16 Things I Would Tell My 16 Year Old Self

It’s funny I can look back at my 16 year old self and see some things that he obviously needed to hear – but I really don’t feel like I have everything figured out now at 28 years old.

So if you’re a 40 year old, and you have some glaring tips for me – please reach out and let me know.

I figured if there are other young men out there who are struggling with figuring things out, I should definitely share what I know I needed in my teens.

I feel like I need to preface this by saying that I’m by no means some sort of guru who has life figured out. But I really don’t think anybody does, so that’s exactly why I’m sharing this post.

That’s me on the right. I was 16 in this photo (or about to turn 16). This post is 100% for that kid right there.

General Tips

These tips can be applied to almost any area of your life, so whether you’re focused on improving your health, career, or interpersonal results – these tips should help.

1. Be Accountable & Take Responsibility

When I was younger I had a tendency to always blame other people or circumstances for things that happened in my life. I think I still fall into this sometimes, but I’ve found that the more you accept that outcomes in your life are a result of your choices and actions, generally the happier you’ll be.

If you continue to think that you would have gotten a promotion, but your boss is a dick. Or you would have gotten in shape, but your partner makes you eat unhealthy. Or you wouldn’t have missed that opportunity, but someone else interfered. You’ll never be happy. With this mindset even if you do succeed, it will be at the hands of someone else.

About a year ago, I read Extreme Ownership by Jocko Willink. Jocko is a Navy Seal who while serving made life-or-death decisions that lead to people getting killed. He explained that when military leaders came to him to ask what happened, he accepted that what had gone down was his fault. This book helped me understand that taking responsibility for your actions, even if they had a bad outcome – will help you win in the long term.

When you take accountability, those around you will know they can count on you to be honest, even if you fuck up.

2. Plan Long Term & Expand Your Time Horizon

I think the best way to set yourself up for success is to set long term goals, plan in decades, not months, and be willing to work towards something for years.

“Most people overestimate what they can achieve in a year and underestimate what they can achieve in ten years.”

Generally I think you’re setting yourself up for success by expanding the time that you give yourself to achieve your goals. If you have a goal that is big enough to pursue for 5-10 years, you’ll be able to achieve greater things than if you limit yourself to working on things you can achieve in a few months.

If you’re actively pursuing a goal for years, and you’re consistently taking action, you’ll still have made progress – even if you fall short of your goal.

3. Never Stop Learning

When I was younger I really thought that I would have everything figured out by the time I was twenty-something years old. How naive of me?!

I think the sooner we recognize that everyone, even our parents, even the smartest person you know, is just continually trying to figure out life. Everyone is experiencing things for the first time, trying to overcome obstacles, and continually navigating their daily life.

Additionally, learning things just because I’m interested in them has enriched my life greatly in recent years. When you’re in school, your teachers and professors tell you both what to learn and how to learn it. After you’re done with your formal schooling, what do you do now?

  • Read books that peak your interest. (Get a Kindle or an Audible subscription – or a library card!)
  • Listen to podcasts about topics you’re curious about and would like to learn more on.
  • Find blogs online that teach you things.
  • Take an online course because it sounds interesting.

Learning new things is fun, especially if you choose what you’re learning on your own. Having these skills or areas of expertise also allows you to connect with more people, and have engaging conversations.

4. Stop Comparing Yourself To Others, Focus on Improving

When you’re young it’s easy to look around at other people and think that they are all so happy. As you get older you realize that people are actually really good at covering up their problems.

I remember hearing about some kid I knew having sex when we were pretty young. My immediate reaction was to think, well why the hell haven’t I had sex? – girls must hate me. That wasn’t a healthy reaction.

I remember looking at people my same age who could just approach and talk to anybody. And although I really admired that trait in them, I would think man, how lucky they are – too bad I’m stuck in this shy person’s body. And that wasn’t the right mindset either.

I needed to take accountability, accept where I was, and work on improving myself to overcome any of the obstacles I ran into.

Comparison can be the ultimate killer of joy, or it can be the ultimate motivator for you to improve yourself. It’s important to find meaning in what you’re pursuing beyond just being better than someone else, but having that drive to succeed and improve consistently has paid off for me in many ways.

5. Don’t Waste All of Your 20s in Bars

I get it, your 20s are a time for having fun, figuring out who you are, and meeting new people (well, so are your 30s, 40s, 50s, 60s, and 70s). However, its easy to get caught in a cycle of living for the party on the weekend. And slowly that becomes going out on Thursdays too. Then add in Monday night football with the boys, Happy Hour on Wednesday, and next thing you know you’re drinking 5 nights a week.

