Buy nice underwear, and funny socks… A list of 40 things.

Phillip J. Clayton
10 min readDec 18, 2022

As I am sitting here, on top of a mountain looking out, I attempt to finish writing something smart. I started writing some days ago sitting in my favourite café — Cannonball Café — I thought about my life. At 39 years old how much do I really know? It’s said that 39 is a pivoting age, 40 is when the new experience begins.

With my 40th birthday approaching, at the time… it is here now, today I am 40 years old. I thought I would share 40 things I have learnt, but I am not sure if I have 40 things. I thought about making a list, but I had already made a list of 20 items (The drugs don’t work). But in life, if anything is guaranteed, it is change, we are never the same person twice, we either become someone else or we mature into our core selves, therefore we must connect with who we are, not who we are expected to be, or assimilate to who we believe we should be.

Who we are is not the same as who we are necessarily perceived to be, we show different sides of ourselves to different people. Influence comes from many areas of our lives, but if we connect with who we are, then there are certain core values that won’t change. As we mature, we become that person, the older we get, the true self is revealed, and it shows up in how we treat others, how we treat ourselves, and how we respond to change, mostly pain.

It is as though we must experience death and rebirth several times in our lives before arriving at a place, a state of being, where peace finds us. When that happens, we make a solemn promise to ourselves, a pact to never return to whatever we were before, we find acceptance in who we are, acceptance for life itself.

There is a popular quote, an aphorism… that has been attributed to Winston Churchill, unfortunately, no records show that it was said by Winston Churchill. It’s not on the International Churchill Society’s website and the director has stated that this is not something said or originated with Churchill.

According to David Freeman, Director of the International Churchill Society, the quote is a classic example of “Churchillian drift,” which is the term we give to any age-old aphorism attributed to Churchill without foundation.

I said all that to say, I used to admire that quote, but then I realized that there are all these aphorisms all over the internet with no attributions, they are either anonymous or falsely attributed to a famous individual. Where did these statements come from? They’re random memes… but some make you think. The truth is, they’re mostly like horoscopes, the right words, the right reader, someone will attest to the validity of these statements.

The quote I speak of reads: “When you’re 20, You care what everyone thinks, When you’re 40, You stop caring what everyone thinks, When you’re 60, You realize no one was ever thinking about you in the first place.”

I can’t say if there is any truth to the statement, but I am sure for some people, it is true, but life is about perception. What I have always focused on is boldness, age is irrelevant, and age does come with experience and knowledge, but going against the grain is not determined by age, it’s determined by giving less of a fuck, being able to say, giving less of a fuck without feeling guilty about saying it…

I recently visited a yacht club I have come to find joy in, and escape. Yesterday, my buddy and I had a chat with an elderly sailor, he was an intriguing man, still joyful, and loving life. The spark is from a pact he made with his friends at 9 years old, which essentially said society sucks. A pact to never be what society wants them to be, to never lose their freedom, or the life of sailing. They are all still friends today.

Today I say, forget the quote about what happens when you’re 20, 40, or 60… we are human, life is an experience and change is a reality. Sometimes we do care at any age, what people think, but it’s whether it has any impact on us that matters. Fear is a reality, it’s not always about being brave, bravery can be stupidity, it’s about being bold, and boldness goes forward despite fear — We don’t have to be brave, but we can be bold.

We are either great leaders or we follow great leaders. Be wary. But mostly, give less of a fuck.

What I know, what is certain, what I cannot deny, what I cannot reject — this is what counts. I can negate everything of that part of me that lives on vague nostalgias, except this desire for unity, this longing to solve, this need for clarity and cohesion. I can refute everything in this world surrounding me that offends or enraptures me, except this chaos, this sovereign chance and this divine equivalence which springs from anarchy. I don’t know whether this world has a meaning that transcends it. But I know that I do not know that meaning and that it is impossible for me just now to know it. What can a meaning outside my condition mean to me? I can understand only in human terms. What I touch, what resists me — that is what I understand. And these two certainties — my appetite for the absolute and for unity and the impossibility of reducing this world to a rational and reasonable principle — I also know that I cannot reconcile them. What other truth can I admit without lying, without bringing in a hope I lack and which means nothing within the limits of my condition? ~Albert Camus

