If I Had It To Do All Over Again, Would I Do Anything Different?

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Jennifer sent me a great email recently that included this question:

Your effort in getting out of debt has been a great inspiration to me and I know it must feel great to have finally freed yourself from the shackles of debt. If you had it to do all over again, what would you do different?

I originally had this question lined up for a reader mailbag, but as I kept thinking about Jennifer’s question, my answer grew and grew.

I think we all look back at the mistakes we’ve made in our lives and wished we could take some of them back. I cringe when I think back at some of the stupidest ways I spent money over the years, and the repeated small choices that led to my debt load are also painful to think about. I can recall relationships and friendships that didn’t end well or faded away without any real reason, and there were at least a few opportunities I should have jumped on but did not.

It’s also really easy to paint a perfect picture of what my life would be like now if I had made better choices then. Would I have a lot more money? Would I have some novels published? Would I still have a connection to a certain few people?

Sure, those things might have happened and I might have a better life if they had.

However, the failures in my life taught me a lot of things.

My failures with the first people I dated eventually helped me build a great relationship with Sarah. I personally experienced some of the relationship mistakes people can make and I was able to build on that to make things work well with her.

My failures with money and overspending eventually helped me to understand the right way to manage my money and how worthwhile it is to be frugal and keep your spending in check. I personally experienced a lot of financial failure, and I was able to draw on those failings to fuel my recovery.

A similar pattern appears with failures with writing, with career moves, and with other aspects of my life. I messed up, but those experiences helped point me toward a better way of doing things.

If I roll back the clock to the mistakes I’ve made, I might find a short term benefit from not making those mistakes, but in almost every case, the long term benefit from the lesson learned was far more valuable.

Without making a financial disaster of things, I would never have learned the value and joy of living a more frugal life. Without making a complete disaster of relationships, I would have never learned how to be a good partner and how to make a relationship work. Without repeatedly failing at various attempts to write, I wouldn’t be making a living at writing.

My life, on the whole, is better off because of the mistakes I’ve made, the ones I’m making now, and the ones I’ll make in the future.

The key to all of it is accepting that I’m not perfect, that I’m going to mess up, and that when I do mess up, there’s probably a better way of doing things.

If I had the opportunity to wind back the clock and undo things I’ve done in my life, I’d turn down that opportunity for almost every regret I have in my life. Without most of those regrets, I would have never found my way to the life I have now. I would have never learned the valuable things that those bad choices had to teach me.

Does that mean it’s a good thing to mess up? No, of course not. You should always draw on your understanding and willpower to make the best choice you can.

Still, we’re all going to sometimes make poor decisions. That’s part of life.

Even with a poor decision, though, there’s something very valuable you can extract from it. If you look at where you messed up, you can perhaps learn something and add it to your understanding of yourself and the world so that the next time you’re faced with a similar situation, you have the knowledge to make a better choice.

For example, if I went back and erased most of the bad financial choices I made over the last decade, I would probably be living paycheck to paycheck right now. I wouldn’t be in a lot of debt, but I wouldn’t have the sense or initiative to save for the future. I’d be spending more than I probably should be, usually on stuff I didn’t really need, and I’d probably be locked into that for the rest of my life.

So, given the chance, I wouldn’t undo those mistakes, or the mistakes I’ve made in many other areas of my life.

Understanding that means that you don’t have many regrets. You just have things you can draw on from your past so that you move toward a better life in the present and the future.

You can’t change the past. You can change the present and the future. The mistakes you’ve made in the past can help you change the present and the future for the better, if you let them. Don’t drown yourself in regret. Instead, look to where you can go from here using what you learned from your mistakes.

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5 thoughts on “If I Had It To Do All Over Again, Would I Do Anything Different?

  1. And if you hadnt made those choices and mistakes you wouldnt have been able to write a successful blog for all these years based on those very choices.

  2. I made plenty of financial mistakes in my first 5- 8 years as an adult that held me back from being able to take advantage of all of the opportunities that came my way. I had many goals that were left unattained because of my debt. However, I agree that I needed to go through those struggles at some point in my life in order to learn what NOT to do. It taught me more than I could ever learn in a book or a blog. So, in a strange way, I’m glad I made the mistakes that I did.

  3. That’s a really unhelpful answer. It’s great that you were able to learn from your mistakes, so why not share some of what you learned so that other people don’t have to learn the hard way? Isn’t that kind of the purpose of your blog (other than making money)?

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