10 Things You Should Do in Your 20s

You will never be more free than you are in your 20s.  You should spend this time focused on personal growth and creating amazing memories.  This will ensure you live a life without regret, and will give you some fantastic tales to tell.

Below are 10 things you should do in your 20s to become successful.

1. Create Good Habits

You aren’t what you do, you are what you continually do.  Practice doesn’t make perfect, practice makes permanent.  In other words – you are a product of your habits.

In your early 20s you need to develop adult habits to will serve you well for your entire life.  Above all else, this will be the foundation for your success.

The first essential habit is you need to take care of your body.  If your college years were like mine, you probably confused the hell out of your body.

I was super-active and fit.  I exercised every day, and was in fantastic shape.  I also drank six cokes a day, ate as much crap as I could get my hands on, and drank a little too much booze.  On the outside my body looked fantastic, on the inside I was poisoning myself.  When I left the college environment that was filled with free time, it was impossible for me to stay in shape and maintain my unhealthy eating habits.

The recipe is very simple to develop healthy habits.  Eat a healthy diet and exercise.  Avoid the obvious things that are bad for you (alcohol in excess, tabaco and drugs).  Wear sunscreen.  One thing you probably aren’t thinking about is stretching.  Getting in the habit of stretching is terribly important if you want to avoid middle age years of aches and pains and soreness.

The second essential habit is to create sound financial habits.  Realize it is not your employer’s job to make you financially stable.  It is your job.  The most certain way to become financially stable is by creating sound financial habits.

You need to learn how to develop and maintain a budget.  Developing a budget is simple.  List all your monthly expenses, and make sure you make enough money to cover those payments.  If you don’t, you need to cut your expenses to get in budget.  This is simple.  The challenge is sticking to the budget.  The first line on your budget needs to be your retirement savings.  Always pay yourself first.  Your budget should have a built-in savings for contingencies, which will happen.  That money is to be used instead of busting your budget.

Avoid debt like the plague.  Unless you are in the extreme minority, you aren’t responsible enough to use credit cards.  The points and perks are not worth using them.  Avoid big car payments.  The more of your budget is going towards debt, the less it is going to building your future wealth.

You will never have a better opportunity to build wealth than you have right now – TODAY.  You need to be saving for your retirement right now.  This is the first financial priority you have.This is the most important part of this entire article – so pay attention.

If you can save $6400 a year for retirement for every year in your 20s, and get an 8% return on your investment, and never deposit another dime after you turn 30, you will become a millionaire by the time you are 60.

If you wait until your 30s and deposit $6400 a-year, every-year for your 30s; then your nest egg will decrease by more than 50%.  If you want until your 40s and only invest in your 40s, it will decrease another 50%.

This reason is the power of compound interest.  Einstein said compound interest was mankind’s most important invention.  He also called it the 8th Wonder of the World.  This is one of the primary reasons why Warren Buffet became so wealthy.  With time, your money will make money.  With more time, that money will make money.  Time is the key factor.

Developing productive habits in your 20s will serve as the foundation for all your future success.  Habits are started one day at a time.  The sooner you start, the sooner they become ingrained and the closer you will be to success.

2. Focus on Self Development

There is so much value in getting a little better each day.  Like the example of compound interest with your finances, that compounding works in your self-development as well.

First, you need to read to get smarter.  This means reading books that improve your knowledge base.  This isn’t reading for fun, even though it can be.

If you read ten pages a day, every day for ten years; you will have read the equivalent of 146, 250-page books in a decade.  You can probably read ten pages in less than fifteen minutes.

And if you are reading the right books, think about how much knowledge you have gained?  If you read 146 books on finance, that is probably the equivalent of an undergraduate degree.

Here’s the thing though.  If you read eleven pages instead of ten, you will have read the equivalent of 160, 250-page books.  One extra page would equal 14 more books over a decade.

If you want to be like one of the richest man in the world, be like Warren Buffet and read 500 pages a day.  That is the equivalent of reading 7300, 250-page books a decade.  And Buffet has been doing that for decades.  It is no wonder he is brilliant.  He dedicated his life to developing his mind.

