve just found new ways to be ignorant and foolish, but, ya know.) And this is something I think about often: should I have pursued my dreams right away or was I better off taking the more traditional path initially?

I spent twenty years on a very traditional path:  I went to college, got a job with a decent company doing something interesting but not amazing, and worked my way up the ladder.

When I look at the six-figures in student loan debt that I took on  (I paid for my MBA myself), it seems like a ridiculous detour from the path that was more true to who I am.

But…

I’ve realized something recently.  That traditional path, if you can navigate it, is a very straight-forward path to financial comfort.

I know a lot of people who don’t think it is.  But, I swear to you, if you tick the right boxes, it is.

What are those boxes?

• A good degree (that means four years at a school with a local or national reputation and you having a good enough GPA to impress employers)
• Sufficient social skills (this means being able to work with others.   You don’t have to be fantastic at it and beloved by all, but you have to be socially adept enough to communicate with others and, especially, get along with your boss.)
• Hard work (you have to be willing to put work first and make the sacrifices that requires.  Long hours.  Assignments you don’t want but are needed.  Tolerating people you don’t like.  Being loyal to your boss or department. Getting your shit done on time and to a sufficient standard.)
• A large company (you need to work for a company that has deep enough pockets and/or enough levels within the company for you to be developed and promoted upward)

Yeah, sure.  Sometimes life sucks and people get laid off or companies go under, but those people who can tick all four of the boxes above?  They land on their feet at the next company.  Or they are the absolute last person to be let go and the one still getting bonuses when everyone else is under a hiring freeze.

Even if you aren’t perfect at ticking those boxes–my social skills are sometimes in doubt.  (I don’t tolerate fools or assholes well.  And if I have to work for or with one, it can be ugly.)–you can still do very well in a traditional corporate environment.

It’s just an endurance race.  It’s showing up day after day for year after year, busting your ass, and fitting yourself into a fairly tight mold of accepted behavior. Do it well and you will be financially rewarded for it.

That simple. (And that hard.)

On the other side is the entrepreneurial path where you strike off on your own.  My dad followed that path.  He wasn’t made to be an employee and with his illness he needed flexibility in terms of hours and requirements.

He did well enough at it.  Not nearly as well financially as he could’ve if he’d been able to take the traditional path.  But he kept his family fed and housed.  He worked his ass off to do it and got to be true to himself, but it wasn’t an easier path by any means.

I think sometimes the mistake people make when they think about pursuing their dreams is they fail to see that the key to success in either path is working your ass off.  And that most people who pursue their dreams fail.

There’s a lot of magic thinking when it comes to pursuing your dreams.  It’s easy to think that as long as you decide to do it life will just magically work out.  But that’s not the case.

And that’s probably why the path I took was the best one for me at the time.  Because it was structured.  I signed up for classes and I had to attend them and pass the tests.  If I didn’t, I failed.  When I went to work, I had to show up every day and turn my work in when it was due and it needed to be a certain level of quality.

And what it let me do was build a ramp that I’ve now launched off of.  I have savings I would’ve never had at 18.  And work experience.  And things to fall back on.  That degree.  The people who worked with me for fifteen years.

If I’d pursued my dreams early and failed I would’ve had a string of retail jobs and temp work behind me and nothing to show for it.  I would’ve been essentially starting off from minimum wage with no easy way to move up because our society is largely built to develop people in their early 20’s.

We each have to make our own choice and I think there is the risk of deferring your dream until it disappears.  But I know too many people in their 20’s right now who are just sitting around waiting for the perfect opportunity or for their dreams to come true when they’d probably be a helluva lot better off just sucking it up, getting that corporate job, and working their way up the ladder for five to ten years.