11 Things I Wish I Had Told My 20 Year Old Self

My 20’s were much like the feelings you get from riding a roller coaster for the first time ever.

Thrilling, euphoric, memorable, terrifying and ultimately… gone way too fast.

At 20 I was a broke college kid who partied five nights a week, delivered pizzas and somehow pulled off A’s and B’s in school.

At 23 I was still broke (but a college graduate) and my lifestyle had finally caught up with me.

Sound familiar?

My goal was always to graduate, but I never gave much thought to what should come next…

I had no money, no goals, and no plans for my future… just a pointless bachelor’s degree.

I felt worthless, and I was more than a little bit pissed off.

But I knew I could change it if I put my mind to it and took massive action.

So I packed my life in my car and moved to Arizona, a city where I knew no one and nothing except the simple fact that I was capable of far more than the level where I resided… I knew I was capable of more but first I had to drastically change my life.

Now, nearly a decade later and just past my 30th birthday, I can say without a second of hesitation that that move was the best decision of my life.

Since moving I built a six-figure career at a great tech company (which I recently quit to pursue my passions), bought a house, published two books, started a blog, and began my writing career.

I would never have guessed the 23-year-old burnout could turn his life around so drastically in such little time.

How did I do it?

Hard work, calculated risks, creating new habits and some good luck.

Ultimately I could have created success much quicker had I known what my goals were instead of just graduating and hoping for the best.

And while setting goals and having a clear plan of action is certainly one of the first things I would have told my 20-year-old self, there are a few more items I would like to add to the list.

And here they are…

1) Invest In Yourself

At 20-years-old it’s easy to think that you know it all and believe that you are invincible.

Trust me, you don’t and you aren’t…

You are just starting your life and won’t believe how much things will change in the coming decade.

As you head into your twenties you should spend as much time as you can learning and investing in yourself.

 “Invest in as much of yourself as you can, you are your own biggest asset by far.” – Warren Buffett

I don’t mean learning like you did in school.

I’m talking about learning about yourself, what you like, don’t like, and finding out what you are passionate about.

If you can discover and create yourself in your early 20’s and develop a deep intimacy with your inner voice, you will be much more likely to:

  • Enjoy your work and career instead of being part of the 80% that hates their job.
  • Make a lot more money because you like what you do for a living.
  • One of the best ways to invest in yourself is to read everything.

Pick from biographies, psychology, personal development, relationships, fitness, or any other topic that interests you.

Unlike your time spent (or wasted) in high school and college, your early 20’s are a time where you get to learn about what you want, not what’s required.

If you’re not a huge reader you can still invest in and educate yourself in a number of different ways…

One of the main reasons people feel lost in their twenties is because they think learning is done once school is over.

It’s not, it’s only just beginning.

2) Learn How to Sell


One of the biggest lessons I learned in my twenties was the importance of being able to sell.

I’m not talking about just selling over the phone or in person at your job.

I’m talking about being able to sell yourself.

When you’re young it’s easy to have a fear of selling because there is always a chance of rejection. (Plus, no one wants to feel like they are working for Ben Affleck in Boiler Room)

But selling is nothing more than communicating well with others.

Why do you need to learn to sell?

Because everyone is being sold something every single day.

By learning to sell in a job or selling yourself you will be able to talk to strangers and give yourself unlimited options.

When you are great at selling, you are comfortable asking for a raise, meeting new people and not being afraid to talk to a girl in any situation.

The best way to learn how to sell?

Just try it, a lot.

“You don’t have to be great to start, but you have to start to be great.” – Zig Ziglar

After working in national sales for most of my twenties I learned that selling is simply a numbers game. No one has a 100% close rate on anything in life.

Some areas will yield higher closing ratios but rejection is part of life, so don’t fear failure, embrace it (more on that later.)

The more you fail the more you learn.

Eventually, you’ll get to be such a good communicator that nothing is impossible.

So don’t be afraid to put yourself out there. Call the client you are afraid of or talk to the girl who you think is too good for you.

The only way to become great at selling anything is through experience.

3) Health is Wealth

Your twenties are the easiest time to ignore your health, fitness, and proper nutrition.

After all… Your metabolism makes up for all of those late night drinks and happy hours.

But if you don’t get started exercising and eating right it will make it even harder when you’re in your thirties and forties.


Exercise and proper nutrition will bring about a plethora of benefits into your life that extend beyond simply looking good naked.

When you exercise and eat healthily you will:

  • Have more mental energy
  • Produce more testosterone
  • Have more confidence

The key is making exercise a consistent, daily activity.

You want to make working out, running, biking, or whatever activity a part of your routine.

Carve out at least an hour per day to exercise in some way.