Warren Buffet’s Reading Routine

There are other ways of self-development.  I’m a huge fan of YouTube.  You can learn anything on there.  I encourage my team at work to start every work day watching a YouTube video about something in our industry.  This serves as a ten minute training session each day.  That is about an hour a week which translates into fifty hours a year.  My guys get fifty hours smarter every year by this habit.

3. Get Out of Your Comfort Zone

If you want to grow, you need to get out of your comfort zone.  You need to make yourself uncomfortable, and you need to challenge yourself to get better.

In my professional career I spent ten years with one company.  This company was great to me, and I worked hard for them.  I was successful.  However, looking back I became stagnant, though I didn’t realize it at the time.  I knew what I knew, and I didn’t know what I didn’t know.  Because I was so successful doing what I always did, there was no need for me to strive for professional growth.  I could go through the old routine and always exceed my objectives.

That all changed when I was recruited by that company’s number one competitor for nearly the exact same job.  I was the coach of the Red Socks, but picked up one day and signed with the Yankees.  This was one of the best career decisions I ever made.

What made the decision so good is how this move challenged me.  I was inheriting a team that I spent the past decade trying to beat – and make no mistake I was beating the pants off of them.  I had to prove myself all over again, because my past accomplishments no longer mattered.  I had to do this while learning a new organization and while completely rebuilding my network.

I worked my ass off.  I rebuilt the team with top talent and aggressively cut the poor performers.  I re-established relationships with key partners and customers that had deteriorated for years.  I focused on market segments where my new company had been traditionally weak, but I could teach them the keys to success.  I used my old tricks to get better, but I also picked up some new ones at my new organization.

The change forced me to get better, and I did.  It was uncomfortable and stressful, but it was incredibly rewarding.

Your 20s needs to be filled with getting yourself out of your comfort zone.  I encourage you to think about how you can stretch your boundaries.

Everyone needs to experience moving away from home in their 20s.  You need to move away from Mom and Dad and all your old friends.  You need to challenge yourself and prove to yourself that you can be independent.

You need to experience different things and challenges.  I spent my twenties working in Italy, and then quitting to join the military.  Both experiences expanding my reality and led to immense personal growth.  The lessons learned from these experiences have been a springboard for success for the rest of my life.

4. Take a Big Risk

Two things happen when you take a big risk.  Either you become wildly successful, which is awesome.  Or you fail spectacularly, which is pretty awesome in the long run…

I want you to fail.  I hope and pray that you fail.  Let me explain.

The entire American culture is centered around the fear of failure.  It is disgusting.  We spend the first twenty years of life in school, fearing academic failure like failing a test.  I can remember as a kid lying in bed before school thinking about faking being sick because I didn’t want to take a test I wasn’t prepared to take.  Those are awful thoughts for a young kid.

We are conditioned to fear rejection when asking a girl out.  We fear not having approval from our peers.  We fear we may say something embarrassing.  We fear we aren’t good enough.

The most maddening fear I have is hitting a golf ball.  I’m afraid of where it may go, and my fear keeps me from being an exceptional golfer.  This is stupid fear, but it shows how deep the concept of fear has permeated our subconscious.

I can go on.  We are afraid at work of getting laid off.  We are afraid at work of getting a bad review from our boss.  We are afraid at home of our kid’s academic development, or how they are adapting socially at school.

Using a sports analogy, we are all playing from our heels.  Bad athletes play from their heels, or a defensive position.  Great athletes play from their toes – always attacking.  We are all on the defensive because we are playing the what-if game in our heads.  Sometimes, this fear and negativity becomes a self-fulfilling prophecy.

I want you to go back to your childhood mentality.  Remember when you were a kid and you’d climb the tallest tree just to prove you could do it?  You never once thought about falling and crashing and cracking your skull.  You played as hard as you could, every single day.  You weren’t worried about getting your clothes dirty.  You didn’t think about wearing a helmet.  You didn’t give a rip what others were thinking about you.  You were L-I-V-I-N…

That is why you need to fail.  You need to realize that there is no failure you can have that you can’t recover from.  The greatest failure in life is taking the conservative and safe path.  You don’t want regret.  The worst possible thing that could happen in anyone’s life is waking up one day and looking back and wondering ‘what if?’

