(#033) Stay vigilant

The bad news first.

Entrepreneurship is not a finite game.

There are no goalposts to tell you how you're doing, or how far you’ve come.

Succeeding once—or several times—is no guarantee of a rerun.

Failing once—or several times—doesn’t say much about whether this is the right path for you.

You might give it a shot early in life, or after decades of experience. You might start when every planet is clearly aligned or against all odds, putting in 100+ hours a week, like Elon Musk—or four, like Tim Ferris—and still hit the jackpot. And then, you might lose it all on the next idea, like me at 31. (A classic, especially if you’re young, and the idea of setting money aside and going again as an underdog eating dirt—like you did the first time—ain’t sexy.)

Or you may read every book you can get your hands on, study every masterclass, dissect every notable success story, dive in headfirst—and still fail. And even then, you won’t know if you should keep going or call it quits. The game isn’t over. The choice to repeat—and risk yet another failure—is all yours. Luck might turn next time. Or it might have nothing to do with luck. You can’t shelve the matter with a clear conscience.

But here’s the good news.

Entrepreneurship is not a finite game.

You read that right. Same statement. Different light.

(Also, I couldn’t resist the opportunity to have two identical pull out quotes in the copy.)

If this feels like your path, then no single outcome—and no single venture—can define you more than the definition you carry in your heart.

I know, it’s cheesy. But that doesn’t mean it ain’t true. And in my defense, I still find it less cheesy than all those guru-theories carved in stone about the "ultimate test" to see if you’re cut out for this, or the top 10 traits that make a “real” entrepreneur.

Being an entrepreneur isn’t about having tried and succeeded—because any single enterprise, and its success, is never the point when it comes to identity.

The point is being incapable of living any other life but one of discovery and creation.

Discovery, because without an attitude of questioning the status quo—seeing the constraints of daily life and immediately running a “what if” exercise—and without resonating with the deep joy of trying to discover something new, there is no venture.

Creation, because once an alternative world is conceived, and a vision is set, the entrepreneur lives his every day in a different version of the world trying to convince everyone else that he’s right. A mentally difficult place to be, but still—far more exciting than the one where everything is exactly the way it’s supposed to be.

An entrepreneur is defined by his ability to navigate the uncomfortable waters between reality and his pursuit of changing the world.

As long as you feel that what you're creating is making the world a little bigger—and adding meaning to your life—you’re on the right track.

Likewise, it’s not a failed venture that should discourage or worry you.

It’s losing yourself in the pursuit.

When the insistence on your goal comes at the expense of the meaning you were trying to create—or your health, or your family—that’s when you know it’s time to run an audit on yourself.

If that’s the case, chances are you’ve fallen victim to your own vanity, chasing external validation (fame, wealth, power, accomplishments easily sold to strangers or peers), and lost sight of the sacred fire that first drove you to change the world.

When the pursuit loses its sense of adventure, when waking up in the morning no longer feels like a mix of excitement, strength, and fear—the excitement for what might happen, the strength of knowing you’re living your truth, the fear of having to start once again to make the next 24 hours matter—when instead your life feels unbalanced, leaning toward some distant event that’s supposed to justify it all... it’s time to stop and reflect.

This doesn’t mean “quit” the moment things don’t feel right.

Just like in a personal relationship, hitting a rough patch doesn’t mean the solution is to walk away.

Doubts, second thoughts, frustration, struggle—they’re all part of the process.

But a bell should go off in your head. You should put your life and agenda under the microscope: Where is that original passion that gave you the first spark? Is it still there?

Chances are, it is. But life got in the way. You became entangled in a thousand chores and surrogate tasks—now strangling both your life and your capacity to continue discovering and creating.

Chances are, quitting is not the answer. The answer is to keep listening to yourself, embracing where the adventure took you, and who it made you.

I’m living this firsthand with my latest venture, Jam Nation. (By the way—look it up in my professional profile, check out some of the milestones I mentioned in my journal here, here, and here, or just visit us at jam-nation.com.)

The original idea was pure excitement: to allow any musician—amateur or pro—to quickly and easily find others to jam with, anywhere in the world. To help people discover the best live music show in town. And eventually, to help musicians reclaim ownership of their audience—cutting through the layers of bars, venues, agents, managers, labels, and producers who add the frosting to the cake and then eat half of it.

That vision still feels nothing short of thrilling—and it still makes me proud.

But the past 17 months—since the day I gave it a go—have been anything but steady excitement.

At every stage, I’ve had to deploy a whole range of life hacks and carefully designed habits just to stay consistently productive, often motivated, and—when lucky—occasionally inspired.

Most importantly, I’ve had to check in with myself again and again, to make sure I was still pursuing the original inspiration: to change the world for the better, and to enrich my life through a meaningful adventure.

Not just keeping up appearances to avoid damaging my credibility in the business world.

Not just chasing profits to silence the anxiety of building something “non-profitable”—or, in less introspective terms, a failure.

Being an entrepreneur is not only about staying strong.

You also have to stay vigilant.

L.F