6 Biggest Regrets of My 20s

I am 33 years old.

By my age, Jesus had managed to save the world. Needless to say, I haven’t been quite so productive. I’ve also made more than my share of mistakes in that time, while Jesus made, at last count, zero.

Thankfully, what Jesus did in His time on earth covers the mistakes I’ve made in mine. But that doesn’t mean I don’t regret some of those things. For a long time I lived under the mantra of “no regrets.” Now, I think that mantra is stupid. I regret all my sins, which still have earthly consequences and kept me for a while from living life to the fullest.

It’s wise to learn from your mistakes, but it’s much wiser to learn from the mistakes of others. Then you can avoid doing those things, and get all the benefits of experience without the pain of regret.

So that those who are a bit younger than me can possibly learn from my mistakes, here are the things I most regret from my years as a twenty-something.

1. Never backpacking through Europe.

This is something I always wanted to do, and would have been both fun and educational. The reason I can’t really do it now is because I have a wife and young children and a mortgage and a ministry. It might be a possibility after the kids are grown, but then I’ll be older and it will be harder to do.

I’m not saying that everyone should backpack through Europe. But there are probably things you want to do, and which would be beneficial to do, that are much easier when you are young and have fewer responsibilities. That freedom is one of the benefits of being single.

It wasn't a sin to not go to Europe, but it was getting stuck in a rut of sin that kept me from going.

2. Thinking that the bar and nightlife scene was “life.”

Go out drinking, pick up girls, wake up with a hangover. Wash, rinse, repeat. I was stuck for so long in a rut of sin, thinking that was how to have fun, yet never actually finding any joy there. Even non-believers tend to realize this problem eventually. Life isn’t found in a bottle or a one-night stand.

It wasn’t until after I started hanging out with a group of Christ-followers that I realized what I’d been missing out on. Sin robs you of creativity. I’ve since had much more fun getting to hang out with people I know and truly care about, and doing something new and creative each week: visiting lake houses, going overseas, throwing a three-day party/concert/retreat for a thousand people, or even just meaningful conversations with good friends. Most importantly, real life is found in trusting Christ and living out what you were always created to do.

3. Dating for fun.

This is closely related to the above. I treated dating like a game. “Winning” was getting the pleasure a girl offers without the commitment. There was a lot of drama; a lot of selfishness; and looking back now, a lot of hurt. It wasn't love, though I threw that word around a lot.

Now I’m married, and realize what love really looks like and the joy that comes with it. But because of my dating history, the first couple of years of my marriage were very, very hard. It was misery, when it should have been one of the best times of my life. Spare yourself from that regret.

4. Spending everything I made.

I don’t want to turn this into an investment column, or say that you need to accumulate money. However, we are to be wise stewards of everything God gives us, including money. In my 20s, I spent a lot of money on things like nice cars, watches, and bar tabs. If I had that money back, with interest, it would be a lot of money. It could be a college fund for my kids, or pay to feed and educate kids who otherwise have no hope.

Financial choices early on in your life have a multiplier effect, much more so than when you are older. One of the most valuable pieces of advice I can give to someone in their 20s can be summed up in four simple words: live beneath your means.

5. Forming bad habits.

As you start living on your own and making your own choices, you’re going to develop some habits. I happened to form some bad ones, which included everything from eating junk food to becoming addicted to pornography. And once habits or addictions are formed, they are very hard to break.

You can use that to your advantage, though, by forming good habits that will then also be hard to break. Habits like working out regularly (though not too excessively), sticking to a budget, and studying the Bible each morning.

6. Not taking discipleship more seriously.

Speaking of investing well and forming good habits, I really regret my lack of discipleship when I was younger.

As believers, we are called to both be disciples and make disciples. It’s the best investment you can make, in yourself and in others. It’s helpful to learn while you are young, so you can avoid mistakes like the ones I made. And because of the way discipleship works, you can literally change the world if you just start early enough and remain faithful.

So those are my main regrets. Learn from my mistakes, so you don’t have to repeat them.

What is your biggest regret from when you were younger?

- JP

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