If you are in your 20s you are young.  You shouldn’t have any real responsibilities.  Real responsibilities are kids.  So take a chance.  Bet big on yourself, and don’t think twice about failing.  If you fail, you are young enough to recover.  Better yet though, you will be armed with the knowledge that fear and failure can’t break you.  You are mentally strong enough to pick yourself up off the ground and try again.

Resiliency is a learned trait.  Learn it while you have the safety net of youth.  If you learn it young, there will be nothing that can intimidate you.

Gary Vee does a great job sharing this same message in the video below that I recommend.  Fair warning though – there is some language that some may find offensive.



5. Choose the Right Career Path

I meet so many people in their 40s that joke and say “I don’t know what I want to be when I grow up.”

How sad is that?  These people have used half of their life, and still don’t know what they want to do.

There is a saying that “You don’t work a day in your life if you do what you love.”  So my suggestion is live that saying.

What do you love?  What do you do for fun?  What are your hobbies?  There are industries and careers built around whatever you are into.  If that is your passion and your interest, why wouldn’t you go into those fields?

Don’t worry about the money.  You are young, the money isn’t important (outside the $6400 a year you need to scrape together to become a millionaire).  Follow your passions and follow what you love.

However, you also need to have a clear understanding of what you love.  You need to know what makes you tick so you know what you are chasing.

This took me a long time to figure out.  For many years, I was one of the “I don’t know what I want to be when I grow up” people.

It took me a while, but I realized I was trying to answer this question the wrong way.  I thought to be happy I needed to be in an industry centered around one of my passions.  I thought I needed to be in the sports industry or another one of my interests.  This pursuit left me unfulfilled in my professional life.

It took me a while, but I eventually recognized my true passion.  I have a passion for leading people.  I love building teams, and then helping those I lead maximize their potential.  This is a fantastic passion, because for me the industry is really irrelevant.  This gives me almost unlimited opportunity to engage in a career that will make me happy.  I can honestly say I have never been happier with my professional life then when I’m leading teams to success.

Do some soul-searching and figure out what is going to make you happy professionally.  The answer is not a pay check.  If you can figure this out, you won’t live a life where you are only looking forward to the weekends.  You will live a life where you are also looking forward to the Mondays.

Here is one of my all-time favorites speeches given by Steve Jobs which does a beautiful job capturing this point.



6. Create a Bucket List

When you are in your 20s you think you have all the time in the world to knock out items on your bucket list.  I hate to be the bearer of bad news, but you don’t.

Typically your 30s and 40s is when you really focus on career and family.  Those obligations make it almost impossible to spend any significant time on your bucket list.  The financial commitments of family also make it challenging if not impossible.  By the time you are in your 50s and 60s your interests and priorities change.

Unless you want to have a life of regret, you need to go on your adventures now.

I am way outside my 20s.  If I had a chance to go back and do it over again, below is what I’d do.  I’m not saying this is what you should do – I’m saying this is what I’d do.

I’m sharing because when I was in my 20s I didn’t have thesame perspective that I do now.  Hopefully this will give you some ideas.

Things I did and would do again:

  • I took a job working in Italy. This was a great experience.  My job was designing laser-guided robot systems.  Pretty fascinating stuff.  I was a working stiff during the week in Northern Italy, and a tourist during the weekends.  I did this for two years and wouldn’t have traded the experience for anything
  • I joined the military. I am one of the people who joined after 9-11.  All of us of that era watched it live in stunned silence.  For many of us this was a call to serve.  Going in, I thought I was the one who was giving to my country.  Looking back, what my country gave to me because of this amazing experience was far greater.  This was incredibly rewarding and was the springboard for my future success.

Things I wish I would have done:

  • I wish I would have spent a football season in Las Vegas trying to become a professional gambler. As the followers of my other site (com) know, this is an interest of mine.  Living only by my wits would have been a great experience (and would have made a great book).
  • I wish I would have spent time as a caddy at Augusta National. An American Caddy at St. Andrews is a book I recommend and describes exactly the experience I wish I would have had, only at Augusta.  This would have been an amazing experience becoming so familiar with the course and being around the high-powered people who play there.
  • I wish I would have studied abroad in college. I never did because I was too busy grinding it out in engineering school.  I think I missed out.
  • I wish I would have spent time in Alaska. I am absolutely fascinated by the 49th  I would have loved to go to Dawson City and learn more about the gold rush.  I would have loved to see Denali.  I want to see the Northern Lights.  I really wish I would have had the stones to spend an Alaskan winter in the bush.  At the time (and even now) I probably don’t have the outdoor skills to pull off that type of adventure.  I don’t care.  I would have loved to go full “Dick Proenneke” for a winter.  Don’t know who Dick is?Check out the video below.

