Mistakes I Made in My 20s

Who doesn’t love to read about big, juicy mistakes? 

You know the ones. The ones where you can’t stop reading, enticed by needing to know what happens next.

Every. Detail. Brings. It. To. Life. 

Unfortunately, this isn’t that article. 

But, it is an article about regret, hindsight bias, and changes I wish I would have made in my 20s. Of course, this is a reflection of having already known how my 20s turned out. 

It’s easy to look back and wish I had done things differently in hindsight. But, maybe my reflection can help someone think about their own life. 

Or, at the very least, reinforce what is important and help me make the most of my 30s. I have another birthday soon, which means one fewer year in my 30s. 

I’ve previously written about 9 Important Money Lessons from my 20s, but not about my mistakes. Let’s dive into mistakes I made in my 20s. 

Not Buying a House Sooner

I fully admit this one is 100% hindsight bias. Plus, it’s only for the money. That’s never a good reason, but it’s making the list because I want others to know everybody has FOMO, yours truly included. 

If I am being honest with myself, I bought a house at the exact right time in my life. I could more easily afford it, felt responsible enough to maintain it, and actually wanted a house. 

I spent my 20s living in Seattle, which saw astronomical house price increases. We are talking about 10%+ increases per year. 

Some people saw their home prices double in 8 years. 

I remember my former colleague telling me I should buy a house in my second or third year of working. I made my case how home prices historically increase slightly above inflation and how I liked the ease of not needing to maintain anything. 

He maintained I should have bought a home. To this day, he still reminds me of how right he was. 

And, he was right with hindsight, but only in an economic sense. 

If I had bought a home when he told me, I’d probably be around $200,000-$300,000 wealthier. 

That’s tough to swallow, right?

Kind of, but only in a monetary sense. 

The equity would be locked inside of my house. I could have refinanced to get money out, but I likely wouldn’t have. That’s not like me to take on more debt. 

While it would be nice to be that much wealthier on paper, I’d have to sell the house to get the equity out. I may have done that one day, but in the meantime, it wouldn’t have added to my feeling of wealth even though it would have increased my net worth. 

From a non-monetary perspective, there was no way I was ready to own and care for a house in my early 20s. 

I had no interest in doing repairs or even knowing what required repairs! 

My budget would have been tighter, too. I enjoyed my cheap rent with roommates. 

On top of that, I got to see many different types of places and make a list of things I liked, which immensely helped when I started house searching. That was one bright side of moving nearly every single year in my early and mid-20s. 

You have to celebrate the wins among the Uhaul trucks, packing, and unpacking. 

So, is it really a mistake not buying a home early? 

Financially, yes. 

Emotionally and for my well-being, absolutely not. 

That’s why the best economic decision is not always the best decision. 

Not Traveling More

I regret not having traveled more in my 20s. Huge mistake. 

I’m feeling this more and more as I get older. 

COVID hit, making travel much more challenging and more of a headache. My fiancée is in residency, which means we have limited opportunities to travel. My dad also was diagnosed with Stage IV Lung Cancer when I was 25, which made me nervous to go anywhere for extended periods of time for the first couple of years. 

I think finding the time to travel and unplugging from as many responsibilities as possible is only going to become harder, at least until I am much older. 

Don’t get me wrong. 

I’m blessed and privileged. I’ve done a lot of traveling in my life. 

In my 20s, I went to Panama, Greece, Mexico, England, Japan, Vietnam, Thailand, Croatia, and Scotland. 

Before that, I had been to Spain, Poland, Nicaragua, and a few other places. 

But, I still wish I had traveled more – both internationally and domestically. 

I was overly focused on saving and investing. I forgot to enjoy life along the way. 

Although not every trip was lovely, and some certainly came with more issues than others, I have fond memories of them. 

I traveled with friends, former colleagues, a former girlfriend, my now-fiancee, as well as alone. I created memories in all of them. 

Traveling solo through Croatia. It was my first solo trip, and it was different to travel at my own pace. 

Staying in the cliff caves in Santorini in Greece. The views were incredible, and the food was exquisite. Absolutely exquisite.  

Visiting my best friend who moved to England. I loved hearing about the cultural differences and catching up. 

Staying a few days in Japan. I ordered something from a menu having no idea what it was. It was the first time I did that.

Driving on the left side of the road in Scotland. We received some tough news about my dad not being able to continue his immunotherapy, which put a cloud on the trip, but I still enjoyed the unbelievably cold wind and the feeling that we were on the edge of the earth in the Isle of Skye. 

We don’t get more time. We can’t create more of it. We can sometimes buy some of it back, but it’s finite. 

Rarely do people regret traveling. 

I’ve always come back having learned something, eaten something delicious, or had a warm, happy memory to look back upon. 

I usually aimed for one major trip per year, but part of me wonders, what if I had tried for two? 

Would it have taken the magic out of it? 

I don’t know, but I wish I did. 

I wish I had traveled more in my 20s. It’s an opportunity to unplug, create memories, and learn about other ways of living. 

Not Taking All My Vacation Days

This goes along with not traveling more. I was one of those people who wore my not taking all my vacation days as a badge of honor. 

It was a badge of stupidity. 

An even bigger stupidity badge because my vacation days didn’t roll over to the next year. 

Take your vacation days. 