But as important as working out is it is only part of the fitness equation.

In fact, I would say that your exercise regimen is responsible for less than 30% of your results in this area of your life.

The other 70% comes directly from how you fuel your body.

If you can learn how to cook and meal prep when you are 20 you will be ahead of 90% of the male population. You will also save money by not eating out and you will also discover the unintended benefit that… chicks dig a guy who can cook.

“The best activities for your health are pumping and humping.” – Arnold Schwarzenegger

You don’t have to be a five-star chef, just learn how to create a few staples and build upon your skills as you get older.

Every man should know how to fire up a grill, cook a filet mignon and entertain girls, friends, and family. Check out videos on Youtube or cookbooks on Amazon to get started.

By focusing on exercise and eating right you will look better, save money, have more energy, and a higher sex drive.

4) Appreciate and Make the Most of Your 20’s

Understand that when you turn 20 you are heading into the decade people love the most in their entire lives.

Appreciate it and don’t take this decade for granted.

This is a time in your life where you get to do almost anything you want.

If you are going to make the most of your 20’s and truly discover yourself, then you need to be grateful for every damn minute you spend in this magical decade.

Most of you won’t have kids or a family yet so take advantage of the freedom you have to travel, start businesses, fail at businesses, try new things, meet new people, and live a truly extraordinary life.

5) Learn to Master Your Money


It’s really easy to not care too much about money when you’re 20 years old because… you probably don’t have much.

With college debt rising to an obscene high and financial literacy courses in short supply, it’s easy to go through your entire adult life without ever truly understanding what money is and how to use it effectively.

Here are four money habits to help you get started early and become a master with your money:

1. Understand Credit

It may not be the most interesting topic but your credit score will impact you for the rest of your life. Your credit score is used when you rent or buy a house, buy a car, and when you get a job.

Pay your bills on time, never miss a payment and don’t max out your credit cards… PERIOD

2. Control Your Spending

It’s easier said than done but it’s essential that you don’t overspend and get into unnecessary debt early in life.

Use a free budget app like Mint to track where you spend your money so you can start saving for the future.

Don’t be an idiot with your money, it will be a painful lesson that you will pay for in your 30’s and 40’s.

“If you don’t get serious about your money you will never have serious money.” – Grant Cardone

3. Save and Invest

Once you start saving money you can then begin to build your savings for major purchases or invest for your future. The younger you are, the more time you have to leverage and grow your money in the stock market.

As much as I want you to earn more than The Wolf of Wall Street, stick with investing in low-cost index funds routinely and take advantage of compound interest.

4. Don’t Grow Your Lifestyle

As you start making more money be careful to not start increasing your lifestyle. If you get a big bonus or a new job don’t move into a bigger place or buy a new car immediately.

Money gives you options and freedom, but only if you use it wisely, save it, invest it, and make it work for you.

If you are able to master your money you will have less stress, more fun, and more options for your future.

6) Travel the World


As you get older and have more responsibility in life you will have undoubtedly have less time to travel.

Luckily, you will never have fewer responsibilities in your life than your twenties.

Before your version of travel becomes business trips and vacations to Disneyland with your family, make travel a priority in your twenties.

Not only do you have more time, but you will also be able to travel much cheaper than in the future. You won’t need fancy hotels, first-class flights, or gourmet food.

Without a wife and kids to think about, the need for fancy accommodations, gourmet foods, and first class flights go out the window and you are able to experience the raw and unadulterated joy of the nomadic lifestyle.

 “Travel while you’re young and able. Don’t worry about the money, just make it work. Experience is far more valuable than money will ever be.” – Anonymous

Traveling is a great way to experience new places, cultures, food, and create memories that will last forever.

Make it a goal to explore two or three new places each year… I promise it’s worth the cost.

As soon as you return book the next trip so you have a new adventure to start planning.

7) Create Lasting Relationships

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Your twenties are the time to meet as many people as you can.

The more people you meet and relationships you create, the more opportunities that will be available in the future.

Make a conscious effort to expand your network of people in your life.


Talk to everyone! In today’s overly connected world, it’s easy to get so sucked into your respective devices that you are too distracted to look up and see the boundless number of possible friendships.

In today’s overly connected world, it’s easy to get so sucked into your respective devices, getting so distracted that you never look up to see the boundless number of possible friendships.

Whether I’m at the gas station, grocery store, happy hour, or the golf course I am talking to people. And let me tell you first hand, there are few things that will prove more advantageous in your 20’s (and the rest of your life for that matter) than mastering the art of networking and connecting.

 “You miss 100% of the shots you don’t take.” — Wayne Gretzky

If you don’t talk to strangers you might miss a huge opportunity to meet someone that could change your life.