Now I’m all about having a good time, I think it’s valuable for building friendships and for de-stressing from work or other stressors. But, drinking wrecks a lot of other parts of your life, specifically your physical and mental health.

When you drink, you disrupt your body’s sleep cycle. You’re staying out later, so you’re getting less sleep. You’re also inhibiting your REM sleep, which is vital for recovery. If you’re going to be healthy, you should probably drink less and sleep more.

Consider Being Sober as an Option

When I was say 21 or 22, I would have never considered being completely sober as an option. I thought that was only for alcoholics and addicts who “couldn’t handle drinking”. But that’s not the case at all. Alcohol is not healthy, and being sober for an extended period of time can do great things for your physical and mental health.

I’ve had friends who have stopped drinking and over the course of a few WEEKS have lost 20-30 pounds. Let that sink in. You could be 20 to 30 pounds overweight simply because of all the extra calories you’re consuming from alcohol.

I was sober for a year when I was 24 years old (we can get into why later). But it gave me a whole new perspective on drinking. I had formed my drinking habits in college and I kind of just thought that how I was drinking (bingeing, blacking out, etc.) was how everyone was drinking.

When I stopped drinking I realized that the people I was hanging around with either stopped calling me, because our friendships were based on partying – or they weren’t drinking as much as I thought.

I’d still go out and dance and party, but I just wouldn’t drink. It was a refreshing year, and I’ve since resumed drinking – albeit with a whole new perspective.


6. You Aren’t Limited By Your Genetics

Saying that you have bad genetics is a cop out. Now I understand we can’t all be Lebron James or Michael Phelps, but you always pursue a healthier lifestyle.

When I was 16 I went from being pretty chubby to being really skinny. Like really fucking skinny. I think I was about 192 pounds at my heaviest and I got down to 148 pounds at my lightest. I was riding bikes a lot and looked at the guys climbing mountains on their bikes as the epitome of fitness.

However, even as I had gotten super skinny, I still didn’t have visible abs. I wanted those things so freaking bad. But I stayed skinny fat, despite my very low bodyweight.

The problem was, my diet sucked and I wasn’t doing resistance training. I focused on eating a lot of carbs because I was doing a ton of cardio, mainly cycling. I also never lifted weights, so I was never going to put on muscle to improve my body composition. I’d do 20 push-ups every so often, but otherwise…nothing.

It took me a long time to figure out how to make my nutrition match my goals. Fortunately I’ve gotten this dialed in pretty well over the past year. Now I focus exclusively on calories in vs. calories out and hitting my daily protein goal. I’ve simplified it and it’s working well. I wish I would have known it was this simple when I was younger, rather than trying all sorts of stupid diets that weren’t sustainable.

I just want people to know that you don’t have to accept how your body looks. Obviously there are some things you can’t change, but don’t give up before you even try. I always had love handles and I thought that was genetic. My hip bones might be, but I got rid of the love handles (if only I would have known there was hope for me at 16).

7. Lift Weights!

Weight training and focusing on building strength has been one of the best decisions I’ve ever made. When I was in college I switched entirely from endurance sports like cycling and running to weight training. I started lifting as part of my cycling off-season to avoid muscle imbalances and to build muscular strength primarily in my legs.

And thankfully, I just never stopped doing it.

I’ve had long discussions about the important of building muscle and getting strong with some friends and we all feel pretty passionate about it.

I love lifting weights for a few reasons:

  • Going to the gym and putting in headphones and focusing totally on my workout is like meditation. I lift heavy stuff, I play loud music, and then I feel good.
  • It has shown me that small gradual improvements lead to big changes over time. Weight training is like compound interest, just keep working and you’ll get big results over time. When I started I could barely lift the empty barbell, now I can confidently move weights that I once thought were impossible.

Want to build muscle? Start here: The Science of How to Build Muscle – Julian Shapiro

Want to get shredded? This nutrition/training protocol helped me: Kinobody Movie Star Body

8. Get Your Nutrition Dialed In

This one is hard, but it really shouldn’t be. One of the problems I see with nutrition is that there are SO MANY fad diets and stories on the news about what is healthy and what isn’t.

These news stories and fad diets focus on minute details of what you’re eating, while ignoring the macro of health and nutrition.

