On Growing Up & Masculinity, From A Young Man To A Younger Man

I was recently asked by a family friend to participate in a minor ‘coming-of-age’ ceremony for her son. He just recently celebrated his 18th birthday and, as a significant age in our society, she wanted her son to receive advice and thoughts on becoming a man.

Jacob Winter
8 min readMay 31, 2021

Due to death in the family, this young man grew up lacking a typical male influence in his upbringing. Several male influences in his life were asked to contribute thoughts on becoming a man and masculinity in today’s world. The notes were given to him as a collection on his 18th birthday. I received permission to post this, but still changed some personal details.

Happy birthday buddy. Eighteen is a big one, and I feel incredibly privileged to be able to share some thoughts with you. I hardly had a grasp on my life on my 18th birthday despite thinking, at the time, that I knew where I was headed. Looking forward, I’m not sure if you plan on pursuing university, community college, work, a trade, or something entirely different. Any of those options are fantastic choices, no matter what anyone else tells you. A college education has historically been pushed by society as the assumed post-high school path if you plan on being successful. I am thrilled with my choice and opportunity to go to college, however, everyone’s experiences are uniquely different and enable each of us to achieve success in different ways.

On a related note to me not having a concrete path laid out to my future, a little bit about where I am right now. I worked for about a year and a half (good trial period, in my opinion) in what my college major got me to. I then decided the environment in that industry wasn’t going to appeal to my interests or contribute to the value of where I see my life going. I’m now living off my savings for a year-and-some. Road tripping, living somewhere new, and exploring my interests. I encourage you to consider doing something similar, but wait until you’re 21+ (bars can be a great scene to people-watch the locals and enjoy some locally brewed beers). I don’t know much of your older brother’s story, but I know he was/is on a similarly explorative path. He’s hopefully been able to share stories of self-improvement, doubt, faith, successes, and failures along his journey. I would be more than happy to share my transformative experiences as well. Moral of the story: put yourself out there in uncomfortable situations and see what sticks. It doesn’t have to be moving to France by yourself for a year. It can be spending a summer working or exploring in a new city or state where you have no close connections. It can be a solo extended backpacking trip. I just personally believe we should all have the opportunity to spend time with ourselves learning about our own minds and bodies, good and bad. I would be happy to talk about ideas and options if you end up deeming my advice legit.

I think experiences like I describe above (learning about yourself and the world) help us decide on and carve out our place in the world as a man, especially in the important transition into manhood that is our late teen/early 20s years. These are years that we start to think seriously about the trajectory of our lives:

  • If and when you want to be married
  • If and when you want to have kids
  • What your skills and interests tell you about what you may want to do for work
  • What types of relationships you want to maintain with friends and family

All of these are questions that adulthood instigates, but by no means will you know the answers right away. A lot of the time these answers change too! These are some of the big picture questions that I still think about daily…and I’m 24! Don’t expect yourself to easily figure your life out similar to just checking a box. Whether in college or not, around the age of college graduation, the mounting pressure of adulthood arrives and our instincts/society tells us, “Buckle up, you’re an adult now. Figure your life out.” It is great to set, track, and meet goals for your life, but these are often ever-changing. I encourage you to not feel like you have to do anything or pigeon-hole yourself into a job or school just because you’ve been told it’s what you’re supposed to do. I’m not saying to easily give up on things. Even a dream job will have its hard days. Always give opportunities a chance, but don’t be afraid to jump ship if something else is calling your name.

Growing up generally in the time you are is probably super strange and plenty confusing. Whether it really is or not, (at least to me) it seems like the world is in constant peril. Media, the internet, and all the other miscellaneous talking heads in our lives can make us unsure of ourselves at times. On top of that, you’ve navigated growing into a man without two incredibly important men in your life. I was so fortunate to know both of them and am happy to pass along some of my takes on masculinity to which I know my time spent with your dad and brother helped form.

