Advice to Myself as a Young Man

This year I turned 40, and along with the realization that I’m now middle-aged (ack!) came some meditations on the life lessons I’ve learned so far (or not learned, as the case may be). As part of that process of introspection, I found myself wondering what I wish I had heard (and taken to heart) as a young man, and how different my life would have been as a result.

I decided to try to write a letter to myself at the age of 15 – giving myself the advice I didn’t have the ears to hear 25 years ago. From that exercise, I came up with a list of things I learned the hard way, and I hope that it serves to help some young man in his path to manhood.

Life Advice to Myself as a Young Man

What other people think of you isn’t nearly as important as what you think of yourself.

It’s common to seek the approval of others, which can lead you down the path of doing things just because they want you to. It isn’t so common to follow your heart and believe in yourself. Learn to love who you are, not who others would have you be.

Rebelling against the status quo leads to burnout. Instead, boldly forge your own path.

Many things about the world will make you angry. But unless you come up with an alternative, your energy is wasted in simply being against something. Find out what you stand for, deep inside, and instead of pushing back against the world, use your heart and mind to become an agent of positive change.

Real men do cry.

Forget that macho bullshit that you hear in the locker room. Learn to be comfortable with your feelings, no matter what they are. Some men cry from joy and some cry from pain, but sooner or later, we all do. Holding your feelings locked inside is not healthy, nor is it manly. Don’t be afraid to feel deeply and to express it to the world.

Memorizing the answers isn’t as important as finding your own.

Most schools teach us to memorize the answers and to spit them back out on demand. They don’t necessarily teach us to think for ourselves, and they don’t teach us what’s really important in life. This isn’t to say you should ignore your teachers and drop out of school, but it is imperative that you question everything and make your own decisions. Never stop learning – every day brings a new lesson, if you are open-minded and not too full of yourself.

Mind your own business.

Gossip and mean-spirited talk about others is a bad habit, and one which leads to small thinking. It’s all good fun until it’s about you, and then you’ll wonder how people could be so mean. Friends that spend their time talking down about others will talk about you sooner or later. Drop them and find positive ones. Let others live their lives as they see fit, and concentrate on living your own.

Stick up for the weak and the small and the innocent.

True strength lies in knowing where and when to show it. Picking on the small, the weak, and the less fortunate doesn’t take strength. Standing up for them does. Be a champion of the underdog, the young, the old, and those who are struggling.

Having a girlfriend isn’t as important as having friends who are girls.

They sure are beautiful, and movies, music, and TV all tell us that we need to have a girl by our side to be whole. What they don’t tell you is that if you feel that way, you’ll always be looking for the next one, a ‘better’ one. If you really want to know about women, make friends with them, talk to them, and listen to them. You’ll learn more that way than you will from any Hollywood movie, and chances are, you’ll have a much richer relationship than one based on how she looks in short shorts.

Sex isn’t conquest.

Again, pop culture will lead you astray, especially when it comes to sex. You won’t be any more of a man if you sleep with lots of girls, but you will have a much bigger chance of getting one pregnant or picking up an STD along the way, and at such a young age the problem is that many don’t even know what do STDs feel like so they won’t know when they have it. I’m not saying you have to abstain or wait for marriage, but I am saying that you do need to consider that every girl is someone’s daughter or sister, and to respect them as you would your own sister. And for god’s sake, make sure you are prepared with some form of birth control. Being a teen dad isn’t so manly either.

Anyone can imitate, but it takes a brave soul to think for himself.

When watching the coolest kids in school, or the best jock, or the most popular guys, it’s tempting to want to be just like them. But if you were just like them, you wouldn’t be following your own true nature. It’s great to learn from others, but to simply imitate them is cheap and fake. Listen to yourself – to what values and dreams are important to you, and live your life in accordance with those, not someone else’s.

Winners do quit, no matter what the cliché is.

If your heart isn’t in it, then it doesn’t serve you to continue doing the things that people think you ought to do. And if you want to be the best didgeridoo player ever, you might have to quit the chess club or the Future Farmers of America, or whatever it is that is taking your time and attention away from playing the didgeridoo. In fact, you might need to quit everything else. But that’s up to you and your dream. Don’t let anyone tell you that persevering through something you can’t stand is of a higher moral imperative than quitting. There’s value in pushing through the tough parts, but suffering for someone else will never be fulfilling or productive for you.