For example, who gives a shit if you’re a vegan if you’re 50 pounds overweight? What difference does it make if you are doing paleo if you’re obese?

It’s not hard to know if you’re eating too much. You can tell by looking at yourself. If you’re overweight, that’s a sign that you’re eating too much.

Fat Person vs. Fit Person

If you look healthy at first glance, you’re probably doing a good job of managing your caloric intake. We can get into the weeds later, but generally, a fit, healthy person is recognizable just by looking at them.

Also if you’re trying to build muscle or lose weight, so much of it relies on proper diet and nutrition. Exercise does play a role but it is much less important.

Here is what I would tell myself at 16:

  • Do you want to gain weight? Eat in a caloric surplus (for an extended period of time).
  • Do you want to lose weight? Eat in a caloric deficit (for an extended period of time).
  • Eat sufficient protein. About 0.82 to 1 gram of protein per pound of bodyweight.
  • Get your bloodwork done. If you have any vitamin deficiencies, use supplements to meet your body’s needs.

I could go in-depth here, but why make things overly complicated?

9. Find Physical Activities You Love!

It’s frustrating to me that people say they don’t like to exercise or workout. I feel like many people associate working out with going to the gym, suffering on the treadmill for 20 minutes, messing around on the machines aimlessly, and then going home.

That sounds horrible to me. I wish I could help people see that there are far more ways you can move your body than suffering at the gym.

These are all sorts of physical activities that can make it easy to “exercise” more:

  • walking
  • hiking
  • riding bikes
  • swimming
  • dancing
  • surfing
  • paddle boarding
  • running
  • group fitness classes
  • tennis
  • pickle ball
  • yoga
  • martial arts (karate, jiu-jitsu, kickboxing, etc.)
  • team sports (basketball, football, soccer)
  • hula hooping

If you can find a physical activity that you love you won’t have to dread exercising, and you can move your body more.


I’m not where I want to be in my career. I am still working to achieve almost all of the goals I’ve set for myself, but I’m still proud of a lot of the progress I’ve made in my career/finances to this point.

10. Set Lofty Goals

Why not shoot for the moon? If you want to be the CEO of a Fortune 500, great! Now get to work. If you want to own your own business, start it now and charge after it.

Don’t take a shitty job because you think that’s what you’re supposed to do. That won’t lead where you want to go anyway.

I was talking to a friend recently who basically said, “THIS IS IT. THIS IS THE THING. THE TIME IS NOW.” Just hearing him say that really put things in perspective for me. I still had the mindset that I was young and working towards something, but in reality now is the time to take massive action and either fail miserably or succeed greatly.

I really love this quote that I heard from Naval Ravikant on the Joe Rogan Experience: “Each man has two lives. The second begins when he realizes he has just one.”

11. Improve Written and Verbal Communication

This isn’t just something that applies to your career, but it definitely helps out there a lot. Improve your written and verbal communication! Written communication is crucial for persuading people, sharing updates, and for getting what you want in a digital world.

Write Better

Writing is simple. To me there’s almost a formula to it. Strong writing skills have applications in almost every field, even ones that don’t place a strong emphasis on writing.

My Tips for Better Writing:

  • Don’t Use Big Words to Sound Smart. When you try to awkwardly work in big words to sound like you’re smarter than you are, it doesn’t work. In fact, when you use those words incorrectly it has the opposite effect.
  • Say More by Saying Less. There are times when context is necessary, but in many cases too much context just hides your main points and makes the message unclear.
  • Write How You Talk. I think people get intimidated by writing for some reason. I’ve had very interesting, engaging conversations with people only to see later that they can hardly put together a clear written sentence. Writing should really just echo what you would say if you were speaking.
  • Practice Makes Perfect. If you suck at writing, just find ways to write more. Make yourself write in a journal every day to get that muscle working. Send emails to businesses telling them you love their products. Write a letter to your grandma. The more you write, the easier it will become.

Speak More Clearly and Coherently

Speaking helps you connect with people. It helps you share your ideas, work through problems, and address conflicts.

My Tips for Speaking More Clearly:

  • Get Comfortable Talking About Yourself. I remember my first job interview. It was terrible. The interviewer was asking me questions and all I could really say was “I don’t know.” If you’re going to crush a job interview, learn to sell yourself.
  • Speak Based On The Situation. Context is key. You are going to speak differently to someone you’re working for than you would with your closest friends.
  • Record Yourself (and maybe even post it). I started a YouTube channel probably 5 years ago. Looking back at my first videos I did a terrible job of talking on camera. I was awkward, I couldn’t arrange my thoughts well, and I just wasn’t engaging. My YouTube videos are still super bare-bones, but my speaking is much better.

