Photo by Josh Hild on Unsplash

The Jaw-Dropping Power of Betting On Yourself

Get scared. Then, do it again. And again.

John Gorman
Feb 21 · 9 min read

I remember the first time I felt truly alone. I mean unequivocally, unconditionally alone. December 29, 2010. I had pulled into an unassuming, cash-only inn somewhere near Paul’s Valley, Oklahoma — the type of slumbering town you’d forget about … even if you lived there.

In the week prior, I’d said goodbye to everyone I’d ever known. Every friend and family member who ever meant a damn. I jettisoned every possession that didn’t fit in my silver 2009 Hyundai Sonata — every end-table, every childhood keepsake, everything other than my cat and the $750 from my latest paycheck — and left the world and my childhood home behind.

Goodbye, Buffalo. Hello, Austin. I watched the snow-cover that marked every winter for 28 winters dissipate into the past, and there I was, in total darkness, at some undefined coordinate between home, nowhere, sanity and my future. I’ll never forget the cool caress of the unseasonably warm wind. It felt like I had ascended into heaven.

I turned on ESPN. I was exhausted, but I could not sleep. This was where it hit me: I was now alone. Officially, purely, finally in virgin territory — a wilderness far from home. I was a pioneer destined for wherever I chose.

I’d willingly uprooted my entire existence … just because I could. Everything I knew, everything I was, everyone I’d grown up and old with, were now somewhere else. I’ve only been back but once.

The old life, the old haunts, the old people and places and things I held dear — they’re growing up, growing old, moving on and moving out. They got new homes of their own and new jobs and new friends and new families.

Their lives are different; their lives have changed. I travelled 3,000 miles to change without them.


I remember the second time I felt truly alone. On the evening of September 17, 2012, I was a beaten-down 29-year-old college graduate who walked outside the shiny glass exterior of one of the largest companies in the world to a maroon-coloured 2011 Jeep Liberty. I had nowhere else to go.

Earlier that morning, I’d walked inside the shiny glass exterior of one of the largest companies in the world to start my new career as a writer. I’d never been paid to write anything before.

The 2011 Jeep Liberty was a rental — my 2009 Hyundai Sonata had been repossessed two weeks prior — and it was also my home, posted up in a Wal-Mart parking lot less than a half-mile from where my apartment used to be. It was still now. Vacant.

Occasionally a drifter would surface down the sidewalk. Walking from god-knows-where to only-god-knows-where. I had to make my last $100 endure all the way until October 3. I ate a lot of fruits and vegetables. I ate a lot of imaginary food. I did this for 16 straight evenings. Destitute. Wheezing because I couldn’t afford my asthma meds.

The nights were steamy. I had a laundry basket of assorted belongings in the trunk. I was restless, and torn between letting fresh air through drawn windows and baking to death in the safety of a completely locked car with blacked-out tint. I charged my wireless at an AT&T Store in the adjacent plaza. I brushed my teeth and washed my face in the morning at the restroom of the H-E-B down the street from where I worked. Occasionally, someone would barge in on me in a bathroom stall.

By the end of the fortnight, I was starving, I had zero money for food and wandered the streets of Round Rock looking for change from anyone who would give me the time of day.

I’d spend another seven weeks holed up alone at a $35/night Red Roof Inn where I was once offered — in no particular order — Old English, crack, prostitutes and weed, almost every night, until I was able to save up enough money to find a place of my own.

I could’ve punted on this dream — gone home, licked my wounds, moved in with my parents or the woman I was seeing at the time who lived in San Antonio. But I didn’t. It was hard. And lonely.


I remember the third time I felt truly alone. The night of October 16, 2014. I’d been discharged from St. David’s Medical Center in North Austin after having shoulder reconstruction done.

I was hooked up to a morphine drip, a cold compress on wheels, and a bag of anesthesia. I was in a sling. I was lit off an insane amount of oxycodone.

My partner who lived in San Antonio? I left her the previous month.

All those years I’d spent in Austin? I never really met anybody, and I was essentially starting again from scratch.

I spent most nights home alone stuffing my face with pizza and tweeting about college football. Some nights I had panic attacks so bad I would drive myself back to the hospital, convinced I was suffocating to death. I complained of a lack of breath that turned me blue and austerity of speech that sapped the character out of my character and rendered me mute, limp and lifeless. Fingers too apathetic to type. Lips to apathetic to move. Sweats in the mid-afternoon that leave me running out the door and gasping at bitterly cold winter air, which turns into a hyperventilation spin-cycle of despair and desperation.

I was also unequivocally depressed. This was an unending, perpetual motion machine of terror. This Ferris Wheel of anti-bliss from which there’s no jumping and no refunds. Too tired to joke. Too lazy to think. Too afraid to die.

I’d start physical therapy in the coming week, and talk therapy later, and I’d slowly work my way out of the sluggish, slogging hellscape I’d retreated to.

I didn’t need the surgery. I didn’t need to be single. I didn’t need to stay in Austin. I didn’t need to start over. But I had to. In my mind, I was crawling my way toward the future. One I hoped would be brighter … even though all I could see was the dark.


What do these stories all have in common? Aside from the loneliness? Aside from the pain and the suffering and the misery and the crippling confusion of it all?

Put simply: These are the three best decisions I’d ever made in my life.

