The Best Investments You Can Make in Your 20s

From your health and confidence to experiences and everyday habits, these are the investments that pay you back for years.

By
Josh Felgoise

Timothee Chalamet

When you're in your twenties, everyone seems to have an opinion about what you should be investing in.

Open social media and you'll see people talking about index funds, retirement accounts, real estate, and side hustles. Open YouTube and someone will tell you the five purchases that changed their life or the products every successful person owns. None of that advice is necessarily wrong, but I think it misses something important.

Some of the best investments you'll ever make don't show up in your bank account.

They show up in your confidence. Your routines. Your relationships. Your health. The way you spend your mornings. The way you feel walking into a first date. The way you look back on your twenties years from now.

When I was putting together this week's Guyset episode, I thought I was making a list of products I thought were worth the money. But the more I talked through each one, the more I realized they weren't really about the products at all. They were about what those purchases had given me in return.

Here's something important:

"A lot of these things improve your life because it improves... they improve the way you think about yourself. And they make you feel better about yourself."

That became the idea that tied everything together.

Looking back, the purchases that have genuinely improved my life weren't the most expensive ones. They were the ones that quietly removed friction from my day, helped me build better habits, or made me feel more like the person I wanted to become.

Invest in Your Confidence Before You Think You Need To

Confidence is one of those things people talk about as if you're either born with it or you're not.

I don't think that's true at all.

Most confidence is built gradually, and it's usually built through small decisions that reinforce how you see yourself.

You start taking better care of yourself, you put a little more effort into how you dress, you develop routines that make you feel prepared, and over time you stop second-guessing yourself as much.

One of the examples I talked about during the episode was grooming. On the surface, buying a quality trimmer or finding a good cologne doesn't sound life-changing. They're small purchases, and they're certainly not the first things people think of when they hear the word "investment."

But I've found they often have a much bigger impact than people expect.

"When you clean up or when you feel good about the way you look, it kind of affects everything in your life. It really does. And it affects it more than you would probably think too."

I think that's because confidence isn't built during the date, the interview, or the big meeting. It's built beforehand.

It's built when you leave your apartment feeling like you've put your best foot forward. It's built when you stop worrying about whether your clothes fit well or whether you remembered to shave. Those thoughts disappear, which gives you more space to focus on the people around you instead of yourself.

That's also why I've written about How to Dress for a First Date. The goal isn't to impress someone with expensive clothes. It's to remove one more thing that could distract you from actually enjoying the conversation.

The same idea applies to buying a good bottle of cologne. It might feel expensive the day you buy it, but if you wear it for three or four years, suddenly it becomes one of the cheapest purchases you've ever made on a per-use basis. More importantly, it becomes part of your routine, and routines have a funny way of shaping how we see ourselves.

Invest in the Things You Use Every Day

One pattern I've noticed is that the purchases I appreciate the most aren't the ones I'm excited to tell people about.

They're the ones I barely think about anymore.

The frying pan I cook with almost every night. The pair of jeans that always fits the way I want it to. The sheets I climb into at the end of a long day. None of those things are particularly exciting, but they all make everyday life just a little bit better.

To me, that's one of the best indicators that something was worth buying.

The purchase fades into the background, but the benefit doesn't.

Style experts at GQ often recommend building your wardrobe around a few timeless staples instead of constantly replacing cheaper, trendier pieces. I think that philosophy extends well beyond clothing. Whenever you're buying something you'll use hundreds of times, quality matters more than people often realize.

The same is true throughout your apartment.

That doesn't mean buying the most expensive version of everything. It means recognizing that there are certain purchases you'll interact with almost every single day. Those are the places where spending a little more often pays you back for years.

Invest in Anything That Gives You More Time

One of my favorite investments has almost nothing to do with the product itself.

It's TSA PreCheck.

Nobody enjoys standing in airport security lines, and nobody looks back on a trip thinking, "I'm really glad I spent an extra forty-five minutes waiting to take my shoes off."

"Time is the only resource that we can't get any of back. And that should be enough of a reason for you to get TSA PreCheck."

The more I thought about it, the more I realized that idea extends far beyond airports.

The purchases that save you time often become the purchases you value the most. Sometimes that's TSA PreCheck. Sometimes it's a better pan that makes cleanup easier. Sometimes it's a product that simplifies your morning routine or removes a small frustration you deal with every day.

When I think about the best investments I've made in my twenties, that's become one of the questions I ask most often.

Will this make my life easier tomorrow?

Will it still make my life easier a year from now?

If the answer is yes, it's probably worth taking seriously.

Invest in Experiences While You Have the Freedom To

One of the biggest surprises I've had in my twenties is realizing that the purchases I remember most aren't products at all.

They're experiences.

A concert with friends.

