Want Adventure AND Security? Just Change Your Timeline

Like most American students, I didn’t take a gap year between high school and college, and I took all of a one-week break between college graduation and the start of my career. (Seriously, why don’t we learn from other countries and give young people time to explore a little before diving into a career path, a mortgage and all the rest? Or at least to work and save up money to avoid all that college loan debt?)

I dove headfirst into adult life, eager to keep finding new outlets for my gold star-seeking ambition. And while that approach has undoubtedly served me well at work (and in my paycheck), it has come at a cost: I felt for years that I’d missed the boat on living a life of adventure, or at least living an adventure interlude.

Because adventure is something only young people pursue, right?

Then we moved to a ski town, and we were suddenly surrounded by all of these people of all ages following their stoke, piecing together a life dedicated to their outdoor passions. People working odd jobs to pay the rent, or bumping chairs at a ski resort in exchange for meager pay but unlimited off-duty skiing. People who started their own small (okay, micro) businesses to give them flexibility to take the day off when the powder comes, or to go on a two-week climbing trip when they feel like it. We are surrounded by people making it work.

The only problem with this model: it often comes at the expense of their current and future financial security. 

I can’t say that it never happens, but I’m guessing that most of the people earning minimum wage as lifties (people operating the chair lifts, for you non-skiers) aren’t maxing out their 401(k)s or putting themselves on the fast-track to financial independence.

Instead, many of the young ski bums talk about having to face reality and “get a real job” one day. Or the older people piecing things together forego a lot of security to prioritize outdoors time or travel. Either way, it’s not ideal, at least from a financial perspective. But there’s another path… and that path comes with a big nudge for those already pursuing financial independence.

The Dirtbag Approach: Adventure First

Psst. “Dirtbag” is a term of endearment in outdoorsy places. Often said with a twinge of envy of the young folks putting adventure first. As always, a hat tip to the Elephant Eaters for coining the perfect term, Dirtbag Millionaires. But today we’re talking about the non-millionaire, just-scraping-by variety.

Let’s say you’re right out of high school or college, and you know you need to get a job at some point, but you just have this overwhelming urge to do something different with your life, this powerful desire to follow your passion. (I’m guessing that feeling sounds pretty familiar to a lot of us pursuing financial independence.)

So instead of getting a job right away, you decide to spend a year ski bumming, maybe waiting tables or bumping chairs to make a few bucks, but devoting as much time as you can to skiing. Your life timeline might look like this:

That big chunk of adventure time must be incredible fun — as an observer, it sure looks like it, but I can’t speak from direct experience. Of course, the problem comes when it’s time to start working.

Now, when you start working, you have no retirement savings, and you are getting a late start. Those early years, when compounding will push your savings to stratospheric levels — those years are gone. You can still save like crazy, and you can make up ground, but there’s no getting those early 20s years back when it comes to retirement savings.

Depending how long an adventure interlude you took, you might also be looking at working later into life, working beyond age 65. When you finally get to that retirement, you’ll truly need the break.

The Security-Loving Approach: Work First

Now let’s say you’re just out of high school or college, you have that desire to do something cool and different, but you just can’t kick the thought that you need to get a job ASAP. You start working, and a few years in, you feel like you missed your chance to be a ski bum or a dirtbag climber, or to backpack around the world.

Have you missed your chance to live a life of adventure?

Absolutely not! In fact, you’ve chosen the way that will let you devote just as much time to adventure — most likely more time, in fact — but without sacrificing your future financial security or retirement. Here’s what your timeline might look like:

All you’ve done is flip the order, putting work first and adventure second, but in doing so, you’ve set yourself up for a fantastic life: more adventure total, and no financial worry along the way.

Now when you’re not working, your investments are growing, instead of collecting tumbleweeds. And when you reach “retirement” age, your adventure may very well continue, because you haven’t exhausted yourself hustling well into your 60s.

The Side-By-Side Comparison

Obviously if you’re pursuing a passion that requires you to be in peak physical condition, nothing replaces those early 20s years. And I would never try to convince you to wait to qualify for the Olympics until you’re in your 40s. But if you are just eager to travel or adventure young because you’re afraid you won’t have the chance to do it later, consider this side-by-side comparison:

With option A, you get the thrill of adventure when you’re young. Maybe it’s traveling when you don’t mind sharing a hostel bunk room with 10 other loud people. Or thru-hiking the Appalachian Trail when you’re young enough that you don’t need rest days. Those are great reasons to go the dirtbag way.

But with option B, what you lose in peak physical ability, you more than make up for with less time worked and more time to adventure, assuming you pursue early retirement of one form or another.

Which would you choose?

Don’t Just Aim for Security

If you’re reading this, there’s a good chance you’re already on the path to early retirement, and you are eagerly working toward your adventure period, however you define it. That’s awesome!

When you picture what you’re aiming for, what images come to mind? Are you picturing predominantly things that represent financial security? Or are you mostly picturing things you wish you’d done when you were younger, but which you can’t wait to do once you retire early? If it’s more the former, it just might be time to expand your vision. Because we can all use this reminder from time to time:

Money is just a tool. It can make your life better, if you let it, or it can change exactly nothing. 

Hitting FI didn’t change anything for us. Paying off our house didn’t really either. What will change our lives is taking action to pursue that life of adventure that we used to worry we’d missed out on.

Define Your Adventure!

Think back to when you were in your early 20s. What did you wish you could be doing then? What did you dream of in your most audacious moments?

Now reflect on what you dream about these days. Is your current dream a lot like what you wanted to do when you were younger, or is it markedly different? If it’s different, why do you think that is? What would it take to rekindle one of your dreams from the past?

We don’t have to push ourselves out of our comfort zone all the time, but pushing ourselves sometimes — including in big ways — is critical to make sure our world doesn’t get a whole lot smaller when we retire.

So today I’m challenging you to define your adventure: What is the grand SOMETHING that scares you a little or at least feels way outside your comfort zone, that you thought you’d missed the chance to do, that you’ll add into your post-work life vision? And then how will you make it a reality?

Twenty-something you will be so proud.

Share share share!

You know we want to hear what adventures you guys are thinking about, so let’s chat about them in the comments. And beyond adventures, who in your life could benefit from thinking through the timeline question, frontloading their earnings instead of the other way around?