a tattoo with a mispelling

I spent the last 10 years mildly regretting the vocational choices I made 20 years ago.

At around 20, I decided to trade passion and freedom for stability. I gave up my entrepreneurial dreams for the safety and stability of regular employment and then spent the next 17 years working for a truly wonderful company, but ultimately not living out my passion or purpose. Trying to transition to work full time on my own business is scarier and riskier today than it might have been back then - now I have a family to feed and a home to pay for… but regret is unproductive if it doesn’t carry us forward.

We must leverage regret into learning if we want to turn failures from our past into the gifts they can be.

Acknowledge you could have done something differently… and then be okay that you didn’t.

The first step in moving past something is to own it.

We all have the choice to either act as a victim or to act as the hero in our own story. Victims are powerless, but heroes have agency.

When you become aware of the feeling of regret, use it as your trigger to dig deeper into why you feel regret. What is it you wish you’d done differently? Then, own the fact that you could have made a different choice. Lastly, accept that the decision is in the past. You cannot change it now.

We must realize that it’s silly to agonize (for very long) over things we cannot change. It’s a waste of time and energy, and it’s a distraction from where we’re at in the present. Time and energy are precious resources, and they ought not be wasted on the things we cannot change.

Instead, make good use of regret by owning it and then leaving it where it belongs: in the past.

Don’t waste regret, learn from it

With that said, regret does have a purpose and it can be useful if we’ll take advantage of it.

No, we shouldn’t dwell in regret, but shouldn’t waste the feeling, either. Rather, we ought to leverage the feeling to make the most of the opportunity we’ve been given.

We’ve been handed a golden moment to learn and improve. Could you have done something differently that would have resulted in a different outcome? I probably had 10 different choices I could have made at the age of 20, but the most obvious thing to me today is this: I could have gone to a less expensive college and then pursued my dream of building a business. In truth, I didn’t need a college degree for what I wanted to do, and the consequences of failure were much less significant at the age of 20 than they are today. But I bought into the fear and the illusion of stability, and that held me back. Instead, I could have embraced the unknown and charged into my fears instead of running away from them.

You can learn from your past, too. Just like I’m learning to charge into my fears and obstacles, you can learn from the things you regret. It’s rare that we only have one choice in any situation and now you have the gift of hindsight - today you may be able to see a better option than you saw in the past.

“Those who fail to learn from history are condemned to repeat it.” ~ George Santayana

Make good use of regret by learning from it.

Move forward with better insight toward the future

That learning isn’t for nothing - now we need to memorialize it for the future.

You’re probably facing other big decisions right now for your business or your life. Now that you’ve just identified something you can learn from the past, how can you apply it going forward?

If I could go back and do it all over again, I’d probably take advantage of my passion, energy, youthful optimism, and freedom to take the risk of starting my own business. Perhaps I would have failed miserably. Perhaps I would have succeeded fantastically. Perhaps I’d be in a similar situation as I am today. I would probably be learning from some different regret, but none of that matters, because I can’t go back and change the past.

What I can do, what you can do, is make better decisions today and tomorrow. I can learn to do the things I’m afraid of, to take some risks. You can decide not to make that same decision again.

”You don’t need to go back in time to be awesome; you just have to start right now. Regretting that you didn’t start earlier is a great distraction from moving on your dream today, and the reality is that today is earlier than tomorrow.” ~ Jon Acuff in Start: Punch Fear in the Face, Escape Average and Do Work that Matters

How this can make you money

As a business owner, you’re faced with decisions every single day.

If you’re not making mistakes, you’re probably not making enough decisions. But here’s the thing: repeating mistakes is expensive.

As small business owners, most of us don’t have deep coffers that render us invincible to our own stupidity. We’re going to make mistakes, but repeating them can be seriously problematic. It’s our responsibility to learn from our mistakes and avoid making them again. If you’re being bold (and you should be), you’re going to make enough new mistakes without adding old ones to the pile.

Save yourself time and money by making new mistakes. Be okay with new mistakes. Learn from them, and fail forward.

“Make new mistakes.”

Action items

You’ve almost certainly made some decision in life or in your business that you wish you hadn’t.

Today is the day to learn from it and fail forward.

  1. Identify a mistake or decision you’ve been wrestling with or regretting
  2. Own that it was a mistake, that you could have done something differently, and then leave it in the past
  3. Learn from it - if you could go back and do it again, what would you do now? Why?
  4. Commit to not repeating that mistake.

Life is too short, and the time you have in your business is too precious to waste. Don’t spend it wallowing in regret or repeating mistakes of the past.

fail forward

Make the most of regret by learning from it and then moving on.

To thriving,