The path to success is not well defined

posted by Jeff | Friday, October 11, 2019, 4:00 PM | comments: 0

I read an interesting career advice essay today that made me realize what I already know, but rarely define out loud: Success, and the path to it, are not easily defined. He was using it with the lens of west coast technology companies and startups, which is not at all representative of most everything else, but still, that itself shows how squishy these definitions are.

For me, I suppose my definition looked like this: Find a field that you are interested in, get solid, white collar jobs, make enough money to retire and own a modest house. That was the basic starting point. Then it got more complicated over time... longevity became increasingly unlikely, especially with economic volatility and tech companies having wildly unpredictable outcomes. The gig economy became lucrative and its lack of long-term commitment had a certain feeling of freedom even with the uncertainty. Then for the better part of the last decade, I've wandered between pure technologist and manager, so the professional accomplishment definition of success has been fluid too. And what does winning look like? A certain salary? Title? I don't know.

If that weren't enough, there's a completely different dimension if you own your own business. I've had a business for two decades, that I started by accident, and outside of the online ad boom 15 years ago, it's mostly been a hobby. I've not deliberately started anything for the purpose of my own sustainment. With all of the experience I've gained in companies from tiny to gigantic, shouldn't I be qualified to do that, and do it well?

This sounds pretty midlife crisis, which is appropriate because, well, that's where I am. At the same time, the late start to parenthood, and starting over with a second marriage, I have the life priorities of someone in their 20's with the life experience of someone with two extra decades. Given what's important to me, defining success can still have a basic starting point, it's just different now. My goal is to be able to provide for my child and my wife, and make sure the latter is well taken care of in a decade when we're empty nesters, even if something were to happen to me. I think as we get older, we transition success from "more" to "enough."

So that's well and good, a solid base to shoot for, but where the anxiety starts to creep in is looking at how we get there. I spent money like an asshole in my 20's, running a negative cash flow for a number of years, and while I had that under control by 30, I didn't really reverse it until later. I'm behind on saving, and suspect that Social Security will be a fantasy when I retire. I've only got half of what I should saved if you don't count home equity (and I sure don't). If financial planning is a measuring stick for success, I sure don't feel like I'm doing it right.

Success for me, today, has more to do with my little family unit. It was never about keeping up with the Jonses. It's always been about personal satisfaction though. I have to combine it with what is practical now, and those are sometimes hard to reconcile.

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