I preferred to be serious. Because the world is a serious place! There are serious things happening, with serious people!

And while that is true to some extent, it was also a very limiting worldview because it misses the more important part: that the world is also a beautifully simple place, filled with love and happiness.

As it turns out, choosing the latter makes for a better life and a better world.

This is a note that I wrote for myself on happiness. Sometimes a reminder is all we need.

1. Be yourself

Act authentically. Speak authentically. Be honest with yourself.

Listen, carefully, to what it is that you really want. Who are you when the walls come down? What is really you vs. what you think is the right thing to say/do/feel? You don’t have to be right, you just have to be honest.

Be uniquely you. Imperfectly you.

Be yourself.

2. Accomplish hard things

Do hard things. Every day.

Occasionally, sign up for something really hard, something you might not even be able to do. Accomplish it. Or fail. But give it your all. These moments will create your future memories. They will put a smile on your face.

When given the opportunity, always choose hard.

Accomplish hard things.

3. Respect the science

Direct sunlight in the morning. Walk. Sweat. Avoid algorithms. Calm your mind. Interact with people in your community. Eat whole foods. Keep it simple.

There are a lot of smart people out there spending their lives in labs trying to figure out how our silly little brains work. Maybe we should listen? Maybe we should commit to trying them for a month. For a year. Maybe they don’t work for us, but maybe they do.

Respect the science.

4. Choose to be happy

In every possible moment, choose happiness.

Did you wake up this morning? Did you walk outside today? Did the sun touch your face? Did you laugh? You’ve likely experienced hundreds of miracles today alone. There’s always an opportunity to choose happiness.

Does it really need to be more complicated than that?

Choose to be happy.

And yet, sometimes you’re just not going to be happy. And that’s ok too. But regardless of how badly I’ve wanted there to be more to this story, the truth (for me at least) has been that happiness is nothing but a simple choice made in every moment. It is not a constant. It is not guaranteed. But it is available to me, and the more I choose happiness, the happier I become.

It famously took James Dyson 15 years and 5,127 prototypes to ship his first bagless vacuum cleaner. 15 years. To build a vacuum. In his own words:

There are countless times an inventor can give up on an idea. By the time I made my 15th prototype, my third child was born. By 2,627, my wife and I were really counting our pennies. By 3,727, my wife was giving art lessons for some extra cash. These were tough times, but each failure brought me closer to solving the problem. It wasn’t the final prototype that made the struggle worth it. The process bore the fruit. I just kept at it.

And he’s not alone.

SpaceX endured nearly two decades of failed rocket launches before they successfully landed their first reusable rocket which now dominates space.

Julia Child spent 8 years in France learning techniques and another 8 years writing her first cookbook, which she didn’t publish until age 49.

Tolkien spent 12 years writing The Lord of the Rings and didn’t see it published until he was 63.

Every time I encounter greatness in the world, I’m reminded of the seemingly impossible amount of time and energy dedicated to its pursuit. I can’t help but think how wildly different that is from my own life so far. The longest I’ve ever even spent in a job or lived in one place was 3 years, and that felt like an eternity.

The world has gotten faster. Time frames have shortened. 18 second TikTok videos are hijacking our attention spans and demanding all information flowing into our brain is summarized into bite sized hacks to make us hot and rich. It’s become increasingly challenging to see the true sacrifice, commitment, and time that is responsible for much of what exists in the world today. But no matter how short Meta wants our attention span, we can’t escape this time based reality. Greatness requires an almost unfathomable level of commitment, that’s part of what makes it great.

This was a good reminder for me. A reminder to commit. To endure. To get back up after the 100th failure and prepare for 100 more. To show up in pursuit of greatness.

But I think there’s more to that story.

Choosing the wrong role models

When I was 19, I went to Silicon Valley for the first time with some friends. Before the trip my friend told me to read the Steve Jobs biography to understand the Valley a bit better (it currently sits on my bookshelf next to me as I write this).

