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, they 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.
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. I’m not saying you need to abstain or wait for marriage, but I am saying that you 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 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 keep 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 cool 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, mostly 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’s 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 life. Making mistakes is how we learn, and the more comfortable we are with failing, the less we are afraid to take chances.
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.]
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Image: Robyn Gallagher at Flickr



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Actually it’s thanks to my parents, who raised me like that.
Emil – your parents deserve a round of applause! Thanks for reading!
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.
Great article and great advice….thanks for sharing…
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.
Great list and great advice. It’s really too bad that we don’t teach kids these things in school now days.
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!
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.
Cheers!
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
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.
Great advice – never cross yourself. Thanks!
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
Thank you, my brother. I appreciate your positivity!
great article, Derek! happy i saw it in your email chat status
really good one
Thank you, Zachary. Cheers!
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!
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!
Thanks for your kind words, and for reading Natural Papa!
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.”
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.)
Cheers!