  1. Moving to Austin.

They were three massive forks in the road where I could have gone the safe route, with the crowd or conventional wisdom, or doubled down on going my own way. I did the foolish thing. The unexpected thing. I ruined my life three times to try and build it ever greater and taller.

Why did I do that? Because it worked.

I got back into running, completing 14 half-marathons and a full marathon. I lost 44 pounds.

I went deeper into music-making a record, playing at venues across Texas. I hit up a litany of music festivals. Threw a multitude of benefit concerts.

I travelled all over the US. Saw both oceans. Saw every friend and every family member I held dear. Met the world’s most interesting people.

I kick-started both a writing career and a brand consulting side-hustle. Then, after my brand went global, one day I quit that corporate job to go rogue.

I fell in love again, and again. I felt and (mostly) fixed my feelings.

I joined the board of a nonprofit preschool. Got involved with various progressive congressional campaigns.

I even upped my credit score 200 points. 10x’d my income. Paid off my debt. Saved a pretty penny for retirement.


I’d go blue in the face running back the litany of ways my life improved because I swerved at those three forks in the road.

They made me stronger. Better. Unequivocally more confident … even my lowest lows — and, yeah, I still have them — are much higher and shorter than the ones that came before.

I’d, of course, be lying if I didn’t acknowledge that luck and privilege didn’t play integral roles in the story of my life. I was born a certain way that’s allowed me to fuck up early, often and forward. If I had been somebody else, I would not have encountered the myriad opportunities I’d been presented.

Still, in the end, it was I who pulled the trigger. It was me behind the wheel on the road less travelled.


I grew up in a culture — both in the home, and in the community, that didn’t encourage risk-taking. You got good grades, went to a good college, got a good safe job, and generally stuck around your hometown to start a family.

I’d be lying if I didn’t tell you I was encouraged to do all those things — by my parents, by my peers, by my neighbours, by my friends. I drank from the doctrine of caution at every turn.

I avoided upsetting the apple-cart whenever possible: Do just enough so your parents don’t yell at you, or your boss doesn’t fire you, and your friends don’t resent you. That was my code of honour for a long time.

It didn’t set my heart on fire; it didn’t make me happy. No, I needed to take three big risks to prove to myself that I could. I had to show a face card and hit.

Many people I know view life as a checklist, and their aim is to complete it as quickly, efficiently and effortlessly as possible. They do what they’re supposed to.

They often ask me about life on the other side with tinges of regret and resignation. I watch their wishes die by a soft 40-watt light flicked on in place of the flickering candle of their fleeting soul. They play it safe and quell their wild sides.


Let it be said: tame is only a letter away from lame. The slightest stone thrown troubles still waters; rushing streams swallow rocks whole.

When you wash yourself in life’s rich pageant (shout-out to REM) — when you speak only of what sparks you — when you believe in the beauty of your own alchemy — you can conjure up the type of magic that can’t be charted in a PowerPoint and presented to your VP at the quarterly all-hands.

To wait is to slumber with one’s eyes open — blind to the beacon that lights our way to the fantastic, the mystical … the rough road that leads to the shimmering stars.

Life is not linear. It is not a list. It’s a blank sheet. An ellipsis. A trail to be blazed. A route to be charted. Explore. Jump. Draw. Write. Sing. Play. Laugh. Move. Seek.

Death is so imminent — so inevitable — that to breathe merely in the interest of breathing again is to waste a breath, when we should focus our being on being left breathless.

Never let the dying of the light extinguish the flame that burns within you.

Never fall for a person you’ll follow into a soft grey glow of neither black nor white nor colour.

Never give your heart to someone who’ll occasionally make you breakfast and treat sex like a chore.


I didn’t want to die in the rust belt. I didn’t want to settle for a career I didn’t want, or live a life on someone else’s terms, or lock down a love that wasn’t enough.

I didn’t want an ordinary working-class life devoid of adventure and adrenaline. So I bet on myself … and I bet big. I bet every last modicum of comfort. Every last penny. Everything I found familiar. (Except my cat. She was the non-negotiable, apparently — and she’s still here beside me.)

Though I was alone, and I was truly afraid, I did what fucking scared me. The money came. The joy came. The love came. The fun came. The loneliness eventually subsided and I found what the self-help industrial complex calls my “calling.”


Today, I’m alone all over again. Doing what scares me. Betting it all on myself one more time.

I’m prepping to live abroad. I’m finding new love. I’m about to get rejected by dozens of publishers. I’m radically altering the way I move through the world. I’m no longer a businessman … I’m a business, man. (Shout-out to HOV.)

I’m risking it all to win it all.

Maybe not all at once.

Maybe not in the way I expect.

Definitely not without struggle and sacrifice.

But will it be worth it? Hell yeah, it’ll be worth it. It’s all I’ve known — behind my greatest risks lay my greatest rewards.

Do what scares you, friends. Only then will you find out you have one less thing to be afraid of.

Bet on yourself. Then, keep betting on yourself until you win. Then, just keep winning.


Mind Cafe

Relaxed, inspiring essays about happiness.

John Gorman

Written by

Essayist, speaker and storyteller on life, liberty and the battle for happiness. Top-100 Medium writer. Words at Human Parts, Mind Cafe and PS I Love You.

Mind Cafe

Mind Cafe

Relaxed, inspiring essays about happiness.

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