Don’t Look Back in Anger

“You can’t go back and change the beginning, but you can start where you are and change the ending.” – C.S. Lewis

Whenever I look back at the life I led early in my adult years, I can’t help but feel a strong twinge of frustration. I see myself wasting tons of money, digging myself into a financial hole that took a very long time to dig out of. I see myself making several career missteps which led me to gradually becoming deeply unhappy with a field that I loved. I see myself not having the faintest idea of what it meant to be a good father or a good husband.

I look back and wonder what could have been had I been smarter with my money and smarter with my career. I have a good marriage and good relationships with my three children now, but what did I miss out on and mess up?

Frustration. Resentment. Shame. Anger. Those are the feelings I feel bubbling up inside of me when I reflect on that big pile of past mistakes. I look back and wish I could take it all back.

I know that I can’t.

It’s sometimes easy to get lost in a whirlpool of “could have beens” and “should have beens.” I could have made different career choices. I should have been smarter with my money. It goes on and on.

There are three key things that keep me from falling into that whirlpool.

First of all, I can’t change the past, only the present (and by changing the present, the future). There is nothing I can do to change the mistakes I’ve made. All I can do is make better decisions going forward.

My life right now is the starting point for the rest of my life. Where is the best place I can go from here? That’s really all that matters. I can reflect on those mistakes from the past, but there is absolutely no way to change those mistakes. It’s just wishful thinking, and wishful thinking doesn’t do anything to improve my direction forward.

I can’t make my twentysomething self not dig a financial hole. I can’t make my twentysomething self not damage a few friendships. I can’t make my twentysomething self not stumble through the early years of my career. There is nothing I can do, so there’s no reason to wonder about it and feel badly about what could have been. It doesn’t gain me anything.

Second, those missteps taught me a number of lessons that are now foundations for how I live my life. All of those financial missteps taught me some hard lessons about personal finance, and it was based on those missteps that I was able to turn my financial life around and put my family on a great financial path.

Let’s say I didn’t make those mistakes. Let’s say instead that I just kept my head above water, bubbling along for years and years with enough debt that I could handle it but not really saving any money. Where would I be now?

Not only would I be in a worse situation than I am right now, I wouldn’t have the knowledge of how to succeed financially nor the motivation to do so. The idea of financial independence or retiring early wouldn’t be on my plate at all.

The same is true for my career path. Over the last decade, I’ve been able to work from home and write for a living, something I never thought was possible. However, it was the career mistakes I made that nudged me toward investing so much time and energy into side gigs. I had put myself into a career position I was unhappy with, so I started spending a lot of my free time on side gigs, trying to figure out something different going forward.

Those mistakes seem devastating from the vantage point of today, but they paved the road for making better moves after those mistakes and they set up the values and opportunities I have today.

Third, if I had done those things “better,” what would I have missed out on in my life? I have a great relationship with my kids, one that I probably wouldn’t have if I didn’t choose to start working from home when they were very young. I have a great job, one that I almost assuredly wouldn’t have if I had made “better” career decisions early on, and this job helped me to have that great relationship with my kids.

The thing is, our earlier missteps sometimes open doors we would have never found without those missteps. Sure, there might have been better opportunities had we moved along a better path, but there’s no guarantee of that.

I’m not willing to throw away something pretty great in the slim hopes of having something just a little better when it’s more likely I just lose that great thing I already have.

So, when I look back and feel that twinge of frustration and guilt about all of the stupid moves that I made back then, I just remember that the place I’m at now was borne out of that. I wouldn’t have the values I have now, the values that put me on a better path. I wouldn’t have some of the great things in my life if I hadn’t made those mistakes early on.

I can’t change the past, but why would I want to?

I don’t look back that often, but when I do, I’m not looking back to wonder what could have been. Rather, I look back to see if there are any more lessons in the past that I missed. Are there any things in those old experiences that can inform my life now?

As the years pass, I look back less and less in anger and more and more with the realization that I was a young man who was bound to make some mistakes, and what really mattered was that I learned from those mistakes. On my best days, I’m still learning from those mistakes and still becoming a better person.

I can’t change the mistakes I made back then, but I can certainly be proud of the values that those mistakes taught me and what I have built with those values.

That quote from C.S. Lewis at the start of the article rings true. “You can’t go back and change the beginning, but you can start where you are and change the ending.” Indeed.

Good luck.

Read more by Trent Hamm

Your Money Missteps Don’t Define You
The Dirty Dozen: My 12 Biggest Financial Mistakes of the Last 10 Years
Breaking the Cycle of Repeated Money Mistakes
Our Nine Biggest Missteps on the Road to Financial Independence, and How We’re Fixing Them

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