“I don’t know.”
As someone who struggles to make decisions, I’ve uttered that phrase more than anyone should utter any phrase.
But in 2013, those three little words transformed from a common refrain to a crippling state of mind.
At the time, I was working as a copywriter for an apparel website in Washington, DC. I was miserable. Like, “Where did it all go wrong?” miserable.
The only thing getting me through the days was the thought of an escape plan I’d hatched years before:
Quitting my job, moving across the country and working as a caddie at Bandon Dunes Golf Resort in Oregon.
On the surface, the plan was simple:
I’d spend my days walking alongside interesting people on some of the world’s greatest golf courses (and getting paid for it), my nights writing about my experiences and absolutely none of my time missing my cubicle.
I loved golf, I loved to write and this was a way to blend both passions.
This could be my “Walden” — with cable and Wi-Fi, of course.
But on a deeper level, it was much more complex.
I was 35 years old and stuck, my life progressing too slowly as life passed me by too quickly — despite the fact I had everything going for me.
I had a family that was always there for me, and a beautiful girl who wanted to spend the rest of her life with me.
I had goals, I had dreams, and beneath my self-loathing and self-doubt, I had the belief I could achieve every last one of them.
Yet there I stood, stuck in place, unable to move.
I had tried breaking free of this inertia before, dabbling in different career fields, exploring different cities and bravely (stupidly?) living with strangers in shared houses I’d found on Craigslist.
But the biggest risks I’d taken — the ones that were in harmony with what I wanted my life to be about — had resulted in my biggest failures.
So like a kid who won’t go near a hot stove after burning his hand, I constructed an existence built around avoidance.
My goal was to maximize security while minimizing exposure to my insecurities.
The dream of going to Bandon actually dated back to 2006, when my father first told me about the resort. I was immediately enthralled. The place seemed to have an almost mystical quality to it, set on the southwestern coast of Oregon, with the Pacific as its impossibly blue backdrop.
That it was home to four of America’s best golf courses only added to its aura.
In 2008, I took a scouting trip there in hopes of convincing myself to make the move.
Those hopes were dead on arrival. From the moment I got off the plane, I was so overwhelmed and so out of my depth, you’d have thought I was trying to relocate to Saturn.
I boarded my return flight convinced I’d never be capable of returning.
But over the next few years, the dream kept coming up. And that had to mean something, right?
Things don’t repeatedly resurface unless there’s a lesson to be learned.
I began wondering if these thoughts were my version of the voice from the movie, “Field of Dreams.”
If they were, they sadly didn’t speak cryptic phrases in soothing whispers. Nor did they offer any actionable clarity.
But they reached a fever pitch in spring 2013, prior to the start of the resort’s high season. They even convinced me to take another reconnaissance mission to Oregon.
And this time, I remained upright.
I visited the resort, met with my potential supervisors and found a place to live.
This was as far into the plan as I’d ever made it.
Now, all that was left was to actually go through with it.
Sitting atop my tipping point, gazing over my divergent paths, I didn’t know what to do.
Should I stay in my safe space, pathetic yet protected?
Or should I risk falling on my face for the chance at something more?
While I’d never had an epiphany, I still held out hope I’d get one.
Maybe I could reenact one of those Hollywood montages in which I walked along the surf, looking out at the ocean, as a song like, “Waiting For My Real Life to Begin” played over my distant stares.
But as poetic as that scenario would’ve been, my “Aha!” moment played out in far less dramatic fashion.
And in hindsight, I’m grateful it did.
My moment occurred in a nondescript office, in a nondescript chair, as I eyeballed the ticking clock in the corner. The din of DC traffic buzzed outside the window, when my therapist asked me the following question:
“Which will you regret more — doing it, or not doing it?”
For seven years, I’d pinballed between pros and cons, examining this Oregon experiment from every angle.
There were logistics to consider, and fears to assess, and finances to calculate.
One minute I was in; the next I was in the fetal position.
It was too much for me to handle.
But this question cut through everything.
It cut through my worries of leaving my girlfriend behind; of quitting my job in this unemployed world; of integrating into a new social/work environment; of adjusting to a part of the country where it’s 55 degrees in June and NFL games start at 10 a.m.
Suddenly, this overwhelming conundrum had been reduced to something more manageable, which allowed me to focus on the perspective that was most important.
There’s an anonymous quote circling the internet that gives the definition of hell as follows:
“On your last day on Earth, the person you became meets the person you could have become.”
That disconnect, that chasm between those two characters?
It’s all the decisions you’d handle differently, the moments you’d do over, the risks you would’ve taken.
By asking myself, “Which will I regret more?” I (metaphorically) transported myself to my last day on Earth.
I was able to look back with the clarity of hindsight and consider what type of experiences I wanted to have, what type of life I wanted to lead and how I wanted to feel about it when it was over.
I was able to see how to best minimize, if not eliminate, regret.
And so it was that I loaded up my SUV and made the 46-hour, 2,952-mile journey to Bandon Dunes.
Though I was only on the Oregon coast for a single high season, I learned more and grew more in those four months than I have in anything else I’ve done.
It’s been four years since my final loop, but in that time, I’ve gotten married (to that same beautiful girlfriend), become a homeowner and thrived in a job that doesn’t make me resent my alarm clock for going off.
You could say my life now resembles that of an actual adult. Almost.
And I wouldn’t have been able to do any of that without asking the question, “Which will I regret more?”
Even better, I haven’t stopped asking it, because it helps me make every kind of decision, from what my next career move should be to what wide receiver I should start in fantasy football.
Oftentimes, it’s the impetus I need to take a chance.
Other times, it helps me see the reward isn’t worth the risk.
Either way, it guarantees that, in everything I do, I come out the other side in a better place. And I can always live with the results.
The fear of the unknown and the fear of sabotaging the status quo are too often what keep people from going where they want to go, doing what they want to do and being who they want to be.
But the next time you’re contemplating a risk, ask yourself, “Which will I regret more — taking it, or not taking it?”
Then play out in your mind’s eye the worst-case scenarios for each decision.
Whichever one will cause you the least amount of heartache on your last day on Earth, that’s your answer.
Eliminate your weaknesses and become a bolder risk-taker, decision-maker and communicator with help from my 5-step strategic video.
Originally published at The Mission.