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As we get older, we have more and more financial history and decisions that go along with this history that we can look back on.

Along with that, it's easy to make a list of things that we would change, because they invariably ‘cost' us money along the way.  Jessica at DebtKid wrote an article outlining things she would change, having had a chance to look back.  Among them:

  1. Would have worked in college versus taking out student loans
  2. Would have eloped instead of having a big wedding
  3. Would have waited to buy a house

All things that, looking back, most definitely cost her money in some fashion.  Loans have to be paid back.  Weddings are expensive.  Houses cost a lot of money and have suffered price drops.  All good points, and all things that may  have resulted in a different money situation had they been handled differently.

So, it's easy to say ‘We would have changed all those things'.

But the more I think about it, I wonder if that's really what people would choose if they did have the ability to make those changes.  I could see changing one, maybe two of the items, but consider:

  1. College is more than what you get in the classroom.  You build friendships for life.  You have relationships that lead you into adulthood and (hopefully) give you the maturity that you need.  Depending on how much you had to work to avoid student loans, you might have missed out on a lot of these important things.
  2. Weddings are definitely expensive and I can see the temptation to look back and say that having paid for one was a decision to change, if given the opportunity.  But, going along with that is that it's probably the biggest party and biggest celebration you'll have in your life.  Your friends and your families are all coming together to celebrate an incredibly happy occasion, not to mention the joy that the bride and groom should have.  Changing that would save money, but the memories that went along with everything associated with the wedding would also go away.  Would you change that?  Many would, but I know I wouldn't change a single thing about our wedding.
  3. OK, I can see this one!

I think in every ‘woulda, coulda, shoulda' discussion you have when it comes to money, I think you have to also look at the trade-offs that you'd give up if you could in fact reverse those decisions.  I look back at all the money I spent going out with my friends back in my single days.  We would go out, pay cover charges, pay for drinks, pay for cabs, paid for going out to movies or wherever else we landed, and not think anything about it.  The amounts were staggering.  Had I saved that,  I could have definitely had more money than I had today.  But, would I change that?

Probably not.  Because while the costs might seem foolish on paper, there were memories made along the way that I'll have forever.  And, in my case, it's an intangible reward I got for those expenses that I am very happy with.