You don’t have to go on vacation. You can stay home. You can rest. You can spend time with friends and family. 

But, take your vacation days. 

I don’t think my not taking vacation days led to any promotions I wouldn’t have received had I taken my vacation days. I don’t think I got paid anymore because I didn’t take my vacation days. 

The only thing not taking my vacation days did was deprive myself of rest and the possibility of new travel. 

Again, we don’t get more time. I was stupid for not taking my vacation days. 

At the end of your life, nobody is going to reward you for not taking your vacation days. There is no grand prize. 

You aren’t going to be on your death bed telling your loved ones, “I’m glad I didn’t take all my vacation days. I’m glad I worked a little more to earn that company a little more profit. I know we didn’t get to travel, and I missed a few key moments in our lives, but it was worth it.” 


Nobody is going to say that. 

Take your vacation days. Live life. 

The promotions will come. The pay raises will appear. The respect from colleagues – well, you’ll get it from the ones who matter. 

Not Continuing the First Financial Blog I Created

Yes, there was an original version of my attempt at blogging about finances. It lasted for a handful of posts, and then I quit. 

I don’t remember what I called it. The writing was terrible. The explanations weren’t great.

But, I wish I had stuck with it. 

I see how other creators often hit their stride in their third or fourth year. I think I started it in 2017, which makes me wonder where I’d be today with it had I not stopped. 

Sometimes you have to pull yourself through the mud of creation. You create the bad stuff, so you can get to creating the good stuff.

I was too worried about what others thought and my own self-imposed idea of perfection. 

It doesn’t have to be perfect. It won’t be. 

Create. Start somewhere. Start before you feel ready. 

Because you will never feel ready. 

I’m still not proud of all the work I produce, but I hit publish anyway.

Do you know why? 

Because it will be better at some point. 

If I don’t hit publish, I lose the continuity. I lose the habit. I create a habit of not creating content.

And at this point, that’s unacceptable to me. 

One blog post every single week. I’ve been doing it for about a year and a half. I love looking back at what I’ve created. 

I have snapshots in time of what I was thinking. I get to see how my thinking has changed.

I even have a few compliments, mostly from friends, thanking me for making financial stuff easier to understand. 

Heck, I know someone in their late 20s or early 30s who used my blog post about a Will at the Thanksgiving dinner table. That was a fun email to read. It made my day.

Despite how proud I am of my little corner of the web, I wonder what the blog would be like if I stuck with it the first time. 

What’s the lesson here? 

Keep going. Keep creating. Even if it’s lousy, continue it. 

Interest compounds, not only financially, but in habits and creating. 

What Mistakes You Don’t See

There aren’t too many financial mistakes here. 

I know you’ll read about other mistakes where people didn’t save for an emergency fund or start investing early. 

I was fortunate enough to do both. 

It’s starting to really compound now, and it’s amazing to see. It felt like nothing for years. It probably will for you, too. 

But, after it reaches a certain point, you feel it. Money makes money. You need enough of it before the compounding can start earning faster than you can save. 

I got term life insurance at the right time. My loved ones are protected if I die. They won’t have to worry about money.

I have disability insurance if I get disabled. I now need to increase my self-employment income, so if I got disabled, there would be a meaningful level of benefits. 

I didn’t speculate while investing. I mostly saved money each month into a 401(k), Roth IRA, and brokerage account. 

I gave myself one or two stupid trades per year with limited money to satisfy the urge to speculate. Investing shouldn’t be fun, and I made sure to separate investing from speculating. 

The financial side of my life is fairly boring. And for most people, that’s how it should be. 

You’re less likely to make mistakes when you have a plan to follow. It may be boring, but it’s working. 

I didn’t buy too much of a house. I didn’t overleverage myself with cheap debt because it was cheap. Even the best strategies can go run with too much debt. 

If your life insurance or disability insurance isn’t in order, focus on those mistakes first. 

Get your investing plan in place. Make an investment policy statement. Create good habits with regular saving and investing. 

Summary – Final Thoughts

I made mistakes in my 20s. 

It’s interesting because almost none of them felt like mistakes at the time. 

Not buying a house didn’t feel like a mistake, and to this day, I still don’t consider much of a mistake when I take into account my well-being. 

Not traveling more also didn’t feel like a mistake. I did my best to travel once a year, and I succeeded in many of those years. I am incredibly blessed for the experiences I’ve had. But, I still feel a tinge of pain having not more fully explored the world. 

Not taking all my vacation days did feel like a mistake at the time. Part of me wanted to take them, but my desire to get ahead won. 

I’m still making the same mistakes. I took a 26-day road trip in the fall of 2021 and should have taken more, but I was too excited to start my new business. 

I haven’t thought much about the first financial blog I created until recently. This one might hurt the most. If I had done what I am doing now, I would have had over 200 blog posts by now. 

I’m learning.

I’ll continue learning. 

That’s the great part about reflection – you take time to understand what you want to change and then you can live your life differently. 

What mistakes stand out in your life? 

Disclaimer: This article is for general information and educational purposes only and should not be considered investment, financial, legal, or tax advice. It is not a recommendation for purchase or sale of any security or investment advisory services. Please consult your own legal, financial, and other professionals to determine what may be appropriate for you. Opinions expressed are as of the date of publication, and such opinions are subject to change. Click for Full Disclaimer