Making lots of money isn’t the point, but neither is it evil.

It would be wonderful if money solved everything, but all it takes is a quick look at a newspaper to see that those who ‘have everything’ also have whole worlds of trouble that you don’t. Because I had but little money, I used to believe that having lots of money was evil, and I denied myself the idea I was capable of earning a good living by following my dreams. Don’t let that be you. Don’t be a slave to the dollar, but also don’t let yourself stay poor out of a moral judgment.

Follow your muse, even if it doesn’t seem practical to your family, friends, or teachers.

People will always try to tell you what you should do with your life, most of it based on what they want from you. Sometimes it’s based on what they wish they could have done, sometimes it’s based on what they did do, and sometimes they simply want to live vicariously through you. Most of the time it is out of love for you, so don’t be angry at them. But at the same time, remember that you’re the one who will have to live with those decisions, so if you are being pushed to go to college, and all you want to do is draw or paint, don’t let others decide for you. Not everyone needs to go to college. There are plenty of trade schools, apprenticeships, and alternative education experiences available to you – and college will always be there for you if you wish. If your heart tells you to play guitar and write music all day, then getting a degree in accounting isn’t going to be fulfilling to you. Listen to your heart.

Don’t take yourself too seriously.

Nobody really enjoys being laughed at by others (well, perhaps comedians or clowns do). However, learning to laugh at ourselves is an important skill to have. If we’re so hung up on always being right, or always winning, or always being ‘perfect’, we’ll miss out on a lot of experiences in life. Making mistakes is how we learn, and the more comfortable we are with failing, the less we are afraid to take chances. And the more chances we take, the more we’ll learn and grow.

Love who you are, not who you think you ought to be.

All of us are born with something special to share with the world. Don’t listen to those who would tell you otherwise. You count. You’re amazing. You’re perfect just as you are. Don’t try to be someone else, and don’t try to be something for someone else. Follow your own counsel always, and trust your heart.

Above all, be honest.

Be honest to your friends, your enemies, your parents, and most importantly, to yourself. If you have the slightest hesitation about your actions or words, think twice. When you look at yourself in the mirror, you want to be proud of yourself and the choices you’ve made. That won’t be the case if you’re not brutally honest with yourself. A true man takes the consequences of his actions and doesn’t try to get out of them or pretend they didn’t happen. If you make a mistake, admit it and make it right. You’ll always have to answer to the man in the mirror, so do yourself a favor and do right the first time.

[After writing over 1500 words, I realized that there’s more to this post than I thought. I imagine I’ll be revisiting this theme in the near future. In the meanwhile, you might also enjoy this piece on anger.]

Image: Robyn Gallagher at Flickr

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  1. I like this advice a lot. I’d skip the part about crying….no 15 year old can hear that….and the world will eventually make you cry, whether you want to or not. There is value in being strong in the moment, and letting yourself grieve afterwards if you need to.
    I’d add this advice too: Learn to handle money by putting off a purchase until you have saved for it, and understand that if you spend your money buying “A”, then you don’t have it to buy “B”. That is how life works, and it works like that because, despite the way our culture tells you to go out and buy this and that and those and these…..the best parts of life are not found on store shelves. The best parts of life are the ones that are so important, we take them for granted: The love of a parent, the respect of a worthwhile friend, the expectation that life holds more hope and joy ahead than it does difficulty.

    Also, I would add that, whatever your religious beliefs, the world and its deeper complexities are pretty much mysterious and magical, even for scientists and atheists. So, revel in the fact that we live, still, among deep mysteries, and beautiful mechanisms that the smartest among us have yet to pierce…each bit of knowledge reveals a deeper layer of mystery and beauty. Nobody knows how the deepest parts of life work, and anyone who says they do is lying. Quantum mechanics, string theory, alternate dimensions, the ability to create life from scratch, consciousness, the ability of the human mind, the abilities of non-human (animal) minds….all these are ultimately still unknowns.Always know that you live in a world that is woven from fabric that is a million times more mysterious and beautiful than we jey fully understand. Live as such. ;-

    • Thanks for your additions!