The traditional man has always been depicted with characteristics like big, strong, hairy, deep voice, aggressive, competitive, and leader. The more modern and progressive man is encourage to be in touch with his emotional side, act more compassionately, and be comfortable straying from traditional gender roles. Similar to most things in life, I think a healthy balance of both extremes produces the best outcome of a successful and happy man today.

Our society has been built on tribes and the family structure since…well, forever. The protective and aggressive instincts we have as males comes from the desire to protect our families and ensure their longevity. However, when pride or outside expectations of this behavior prevent us from addressing issues within ourselves or with others, i.e., letting emotion bottle up in us, it can become an issue. We don’t need more men holding in feelings to then explode in anger, overindulging in our aggressive instincts. That is what can happen when “being a man”, unprocessed emotion, or pretending that men don’t cry isn’t well-balanced. A strong man is thoughtful and can communicate in a non-impulsive way. I believe it’s just as important for a man to protect, compete, and love the outdoors as it is for him to be emotionally available, thoughtful, and able to present himself. The protectiveness we exhibit over friends and loved ones is a result of our care for these people. It’s important to embrace the “why” of acting how we do as males as much as the “how” we show our masculinity.

In ancient Europe, the term “renaissance man” was used to describe a man who was well-rounded. A man who can talk politics and astronomy. A man who enjoys theatre and the outdoors. This general idea is the lens I put on my life. There are so many incredible and beautiful people, ideas, and places out there. Be curious and open to anything!

What I think a man does NOT do includes:

  • Belittling the women in his life
  • Putting others down, in general, with an intent to hurt
  • Contribute to any negative outlook of a group when in a sticky situation. Be a problem solver! Have faith in yourself!
  • Intentionally call to attention the differences in others to build himself up or put others down

Your dad and brother were big parts of my life, both as I stepped into puberty and as I began finding my manhood early in high school. These are two very transformative points in a boy’s life! Your dad was my first coach that really pushed me to my physical and competitive limits while being an example of a caring and fun-loving man. At 10 years old, he taught me how to work hard and how to never fail in finding humor in a situation. Your brother and I were on relatively similar paths toward manhood in middle and high school. He loved to laugh, make people laugh, and get himself into trouble occasionally, but held such a high respect and understanding of the role models he grew up around (church, soccer, school, etc.). Your dad and brother found their masculinity in extreme competition, snarky humor, and building others up because they truly cared to do so.

I know this has been lengthy, but I’ll leave you with just a couple more notes. Some random points of advice:

  • Read and write. I got plenty burned out of reading for pleasure in high school and college. But don’t give up on it for good. There are an infinite amount of incredible thinkers out there to read that help you understand yourself and others like nothing else can. Also, writing can be great meditation/therapy.
  • Minimize your cravings and it will minimize your suffering. I got this one from my brief study of Buddhism and is one of my most important life mottos. There are many things in life we can’t do anything about. Instead of letting these things bother you, accept them and be present. If you’re angry, sit with your anger. If you’re sad, sit with your sadness. If you find yourself in an unideal situation you can’t change, see what you can learn from it.
  • Engage other people. A major contributor to my successes has been my willingness and ability to listen to others and open up to them, provoking a connection or conversation. Be interested in others, ask them questions. It never hurts to have more contacts, only less.
  • Act like you’ve been there before. People don’t like cocky people. It is so okay to be excited or proud of yourself for something you accomplished. Just don’t wave it around in people’s faces inappropriately, dependent upon the situation. We all struggle with pride. Just be observant of it in yourself and adjust how you see fit.

Many parts of this message are explained in a very absolute way. There are always exceptions to the rule and I hope my takes will be used in conjunction with many other perspectives to form your understanding of masculinity in the world.

I feel like I haven’t been incredibly involved in your life, but I’m someone who will always hold a spot for you in my life, no matter how much time passes. I’m so proud of you and am always open to talk about anything I wrote here or anything else!

Love From,

Jacob Winter



Jacob Winter

25-year-old exploring history, religion, & philosophy