That’s the high explosive bomb that blew my mind at 4 am this morning. As I lay there thinking about my commitment to a new business venture, the horrific fear of doubt started creeping in. What if it doesn’t work out?

I’m placing our future on the hopes other people will follow through. It’s a scary place to be and I don’t like it because I’ve been here before.

The past failures still haunt me.

Getting screwed over in business partnerships is enough to make anyone’s butt pucker. When you contribute your blood, sweat, and tears into a dream only to have it obliterated by people you trusted, it’s hard to recover and drive on. When you allow it to happen multiple times, bitterness and cynicism become your best friends. You also begin to question your sanity!

Unfortunately my past is littered with failures in working with others.

Perhaps my expectations were set too high for others or I was unbearable to be around. It really doesn’t matter whose fault it was in these circumstances. We all make mistakes. But those scars and memories still haunt me.

Here we go again …

What if it doesn’t work out?

Letting go of fear and doubt isn’t easy.

Maybe you’ve experienced the same past hurts or failures. A terrible relationship or divorce; a failed career or profession; a broken dream to travel or get away from home. The reality is most of us have encountered some sort of traumatic event that conjures up fear and doubt.

What the hell do we do with that?

It’s been said that we shouldn’t let failures or hurtful experiences define us, but it’s not always easy to overcome them. You can’t always “just get over it” and move on with life. It takes time to process and understand before we can take the negative and change it into a positive.

But letting go and moving on is exactly what we need to do.

If we continue to always hold onto the past we will never get to embrace the future. A sailboat tied to the dock will never experience the thrill of riding the waves of the ocean. The same goes for us and our lives.

What if it DOES work out?

I’m no jacked up Tony Robbins or botox smiling Joel Osteen. Seeing the cup half full instead of half empty has not been my strength in life. I’ve gone through some bad shit since childhood and it’s tainted my world view.

HOWEVER … I have learned to be positive and find happiness despite those challenges. I’ve learned to think differently about turning trials into triumphs. I’ve learned that how you ask the hard questions changes your perspective on the outcome.

  • What if this new job leads to a rewarding career?
  • What if this person truly loves me and brings great joy in life?
  • What if this crazy travel idea brings me total happiness?

There is no guarantee the path in front of us will lead to the fairytale ending but that shouldn’t stop us from taking the risk. We will never know unless we’re willing to go roll the dice.

Sometimes you lose but sometimes you win!

Life is a gamble but I believe we have better odds at winning there than at the casino. How come we don’t bet on ourselves more?

There have been times when I lost big. But there have been times I’ve hit the jackpot too!

When I asked Donetta to marry me at the age of 18 – having dated only three months – that was rolling the dice. Yet we’ve been married almost 30 years and have had a wonderful life together. When I gave the finger to corporate America to pursue my dream of entrepreneurship, I was gambling with my family’s future. But we made a great living and lived by our own rules. When we decided to sell everything to travel the world during a global pandemic, it was all in or nothing. And here we are having the best time ever.

You get the point.

The failures or hardships we encounter are a good reason to ask what if it doesn’t work out. There might be a lot of losses under our belts. But we’ll never hit the jackpot if we don’t play the game either.

I don’t know if this has helped you at all, but it has reminded me to keep doubling down and bet on myself. If my new business venture doesn’t work out at least I have tried and that makes all the difference.

Ante up!

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