What I Would Tell My 20 Year Old Self


Imagine yourself 5 or 10 years ago.

What did you enjoy, what did you like to do? What decisions did you make and what lessons did you learn?

If you had something to tell your younger self, what would it be?


My Younger Self

I recently found a picture of myself when I was 20 years old, that was 17 years ago as of this writing.


What’s amazing is, I didn’t even recognize myself when I found the picture. I thought it was a picture of one of my brothers.

While thinking about my life back then, I got to wondering about all the experiences and lessons I have learned since that time. Mistakes I wished I could do over or experiences I could relive.

I got to thinking that if I could sit down with my 20 year old self today, what could I teach him? More importantly, what can I share with younger people to pass on some wisdom?


Mistakes To Avoid

I’m not saying I would change what has happened in my life, but some mistakes are more costly than others. These lessons have shaped me into what I am today.

However, if I would have listened to others I could have avoided a lot of problems. Here are a few below:

  • Don’t stop learning - Write and read daily, take up activities that mentally push you. Sharpening your mind gets harder as you get older and have less time due to other commitments.
  • Eating junk food – Treat your body as a temple. When you are older this is so important. Kicking a junk food habit gets harder as you are older. Losing weight is also the same.
  • Lazy or comfortable – Don’t push off anything. Do it now, develop a habit of doing. Once you get lazy or comfortable, it is 30x harder to get motivated to do things.
  • Not exercising – Exercise not only has a physical benefit, but a mental one. You don’t want to be the parent who can’t climb a flight of stairs without being out of breath.
  • Shitty relationships – No reason to be in them as women are everywhere. These relationships will harm you more the longer you are in them.
  • Spending money – Start saving early. Live on 15% less. Not just for retirement, but to build the habit easier. Max out your 401k, then a Roth, then Index funds.
  • No family time – Make the time. Tell people you love them. They will be gone one day soon.
  • Not Letting go – From shitty friends, jobs, partners, and family members, just learn to let things go. It’s not good for your health to carry on pain or anger.
  • Perfecting – Stop it. No one is expecting perfect “anything” from you. If they are, you are with the wrong crowd. You are wasting your time perfecting.

I don’t dwell or think about changing all the mistakes I made in my life. Doing so waste time and prevents me from going forward.

“It has been a mistake living my life in the past. One cannot ride a horse backwards and still hold its reins.”
― Richard Paul Evans


What I Would Relive

As I get older and come across more opportunities, I sometimes ask myself, “Why haven’t I done more of this?“. Sometimes I think about why I didn’t do more of a certain experience as well.

Here are a few things I would tell my younger self to relive and do more of:

  • Traveling – This is one of the best activities I have ever took up. I love seeing new places, people, tasting new foods, and getting outside of my comfort zone.
  • Date nights with the wife – Your career, kids, bills, and other commitments can get in the way as you get older. Spending time with that special someone is enjoyable.
  • Debate – Challenging the status quo and taking a stand loses its edge as you grow older. Those can be the most defining moments in your life.
  • Working with your hands – Cutting down a tree, building a house, fixing a car, or hunting gives a satisfaction that can not be replaced.
  • Music – Jamming out with friends on the weekend or playing some of your favorite tunes on the drums can be relaxing and fun.
  • Being naive - Not knowing can work to your advantage. When you don’t know the failure points of an idea, you trust you can execute on it. Nothing stops you before you start.
  • Taking more pictures – Your mind will fade, finding this picture of my younger self made me relive my youth.
  • Being broke – Learning street smarts and developing a passion to give myself more and better opportunities came from this hardship. Also made me humble. Sometimes you need this slap in the face more than once in your life.
  • My children’s youth – Time passes so fast and sometimes life gets in the way of enjoying the youth of your children. The many memories of us at Disney, their birth, beach vacations, and joys and tears of their early life can not be replaced.

Some experiences are worth living over several times.

In Conclusion

Don’t get stuck in the past thinking about what you should have done, and don’t ever regret how you lived your life.

Take note of what you have done, how it could have been different, and what you learned from it. From that point you can grow with your existing self and improve upon yourself.

Learning from your mistakes will make you a better person.

Leave a comment below on what 3 things in your life you wish you could “relive” and do more of.

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Hi! I'm Jason Brown and I’m a 36 year old digital marketing intrapreneur living in beautiful Louisville, Kentucky. I've been involved with the Internet since 1996 and have personally made millions online with my creative marketing tactics and persistence. I blog about marketing, money, and motivation. Thanks for stopping by!


  1. Gent   •  

    Great article, Jason!

    As a 20 year old, I really appreciate you breaking down the things you’ve found to be the most important in life. There’s a lot that you can learn from people older than you and who’ve lived enough to know how life really is, especially when they share the mistakes to avoid in life, like you did in the first part of this post, which I really enjoyed. Experience is the best teacher.

    I think that being physically healthy and mentally active is a great start to live a good life.

    People are scared from failure, that’s why they keep seeking stability and security all the time while settling for boring and mediocre lives. I was lucky to start early in my entrepreneurial journey, while I was naive enough not to know the risk, as you wrote in this article, and, yeah, I’ve failed. A lot!

    But with each failure I learnt something that I didn’t know before, and that alone was worth it. I see failure not as the opposite of success, but as an important part of it.

    Everyone can and should live a great life!

  2. David Nguyen   •  

    I wish I could have done more physical activities in high school.

    I wish I was more socially active in high school.

    Last wish, I wish nothing changed in high school.

    As you can obviously tell my teenager life was the biggest down side — young, dumb and scared.

    I am making some huge progress overcoming all that. I’m 25 years old today, not perfect but trying.

    Good article Jason.

    -David Nguyen

  3. Tom   •  

    Great post.

    Back To The Future style, I’m now thinking about what future me would tell now me to do/not do.

    Top of the list would probably be get off the computer and go outside more…then again, that’s what smartphones are for!

  4. Kurt Yazici   •  

    Thanks for the great tips Jason, this makes a lot of sense to me. I’m 30 and just now getting started out in AM.

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