Everything I Know About Business I Learned from Kenny Rogers

A pair of aces is arguably the best hand to be...
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My big lesson learned this week is actually an old Kenny Rogers song, The Gambler. “You gotta know when to hold ’em. Know when to fold ’em. Know when to walk away. Know when to run.” As a burgeoning business owner, I have had the thrilling opportunity to feel like holding, folding, walking and running all at the same time…all the time. And when I say “thrilling,” I mean “nauseating.” I have been in flight or fight for about a week now with no apparent reason to be. I am healthy, safe, and in a mentally sound relationship with my spouse, friends, and family. I have no predators. I am not lack for shelter. I eat three (or more) balanced meals a day. But with all that, I am terrified of losing everything and dying alone by lunchtime Tuesday. So what gives? What is this near-panic, country song chaos that is my brain? How did it start?

I had an idea.

It has not proven to be a good idea. It is too new to be a bad idea. But it is an idea that I decided to put into motion. Because I know objectively that I haven’t given this idea a fair chance, I want to keep trying (hold). But because the world didn’t run to me, begging to be part of what I didn’t tell them I thought up, I want to give up (fold). Because I’ve gotten a small amount of feedback that feeds my fears this may be a bad idea, I am prematurely dying of embarrassment (walk away). Because I am a catastrophic thinker, I assume this tiny amount of feedback is actually what everyone else thinks but is afraid to hurt my feelings and really the whole world is laughing at me. Who cares I just admitted three sentences ago that I’ve only told a limited few. Who cares I only told them a couple times and if the theory of “three times told equals one time heard” is true, I actually haven’t told a single soul. The whole world is laughing at me. (Run).

And there is rarely a moment that I am sitting in any of those, because as soon as I do, an event happens. An email saying no when I am relying on it saying yes for a series of events to unlock. An email saying yes the moment I’m considering shutting down the blog and deleting all facebook posts. A downvote on reddit (three actually) put me in a funk for days. And the whole reason I started was from a “like” on my facebook status mentioning it. Both are not reasons to start or stop a business idea. But both were all I needed in my rapid heartbeat, reactionary mind. I am not generally this scared. I have ideas. I pursue. I succeed or give up. Whatever. Life happens. But ever since this particular idea, I have been a tumbleweed of raw nerves. I can’t get a grip on my confidence. It’s either large and unwieldy, overbearing in its insistence to push forward, or tiny and weak, frozen in terror like a mouse under the glowering eyes of a snake.

But for every day I hold ’em, I’m realizing the best case scenario is success and the worst case scenario is knowledge. Unlike the world of a gambler, I cannot lose if I keep playing the game.

This lesson is profoundly obvious to successful people. Anyone I talk to who has reached some level of self-made success in their passion merely nod. Yep, all you got to do is be standing when the dust settles. Yeah, get done with those nine no’s to get to your one yes. Sure, failure only happens when you give up. It’s obvious to them. You know who it’s not obvious to? People who have given up. The “pragmatists.” There will always be someone giving us a reality check. They are never successful at their passion. Coincidence? Likely not. So when I want to fold, hell, to run, I remember that Kenny Rogers song. I know who’s at the table. I want to stay at the table with these players. I want to keep playing. And I like my hand.


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