Things I Wish I'd Known at 25, From a Guy in His Thirties

Things I Wish I'd Known at 25, From a Guy in His Thirties

Jake Holden||11 min read

I turned 34 last month. I celebrated by going to dinner with my girlfriend, having two glasses of wine, being in bed by 10:30, and sleeping nine hours because my body now treats staying up past 11 like a personal insult. It was a great birthday. At 25, I would have called it pathetic. At 34, I call it peak performance.

That gap -- between who I was at 25 and who I am now -- is the most interesting thing about getting older. Not because I've become some enlightened sage who meditates at dawn and journals about gratitude (I don't, though I probably should). But because I can see, with painful clarity, all the things I got wrong, all the time I wasted, all the lessons I had to learn through expensive trial and error when they were available for free the entire time.

I'm not going to pretend this list is comprehensive or universal. Your twenties are different from mine. But these are the things that, if I could send them back in time to 25-year-old me via some kind of temporal advice delivery system, would have saved me money, time, heartache, and at least one truly regrettable haircut.

Your Salary Is Not Your Wealth

At 25, I got my first "real" paycheck and immediately spent it like I'd won something. New apartment. New furniture. Dinners out four nights a week. Clothes I didn't need. A subscription to every streaming service that existed. I was making 52,000ayearandspendingapproximately52,000 a year and spending approximately 52,000 a year, and I felt rich because money was coming in, not realizing that money was also leaving at exactly the same rate, like a bathtub with the drain open.

Here's what I wish I'd understood: your salary is the money that flows through your life. Your wealth is the money that stays. And at 25, almost none of it was staying. I had a 401(k) that I was contributing the bare minimum to (3%) because my company matched it and someone in HR told me to. Beyond that, I had a savings account with about $800 in it and a vague sense that "I'll start saving seriously later."

"Later" is the most expensive word in personal finance. Every dollar I didn't invest at 25 would have been worth roughly $7 at retirement, thanks to compound interest. Every year I delayed contributing seriously to my retirement account cost me tens of thousands of dollars in future wealth. I'm not saying you need to live like a monk in your twenties -- please don't, your twenties should be fun -- but the gap between "spending everything" and "saving 15-20% while still having a great time" is smaller than you think, and the long-term difference is enormous.

If I could go back, I'd max out my 401(k) match from day one (free money that I almost left on the table), set up an automatic transfer of 15% of every paycheck into savings/investments before I could touch it, and learn to live on what remained. Which, honestly, would have still been plenty. I didn't need four streaming services. I didn't need dinner out four nights a week. I needed a system that made saving automatic and spending intentional.

Nobody Cares About Your Career as Much as You Think

At 25, I was convinced that everyone at my company was watching my career trajectory with great interest. I worried about what my boss thought of me. I agonized over performance reviews. I stayed late to demonstrate "commitment" even when I had nothing to do, because I thought being seen at my desk at 7 PM communicated something important about my character.

Here's the truth that would have saved me hundreds of hours of unnecessary stress: nobody at your company is thinking about your career. Your boss is thinking about their boss. Your colleagues are thinking about their own lives. The CEO doesn't know your name. You are one of hundreds or thousands of employees, and your presence at the desk at 7 PM is noticed by approximately zero people.

This isn't depressing -- it's liberating. Once you realize that nobody is watching, you stop performing and start being strategic. You focus on doing excellent work during work hours instead of doing mediocre work during extended hours. You invest in skills that are portable -- that make you valuable everywhere, not just at this one company. You take risks (apply for that stretch role, pitch that idea, ask for that raise) because the downside of failure is way smaller than you imagine when you think everyone is paying attention.

The best career advice I got in my twenties was from a director who told me: "No one's going to manage your career for you. HR won't do it. Your manager won't do it. You have to do it yourself." He was right. I just wish I'd listened three years earlier.

Your Body Is Not Indestructible (Start Acting Like It)

At 25, I ate like a raccoon, slept five hours a night, drank four nights a week, and exercised when I felt like it (which was rarely). I could do this because at 25, your body is running on factory settings and factory settings are generous. You can abuse the machine and it keeps performing.

Then, somewhere around 28, the warranty expired.

My back started hurting. Not from an injury -- from years of sitting in bad chairs with bad posture. My energy levels dropped. Not because of a medical condition -- because of years of bad sleep and worse nutrition. I started getting headaches every afternoon. Not from stress -- from dehydration, because I drank coffee all morning and nothing else until dinner.

Every single one of these problems was preventable. Every single one of them was caused by habits I'd been building since 25 without consequence. The consequence just arrived on a delay, like a credit card bill for years of physical neglect.

Here's what I'd tell 25-year-old me: start exercising regularly now, even if you feel fine. Lift weights -- it builds bone density and muscle mass that you'll lose starting in your thirties if you don't maintain it. Drink water. An embarrassing amount of how you feel on a daily basis is determined by hydration. Sleep seven to eight hours. I know you think you're productive at 1 AM. You're not. You're just awake. Fix your posture. Sit properly. Stand up every hour. Your 35-year-old back will thank you with every pain-free morning.