It could be a best friend, significant other, or a mentor to help your career. There is no harm in trying.

Once you do meet people be sure to stay connected with LinkedIn, social media, and events.

8) Set Big Goals 

One of the most important things that I would tell my 20-year-old self is to set clearly written goals, and big ones at that.


Don’t get in the habit of thinking small or being “realistic.”

With hard work and a plan, you accomplish anything.

And the great part about your 20’s is that you will have more energy, enthusiasm, and youthful naivety to pursue these hairy audacious goals than you will at any other time in your life.

“Life takes on meaning when you become motivated, set goals, and charge after them in an unstoppable manner.” – Les Brown

To maximize the chance of crushing your goals make sure you:

Write Down Every Goal: Your brain will see them in your own handwriting and start to think it’s possible. Once you write them down put them somewhere in your house that you will see them daily.

Share Your Goals with Family and Friends: Studies have shown that the likelihood of accomplishing your goals goes up significantly when you share them with others.

Visualize Your Goals: If you don’t see yourself accomplishing your goals it may be hard to keep working when it feels like you feel unmotivated.

Spend time by yourself visualizing yourself reaching a goal and think how it will feel when you accomplish it.

Imagine in detail how it will feel when you hit your goal weight, get the job promotion, or finally talk to the girl you see at the gym.

Create goals for all areas of your life, not just fitness or the amount of money you want to make.

Break them into personal, professional and fitness goals.

Be the guy that dreams big, works his ass off, and crushes his goals.

Your 30-year-old self will thank you…

9) Cherish Your Family


If you’re following the previous eight pieces of advice you will be busy… Really busy.

But never, ever be too busy and forget to spend time with your family.

I don’t mean to sound like Dominic Toretto but the most important thing in life is family.

Life is short and I’ve experienced first hand the heartbreak that comes from losing a loved one and knowing that you didn’t prioritize the relationship because you were too caught up in your work and the daily “grind”

“Family is not an important thing, it’s everything.” – Michael J Fox

Call your family, spend time with them outside of the holidays, and don’t be afraid to express your love and gratitude.

If things ever go bad in your life your family will (almost) always be there for you.

You only get one family, spend time with them and love them. Go on trips, make memories, and treat them right.

If you don’t, I guarantee you will have regrets when they are gone.

Never be too busy for family, cherish every moment you spend together.

10) Don’t Be Afraid to Fail

It’s easy to think that successful people like Mark Cuban, Michael Jordan or Bill Gates never failed because we only know their work once they made it big.

But they all failed hundreds or thousands of times before they truly became successful.

Success is not linear, you will have ups and downs.

You will have victories and failures, it’s part of the process.

I didn’t take enough risks when I was 20, I played it way too safe. I wish I would have acted on more ideas and taken more calculated risks.

Don’t be afraid to taking risks when it comes to your career or business ideas. At 20 years old you have so much time to figure it out and bounce back.

“Don’t be afraid to fail. Be afraid not to try.” – Michael Jordan

The more you fail at things the more you learn, success is a poor teacher.

Keep trying, keep learning.

Whether it’s learning a new skill, starting a side business, or whatever else… don’t be afraid to fail.

Failure is just part of the process of success.

11) Give Back

The easiest way to be happy is to make someone else happy. It feels great when you take a girl on a nice date, pay it forward at the coffee shop or donate your time to volunteer.

It’s easy to think that since you don’t have much money when you are twenty you don’t have much to give back.

However, giving back is more than just donating money, you can always volunteer your time to help others.

Find a charity or cause you believe in your community and spend time helping others.

“The secret to living is giving.” – Tony Robbins

If you don’t give a dollar out of a $100 you won’t give a $1,000 out of one million in the future.

It will all come back positively in some way in your life and you will have instant gratification when you are making others happy.

Final Thoughts

If I could tell my 20-year-old self these 11 pieces of advice I’m confident I would have found success much sooner.

Even if you are 25 or 35 you can still use most, if not all of these tips to build a strong, grounded life.

By 29 I realized life wasn’t all about money and decided to quit after contemplating for a year. I decided I was going to bet on myself and follow my passions.

Life is too short to be chained to a desk at a job you aren’t passionate about.

Enjoy your twenties.

Find out who you are, invest in yourself, experience new things, travel to new places and dream big.

Don’t worry what others will think about your choices as long as you are happy.

Your twenties are the time where you are allowed to make mistakes and grow as a person.

Don’t be afraid to fail, you can bounce back from anything at this age.

Take massive action to conquer your goals and live your dreams.

Your 20’s are a roller coaster with plenty of thrills and terrors. Love every second, don’t forget to enjoy it all.

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