I like to joke that I am who I am today because I did everything wrong in my 20’s. I’ve always been fearless, and it often got me in trouble. I wasn’t afraid to start a business, borrow a bunch of money, or quit a well-paying job to travel the world.

At the same time, the fact that I took chances (and often failed) gave me the wisdom that I have today. Lessons learned through failure tend to be much more meaningful than lessons learned otherwise.

Now that I’m in my 30’s, life is pretty good. While I haven’t learned it all, I feel my head is screwed on straight enough that life is much less stressful. I’ve come into my own and built the foundation for a secure and prosperous future.

Even though things are going well, I often imagine what it would be like to go back into the past and teach myself what I know now. I know enough to be certain that I lost most of my twenties to a struggle with debt and poor decisions. If I had done things differently, maybe I could have been where I am now at age 22.

Could you imagine? Self employed and almost financially independent at age 22? No… not almost. My expenses were much less back then… I would have been financially free!

I know, it doesn’t do any good to ask what if. If I had known it all at age 22, I probably would have been a little cocky. Doing things the hard way seasoned my character. I like who I am and I wouldn’t change a thing.

But what if…

What I’d Tell Myself at 18

Sometimes I imagine that I’m in a fishing boat, thousands of miles away from the life I know, slowly drifting across a lake. As I recline at an uncomfortable angle created by the wood bench and aluminum hull, I glance over at the 18 year-old version of myself and upload my wisdom to him.

Here’s what I say:

Don’t be so Serious

Relax… You’ve got your whole life ahead of you. I know it can seem like the most important thing in the world is fighting the good fight, but don’t let your life pass you by in the process. There’ll be plenty of time for starting businesses, writing books, creating art, and solving the world’s problems in your head.

It’s impressive that you do those things at such a young age, but life is really about experiences. Above all, it’s about sharing experiences with other people. Sometimes when you’re all wrapped up in your own head, doing the things that you are determined to do, you miss a chance to connect with other people.

So take it easy. Have some fun. Do something crazy. Let loose. Call up some friends and share some great moments together.

Don’t Be in Such a Hurry to Grow Up

A funny thing happens as you age: The older you get, the less of a hurry you’re in. You’d think it would be the other way around: the less time you have, the more of a hurry you’re in; but it’s actually quite the opposite.

At 18, it seems like you have to rush everything before you get too old. You think you have to graduate college, get a good job, and get married before you turn 22, because (for some reason) you think 22 is old.

Don’t take being young for granted! Being a kid without responsibility is a thing of beauty. I know you don’t appreciate it now, but you will when you’re my age.

22 is just getting started! In fact, life gets more enjoyable as you age. As you learn more about yourself and the world, it gets easier to enjoy what the world has to offer.

Your 20’s are the perfect time to explore the world and experience new things. If you grow up before you turn 22, you’ll have missed a perfect opportunity. Experiences at 18 are just not the same as when you’re 25.

Travel, art, culture, sport, and adventure take on a whole new meaning when you have had some experience to build on. As you add layer upon layer, each experience is more rich than the last.

Choose Experience over Material Possessions

If you’re ever faced with the choice of upgrading your lifestyle (an apartment by yourself, a new car, new clothes, etc.) or working less so you can experience more; chose the latter.

When I was your age, I thought I needed to have nice stuff so girls would like me. I ended up working so hard to pay for the stuff that I didn’t have time to meet girls.

Working hard is for grown-ups. Be a kid for as long as you can, even if it means living with a roommate in a crappy apartment and riding your bike around town.

Besides, girls aren’t going to like you for awhile anyway. What they really want is a man with a little confidence and life experience under his belt. Working too hard will just delay that process.

Be Confident

Oh yeah, you might as well get a head start on your confidence. Believe in yourself no matter what. Don’t let self-doubt ruin your chance to meet a new girl or to try something new.

I know I just said that girls aren’t going to like you anyway, but that’s not entirely true. While you are accumulating the wisdom that comes with life experiences, your best shot is to project confidence.

Always act like you know what you’re doing, even if you don’t. The biggest turn-off for a girl is self-doubt. If she still doesn’t like you, take it with grace and move on quickly.

Don’t start doubting yourself if you get turned down. You’re going to get turned down A LOT before you finally get the girl.

Don’t Get Attached

When you finally do get a girlfriend, take it easy. Along the same line as not trying to grow up too quickly, don’t fall into the trap of thinking that this is the best girl you’ll ever get. The second biggest turnoff for a girl is an 18 year old guy who’s already thinking about marriage.

Relax a little and enjoy the moment. Besides, you’re going to have several girlfriends before you find “the one.” How are you going to be able to know what you want if you don’t have anything to compare it to?