Create your list, and go make memories and have adventures.  Then spend the rest of your life sharing how awesome you are.

7. Develop Expertise

My Mom loves the saying “Go narrow, but go deep.”  This advice gets even more valuable every year.  The world is becoming more and more specialized.  Generalists are not as valuable in the new economy.  Expertise is.

In your professional life, become the subject matter expert on something.  You want to be the go-to person on some topic.  Being the expert on your markets or product or industry is obviously ideal.  Don’t discount being an expert on the obscure though.

Case-in-point – I got my first corporate management gig before the 2008 recession.  My industry was impacted like everyone else, and we had a targeted layoff.  There was a great deal of debate on two individuals.  Both were dead weight and underperformers in my opinion.  I remember actually being surprised that there we even a discussion on keeping those two employees.

The entire room knew and acknowledged each of these individuals shortcomings.  It was unanimous that these guys were underperformers.  However, there was heavy discussion on both of them because of the unique skills they possessed.

The first individual was a whiz at Microsoft Excel.  The entire business was run on Excel, and this guy could make that program sing.  I bet he could program a macro to make him a peanut butter and jelly sandwich if he wanted.  He was that good.  He was always tasked with whatever important spreadsheets needed to be built.

The second guy was the chemical guy.  He know what chemicals were needed for our processes.  He knew the regulations required by the government to have these chemicals.  He know how and where to reorder and how often.  He owned this little niche of our business, but without his knowledge the entire business would stop.

At the end of the day, both of these guys kept their jobs despite being woeful underperformers.  They had made themselves valuable and non-expendable.

It is also important to be an expert at something in your personal life.  Be passionate about life.  Have a zest for living.  Above all else, be interesting.

Success in your professional life depends on several things, but probably the most important is the ability to develop relationships.  How you do in the sandbox in kindergarten is shockingly similar to how you do in the corporate world.  Those who can get along with others are the winners.

I strive to get the most out of life, but I also strive to be interesting.  I want people to be attracted to me and interested in me because it helps my career.  Most of the people in my industry are men.  Most men are either sports guys or outdoors guys.  Many are interested in booze and most are interested in the military.

I am an avid sports guy.  Like any good bettor, I can give a person a perspective on games that the non-degenerates have never thought of.  This insight is fascinating to the non-gamblers.  I can talk golf for hours.  I have a handful of great sports stories that I can lean on (talking my way into the Super Bowl as a 12 year-old kid, winning $100k on a football game, attending the Masters a bunch of times).

I recently became a hiker/camper.  My boy and I are section hiking the Appalachian Trail.  It isthe best thing I do, and people love to hear our stories.  The outdoor types especially love to hear about our adventure.

I became a huge bourbon guy.  I love collecting, and more than that I love telling the stories behind the different distillers.  An example – I can talk for hours about how to get your hands on Pappy Van Winkle.  I am very often at corporate dinners, and dropping a few bourbon stories always entertains my dinner company.

I served in the military for five years.  I deployed to the Middle East twice.  I survived a bunch of hairy situations.  This makes for some good stories.

The point is two-fold.  Develop expertise and a passion because it makes your life richer.  However, it also makes you more interesting, and that will help you when you need to develop relationships.

8. Spend Your Money on Experiences

Don’t waste your 20s buying stupid crap.  Consumer debt and making foolish purchases will make you a slave to a paycheck.  You can’t live your best life if you are wasting your money.

I was the king of foolish purchases in my 20s.  The day after I was commissioned in the Air Force I bought a brand new Chevy Tahoe.  I had no business buying a Tahoe.  You can’t afford a Tahoe on a 2nd Lieutenant’s salary.  I bought the best golf equipment which had no impact on my ability to score.  I had expensive clothes even though I wore a government issued uniform everyday, and wore a t-shirt and jeans when I hung out with my buddies on the weekend.

This was stupid.  I missed out on so many experiences because I chose to spend my money on junk.

