TRM41: The Art of Quitting

An Entrepreneurial Virtue

In the startup scene, there's a saying I've grown fond of: “Don't just quit, rest.” Sure, we hear it all the time that you have to stick it out, that true success comes from never throwing in the towel. And I get it. There’s a ton of value behind sticking with it. But, there's another side to that coin, one that doesn't get enough limelight: knowing when to bow out gracefully, or what I like to call “walking away.”

Walking away is an art in itself. It's not just a last resort; it's a savvy move. History's littered with stories of folks who knew when to fold their cards – from ancestors who ventured out for a fresh start to entrepreneurs who could spot a dead end a mile off. My own grandparents packed up their lives in Southern Italy back in the 50s, chasing a dream that paid off for generations to come, a stark contrast to the fate of those who stayed put.

From a business perspective, take it from the top dogs in the boardroom: quitting is part of their playbook. They've got this knack for spotting a flop early, shifting gears, and hitting the gas towards new horizons. Take Jeff Bezos – the guy's no stranger to costly blunders, but it's that same readiness to cut losses that set him up for the big wins.

Chasing the dream is risky business; failure's part of the deal. To hit the jackpot, you might have to ditch a few jobs, say goodbye to some pals, or drop a dud investment. Those "overnight successes"? They’re usually the end product of years of grinding, failing, and strategic quitting.

But let's not forget: the market's bigger than any of us. Success can be as unpredictable as the weather, and failure's often out of our hands. It's all about staying grounded when you're riding high and not beating yourself up when you take a tumble. Quitting isn't a sign you're giving up; it's just you steering your energy where it counts.

We humans, funny enough, hate to admit when we’ve sunk our teeth into a bad apple. Our brains trick us into sticking with a losing game. But, you got to play smart, not hard – and that means letting go.

And guess what? Most of the time, nobody else even notices. Fear and pride can freeze us in our tracks, but owning up to a bust without making excuses? That's where the magic happens. Failures can fling open doors we never even noticed.

In the end, business is a constant toss-up between sticking it out and knowing when to pack it in. The real champs are those who can stare reality in the face, embrace their failures, and still hold faith in the end game. Out of the eight businesses I've launched, most never took off. But man, did I learn a truckload from each crash and burn. Those experiences loaded me with enough knowledge to truly understand the difference between 'quitting' and 'knowing when something is over.’

So, here’s the scoop on entrepreneurship: it isn’t just about the chase; it's about having the smarts to know when to take a different path. Walking away isn't the same as giving up—it's choosing to jump onto a new track because the one you're on is leading nowhere. At the end of the day, you can drop a project, idea, or even a team, (what I call micro walk aways) but you never drop out of the race (what I call macro staying power). So, when do you know when to walk away or stick it out? Great question. For me, it's about asking one simple question: Am I happy?

Both life and business begin and end with your happiness — what else truly matters? If, upon self-reflection, I realize that I'm not happy, that realization empowers me to make the decision I need to make decisively.

So, as we hustle along, let’s celebrate the power of knowing when to walk away or when to try harder. And like always, Let's Continue.

P.S….I'm working on a book.

I love books, and truthfully, I have more than I can read, but they're on my list and I'll definitely get to them. I honestly believe that a mentor doesn't have to be a person. Don't underestimate the power of finding mentorship through books. People literally put years of experience into 300 pages for you! With that said, I am putting my 15 years of entrepreneurial, SMB M&A, and leadership experience on paper for you all. I promise it's going to be an easy read and something you can share with everyone in your family. I would love for you to be on this journey with me. I'm unsure what the journey is going to look like, but I promise to add value. Join here.