A weekend trip that came together at the last minute.

A dinner where everyone stayed long after the plates had been cleared because the conversation was too good to end.

Those moments have stayed with me far longer than almost anything I've ever ordered online.

"I've never regretted spending money on a concert. I've never been like, I shouldn't have gone to that."

The reason isn't just that concerts are fun.

It's that they begin long before you walk through the doors. You buy the tickets weeks or months in advance, you talk about them with your friends, you count down the days, and you spend time looking forward to them. Then afterward, you carry those memories with you for years.

That's something most material purchases simply can't do.

Researchers writing for Harvard Business Review have found that experiences often create more lasting happiness than material possessions because they become part of our identity and are frequently shared with the people around us. Looking back on my twenties so far, that feels exactly right.

I've forgotten plenty of things I've bought.

I've remembered almost every concert, trip, and great night with friends.

I also think your twenties are one of the best times to prioritize those experiences. Responsibilities have a way of growing as you get older. Careers become more demanding. Families begin. Schedules get fuller. That's not a reason to spend recklessly, but it is a reminder that you won't always have the same flexibility you do today.

Some of the best investments you can make aren't things you'll keep on a shelf.

They're stories you'll tell for the rest of your life.

Invest in Habits That Make Every Day Better

When people think about investing in themselves, they often imagine one big decision that changes everything.

In my experience, that's rarely how it happens.

Life usually changes because of small habits you repeat over and over again.

That's one of the reasons I believe a gym membership is one of the best investments you can make in your twenties.

It isn't just about getting stronger or looking better.

It's about creating a routine that positively affects everything else you do.

During the episode, I talked about how I used to tell myself I'd work out after work. Almost every evening, something got in the way. I'd be tired, I'd have dinner to make, I'd want to meet up with friends, or I'd simply lose the motivation I'd had earlier in the day.

Eventually, I stopped trying to fit the gym into my schedule and started building my schedule around the gym.

That one decision changed far more than my workouts.

It gave my mornings structure.

It gave me somewhere to be.

It made me feel like I'd already accomplished something before most of the day had even started.

I've written more about this in How Do You Build Confidence at the Gym (And Stop Feeling Intimidated)?, because consistency usually isn't about finding more motivation. It's about creating an environment where the right choice becomes the easy choice.

The same philosophy applies to other parts of your life.

A notebook you actually enjoy writing in makes it easier to plan your day.

Good cookware makes you more likely to cook at home.

Comfortable sheets make you look forward to getting enough sleep.

None of those purchases are life-changing on their own.

Together, they shape the routines that define your everyday life.

The Best Investments Compound Quietly

One thing I've noticed is that the best investments rarely feel dramatic in the moment.

You don't buy a quality pan and suddenly feel like a different person.

You don't join a gym and wake up confident the next day.

You don't book one trip and instantly become happier.

The return comes slowly.

Almost quietly.

You cook more often because it's easier.

You work out because it's become part of your routine.

You feel more comfortable in your clothes because you've invested in a few pieces you genuinely like wearing.

Months later, you look back and realize your life feels different.

Not because of one massive decision.

Because of dozens of small ones.

That's what investing in yourself actually looks like.

And Here's The Thing

Your twenties are full of decisions about where your money should go.

Some investments will grow your bank account.

Others will grow you.

Looking back, the investments I'm most grateful for aren't necessarily the ones with the biggest price tags. They're the ones that helped me build better habits, become more confident, spend more time with people I care about, and create a life I genuinely enjoy living.

That's why I don't think the best investments in your twenties are just financial.

They're personal.

They're the purchases that remove friction from your day.

They're the experiences that become lifelong memories.

They're the habits that make tomorrow a little bit easier than today.

Those are the investments that continue paying you back long after you've forgotten what they cost.

Frequently Asked Questions

What are the best investments to make in your 20s?

Some of the best investments include your health, your confidence, your relationships, and your daily habits. Financial investments matter too, but investing in yourself often creates benefits that influence every area of your life.

Should I spend money on experiences in my 20s?

If they're within your budget, experiences can be some of the most rewarding investments you make. Concerts, travel, and meaningful time with friends often create memories that last much longer than material purchases.

Is a gym membership worth the money?

For many people, yes. A gym membership can improve your physical health, mental health, energy, confidence, and daily routine, making it one of the highest-return investments you can make in yourself.

What everyday purchases are worth spending more on?

Items you use regularly, like quality clothing, cookware, bedding, or products that simplify your routine, often provide better long-term value because you'll benefit from them almost every day.

How do I know if something is a good investment?

A helpful question to ask is whether it will continue improving your life months or even years after you buy it. If it saves time, builds confidence, strengthens relationships, or helps you develop better habits, it's often a worthwhile investment.