(Book: The Myth of Sisyphus

So then, here is my list…

  1. The keys to life are discipline, patience, and kindness. In life, dedication is great, but there is great power in having patience. Endurance is mostly what we have.
  2. Be self-aware — You can still be your truest self while only allowing people to know what you wish them to know about you. People experience different sides of us, but there should be a general understanding of your reputation. Some will be ok, others won’t, but they all respect it — boundaries. In matters of personal and professional.
  3. We must be careful how we use the word interesting — some folks use it fast and loose.
  4. Innovation is given birth from pain, or from the ashes it may leave in its wake… I cheer on those bold enough to try, I celebrate their success as much as their failing forward motion.
  5. Self-authoring is good; “The best self-care is quitting the people, places, and things that are keeping you from evolving into your best self.”- Nidhi Tewari, LCSW
  6. Don’t become everyone’s cup of tea… there is something liberating about that — Advice comes from everywhere, know what you want, and stick to it. As long as you can live with the consequences.
  7. Love someone at least once, the pain that follows will change your life forever. This is good.
  8. Don’t fall in love too early, it’s easy to confuse sensuality with love, but more importantly… find yourself first, love that person in the mirror and then share that love with someone else that has also done the same. Choose to be productive, focus on your career and life, and radiate your joy and love so it can one day return to you, do not seek it.
  9. Life is hard and everyone is fighting their own personal battles. Help them through it, kindness is powerful, try to understand their battle — Be a good person.
  10. The person who mistakes money for wealth will mistake a life of owning for a life of living.
  11. Life is one big lesson and the older you get the more you’ll realize how little you know. Have an endless and unquenchable thirst for knowledge and understanding.
  12. In matters of career, have a personal life goal, what is the life you desire most to have? This will dictate all your decisions.
  13. I found this interesting, happiness is a place we arrive at, not something we find — Don’t do something you love. Do something other people will love you for doing. The path to success isn’t always doing what you love. I have found, doing things that other people love has its own rewards, but they must also compensate you for doing those things (contextualize appropriately).
  14. The Olympic Creed says “the most important thing in life is not the triumph but the struggle.” All of life is a struggle, but working through the struggle is how we grow and improve. Doing anything meaningful is never easy but find meaningful things to do.
  15. Give willingly, the more you give the more you get. This is not a Zen mantra; it is a schematic of how life works.
  16. Marry your best friend. The person you marry is someone you’re going to agree to have tens of thousands of meals with. You’ll spend countless hours watching TV and talking to them. They’re the person you’ll argue with and love most. Make sure it’s someone you really, really like to be around.
  17. Be selective with the people you spend time with, there are beautiful people in this world — Surround yourself with people who will make you better.
  18. Hell is real. At some point in your life, you will be forced to endure great levels of turmoil — If you endure long enough, you can find your way out of hell. You will be forever changed, never to be the same again, hopefully, you will be better for it.
  19. Pain is a great motivator.
  20. Fear is a reality; we do not kill fear or remove it from our lives. Understanding risk removes the crippling effects of fear. Taking risks isn’t necessarily brave, from an informed position, it is bold because you made a choice to go against fear — We must ask, “What am I prepared to lose?” and if you don’t lose you have everything to gain.
  21. The greatest thing in the world is to know how to belong to oneself.” — Michel de Montaigne. If your inner voice is harsh, judgmental, overly critical, pessimistic, and sometimes cruel, there is a good chance you are struggling with low self-esteem. Change how you perceive yourself and speak to and about yourself.
  22. Buy nice underwear and funny socks… Life can be spontaneously pleasant as much as it can be embarrassing.
  23. You can have anything you desire most in this world, you’re capable of a lot more than you think. But you must want it and you must want to invest in it. Mental conditioning trains your mind.
  24. Morgan Freeman as William Somerset in the movie ‘Seven’, said: “Ernest Hemingway once wrote, ‘The world is a fine place and worth fighting for.’ I agree with the second part.” — Embrace change in a world that is always changing.
  25. With age comes wisdom, knowledge has more meaning, and you will one day realize that someone always has more than you. You will never have it all. But you will also learn that having enough is not that different.
  26. It all goes a lot faster than you think. You have no time… Don’t wait to do the things you want to do.
  27. While never stop learning, also, never stop teaching. Whether you realize it or not, there are people who look up to you, you have a responsibility.
  28. Have large goals, and give yourself something worth fighting for. You will fail but you will learn to endure.
  29. Relationships are mostly about compromise. The best relationships that are worth the most are the ones you give the most to.
  30. Learn to say you’re sorry.
  31. Embracing change also means embracing failure, but it is more important about learning from those mistakes. Failure is all part of the process.
  32. We are always selling, negotiating, and leveraging something about ourselves, those who do this effectively are masters of selling themselves. You’re great. You can be even greater. But no one is going to believe that until you first believe it to be true.
  33. Stop thinking of yourself as someone filling a job, be a problem solver, and present yourself as a solution. Remain curious and explorative.
  34. Ask for help.
  35. Don’t network, connect, and have a genuine desire to build relationships with other people.
  36. Learn to say no. No often leads to a powerful yes. The right yes.
  37. Almost everyone, no… everyone is looking for something to believe in, we question what the truth is and what is the lie. The truth usually exists somewhere in the middle, but your life is a journey, you will discover things, so try to relax more.
  38. Don’t fear vulnerability or emotions, they are required to become better, stronger, and incredibly intelligent when it comes to processing life’s pain.
  39. Don’t forget to smile.
  40. Protect yourself at all times.

It turns out, coming up with a list of 40 things is a lot more difficult than I realized, I then realized there are a lot more than 40 things one could write about life. The difficult part is, coming up with 40 helpful things. I hope it was helpful.

The view isn't horrible from here.

“Go without a coat when it’s cold; find out what cold is. Go hungry; keep your existence lean. Wear away the fat, get down to the lean tissue and see what it’s all about. The only time you define your character is when you go without. In times of hardship, you find out what you’re made of and what you’re capable of. If you’re never tested, you’ll never define your character.”

— Henry Rollins



Phillip J. Clayton

Brand consultant | Strategic advisor | International brand & marketing design judge: | Writer | Creative director