What should one do in their 20s to avoid regrets in their 30s and 40s?

Article Author: Ryan Holiday Created: January 28, 2020 1:33 PM Property: Processed Updated: July 18, 2021 1:57 PM

Your 20s are a paradoxical point in your life. You’re all grown up, yet most people consider you a young person. You’ve come so far, but there’s still quite a long way to go. You’ve learned a lot over the years (or so it seems right now), but so much remains to be discovered. You have more freedom than you’ve ever had before, but what good is all that freedom if you’re just coasting along, feeling unfulfilled and unsure of your next move?

If you’re reading this, you’re probably in your 20s or almost there. You should be excited! If done right, your 20s will be some of the most exciting and enlightening years of your life. You may not find all the answers, but you’ll get started. You’ll overcome obstacles. You’ll learn more about yourself and other people. You’ll grow… a lot.Years from now, when you’re in your 30s, you’ll look back and think about how young and naive you were. It’s inevitable, and it’s not a bad thing. What would be bad, however, would be to look back and wonder what you’ve really accomplished, where all the time has gone, and why you didn’t make the most of those years.

On that note, here are 20 things you should do during your 20s to avoid regrets in the decades to come.

1) Read books. Lots of them.

Reading should be as integral to your daily routine as eating or sleeping. Make time for it. My whole life and career, I’ve been seeking out, reading, and taking notes on books that can teach me things. How to live. How to learn. How to find happiness. How to understand the past. How to prepare for the future. How to succeed. How to manage relationships. How to be a good person. There’s no limit on what you can learn from books, if you know where to look. (For a list of great recommendations, go here.)

2) Quit dicking around.

The books I’ve been fortunate enough to write were not the result of mad sprints of intensity. I get up every day and work on them. One right after another. While I’m waiting for one to come back from the printer, I am hard at work on the next one. Basically, I’m not dicking around. 30 years is so much time. One year is so much time. Wake up every day and do a little more. Dick around a little less. See what happens.

3) Live in New York or Los Angeles (or a city like that).

but not for long. It’s good to test yourself in a big city. It’s good to feel the energy of millions of people coursing through your veins. But leave before you become jaded by it or addicted to it. Leave before it changes your lifestyle.

4) Exercise every day.

Exercise becomes harder over time, and not just because your body starts to age. Getting older means having more things to do and having more people around you who demand your time. Do yourself a favor and make exercise part of your job, part of your duties as a human being, starting now. Let endorphins be something you give yourself every day.

5) Steer clear of the Charlatans and the Toxic.

The real problem with these people is that they steal your time–your most valuable resource–without you even realizing it. Don’t hesitate to eliminate them from your life. You become who you know. You conform to your surroundings. Make sure those two facts are taking you in a direction you want to go.

6) Do it now.

Casey Neistat has a great line: “the right time is right now.” It’s a great mindset to adopt. Let it motivate you to go exercise, to get out of a job you can’t stand, to make a significant lifestyle change. When I moved to a farm, do you know how many people I heard from telling me they’ve always wanted to do that? Let me tell you, it wasn’t a tough vetting process. It’s not like getting into Harvard. If you think you want to do something, do it. Life is short. Why wait?

7) Have a philosophy.

Pete Carroll talks about his turning point as a coach, when he realized he was just winging it. So he stopped and wrote down his entire coaching philosophy. Now he has something to measure himself against. Well, what’s yours? Don’t wing it through your 20s. Focus.

8) Study the lives of the greats.

The dissections of the lives of powerful, ambitious people will teach you so much, and save you some much disaster and heartache and regret. Any fool can learn by experience, I prefer to learn by the experiences of others, is how Bismark put it. The amount of dumb things I’ve managed to avoid because I learned the lesson in advance? Too many to count.

9) Stop wasting time and energy on useless shit.

So many activities that seem “normal” are really just devouring your time and offering you nothing in return. It’s time to replace these bad habits with better ones. How many hours of your life have you poured down the drain playing games on your phone? Delete Candy Crush and pick up a book. What good has fighting with people online done you over the years? If you must vocalize your opinion, do it in a healthy and productive way: Get off Facebook and have a real conversation with someone you disagree with. How much precious time have you wasted being negative? Getting envious or jealous or hating on someone just makes you unhappier.

10) Don’t compare yourself to other people.

