Rented Headspace: Your Past, Your Future, and How to Build a Bridge Between The Two

Something happens when you decide to step out your front door and go on some great journey the likes of which you’ve never been on before.

To describe it would be to claim to know all the ways of the Universe: Its inner workings, its greatest mysteries. Even its beginning and end.

But when you set off on your way in a direction of your own choosing – and it is indeed the very course your life ought to take – it is as if you are shaking hands with the very same power that hung the stars in the night sky.

You are making a pact with the Creator, Mother Nature, Father Time.

Because in the moment when you realize no one is coming to save you or do any of the work you alone are best equipped to do, you are not just taking a step in some arbitrary direction.

You are beginning a journey on which no one in all of human history has ever embarked. And your journey only ends when you meet the person who represents the fullest potential that you as an individual can achieve.

Raindrops and Bus Stops

When I first had the idea to embark on my bike ride, it felt similar to how it feels when a drop of rain hits you on your nose.

Sure, you may have seen a few clouds gathering overhead. But until that first drop wets your skin, you’re not totally sure it’s going to rain.

“It’ll pass over top of me,” you might think. “Nothing to worry about. Stay the course and those clouds will blow out of sight in no time.”

Then it’s business as usual. Just another sunny day on the long road of life. The bills are paid. There’s food on the table. You have a warm bed and can take a hot shower whenever you wish.

But then the second rain drop splashes on your cheek.

“Oh, nothing to fret about,” your internal voice declares, somewhat less enthusiastically than before. “If anything it’ll just be a light sprinkle. No need to break out the umbrella.”

And off you scamper down the sidewalk, subconsciously noting a bus stop just ahead that you could duck under if need be.

The third, fourth, and fifth drops hit you. You pick up the pace towards the bus stop.

But upon reaching cover, you find the bus stop is already filled with people all crammed beneath the tiny awning, their faces buried in their phones or expectantly glancing down the road for an approaching bus.

The skies open, and rain begins to pour down on your unprotected head.

The bus does approach, the people jostle one another as they squeeze through the door. And then, upon finding their seats, they once again bury their heads in their phones.

And you are left standing in the rain because the bus is going in the opposite direction from your destination.

Dreams and Reality

That is something like how it feels when you first set off down the long, lonely road towards that “best life” everyone is telling you to go out and get.

It’s ironic, though, that the same people telling you to “go for it” are the ones on the bus scrolling through their phones trying to find anything they can to distract them from the kind of lives they could be living.

The point here is that dreams, while undoubtedly worth chasing after, are the ultimate unreliable narrators in life.

They tempt you with brochures showcasing streets of gold and fields of plentiful harvests.

When in all actuality they will lead you down overgrown paths that haven’t been trodden in years. Not since the last sorry sack – or should I say brave soul? – determined it was his duty to walk that formidable trail towards his own fullest potential.

Now, to be clear, a dream will always be worth chasing, even if it leads you down a completely different path than the one you first intended to walk.

Having a vision for your own future is far better than simply “winging it” through life. It will seem strange to most, utterly baffling to a few, and potentially even downright insane to the people closest to you.

None of those are good reasons not to set off on your own unique journey, though.

In fact, other people’s doubts or questions about your sanity may just be the very catalysts for the change you seek to make around you.

But you simply won’t know until you actually begin taking strides towards making them.

Which brings me back to what it was like when I first decided to set out to ride a bicycle across North America.

What Lives Between Your Ears

I was lying awake on the hard bed I’d made for the dry cabin I was renting in Fairbanks during the winter of 2025.

I knew I wanted to take off on my ride that spring. But that’s about all I knew.

And then an image crept up in my mind and lodged itself there, taking up residence, ironically, right next door to another tenant in my brain named Self-Doubt.

Now, Self-Doubt had been living inside my head for as long as I can remember. But this new tenant didn’t take kindly to Self-Doubt playing his loud music late at night and keeping me, the Landlord, awake past my bedtime.