What I should have done is take that money and invested it.  Or better yet, taken it and knocked out a few more items on my bucket list.

Years later you will look back and you won’t have any of that stuff anymore that you thought was so important.  If you spend your money on experiences though, you will have solid memories that you will treasure forever.

So live like a college kid as long as possible.  Drive your beater car. Eat more sandwiches.  Shop at Marshall’s instead of Macy’s.  But use the money you save to live your best life.  Take expensive trips.  Create once-in-a-lifetime experiences.

That is the best way to spend your income in your 20s.

9. Give Back

I’m a big believer in giving back.  The secret is when you give, you end up getting more back in return.

After I graduated college I wanted to have a volunteer activity, so I volunteered at the Duke Children’s Hospital.  I would show up a few times a week, and hang out with kids in the waiting rooms while their parents talked to doctors or when they were waiting for their treatments.  There was an original Nintendo there, and I would dominate those kids on that thing.  It took me a bit to realize that they were children of a different generation, and never had even seen an original Nintendo.  I had a distinct advantage.

This was an incredibly rewarding experience.  To see the fight in those kids as the dealt with adversity that no child should endure was humbling.  I learned a lot spending time there.

I joined the military because I felt a call to serve.  I wanted to give back to the country that gave me so much.  My experience gave me an even deeper love for my country.  While in Iraq I had an Iraqi as my interpreter.  His name was Zack.  Zack was a talker.  Very often, in his ramblings he would talk about how great his country was before Saddam.  He would often cry when talking about how appreciative he was that the US removed that tyrant and gave Iraq its country back.

While deployed to Kuwait, the gratitude is hard to imagine.  While most American’s look at Kuwait as a blip on the timeline of history, this was a significant event in their world.  Iraq invaded the country, and brutally attacked the men and tortured the women and children.  We came in and liberated the country, and they remember that the US was there for them in their time of need.  When nomadic goat herders in the desertsaw me in uniform while driving off-base, they would snap to attention and salute me because they knew I was an American.  It was very rewarding knowing the good we do for other people.

In addition, don’t forget to give back to those that are important to you in your family.  You should feel blessed if you are in your 20s and still have grandparents who are alive.  Spend time with them.  Call them.  Ask them questions.  Learn about your family history.  Help them with chores that are difficult for older folks.  I was very tight with my grandparents.  My last grandparent passed a few years ago.  Now that I’m older, there are questions I wish I would have asked.  Those opportunities are gone forever.  Treasure the remaining opportunities you have with yours.

10. Learn to BeHappy with Yourself

Being happy with yourself is so hard for so many people.  It is vitally important though if you want to live a happy life.  There are several areas where you can focus which will improve your self-worth and self-confidence.

First, don’t compare yourself to others.  My Dad gave me the best piece of advice he ever gave me in a note when I graduated college.  He told me to remember that thoroughbreds don’t look at the other horses. They run their own race.  He also told me that he raised me to be a thoroughbred.

This is so true.  You need to live your own life, and make your own decisions.  You need to do what makes you happy, because at the end of the day you are living your life, not somebody else’s.

Second, don’t be too hard on yourself.  Don’t beat yourself up over your shortcomings or failures.  There will be plenty of jerks in life that will do that for you.  Take pride that you did your best, and you did what you can control.  Learn your lesson, move on and don’t dwell on the past.

Third, no one cares what you are doing.  Everyone gets so self-absorbed in their own lives, that they have a hard time being comfortable over fear what others may think of them.  News flash – everyone is so busy with their own stuff that they don’t care about yours.

Four – there is a saying that you are combination of the five people you associate with the most.  I think there is a lot of truth to that.  If you want to be an achiever, hang out with achievers.  If you want to be rich, hang out with rich people.  If you want to be a drug addict, hang out with drug addicts.  Be very selective about the people you hang out with and realize that you will become more and more like them over time.

Fifth – At all costs protect your character.  Don’t compromise your morals and integrity for anyone or anything.  Keep your promises.  Be trustworthy.  Don’t speak poorly of others.  At the end of the day, if you can keep your character clean in all circumstances, you can sleep easy at night.


You will never be more free in your entire life than you will be in your 20s.  My sincere hope is you take advantage of this time in your life, and you are rewarded with priceless memories that you will treasure for the rest of your life.


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