I think this was the first time in my life that I really experienced greatness. I could see it, feel it, smell it in the air as I walked through Cupertino staring up at the glass spaceship that was about to house Apple’s HQ. All of this, from Steve’s vision. His pursuit. His greatness.

I craved that feeling. Something about the aura of greatness consumed me. There was an issue though.

It turns out I really don’t want to live like Steve Jobs.

Or like Dyson, or Buffet, or any of the other greats I can think of. These are tortured beings. They neglected their families, their bodies, their minds, because they felt they had no other choice. They risked everything. They were obsessed to the core. Singularly focused on being the best in the world at one thing or accomplishing something nobody else possibly could. I’d be willing to bet that you’re reading this on an Apple device, or that you have a Dyson in the closet.

I have no judgement on whether their approach is right or wrong, people ultimately live the life they need to live. I’d argue the world needs more people willing to sacrifice everything for breakthrough innovation. What strikes me about these figures isn't their methods, but their complete commitment to something that matters to them. They're so unapologetically consumed by their purpose that you can feel it just by looking at them, or by listening to them speak (David Senra comes to mind here).

So what now? I’m not like Steve Jobs. I’m not like Dyson. I’m not like anyone. I’m me.

And I’ve been me for as long as I can remember.

Being great at being me

Greatness needs a rebrand.

Take my wife for example. She teaches six-year-olds, without a doubt one of the most challenging and important jobs in the world. For a brief moment in time she is the most important non-family person in a child’s life. Her daily presence, actions, and energy will form how these little humans show up in the world. She doesn’t have a biography, and people aren’t going to visit her classroom like they do the Apple headquarters, but what she does get is a drawing every day from someone in her class saying “I lov yu Ms Killum”, and they mean it. If that isn’t greatness I don’t know what is.

Is there an opportunity to pursue my own version of greatness? One that feels authentic, maybe one that looks crazy or boring to other people, but one that feels like me.

I think the same principles apply whether I’m building a vacuum or building a family: do what I feel called to do, and give it my all. The question isn't whether to pursue greatness, but how to define it on my own terms. What if greatness for me isn't about “changing the world”, but about being fully present in my own? What if it's not about being remembered by history, but about being there for the people who matter most?

These questions don't make the pursuit any easier, they just make it mine. And maybe that’s exactly where greatness begins.

I recently listened to a great podcast, Chris Sacca (a certified legend) on Tim Ferriss.

They’re talking about dating and Chris shares a hilarious story about a dinner party where he tried to set Tim up with a mutual friend.

So Tim and this woman are sitting next to each other at the dinner table. Vibes are high, conversation is flowing, and the woman asks, “Tim, when do you feel most present?”

With everyone at the table listening, Tim replied with a straight face, “while I’m having sex, doing psychedelics, or hunting.”

Needless to say, things didn’t work out between them (she’s vegan). I mean, it’s an outrageous thing to say at a dinner party, even at a table full of the eclectic elite that Tim Ferriss hangs out with.

But hold on. Tim’s response of sex, psychedelics, and hunting aside, is that not the ultimate question?

The lady at the table asks, when do you feel most present? Is that not beautiful? What could be more real, more magical than the moments when we feel most present, most alive?

When do you feel most alive?

When you’re driving with the windows down and the right song comes on?

When the first ray of warm sunlight hits your face?

When you look at someone you love and everything else fades into the background?

Whatever it is, isn’t it…beautiful?

I get it, we’re all out here trying to be Serious People. Trying not to look silly. Trying our best to keep up. Trying, desperately, to be a part of something larger than ourselves. I also wonder if at times we let life get in the way of the simple experiences that make us feel most human.

At the end of the day, at the end of our lives, I suspect those moments are the only ones that really matter.