The new tenant, I quickly learned, was named Self-Belief. And he looked a lot like me, only he had an ear-to-ear grin on his face and was lifting my bicycle above his head in front of the pillar marking the southernmost point of the contiguous United States in Key West, Florida.

I have yet to ask Self-Belief why he decided to indefinitely strike this very specific – and likely quite tiring – pose. But as long as he was able to keep the music down and let me get my beauty rest, I didn’t much care.

And so I allowed Self-Belief to continue his residency inside my head, free of charge, as long as he could stand to continue hoisting my bike above his head.

The Thing You Can't Stand to Lose

So where am I going with all this talk of raindrops and ambiguous ideas rolling around inside my brain?

Well, put succinctly, I am going exactly where I intended to go, albeit via a very different route than the one my much younger self envisioned.

And therein lies the point of this article: If you want to get to wherever it is you intend to go in life, you first have to determine in what direction you should take the first step.

I knew that I had to use the majority of the year 2025 riding a bicycle across the US and Canada. How did I know that? Because it was the very thing I simply couldn’t get out of my head.

As hard as I tried, as much as I pictured another course of action – be it a job opportunity, a career move, or a physical move to a new location – all those thoughts kept leading me back to my bike ride.

If I got a whiff of some new idea that would force me to have to sacrifice the ride, my heart sank.

If a thought popped up that tempted me to give up my ride to earn more money and take another year to prepare, that Self-Belief chap I talked about earlier would knock on my door and tell me to quit putting off the very thing I knew I needed to do.

But mostly I knew I needed to set off on my journey because it was the answer to one question in particular that kept creeping back up inside me.

Big and Small

That all-important question: What decision would lead to a bigger life?

My friend, that is the question you and I ought to ask ourselves when faced with any decision, big or small:

• Do I quit my job and go all-in on my profitable side hustle?

• Do I ask my girlfriend to marry me?

• Do I move to a new state and pursue a totally different opportunity from the stable one I have now?

  
  

To find your answer to any one or all of those questions, just ask yourself: What decision would lead to a bigger life than the one I’m living now?

Hint: It’s probably the scarier one that fills you with more questions than answers.

Because life isn’t about having all the answers. Life is about asking better questions.

Rewriting the Script

I’ve heard people say that if they were to return to their past selves, they wouldn’t change the decisions that got them where they are at present.

I can appreciate the sentiment and the “no regrets” mentality. But I respectfully disagree with it.

I’ve found that revisiting my past decisions and reversing the course I ended up taking – at least within my own head – helps me better come to grips with what I ought to do in the future.

For example, I mentioned in a previous post that I studied creative writing and classical studies at a university known for its STEM programs.

In the decade after graduating, I’ve determined that I would rather have had my late teenage self follow a much different path into my early adulthood.

The biggest mistake I made at the end of my high school years was getting so caught up in the “College or Bust” mentality.

All my friends were doing it. And I was an honor’s student after all. High school students with good grades went straight to college. Period. No questions asked.

But that’s the lesson here: I didn’t even bother asking myself what I wanted, regardless of what anyone else might think of it.

I didn’t know it at the time, but there is a whole host of options I had following my high school graduation.

I could have gotten a well-paying day job learning a valuable trade while I took community college classes part-time. By following that route, I would have knocked out some or all of my general education college credits before committing to a Bachelor’s program.

And in so doing, I would have gotten a better sense of my own interests before taking the next life-altering step towards my professional aspirations.

Looking back now, if I’d gone that route, I would have saved a ton of money. I would have developed valuable skills that would have served me well in virtually any work environment.

And I would have entered college with a plan for my own future rather than simply stumbling through what people told me was the next right move for me.

Instead of pointing to a map and choosing a college essentially at random, I would have likely headed west to Montana, Wyoming, or the Pacific Northwest and studied forestry or some other field in natural resources with a minor in English.

