Charge It To The Game
We've all made bad investments. You can't keep punishing yourself for decisions you made when you didn't know what you didn't know.
Every business owner has made an investment of time or money they wish they could get back.
Maybe you borrowed money to invest in an online course or a program promising the breakthrough of a lifetime.
The marketing strategy that was supposed to have new leads breaking down your door.
Joining a networking group or investing in office space hoping it’ll lead to more business and referrals.
The conference, the coach, the software subscription, the partnership, the ad campaign that looked like the missing piece.
And after thousands of dollars and weeks/months of your time you realize it wasn't the answer.
As much as those mistakes may have cost you in resources, there’s a bigger mistake I see entrepreneurs and business owners making after that — shaming themselves long after the fact.
I was thinking about this after a conversation with some fellow entrepreneurs and business owners in one of the salsa dancing communities I’m part of.
One of them shared about how they had secured space in a coworking office about an hour from where they lived with the intention of being able to network and get new business.
Now it’s easy to judge in hindsight but if I were to truly list both the dollar and time amount I’ve personally wasted on swings that ultimately lead to nothing, it would dwarf that scenario by 15-20x.
Seriously. I once invested nearly $10K into a Facebook Ads course at the height of FB ad craze, thinking it’d be an “easy” add-on to my existing marketing services. But the main people responding to my ads were other people in the course and community with me…
The things I would do differently now…
But that’s just it — I didn’t know what I didn’t know.
And I didn’t know that I didn’t know what I didn’t know.
Yeah, have fun saying that three times fast…
I can cringe at that and many other examples but what would be the value in shaming myself for it?
The thing about entrepreneurship—especially when viewed by those from the outside—is that it has a way of making every wrong turn feel like a personal failure.
I’ve replayed conversations. I’ve questioned my instincts. And even after FIFTEEN YEARS, I still have the occasional thought of whether I’m actually cut out for this.
Social media doesn’t help either. It’s filled with people claiming they built six-figure businesses with one simple funnel, one perfect offer, or one secret strategy.
A large majority of that is absolute-fucking-bullshit by the way. Nobody’s posting their trip to the dollar menu or 4th night eating Ramen noodle to their Instagram highlights.
They’re whole job is to sell you on the idea that if only you had their course, followed their blueprint, you, too, could be taking pictures next to someone else’s private jet or Porsche 718 Cayman GT4 RS.
The reality is there is no definitive playbook.
Business schools can teach concepts and principles. Coaches can share experience. Mentors can shorten the learning curve.
But not a single one of them can eliminate uncertainty.
Every successful entrepreneur has to reach a point where they’re comfortable making decisions with incomplete information.
That’s the job.
You take a swing, you learn, you adjust, and keep moving forward.
Some lessons cost fifty dollars. Some cost five thousand. Some cost an entire year.
At some point, you have to stop treating every failed investment like evidence that you’re bad at business and start recognizing it as the price to be paid for the experiential education called entrepreneurship.
Charge it to the game.
People think the challenge is finding the perfect strategy, the perfect tool, or perfect employee, etc.
But the real challenge is surviving the lonely nights when nothing seems to be working. It’s making it through the lean months when the inbox is crickets, the pipeline is empty, and you’re wondering if everyone else figured something out that you somehow missed.
(And try dating or being in a relationship while enduring all that…)
There’s no masterclass for that.
No certificate.
No guru can teach the discipline of holding onto a vision that nobody else can see but you.
That belongs to you.
So if you’re carrying around regret for money you spent, opportunities you chased, or ideas that never became what you hoped they would be, maybe it’s time to close that mental tab.
Take the lesson.
Keep the wisdom.
Leave the shame behind.
Every entrepreneur pays for an education.
The only real waste is paying for the lesson and refusing to learn from it.
Ali J. Taylor is a NJ-based business consultant and TEDx speaker. He writes about work, identity, creativity, relationships, ambition, faith, and the stories we tell ourselves about who we are and what’s possible.
Some of those stories deserve to be honored, while others deserve to be rewritten.
Learn more at alijtaylor.com or his consulting framework here.