Link to the episode:

Over the past year I’ve experienced a growing desire to write. The universe blessed me with endless topics to explore. So I wrote often. I wrote about money. I wrote about modern work. I wrote about meaning. I wrote about great books, podcasts, and movies. I wrote about simple ideas that changed my life.

There was just one massive problem. Most of the time, I couldn’t hit publish. I had the Fear. Fear that I’m not a “writer”. Fear that it wouldn’t resonate. Fear that I need to choose a lane. Fear that I’ll write something today and disagree with it a few months from now.

It turns out that there are only two things standing in the way of me being a writer: writing and hitting publish.

Turning Pro

In some areas of my life I am a pro (to use some Steven Pressfield verbiage).

For the past ~10 years I’ve (mostly) worked on growing software companies, and when I show up at work I am a pro. When I’m investing and researching businesses, I am a pro. When I look at my bookshelf, it’s clear that when it comes to reading I am a pro. From the moment I put my wetsuit on until the moment I get back to the car after a surf, I am a pro.

To clarify, I do not mean pro in the traditional sense. Despite my fancy Excel sheets and thousands (?) of hours spent researching and investing, I am not a “professional” investor. I haven’t gotten through a Dostoyevsky novel (yet). I’ll drive 4 hours in the middle of winter to go surfing and catch one good wave if I’m lucky. But I show up, and I show up like a pro.

A professional shows up every day.

A professional does not fear failure.

A professional pursues excellence but is not shackled by perfection.

A professional writes and hits publish.

And therein lies my issue. When it comes to writing, I’ve been acting like an amateur.

Leaning in is the only way forward. I must do the work. I can’t be sure anyone will care, or that it will find the right eyes. The only thing I can be sure of is that I will write about what energizes me and it will be great work, because I will show up like a pro.

Thinking and Feeling

Welcome to Thinking and Feeling, a Substack that actually gets published :)

If the past year of writing journaling (shout out to my friend Ian for this post that has been living in my head rent-free) is any indication, I suspect I will write mostly about money, meaning, and modern life. I also suspect that I will go off script and explore new frontiers.

I will write often, I will write authentically, and I will hit publish.

I’d love to have you along for the ride (to the 40 of you who aren’t my Mom).

Time to lean in.

Thinking and Feeling

An experiment in early mornings, strong coffee, and a commitment to doing the work. Writing about money, meaning, and modern life.

By Finn Killam

Shout out to Adam, a pro, who used a skillful combination of knife and feather to help me see more clearly that which was right in front of me.

1. I am fully in control (of nothing). There is only one thing in my life that I can control. One. The only thing I have any control over is how I respond to reality. There is what is, and then there is how I react to what is. This is the only real choice I get. My reaction becomes my reality. Something “bad” happens to me. I am in full control of how I deal with that reality. I make it bad or good, meaningful or meaningless. This is such a freeing concept, and it has improved my life on every conceivable axis.

2. Sleep well, make money. The single most important financial decision I’ve ever made is to prioritize getting a good night’s sleep. What do I mean by this? Investing is a tough sport. It’s endurance above all. Success comes from thousands of good decisions compounding over a lifetime. What I’ve realized is that the only way to achieve this sort of longevity is to do what feels right for me. I used to think optimizing for the perfect strategy was the goal, but what turned out to be more true is that I need to optimize my investing strategy for myself. The optimal strategy for me is the one that helps me sleep at night. A bit of extra cash. A bit of stock picking so I avoid the FOMO. It’s not objectively perfect, but it’s perfect for me. If I get this wrong, even the “best” strategy will fail because I won’t be able to stick with it.

3. Hard days, easy life. It’s true. It sucks, but it’s true. Doing challenging things has made me a better person. I’m trying to default to doing something hard every day. Some days it’s a hard workout, some days it’s a walk, and some days it’s as simple as sending a text or making a call I’ve been dreading. I don’t have to go full David Goggins mode, I just need to step out of my comfort zone that day and do something that feels hard to get that sense of reward.