      As far as crying – I was imagining that because I was ‘taught’ by society that boys don’t cry, learning that they do indeed would have greatly changed my attitude about it. (And I wasn’t advocating breaking out in tears at any moment, I was trying to get at the message behind it – that men don’t cry, and because of hearing that message, many of us are not comfortable with our feelings.)


    • Justaguy: thank you for the incredulous thought process! I just edited and posted on our family “wall” for my 3 step-sons who are suffering lack-of-father. Literally printed and hung…

  2. Oh, and look people in the eyes when you speak to them, and if you make a promise, keep it. If you don’t want to make a promise, say, “I cannot make that promise.”

  3. I thought this was great advice for boys and girls!

    So many of us struggle with being true to ourselves, and I think that’s at the heart of so many of our problems. These are actually all great tips for me to remember, and I’m in my 30’s! 😉

    Also, I thought the gender-specific advice about crying, relationships with women, and sex as conquest was perfect. My wish is to see all men treat women as equals with honor and respect, but we have to teach that. You’re doing a great job!

  4. Great post! I think this could be given to a 15 years old, and again when he is 20. It’s hard to make the “making money” choice over what we like to do, and we too often take the first path. (I did!) It’d be good at this age to hear someone say “no matter what you do, you will be just fine” instead of “this is economic crisis, you need to go where there are still jobs!”. Like you said, our family, friends…just want the best for us but, they also dump their worries about life on ourselves. Having said all that, you can ALWAYS change your path, so no need to be angry at your family, for after figuring this out, you can just stop right there in your tracks and try something else. You were wearing the wrong shoes anyways.

    • Definitely true – to revisit these words after some time has passed (I’m still working on them…). Thanks!

  5. Pingback: Something Borrowed « Brave New Girl

  6. Another great post, Derek — truly words I wish I had heard when I was younger & that, frankly, I am grateful to be reminded of even now :)! Your son is lucky to have you, as are the rest of us. Keep spreading the light, my friend! — Michael

  7. Hey Derek, Great post. I ran across this through stumbleupon. I just turned 52 and can ‘honestly’ say, I have made mistakes in every one of these categories. I too, have learned things the hard way, the school of hard knocks. I still do in fact make bad decisions in some areas of life, but we are always growing till we die. A strong finish is better than a strong start. As the sayings go, “Know thyself.” and “To thine own self be true.” A friend of mine once told me 32 years ago, “Never cross yourself.” There is more to that than I realized at the time. If you do things you’ll be ashamed of, you’ve crossed yourself. If you make foolish decisions, you’ve crossed yourself. If you cross your legs when you should go visit a sick friend, you’ve crossed yourself. If you cross your arms when you should lend a hand, you’ve crossed yourself. And on it goes. If cross others, You’ve crossed yourself.

  8. Part of me wishes that I had listened to this type of advice as a teenager. But, I know that I wouldn’t be where I am at if I hadn’t made the mistakes that I made. Great post! These apply to both men and women!! Thank you!
    .-= Shannon´s last blog ..Rainbow Baby =-.

  9. Dear Derek, This is FANTASTIC! Wow!!! I wish I’d had this list when I was younger. This is so so soooooooooo good. It is a list for EVERY human being, male or female, and ALL ages. It is one I will print out and keep just to remind myself when I need it. I also think I will make one of my own. What a fabulous idea.

    I can also think of a few young people I will refer to your site who are in a place in themselves where they would soak this in and use it. Bless you for your authenticity. And many good “experiences” to you and your family in the new year. Hugs, Robin.
    .-= Robin Easton´s last blog ..When You Know You’re Alive =-.

    • Thanks, Robin. When I reached (what I thought was) the end, I realized that there’s a lot more to say about it, and I am planning to continue the thought in another post. I also would love to see what others would write about it as well – I look forward to reading yours.


  10. Thank you for sharing this advice. Self-honesty is always key, as is loving yourself for who you are and not who you may want to be. I’m a 22 year old guy trying to find his place in the world, and a lot of this really resonated with me. So thank you for sharing, and I hope to see more posts on the topic. I don’t think there’s nearly enough candid, real talk from adult men in this society to people my age. I, for one, appreciate it and wish it happened more often.

    • You’re welcome, Auren. I’m glad you got something out of it, and that’s more than enough reason for me to pursue some other posts on similar topics. Thanks for reading!