That way, I’d actually, y’know, have something to write about.

Train Wrecks and Small Steps

I’m well aware that the act of writing out all these possibilities for one’s younger self doesn’t change anything about how things will turn out in reality.

But the act of painting a word picture of your own alternate past life can help you feel out the next right step you should take in the present.

And it doesn’t require you to make any big life-altering commitments from the get-go.

Because the further you can get from seeing your life as a short series of big irreversible commitments and instead look at it as a long line of small decisions that can be swapped out and moved around as you wish, the more peace-filled your life will be.

Why? Well, because you’re less likely to go all-in on a decision that ultimately doesn’t pan out like you thought it would. You will still have some chips to play. And you’ll be more cautious in your risk-taking.

You’ll still take risks, for sure; you’ll get nowhere in life if you don’t.

But those risks won’t lead you to a free person’s equivalent of a life sentence. You won’t be shackled by a pair of golden handcuffs that you latched onto your own wrists.

You may still be sidelined for a short time in order to fix a mistake you made, but that’s just the price of admission to the kind of meaningful life you will be working to build.

If you get somewhat off-track, no big deal. Get around the roadblock and keep on keepin’ on.

That approach is far better than you careening off a cliff because you were too stubborn to change direction when you knew you should have done so.

Your Next Right Move, Defined

Let’s end with a short and sweet exercise you can do right where you’re sitting.

Whip out a pen and piece of paper. Draw a line down the middle of the paper. On the left side, describe where you’re at right now in 2-3 words per line.

• What’s your job?

• Where do you live?

• What do you drive?

• What do you do when you’re not working or sleeping?

• What are you reading/watching/listening to?

• How much money do you make?

• Who are the most important people in your life?

• What beliefs do you hold that are the most meaningful to you?

Once you have a half-page or more, stop writing. Look back over what your life looks like from an outsider’s perspective.

Now, make marks next to the aspects of your existence that you’re happy with, dissatisfied about, and/or want to change.

After you’ve taken a good look at how things are, move over to the right side of the page and write out how you want things to be:

• What’s your dream job?

• Where do you want to live?

• What do you wish you could drive?

• How might you better spend your free time?

• What are you curious about (i.e., What do you find yourself daydreaming about?)

• How much money do you want to make per year or per hour?

• What do you want your relationships with the people closest to you to be like?

• What questions do you have regarding your own beliefs or values?

Admittedly, this side of the page is likely to take you far longer to think about than the other side.

That’s fine. Take all the time you need. Go for a walk if that helps you think.

But once you’re finished, know that you’ve now painted a clear picture of what your life looks like at present and what you want all components of your life to look like in the future.

That is a huge step. You’ll probably get a tremendous night’s sleep once you’re done.

And if you’re having trouble filling out the right side of the page, put it in a drawer and step away from it altogether.

But don’t abandon it. Take time to ask yourself two questions:

• What does a “bigger life” mean to me?

• What decisions will I be happy I made one, five, ten, or even 30-50 years from now?

  
  

Stew over those thoughts for as long as necessary, then return to your paper and finish the exercise.

And know that your future, your happiness, your sense of meaning and purpose are all wrapped up in this. So it’s not going to just “come together” in an afternoon.

You should challenge yourself to revisit this document regularly. Every year, quarter, month, or week. Because goals should change.

Final Thoughts

We’ll continue on this thread in the next article.

For now, just remember, the next thing you ought to do is on the other side of discomfort. It will fill you with questions. Doubts will flood your head every time you think about it.

But none of those are viable reasons why you shouldn’t set off down the path anyway.

And if you’re wondering, no, you don’t need anything besides what you already have.

There’s no special course, coach, or magical tool you need to get started. All you need is a clear picture of where you are and where you intend to go.

Oh, and just a little bit of phlegm. That’s important, too.

We’ll go into what I’m talking about in the next article.