“Man suffers only because he takes seriously what the gods made for fun.”
—Alan Watts
My client, Jon, asked if we could meet for lunch in Asheville, NC. He was flying in from Austin on a buddy’s plane and said he needed a face-to-face session. I could already sense it: struggle.
I chose a fun tapas place on Biltmore Ave with impeccable vibes and food, sure to elevate any mood. We sat at the bar so we could watch the chefs make their magic.
We studied the menu in silence for a minute before Jon twisted his torso toward me and leaned on his left elbow. Wearing a backward ballcap, crisp white tee shirt, and Patagonia shorts, he looked athletic and preppy. And much younger than his biological age.
“I feel like I’m doing the opposite of what they tell you to do in driver’s ed,” he said.
“Oh, yeah? I asked. “How so?”
“I’m not steering into the skid,” he said. “In fact, I’m jerking the wheel hard in the opposite direction while watching a telephone pole about 30 feet in the distance get closer and closer.”
“What’s the source of the skid?” I asked.
“Mmmm, nothing,” he said. “Well, everything.” He chuckled.
Jon took his cap off and set it on the bar. An indented red ridge ran horizontally across his forehead from the cap’s band. He did his signature move when nervous—running his right hand through his wavy, brown hair.
I already had a hunch, but waited for him to say more.
“I feel like I’m doing everything wrong,” he said. “Not enough, for sure.”
When I asked why, he listed nearly a dozen reasons for his struggle. His latest startup should be growing faster. He should have launched that new product already. He should be publishing more. He should be a better leader for his team. He should be waking up earlier. Sleeping better. He should be spending more time on strategy. He should stop drinking alcohol entirely. He was pretty sure he wasn’t getting enough protein macros. He felt pressure to connect more with his wife, but didn’t have the energy or the desire to close the yawning gap between them (and was afraid of what that meant).
And then, he said something I hadn’t anticipated.
“You know, I’ll be 56 this summer,” he said as if he were disclosing a shocking diagnosis.
“I know,” I said, not taking the bait, but knowing fully what he meant. “You’re my favorite Leo.”
Jon finally smiled. “So, what’s my path out?”
I had dreamed up a metaphor during a client session the week before and knew it was perfect to share with him.
“As you took me through your skid list, all I could see in my mind was a mean witch running behind you, wielding her broom like a whip, threatening to bludgeon you if you stood still or relaxed,” I said. “Beat you senseless if you took a breather. Or looked around and got your bearings. Brutal, never-ending pressure to perform, improve, relentlessly chase, but never arrive.”
Jon turned away from me and faced forward. He grabbed my wrist with his right hand as if to steady himself on the barstool and said, “Jesus. That’s true.”
“But, wait,” he said, turning back toward me. “Who’s the witch?”
“You, my friend,” I said. “Well, your brain and all the cultural messages you have absorbed since birth.”
The Self Inflicted Struggle
Jon’s suffering came from his very typical human brain (one that barked scarcity and survival chants via a litany of you’re-not-enough nasty grams) and an endless collection of rules he had accumulated over the years.
Rules from well-intending parents, teachers, and peers. Rules from social media, movies, books. Rules borrowed from people whose lives looked nothing like his own.
He had built a very successful company and life. Then he had built a prison around all of it.
There is a strange badge of honor that we creators and entrepreneurs wear without realizing it.
We celebrate the late nights, the packed calendars, the endless optimization. We turn difficulty into evidence that we are doing something important. If a project feels effortless, we question its value. If a day feels spacious, we wonder whether we are falling behind.
Somewhere along the way, struggle became an enormous part of our identity. The irony is that most of us did not begin our work this way.
We become addicted to the struggle.
The writer started because words felt alive. The founder started because building something felt fun, exciting. The artist started because making things was an adventure. There was curiosity. Expression. There was experimentation. Passion. There was room to wander.
Then the rules arrived.
Rules about growth. Rules about productivity. Rules about what success should look like and how quickly it should happen. Rules about the correct path, the proper strategy, and the milestones that supposedly separate the serious from the amateur.
At first, these rules seem helpful. They offer structure in a world filled with uncertainty.
Over time, however, something subtle happens. The map becomes more important than the territory.
Instead of engaging with the work itself, we begin managing our relationship to an ever-expanding collection of expectations, obligations. We stop asking whether we are interested and start asking whether we are efficient. We stop noticing what sparks energy and start measuring ourselves against a scoreboard that never stops updating. We wonder, without ceasing, are we enough?
The result is a life that feels heavy, dull, and with limited oxygen.
Struggling as a Means to an End Will Not Lead You to Your Destination
Meanwhile, the most remarkable creators often share a different quality. They approach their work with a certain looseness. A willingness to engage fully without gripping everything so tightly that color leaves their knuckles.
They understand that not every experiment needs to succeed. Not every idea needs to become a business. Not every chapter needs to be brilliant.
The musician plays new riffs and arrangements from spontaneous, spirit-filled combustion. The inventor tinkers and putters and pokes around potential solutions. The entrepreneur explores, collecting insights and nuance like shells in a beach towel apron tied around her waist.
There is effort, certainly. Hard work. Commitment.
But there is also a lot of play.
And play has a surprising way of accomplishing what furrowed-brow force cannot. It invites possibility back into the room. And when we get a whiff of that delicious freedom, joy joins the chat.
When we loosen our grip, something unexpected happens. We become more creative, energized. Present.
The question is not whether we are working hard enough. Or life-maxxing enough.
Perhaps the better question is whether we have become so attached to struggle that we no longer know how to exist in ease.
A life built entirely around rigidity and pressure to perform is difficult to inhabit. A life that leaves room for curiosity, experimentation, and even a little mischief becomes something else altogether.
We do not need to earn our place here through constant exertion or improvement.
The richest, most rewarding moments in life arrive when we stop trying to force certain outcomes and make room for surprise, delight, and passionate connection.
In that space, safe from the struggle, we rediscover what has been waiting for us all along— the experience of being fully alive, most especially while our story is still unfolding.