4. Simple mornings and evenings. I’m a classic optimizer, always looking for the perfect way to do things. While optimizing feels good in the moment, I’ve learned that it rarely actually works. If I try to optimize, I never stick to the thing because there’s always a better way—I can always optimize further. In the spirit of un-optimizing, I’ve been trying something for my mornings/evenings that has been working very well. My mornings and evenings only have three hard rules each, the rest is noise. Most importantly, I don’t aim for perfection, I just try to show up often.

   1. Morning: 1) Wake up early and at the same time every day, 2) Exercise or get outside for a walk, and 3) No phone for as long as I can (usually the first 60 minutes).

   2. Evening: The 3-2-1 rule: No food 3 hours before bed, no liquids 2 hours before bed, no screens 1 hour before bed.

5. Follow the light. I know it sounds cringey or like something you’d hear at a South American ayahuasca ceremony, but hear me out. The light, for me, is basically interest. Things that I encounter and feel a connection to. It’s a feeling and a knowing that a particular thing is unquestionably relevant for me, right now. The challenging part is that the light is not always visible. Sometimes it’s dim, sometimes I’m looking in the wrong direction, and sometimes it’s blinding me. That said, it’s always on, and it’s always pointing the right way towards what is uniquely relevant and interesting for me.

I’ve spent a considerable amount of time (for a normal member of society - the Quebecois ski bums would scoff) in the backcountry putting animal hair skins onto the bottom of my skis, strapping on a 20 pound backpack, and walking 8 hours up a mountain in -25 degree temperatures. Why? I haven’t figured out exactly which screw in my brain is loose, but, being hours away from any other humans in a pristine mountain landscape, with clear blue skies and untouched champagne powder at a 37-degree angle as far as the eyes can see? It doesn’t get much better than that.

As I’m realizing is the case with most of life’s pursuits, my time in the backcountry has taught me a lot about the world. Things most of us know, but often forget.

Embracing challenge

The modern world is set up for you to endure the least amount of pain possible. You have all your needs met - food, water, shelter. I think there’s something to be said about people engaging in meaningful challenges, doing things that are hard. Running marathons, doing Ironmans, getting up early, working around the clock on something important, having hard conversations. Looking at a ski resort and thinking “why wouldn’t I just pay to take the chair up? It’s way faster and easier and the skiing is still fine.” is missing the point of life. The metaphorical ski down is only as rewarding as the walk up. Doing hard things is hard - that’s what makes them meaningful and rewarding. Don’t shy away from challenge, and don’t just choose the easiest option that society has to offer. Embrace meaningful challenges and know that they will lead to a meaningful life.

Managing risk

Backcountry skiing is “risky”. There is risk involved in everything you do, from the icy highway that takes you there to the cornice hanging off the ridge above you to the unstable snowpack beneath your feet that could trigger an avalanche (this is the main one people seem to fixate on - I see this as the equivalent of shark attacks for surfers; nowhere near the most dangerous part, but by far the scariest and most thought about.)

You can easily tell someone’s risk tolerance based on what they do for fun, and you can tell someone’s understanding of risk based on how many times they’ve been to a casino in the last year. Something to note about risk is that risk itself is not inherently good or bad. I’ve been guilty of being incredibly risk-averse throughout my life. I would over analyze every decision and not do anything that carried the risk of me failing. In my opinion, this is a limiting perspective. Risk is complex and our brains are bad at evaluating risk, which makes it hard to navigate in the real world. It can be helpful to understand the risk/reward profile of any given activity and then decide if it makes sense for you to take on. As you get feedback (ie. a risk you took resulted in something negative or positive) your understanding of your personal risk-tolerance will become clearer. If the risk you’re taking carries a significant chance of death or complete loss, then carefully consider if the reward is worth it to you. While skiing in the backcountry, there are often situations where the shortest path up a mountain or the best line down a mountain involve catastrophic risks - ie. if something out of your control were to go wrong, you could be seriously injured or die. This is why we often choose the longer route up or the slightly less fun line down, and enjoy a cold beer at the bottom.

