I have weird visions of what retirement looks like.

In one version, I’m living in Key West. On the beach. I’m a juggler, busking for enough money to pay for meals, sleeping in a tent under the boardwalk, enjoying the sunsets every night.

In another version, I’m living in a lighthouse – polishing the mirror in exchange for lodging – and I spend my days painting the clouds and the sea. For decades I’ve had this vision of a huge canvas with every kind of cloud painted on it.

Yet another has me living in one of my daughter’s attics, which happens to look just like Mark Twain’s study. I sit up there and write stories and words of wisdom that are published and appreciated by…well, somebody.

Now, of course all of these are pretty ridiculous, ignoring factors like arthritis, hurricanes, GPS, the fact that I don’t paint, or the odds of any of my daughters having an attic they’re willing to let me live in.

But I should probably start working on a more realistic plan soon, right? Since I reach retirement age in a mere seventeen years. It’s amazing how much younger sixty seems the closer you get to it…

Stretched Out and Sped Up

But here’s a question for you: how can you really prepare for something that far in the future?

It’s a serious question. People who thought they had planned well for their retirement have found their pensions plundered, devalued, or simply eliminated. The state of healthcare is uncertain even a couple of years in the future, much less ten or twenty. Heck, even those people who were smart enough to take jobs that would pay off their student loans are finding out that the fine print might not have been what they thought it was.

At the same time that things are changing at a dizzying pace, we are all living longer. Much longer. The retirement age of sixty-five was predicated on the anticipation of death within about a decade. What happens when you stretch that out to two, three, four decades? Or even, as some futurists speculate, immortality?

Well, let’s leave health and career obsolescence and inadequate relationship models aside: what about just getting bored? The old life model of “learn for twenty years, work forty, do a hobby for twenty, die” doesn’t work anymore.

Luckily, another part of the speeding up of life is that the resources available for you to learn new things is also much faster. I’m not talking about learning programming, either; want to be a woodworker? Youtube videos teach you, eBay or Amazon has used tools, or there is some MakerSpace in your town with people who want to share your passion. Ditto for dance, for plumbing, for accounting, for writing, for architecture, for pretty much any career.

“But What If I’m Not Good Enough?”

sigh. If there is one thing that will contribute to the fall of civilization, I think it is the double-edged blade of fear of failure combined with anything but the best is failure. I get it, competition can be healthy – but at some point we stopped giving people credit for being their best selves, and instead created an arbitrary (and usually unrealistic) standard to measure people by.

Along the way career counselors ignored factors like luck, privilege, home environment, and other factors to create the myth of the self-made man (and yes, it’s usually the man). “Pulling yourself up by your bootstraps” conveniently ignores the question: where did you get those bootstraps to begin with? Were they given? Stolen? Are they your father’s bootstraps?

Instead, let’s adopt some different principles.

1. Failure teaches. Within my work in the aerial arts, the scariest kind of performer is the one who has never had anything go wrong, because they don’t know how they will react when something does. Every time we fail, we have learned something; we can use that information for the second principle:
2. Iteration is Sexy. Change is going to happen, one way or another. Time takes its toll, etc. What we do is harness the power of change to try and influence it towards being ever-so-slightly better. Sometimes it works, and we say “Success!” And sometimes it doesn’t, and we go back to the first principle.
3. Enough is better than more. This is a big one. Brené Brown has talked about this extensively: “We don’t need to hustle for our worthiness.” Learning to accept that we are ok even with what we perceive as limitations is essential to a sustained life; the word for unrestrained growth, after all, is cancer.

The answer to the question “What if I’m not good enough?” is some variation of “Good enough for who?” In a world where no one knows what occupation will be next to be replaced by a robot, it doesn’t really matter how good you are – what matters is what you bring to the table.

Will other people judge you? Certainly. Your waistline, your bank account, your likes, your children (or car), your hairline or whatever.

…we begin to sense that we may be living on the reflections of ourselves in the eyes of others. Drowning our sincerity and integrity in the applause of others, applause for performing our role, for keeping our poses…we develop an internal sense of self as the decision maker and the person responsible for the choices of life. We have finally worked free of the concepts Authority and Right Career. We are the Authority and we have options.
– Robert Jay Ginn

It’s not about learning to play the game, or refusing to play the game – it’s about creating your own game. And, barring unforeseen accidents, it’s going to be a pretty long game – so don’t you think it’s time to start figuring out what you want the rules to be?