  11. I love this…all good points. I would only add that I really think a “mistake” isn’t such if one can look back on it and realize they would have altered their decisions. Clarity is a great gift, and if it means taking some tough turns on our journey to absorb wisdom, then put on your seatbelt! 😉 I’m glad I found your voice. Cheers and Blessings.

  12. Thank you very much for this post. It’s weird how i realized that although I’m just 14 I know and follow most of the things you said.

    • Thanks, Mocha Dad. That was the reason I wanted to write about it – because I never heard these things growing up. Cheers!

  13. Best post I’ve read in a long time. I dig the retrospect and The advice is beautiful! Of course who you are is based on the mistakes and lessons; they all served you in some way. With that said, it doesn’t mean others can’t learn from your wisdom and go learn different lessons of their own. Thank you very much for sharing this! And hey who says you’re “middle aged”? If you don’t plan to die at 80 don’t let society tell you when you’ve reached the half way mark!

    Peace & Prosperity ‘
    Dallas Cyr

  14. I read through these pieces of advice not thinking of it as advice for a fifteen year old, but with the fresh eyes of a 25 year old with something to learn.

    I’ll tell ya, I learned a few things. And a few things that you said were like wise old pieces I’d heard before, like from my grandmother, who I’ve been listening to for a long time.

    Great post, Derek. I can see why this is your most popular piece.

    Much respect,
    .-= Kaitlin Rose´s last blog ..Home Birth on Capitol Hill =-.

  15. Hey Derek,
    Great post, I know you put this out several months ago but the info is timeless. As a pediatrician in my 40’s, I can relate on a personal level as well as professional level to your words of advice to the 15 year old in all of us. I have a particular interest in helping parents of those 15 year old teenagers of today to be able to impart the words of wisdom like you have so eloquently put here.

  16. Derek, This is a great piece. It’s funny but I wonder do you think anyone can know all the above at 15? Can you hear the wisdom without having some of the life experiences that are necessary to understand the truth of what is being said. Reading through at 35 years old I know all the above to be true and yet still find myself having to step back from what I do on a daily basis to ensure I’m following my own path. Oh and quitting, I think learning to quit without feeling like you failed might just be the hardest thing of all.

    • Kevin – I think you’re right – a 15 YO probably can’t know all of the above without the experiences to support them. However, I did this as an exercise to help me understand what I’ve learned, and in hope that I’ll be able to cultivate the type of relationship with my son in which he *might* be able to hear this kind of advice.


  17. Hello,
    I really admire your taking the time to construct such a positive message based on your own experiences on this world. ;] … Despite what previous people may have commented about a 15 YO not understanding the meaning of this post, I will say regardless of that this post is still more precious than gold. For no matter what age you are at, this will never be understood unless you possess the desire to understand it!.. I am 21 years old living in Southern California, and I have had my share of negative and positive experiences and can relate to every single point you have elaborated on… in my opinion, if your post even touches the mind of 1 person in a positive way, young or old, you have achieved a noble task!!!.. And I am 1 person… May you continue to promote positivity and enjoy all you have been blessed with!!!

  18. This is awesome… I’d also add that your mind, your body, your emotions are all important and wonderful aspects of your being… but if you let any of them rule you, they may just destroy you… you need discipline to keep your will- your true soul desire & conscience running the show. And wisdom is better than knowledge.

  19. Oh soooo true. You just helped me realize my 21 yr old grandson, whom we lost just shy of 2 yrs ago, WAS living much the way you suggest. I, of a different generation, was unable to see and accept that.. . it is tooo late now to tell him “I understand and you go for it Thommers”. But I feel such peace in realizing how much he DID live his life and how MUCH HE Gave and Received back in living his life as he did. Now we have a 9yr old Great-grandson,a 4 yr of Great-granddaughter and his 3yr old son. I may not be here by the time they reach 15 or 20, so I am printing this out and tucking it into the old ceder-chest that belonged to my mother. Everyone know “All Important Stuff” is kept there.. I hope someone finds it and shares it with all 3 of them. Thank you for the words everyone should hear more than one time in their lives. Also, thank you for the article “what NOT to say to a parent when a child dies.” Re-posted it on my status on Facebook. Hope that was ok. You got the credit. Powerful Thank you again. You have made my day seem worth while. Bless you from an Old Great-Gam.

