You learn a lot about personal finance in 30 years. Many folks get married and buy homes. There's a lot to learn just there, but here's a total of 30 things I've learned over the years.

With this milestone approaching, I’ve already passed a late night or two sipping bourbon and meditating on my first three decades of life—successes, failures and what, if anything, I learned from them.

Today, I want to share a few of these points on money. I’ll offer brief explanations of some; others stand alone.

(Having spent almost five years writing about finances, I could easily pen a list of 200 or more “money lessons”, but I’ll stick with 30 of the most personal and, hopefully, most prescient.)

1. People love to judge the financial decisions of others.
Try not to. Personal finance is personal.

2. Armed with credit cards, anybody can live richly for a year or two.

3. Doing so causes a world of pain.

4. Being ensnared in debt was the most difficult thing I have experienced in life.
Debt’s effects are widespread: emotional, psychological, and even physical.

5. Poor financial decisions also mean lost opportunities.
Debts tie you down, and when you’re tied down, you can’t take risks.

6. It’s hard to reach financial goals until you know where you’re going.
Make a financial plan. Get specific, put it in writing, and set deadlines.

7. When it comes to reaching financial goals, BABY STEPS really do work.
Set a small goal. Celebrate achieving it. Set a bigger goal. And so on.

8. The less you have to think about money, the better.
Without a doubt, paying yourself first and automating retirement contributions and debt payments has consistently helped me reach financial goals sooner.

9. It’s a GOOD idea to admire people who EARN MORE money than you.

10. It’s a BAD idea to admire people who SPEND MORE money than you.

11. Over time, I regret spending money on ordinary things.
A new bicycle, a $200 set of poker chips, an Xbox 360, and more guitars than I can count. All things I bought with credit when I shouldn’t have. Most of them I later sold on eBay when I smartened up. And I don’t miss any of them. Although making a new purchase leads to a kind of high for a couple of days, it inevitably leads to remorse…especially when you buy it with credit.

12. Over time, I DO NOT regret spending money on extraordinary experiences.
If I were to tally up all the things I financed with credit cards years ago, the single biggest line item would be this: PILOT’S LICENSE ($4,500).

That’s right, I spent several grand I didn’t have on flying lessons. Idiotic? Yes. Irresponsible? Of course! But do I regret it? Well, not exactly.

In hindsight, I wish I had never gotten a credit card so young, which would mean I would’ve never purchased flying lessons. But quite honestly, learning to fly was one of the best and most unique experiences of my life. I know people who dream their entire lives of doing something like this but never get around to it because they don’t have time or because spending the money on something so indulgent isn’t the responsible thing to do.

But in this case, I chose to trade in a dream for a memory, and I don’t regret it. Flying was awesome. And once everything else in life is paid for, I hope to do it again someday. But if that never happens, at least I did it. That’s how I feel about experiences. If you have the opportunity to do something you really, really want to do, it might be time to throw pragmatism to the wind.

13. Having “enough” money is a really good feeling.
Does money buy happiness? I don’t think so. But getting out of debt and having a few dollars in the bank sure makes a lot of problems disappear, if you can swing it.

14. The less money you have, the easier it is to gamble it.
Ironic, isn’t it? When I was in the depths of indebtedness, working two jobs just to cover minimum payments and rent, I started playing casino blackjack. I was deluded into thinking a big win would wipe out all my debts and let me start over, easy as pie.

You know, the classic gambler’s dream. The easy way out.

Of course, all I did was make my debt worse by gambling money I couldn’t afford to lose.

Although gambling itself wasn’t the source of my debt (thank God), gambling became a roadblock to getting out of debt. Whenever I had some spare cash, instead of making an extra debt payment, I gambled it. Sometimes I won and used the winnings to pay debt. More often, I lost, and once again had to turn credit cards to pay the month’s bills. But because I had so little money, gambling was really exciting. It was all or nothing. Go home with nothing or go home with a couple thousand dollars which, at the time, was a huge sum of money. This is why, I think, casinos are filled with the old and the poor. Gambling is most exciting when you have the most to lose. The dollar amount doesn’t matter, only the relative sum.

15. The more money you have, the more you want to protect it.
Something interesting happened when I emerged from debt and watched my savings and investment balances grow. Spending money became more painful. For the first time in my life, I could actually afford some of the things I once racked up debt to buy, only now I didn’t want them. Knowing how hard I worked for the money in my bank account (and to pay down all that debt) puts purchasing decisions in an entirely new light.

16. Don’t blindly trust investment advice.
I think you have to ask yourself: If somebody pitching stock tips is so smart, why aren’t they just investing for themselves? (For one, because selling investment advice is a sure-thing whereas any investment, by definition, is a risk). Now I’m not saying there isn’t good investing advice out there, but I am saying you can’t always tell the difference. Ignore most investing advice, and ignore the stock market, too.

17. Talking about money with your (future) spouse is so important…and extremely hard.
My wife and I have been totally open about money since before we were married, and this has enabled us to jointly make some smart financial decisions. I honestly can’t imagine being in a relationship in which I couldn’t talk about money. That said, I’m not saying the conversations are always easy.

Your financial values will never be the same as your partner’s, and whenever your values differ, there is the potential for tension. The sooner you learn to to talk about your differences and reach compromises, the happier (and wealthier) you both will be.

18. Pay your taxes (and double-check your returns).
Just sayin’.

19. Practicing earning more money is a lot more fun than practicing spending less money.

20. The first dollar is the hardest to earn.
Nine out of ten business/freelance ventures I’ve attempted have failed to earn a single dollar. Then one got off the ground, made some money, grew, made some more money, inspired another idea which made some money, and so on. With persistence, success can be exponential.

21. You don’t have to be a “numbers person” to make smart financial decisions.

22. Being pragmatic doesn’t have to mean being boring.
Back in my spendthrift days, I used to tell myself that being frugal meant being lame. I was all about living for the moment, something boring people who saved their money obviously never did. I’ve since learned that it’s not only possible to enjoy today while saving for tomorrow, life is more fun when you pay in full.

23. Talking about money is more taboo than talking about sex.
Unless, perhaps, you’re with a bunch of personal finance bloggers.

24. Contributing to your 401(k) and/or starting an IRA while you’re still in your twenties is really, really smart.
And it’s not as hard as you think once you learn the basics.

25. Big banks assume their customers are stupid and treat them like crap.
Most of us put up with it for the sake of convenience.

26. When it comes to our economy, the only certainty is uncertainty.
Be prepared for anything.

27. Owning your home (as a financial strategy) is overrated.
It’s okay to rent.

28. Budgeting takes discipline most people don’t have.

29. When it comes to money, most people are ostriches; they have their heads in the sand.
Most people will never regularly read a financial blog. Most people will not make a plan to save for different financial goals. Most people will not take the time to learn even a little bit about investing. Most people won’t even save enough to cover three months living expenses if they lose their jobs. The good news? It doesn’t take much to do better than “most people”.

30. Time is a scarcer resource than money.
Spend it wisely.

So that’s a wrap: 30 years, 30 lessons! What about you—what’s the most important lesson you’ve learned about money in your life so far?


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