12. Get Over Imposter Syndrome

I still haven’t figured this one out, but I’d love to convince my 16 year old self that it’s possible. In my jobs I always assume that I’m going to get “found out” and subsequently fired. But so far, I haven’t.

The fact that I can show up every day and do the job I was hired to do shows that I am not an imposter at all. In reality, I’ve achieved some great results that I’m very proud of. That should be enough to give myself some confidence that I am here because I earned it, but it just doesn’t feel that way sometimes.

I think we all could be more open about this, and I think it would help settle a lot of uncomfortable feelings. I know other people I’ve worked with struggle with this too, but from the outside looking in it seems totally unjustified – because they show up every day and get their work done.

(If you’re a doctor, but didn’t go to medical school or pass any licensing exams – you’re an imposter. But if you just don’t feel like you’ve earned your spot in your career, you’re probably not)


I’ve built some really great relationships in my life. I’m proud to have some amazing friends that I’ve stayed in touch with for years and years. My friends and family are without a doubt my greatest asset. Here’s what I wish I knew when I was younger.

13. Go Meet PEOPLE! Get Off Your Phone.

I turned 16 in 2009. Smartphones were still fairly new, but I still was sucked into my phone. I would look at my phone while walking down the hall in high school to avoid making eye contact with people.

There are so many interesting people out there and you need to go find them!

I wonder how many hours I’ve spent scrolling through social media looking for social connection, and never finding it. It’s probably a terribly depressing number.

Find people you connect with and make an effort to spend time with them. It’s the best thing you can do for your mental health and to enrich your life.

Also, don’t be afraid to talk to people. I’ve avoided talking to people a lot and I’ve later regretted it. The occasions when I’ve gone out of my way to talk to someone have often blossomed into friendships or cool conversations.

14. Say No More Often.

When I was younger, I found myself habitually saying YES to any and every opportunity that crossed my path. I think as a result I was able to find myself in a lot of exciting places doing a lot of exciting things.

However, as I said yes to more and more things, my output in each would decline. You have to be very selective about the opportunities you pursue, because of the idea of opportunity cost. Even if you feel like you’re handling everything well, eventually you won’t be able to and you’ll suffer from burnout.

If you can find the activities that make you the happiest and provide the most benefit, you should say FUCK YES to those things and NO to everything else.

Fuck yes, or no.

This framework for decision making is simple, but can help you make better decisions:

15. Be Authentic.

I’ve struggled with this a lot as an adult. Doing things because I feel like I’m supposed to. Or not expressing my full self for fear of judgement or retribution.

The feeling of being in situations where I’m comfortable enough to fully be myself is unmatched. I seek these opportunities out like crazy, whether it’s who I’m hanging out with, where we are, or what we’re doing.

If you’re in a situation where you feel like you can’t be yourself, that’s not an ideal situation to be in. You’re sacrificing yourself for the sake of other people.

It takes some deliberate effort, but being yourself will be more fulfilling than pretending to be someone you’re not. And overtime you’ll drain yourself trying to put on a front for other people.

You may end up turning people away, but these probably weren’t the people you wanted to be around anyway.

16. Let The People You Love Know You Love Them

As people grow older, it seems like they generally become more comfortable with this. But I believe it’s very important to let people know when they are important to you and that you love them.

When I was 16, I had lost people I loved – specifically family members. Since then I’ve lost others too, friends and acquaintances. These losses helped me see the importance of letting people know you love them when you have them. Life is finite and for that reason we need to savor every moment we have with people, because it could be the last time.

It can feel uncomfortable to tell a friend that you love them, but it can mean so much to someone who may not know how you feel.

When people have gone out of their way to let me know how they feel, I’ve never reacted negatively. And it means so much that I know how they feel, and that they were willing to be vulnerable with me like that. It can help enrich your relationships – and you never know when you’re spending time with someone for the last time.

Published by stewofkc

I write stuff in Kansas City.

4 thoughts on “16 Things I Would Tell My 16 Year Old Self

  1. Accountability really is a huge one, and I’m glad it’s first on the list. So many of us tend to blame others for everything, but once we take responsibility for even things that doesn’t seem like our fault at first glance, our lives start getting so much better. Anyway, thanks for this post!

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