  20. speaking as someone heading for the big “four-oh” and still learning every day and still making more than my share of “mistakes” – i really want to show my 2 boys that they can go their own way in life – and that it you have never made a mistake, you have never made anything!

  21. The most comprehensive list of brilliant advice I’ve seen recently 🙂 An awful lot of the conclusions I’ve been starting to come to lately too…

  22. Hello Derek,
    I happened upon your words of wisdom through doing a search for: life advice for young men. I have been looking for something that I can send my 20 year old grandson, who really needs a wise male mentor. Both his father and grandfather, unfortunately, are not equipped to offer him advice, as they are the results of inadequate fathering themselves. I think your advice is just right, and would like to print it off and send it to him. But I am wondering whether you may already have written something similar in published form, as I think it is two years since the above article appeared?
    There seems to be a lack of such information for young males…especially those who need information presented in a manner which “speaks” to them easily.
    I would love to hear about anything you may have published on this subject, and thank you for doing this article.

  23. I am consistently learning and trying to reform my life in terms of how I view things and the way I think, act, and speak. I am working on a blog and this really helped me think about somethings I don’t necessarily think about until I read them. great article.

  24. Hey, I am a 14 year old teenager. My mom emailed me this post because she thought that it could help me. She was right. I have been looking for some answers about girls, who I should be, what I should do, and what I should try to achieve from someone other than my friends and family because they will just tell me don’t give up, take it slow, and a bunch of stuff like that. This really helped me answer soen of those questions. Thank for writing this and I hope you keep this blog up

  25. If I had to summarize this fabulous post, I would do so with “Be YOU.” Being you as in owning up to your shit, knowing who you are, living out your purpose, and having a good reason for all the things you do.

    We get so caught up in this idea of needing material things, sexual attention, high status positions, and on, and on, and on. They only ever fill a hole though. When you REALLY know who you are and you REALLY care about your influence on the world, then you’re sure to do great things. It’s not what you have, but what you do. When you do great things, you’ll have great things.

    P.S. As a woman, I admire what you have to say about relationships and sex. It’s so important that a woman be valued as a person rather than be seen as a “good time.” I hope all men reading this get that and can see how the way the treat a woman will always mean 1000x more than matters of size, speed, and duration.

  26. I happened upon this website looking for quotes, sayings to write to my growing boys (16). This advice is truly perfect. I am putting together a nice booklet for them. I hope it is only to take some of these points.

    Thank you.

  27. hi Derek, i found this gem whilst doing some research for my company on tips for what men need.I will be 26yrs old 16th september,next month . guess what?! this is one article i love so much. Thank you for touching so many lives with this.I will share this to as many as i can . its a great one .

  28. Hi Derek, My son’s 15th birthday is today. Need I say more!! In addition to regular 15 year old boy problems, my son (who has a great heart) has battled with behavior problems his entire life (he met criteria for ADHD, ODD, and Conduct Disorder- not to be used as a label, merely helpful in identifying issues he deals with) Life with him has not been dull and has been full of challenging and growing experiences for me. This last while, I’ve asked him to think of what he’d like to accomplish this year- goals, activities, plans (a bucket list, so to speak!) It saddens me that he doesn’t really have one. He wants to buy stuff (and play videogames, of course) I see your article as an amazing tool that should be used in schools and discussed and reports could be done on it to get kids to start thinking about how they would like to shape their lives. Where would they like to be and how are they going to get there. I think it’s a perfect article to have stumbled upon. As a mom, I cannot give advise from other than a female’s perspective. Thanks so much 🙂

  29. “You’re amazing. You’re perfect just as you are. Don’t try to be someone else, and don’t try to be something for someone else. Follow your own counsel always, and trust your heart.”
    These words really inspired me. This is whatthat everyone should understand and follow. Definitely all the things that mentioned here is really true. Well said.

  30. What a wonderful article even to those who are in their middle age and beyond. We all need reminding of the simple truths that failed us while growing up. As a grandmum, this is an amazing article to share with my 14 year old grandson who is not short for anything but experience..his biggest teacher yet to meet.

    May I also add even us ladies can resonate with the advice and it is not strictly for the gents..Thank you.

    Peace & Good Health for 2018 & beyond