Most of Your Friendships Need Active Maintenance

In your early twenties, friendships happen automatically. You're in college or you just moved to a city and you're going out constantly and you accumulate friends the way a sweater accumulates lint -- passively, by proximity, without effort. You see the same people at the same bars and at some point you're friends.

Around 25-27, that stops. People get into serious relationships. People move. People get busy with careers. The passive friend-accumulation machine breaks down, and if you don't replace it with active effort, you'll wake up at 32 with a group chat full of guys you used to see weekly and now see twice a year.

I let several friendships that mattered to me atrophy in my late twenties because I assumed they were self-sustaining. They weren't. By the time I realized it, rebuilding them required significantly more effort than maintaining them would have.

The fix is simple but requires intention: be the person who makes plans. Text first. Suggest the hangout. Don't wait for someone else to organize it. Most people aren't drifting away because they don't want to see you -- they're drifting away because both of you are waiting for the other person to initiate, and neither of you does, and weeks become months become years.

Also -- and this took me way too long to learn -- it's okay to make new friends in your late twenties and thirties. Join a sports league. Take a class. Say yes to invitations from people you kind of know. Adult friendships require the same vulnerability as dating: you have to put yourself out there and risk rejection. It feels awkward at 30 in a way it didn't at 20, but the friendships you build intentionally are often deeper than the ones you fell into by accident.

Stop Buying Stuff, Start Buying Experiences

I spent a truly embarrassing amount of money on things in my twenties. A TV I didn't need (the old one was fine). Sneakers I wore twice. Tech gadgets that seemed essential for about a week. Clothes that were trendy for one season. Every single one of these purchases gave me a brief dopamine hit followed by complete indifference.

Meanwhile, the things I look back on fondly -- the road trip to Big Sur with three friends, the weekend we rented a cabin in the mountains for someone's birthday, the time we drove five hours to see a concert in a city none of us had been to -- cost the same or less than the stuff I bought and forgot about.

Research backs this up: spending money on experiences makes people happier than spending money on things. Experiences become part of your identity. They generate stories. They connect you to other people. A 200concertwithfriendsisamemoryyoullhaveforever.A200 concert with friends is a memory you'll have forever. A 200 pair of shoes is in the back of your closet in six months.

This doesn't mean never buy things. It means shift the ratio. Spend less on stuff, more on doing things. Your future self will remember the camping trip. He will not remember the fourth pair of sneakers.

Learn to Cook. Actually Learn.

I mean learn five to ten meals that you can make well, from memory, without a recipe. Not "I can microwave things" and not "I follow a recipe sometimes." Actual cooking. The kind where someone comes over and you make dinner and it's good and they're impressed and you feel like a functioning human adult.

Cooking saves money (dramatically -- eating out is 3-5x the cost of cooking the same meal). Cooking is healthier (you control the ingredients). Cooking impresses dates (I cannot overstate how much mileage I've gotten from being able to cook a decent pasta and a pan-seared salmon). And cooking is genuinely enjoyable once you get past the initial learning curve where everything takes too long and nothing turns out right.

I started learning at 28 and I wish I'd started at 22. By 25, I could've been the guy who hosts dinner parties. Instead, I was the guy who suggested ordering DoorDash at every gathering. Don't be that guy.

Your Mental Health Is Not a Side Quest

At 25, I thought therapy was for people with "real problems" -- meaning problems bigger than mine. I was stressed, sleeping badly, occasionally anxious in ways I couldn't explain, and generally operating at about 70% of my capacity, but I figured that was just what life felt like. Doesn't everyone feel this way? Isn't adulthood just low-grade exhaustion with occasional highlights?

No. It's not. Or at least, it doesn't have to be.

I started seeing a therapist at 29, and within six months, I understood patterns in my behavior that I'd been blind to for a decade. Why I procrastinated certain things. Why certain conversations triggered outsized anxiety. Why I defaulted to sarcasm when I was actually hurt. None of it was earth-shattering revelation. It was just... useful. Like finally reading the user manual for my own brain.

Therapy isn't mandatory. But if you're living with a vague sense that things could be better and you're not sure why they aren't, talking to a professional is the most efficient way to figure it out. It's not weak. It's not dramatic. It's maintenance. Same reason you take your car to a mechanic -- not because it's broken, but because regular maintenance prevents breakdowns.

The Summary I Needed at 25

Save money before you spend it. Nobody's watching your career -- take risks. Take care of your body before it forces you to. Maintain your friendships actively. Spend money on experiences. Learn to cook. Talk to someone about your mental health.

None of this is revolutionary. All of it is stuff I'd heard before and ignored because I thought I had time. I did have time. I just used it on things that didn't matter as much as I thought they did.

For the specific money stuff -- the tactical, numbers-based advice on how to stop being broke in your twenties -- I've written about that separately. And if you want to start rewiring how you think about building wealth, these 10 books about money are the ones that changed my perspective the most.

You're 25. You've got time. But time is less infinite than it feels. Start now.