As you get older, you’ll naturally become more attractive to women. I had no idea this was true when I was your age. I thought that I was as attractive as I’d ever be. Not true.

It gets easier, I promise.

Don’t Get a Credit Card

If I didn’t get a credit card when I was your age, I would have saved myself 10 years of financial struggle.

I know it seems like you have to be a grown up and have nice things, but you’ve got to think long-term. If you can just have the patience to hold off a few years on the nice stuff, you’ll be able to afford more of it than you can imagine.

Buying something today on credit because you can’t wait will impact your financial situation for years to come.

Simply have the mind to save up for what you want to buy. If you buy with cash, you’ll always own what you have, and be free to do what you want.

When people build up debt and monthly payments, they become slaves to their job. They have to work to pay for all the junk that they put on their credit cards.

Put Money Away Every Month

Take this advice and you’ll never regret it. Open a savings account and set up an automatic withdrawal from your checking account each month. Don’t touch the money, NO MATTER WHAT!

Even if you can only afford $10 a month, you must stick to this plan because it’s your ticket to freedom. In five or ten years (whenever you decide to grow up), you’ll use this money to invest in something that makes passive income, like real estate.

Travel and Learn a Language

One of the wisest decisions I ever made is to live in another culture long enough to learn the language. (Read The Secret to Learning a Language for detailed instructions.)

Don’t just take language classes and backpack around Europe at a furious pace; immerse yourself in a culture. Pick a place and stay there for several months.

The best time to do this is the year after you graduate from college. You’ll be old enough to appreciate the experience, but young enough that you won’t have any responsibility.

If you took my advice about taking your time to grow up, you won’t yet be attached to a mortgage payment, a job, or a girl. Move all your stuff into a corner of your parent’s basement and live abroad.

It’s actually a lot more affordable that you might think, especially if you don’t have any expenses at home. Get a job in your chosen country if you need to.

Don’t allow yourself to hang out with other English-speaking people. That’s too easy. Force yourself to learn the language. It will be frustrating at first, but the life-long benefit will be greater than you can imagine.

Keep a Journal

Get a Moleskine Notebook and carry it in your back pocket wherever you go. Don’t be a perfectionist with it, just jot whatever comes to your mind in it.

Having a journal will help to solidify your thoughts. The act of writing helps to close the circle of ideas from your head to your hand and back to your head.

Plus, you’ll have a record of your thoughts for generations to come.

Get to Know People

As you travel and try new things, make it a point to meet people. As I said before, the most valuable things in life are shared experiences with other people.

There is so much you can learn from people. Open your mind and take in different perspectives. Put yourself in their shoes and try to understand why they think the way they do.

Your success in life will depend on your network of people. It’s impossible to achieve success in a vacuum. You never know what opportunities will present themselves when you meet new people.

There’s No Rush to Have it All Figured Out

When I was your age, I felt pressure to have my life’s purpose figured out. I think a lot of young people think there’s something wrong with them if they haven’t “found themselves” by age 22.

Most people don’t figure things out until much later in life (if at all). That’s what your twenties are for: exploring different paths, making mistakes, falling on your face, and building your character.

Take your time figuring it all out. You don’t want to rush such a grand decision as your life’s purpose.

Savor the Moment

Experience the textures, sights, sounds, and feelings of each moment. Time moves faster than you think. Your youth is special and you’ll want to remember it for the rest of your life.

Start Businesses Without Borrowing Money

When you decide to start a business, don’t go into debt over it. Most businesses fail, and it’s better to be left with nothing than to not have anything and still owe someone else money.

Pick a business that doesn’t cost much to start and grow slowly, reinvesting your earnings.

Choose a business that’s as passive as possible. Bulk vending is a good one to start with while you’re young.

Stay away from services. I made the mistake when I was your age of starting a T-shirt design service. The problem with services is that you have to re-create your work if you want to get paid again. Find something that pays you over and over for work done once.

Pick Something and Stick With It

Once you’ve had your fun traveling the world and being young, find a line of work that you are passionate about. Don’t worry about the money, that will come with time. As long as you are out of debt and putting money into savings each month, you’re going to be just fine.

Don’t get into the habit of changing your mind all the time. Each time you change course, you lose all your start-up energy. Learn how exponential growth can affect your level of success in your chosen field.

If you are passionate about what you do, and stick with it, you can’t help but be successful.

Back to Reality…

It’s fun to think about what might have been, but in reality, we can’t change the past. Ten years from now, I’ll have a whole new list of things I wish I knew in my 30’s. I would do well to take my own advice, and enjoy each moment.

(Featured photo by Mark Fischer)