Regret, Ughhh……

A little more than 12 years ago I missed out on an opportunity that I still think about from time to time. I really don’t talk about it, I just think about it. And it eats at me. It is something I completely regret not doing.

The company I worked for was, and continues to be, a very large and successful corporation in its industry. Each year they have a national meeting for thousands of leaders from across the country who get together to plan and shape the future of the company. As an HR leader with the company, I was honored to be invited each year to help participate and watch my company grow and thrive.

At one point during this conference 12 years ago, the CEO of the company challenged everybody in attendance to come up with a clever and unique name for a process that was in development to be implemented in the coming year. He asked all to be very creative and to not hold back with our ideas and the winner would receive a cash reward of several thousand dollars.

Now, I am often known for being a little bit goofy and telling bad dad jokes and using puns whenever possible. When the contest was announced, I immediately came up with a silly name that I thought was hysterical for the process and I wrote it down to be submitted. The name was not inappropriate and it did fit the meaning and theme of the process. It was just a little unorthodox, if you know what I mean.

Several of the people at my table started to share their ideas for a name and all of these, without exception, we’re very “professional” in nature. When I read what I had written down, mine didn’t quite measure up to those who were submitting responses. My idea was simply a play on words and my reasoning for choosing this name was that it would be memorable.

Out of fear of looking silly to those who would review the submissions, including the CEO, I decided at the last minute not to submit my entry. And then I quickly moved on, got back to work and forgot about the contest.

On the last day of the conference, the CEO reminded all of the contest and said that there was a three-way tie. He stated that the name was so clever that he decided to give the same monetary award to the three individuals who had submitted that name. They didn’t split the prize, they each received the same amount. I immediately thought to myself, “there is no way this name is more clever than mine.”

To my absolute amazement and astonishment, the name that was announced was the exact thing that I had thought of for submission.

Now to be honest, my first thought was not about losing the big monetary prize. My first thought was, “WOW! there are three other people here, out of everybody in attendance, who think like me!” And then I thought about the prize that I missed out on. Have you ever had that feeling of being punched in the gut even though you were not punched in the gut? That feeling you get when you realize you can truly be a “bonehead.” That feeling of complete… regret! That prize should have been mine!

When I saw the three people walking up to shake the hand of the CEO for winning the award, I reached into my pocket and read the name I had previously written down. I squeezed it as hard as I could into the smallest possible ball and threw it in the trash on my way out of the conference later that afternoon. I had not only thrown away a piece of paper but I had thrown away the opportunity to win a big award and be recognized in front of so many people by the CEO of the company.

It’s been more than 12 years and I’ve never spoken about it, much less written about it, until now. I don’t think I’ve even told my wife about this unfortunate event. She’s going to be reading this blog post and ask me more specific information about how much money we missed out on and probably tell me how much she loves me, but she sure wished we could have gone on a nice vacation, or put some additional money in savings, or buy something that she wanted… uh… I mean we wanted, or something like that if I would have only submitted my entry.

Yes, I still think about that missed opportunity. I learned a very important lesson from my unfortunate decision. I should never be afraid to be myself. I have a lot to offer. That’s one of the reasons I tell dad jokes at the end of every single one of my blog posts. If I make one person smile, or even laugh, the post has been worth it. I should try to remain confident about my abilities and what I have to offer.

As I think about it now, I don’t even remember the name that I came up with that day. I probably blocked it out of my memory for some psychological reason. But I do remember that I missed an opportunity that I completely regret!

So, what does this have to do with running an online business? Well, I’m glad you asked!

Confidence plays a huge role in every decision we make, especially when running an online business.

Whether it’s launching a new product, trying a new marketing idea, or even posting your first blog or video, there’s always that small voice whispering, “What if this looks silly?” or “What if no one likes it?” But here’s the truth. The only thing worse than trying something and failing is never trying at all. Regret doesn’t come from what we did, it comes from what we didn’t do.

That moment 12 years ago taught me something that still applies to business and life today. Playing it safe might keep us comfortable, but it rarely helps us grow.

Every successful entrepreneur, creator, or innovator you admire has one thing in common. They took a chance when it felt risky. They trusted that their ideas were worth hearing. And even if they stumbled, they learned, adjusted, and grew stronger.

So, when opportunity knocks, answer it! Even if it sounds a little unorthodox. Even if your idea makes people raise an eyebrow. Because sometimes the thing that makes your idea different is exactly what makes it powerful.

Here are five reasons you should take risks (even when you’re scared).

1. Growth only happens outside your comfort zone. You’ll never discover how capable you really are until you step beyond what feels familiar.
2. Failure teaches more than success ever will. Each risk brings lessons you can’t learn by standing still.
3. You might surprise yourself. Confidence isn’t built by waiting to feel ready. It’s built by taking the first step anyway.
4. Unique ideas stand out. The world doesn’t reward “safe.” It rewards boldness, creativity, and authenticity.
5. Regret lasts longer than failure. You can recover from a setback. But you can’t go back and take a chance you never took.

We all have moments that make us second-guess ourselves. But every time you lean into your abilities, trust your instincts, and take a chance on something new, you’re rewriting your story.

Confidence doesn’t mean you’ll never feel afraid. It means you act anyway, knowing you’ve got what it takes to handle whatever comes next.

If you’ve been sitting on a business idea or a bold new direction, don’t let fear or self-doubt talk you out of it. Take that chance. You might just surprise yourself, and more importantly, you’ll silence that future voice that whispers, “I wish I had.”

Your next opportunity might be the one that changes everything if you’re brave enough to submit it.

OK, now that I’ve finally talked about this, I can move on. I better hurry up and finish for the day or my next regret will be showing up late for the wonderful meal my wife has been cooking. Now that would be a real shame!

“Only those who will risk going too far can possibly find out how far one can go.” T.S. Eliot

“You are braver than you believe, stronger than you seem, and smarter than you think.” A.A. Milne (Winnie the Pooh)

And of course, a few VERY BAD Dad jokes:

I told my wife I regret not becoming a banker. She said, “Why?” I said, “Because I really lost interest.”

I missed my chance to join the orchestra years ago. Now I just live with the “repercussions”

Until next time, STAY FRESH, Friends!

 

 

 

 

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