This could fit under the “useless shit” umbrella, but this shit is so useless (and insecure and destructive) that it deserves its own section. Thinking about how you stack up against your peers, in addition to being a huge distraction, will leave you permanently unsatisfied. And not unsatisfied in a positive, hungry-for-more way that athletes talk about it. You will be disappointed and miserable. Who cares whether so-and-so did this or that earlier than you? Who cares that so-and-so had more? Measure success on your own terms.

11) Balance out risk-taking and being responsible.

I have a life insurance policy. I have money saved. If something happens to me, people I care about will be taken care of. The reason they will be taken care of and that I feel creatively and professionally satisfied, is that I have taken a lot of big risks. I dropped out of college. I left a good job. I bit off more than I could chew many times. Why could I take those risks? Because I had been responsible. I had money saved. I knew what was important to me. I had built a support network. I eliminated the tiny risks so I could take the right ones. As I said, do the irresponsible things–because it averages out the ultra-responsible choices you made elsewhere.

12) Travel (with purpose).

Nothing has wasted more millennial time than the cult of travel for its own sake. So you’ve been to Africa? And? So you’ve spent a month in hostels in Thailand? Yes? What did you really learn there, that you couldn’t have gotten from some other source? What did you really do? What was the purpose of any of it? Wisdom doesn’t come from going places. Not if you, as Emerson said, “brought ruins to ruins.”

13) Remember the law of diminishing returns.

For instance with travel — it’s great, but two years of backpacking through Europe is two years of your life. Who is to say you have that much time? Chances are, at some point, you extracted most of the value of whatever it is you’re doing, but you’re just coasting now. A year in New York can be transformative, ten years will ossify you. Be willing to call things when the diminishing returns set in, it’s how you move on when others are stuck.

14) Design the ideal day.

So many people have big goals for the future. I think it’s better to know what your perfect day looks like. Then you can ask yourself with each opportunity and choice: Is this getting me closer or further away? I know my ideal day and more importantly, I know when I have gotten too far from it. Life is too short to not live the way you want.

15) Take notes.

It’s very easy for learning to go in one ear and out the other. Making a concerted effort to record and process what you’re observing and being taught helps prevent that. If you read a lot, take notes on what you read and transfer those notes into a commonplace book, where you can organize your thoughts. Repeating and reiterating what you’ve learned helps make connections and improve memory. Organizing it into a system means it will be so much easier to retrieve when you need it. It might seem time consuming at first, but it will save you loads of time later on. Trust me.

16) Have a to-do list every day.

Every day have a to-do list. Even on the weekends. Not to drown yourself in work, but so you can always be moving forward. Check the stuff off, don’t wing it.

And while you’re taking a bit of time out of each day to write something down…

17) Keep a journal.

Not for looking backward, but to force you to think about what you’re doing now. I should have done this earlier.

18) Do whatever you want.

Doing what’s “comfortable” and “normal” is easy, but you’ll regret it when you get older. That Steve Jobs line about how the rules were made up by people no smarter than you. Make sure you’re not conforming to needless constraints about how to dress, how to live, what’s important, how things must be done. The more value you deliver in life, the more freedom and power you have.

19) Meditate on your mortality.

A weird thought occurs to me from time to time. When I am on a plane and the turbulence hits, when a car veers out into traffic, when I hear about someone I know who died suddenly: I don’t get scared. I just think, “If this is it, alright.” This might seem morbid to say that I’d e happy going at any moment, it’s actually a wonderful way to live. It’s something I feel quite lucky to be able to say. Don’t shy away from thinking about death. Think about it a lot. I like this line from Marcus Aurelius: “Are you afraid of death because you won’t be able to do this anymore?” For “this” plug in so much of the crap we waste our time with.

20) Get the big things right.

There’s the old Benjamin Franklin line about being a penny wise but a pound foolish. It’s the same thing with time management.

The famous journalist HL Mencken once said, “Looking back over a life of hard work… my only regret is that I didn’t work even harder.” If you can echo this sentiment at the end of your 20s, you’ll be light years ahead of most people your age. Enjoy yourself, but have a sense of urgency. Take advantage of your youth, but also of your maturity.

It’s on you to make good use of your precious time on this planet. If you haven’t done so in the past, start now. It’s not too late to start making better decisions, but you aren’t getting any younger.

Hell, you’re almost 30.

The clock is ticking. Good luck!

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