Finding focus in your pursuits

Find a few things you really love doing and take them to the limits. There are infinite hobbies or activities to do. People will ask to join their soccer team or to come golfing with them or to join a book club. When you’re young it makes sense to try many things (and I imagine it also makes sense to continue experimenting and exploring throughout life) but put some effort into finding what you really love doing, not necessarily what everyone around you enjoys doing. Focus on your things. Spend your free time doing them. Find other people who also love doing them. Go deep, and try to find the limits of those things. Similar to an investment, time spent will compound and you’ll start experiencing outsized returns - one good day in the backcountry can yield the same joy as an entire season at the resort. This is only possible because of time and dedication towards pursuing that activity. You earn the right to reap the reward by committing to something, focusing on it, and taking it beyond the basics.

Disconnecting

We are so, so connected. Always up to date on the latest news, always seeing what our friends and that random guy we went to university with is doing, always checking the stock price, always replying to our Slack messages. On the one hand, it’s fine. This is the world we live in. Meditate, read for a bit, go for a walk, keep working, whatever you personally have to do to find some balance. On the other hand, I strongly believe we need a factory reset every once in a while. Get off grid for a while. No phone. No laptop. No internet. No news. Just good friends, doing something you love in the real world for 24 hours a day. Experience the slowness. The stillness. The sun rising and setting. Experience how the food tastes better. The coffee is stronger. The Kokanee’s are colder. Do something fully. Don’t film it, don’t think about something else, don’t worry about how you’re doing it. Just do the thing, fully. Be present doing something you love. This is the ultimate form of meditation.

Is any of this novel information? Certainly not. Does it serve as a useful reminder that the world is a beautiful, complex, and meaning-filled place that is yours to discover? For me, yes it does.

I’ve learned a lot over the past few months of self-inflicted unemployment. This post is an attempt at summarizing those learnings to (selfishly) learn and grow from them.

I love this quote from Jerry Seinfeld’s recent commencement speech at Duke:

Making work easier, this is the problem. So obsessed with getting to the answer, completing the project, producing a result, which are all valid things. But not where the richness of the human experience lies. The only two things you ever need to pay attention to in life are work and love. Things that are self-justified in the experience, and who cares about the result. Stop rushing to what you perceive as some valuable endpoint. Learn to enjoy the expenditure of energy that may or may not be on the correct path. 

The end result that many of us pursue often lacks the richness of the human experience. Work (and love, but we’ll save that topic for another day) is a self-justified experience – its meaning comes from the act of doing rather than the final destination. That is great career advice.

What I’ve learned on my quest (so far)

• Finding work you love can be incredibly hard. I suspect this is what makes it meaningful.

• Not everyone is on the same quest as you, and that’s ok - a lot of people are genuinely content in their career, they’ve found what other’s are looking for, and that’s a blessing.

• Work is about more than just the job itself. It’s about the people you spend time with, the freedom it provides you (both financially and your time), and the less romantic day to day tasks. It’s about what you are actually doing vs. some fancy title or job description. A helpful way to tell if you’ll enjoy a certain type of work is to actually do it (for example, if you think you want to be an investor, then trade with a paper portfolio for 6 months). You will find out very quickly if it’s something you like and are good at.

• Inspiration is like a poorly trained dog, it does not usually come when called. Learning about yourself may require a different way of thinking. Career focused people are often used to fast paced, relentless hustle. Introspection and inspiration are part of a different game - one that has different rules. I’ve found engaging in activities that promote creative states (exercise, sauna, walking, reading fiction, meditating) can help but sometimes you just have to be patient and try again later.

• Action is the path. There are no shortcuts (trust me, I’ve tried). There is no other path. You must eventually do the thing. Write the essay, build the app, have the meeting, do the thing. If it turns out to be the wrong thing, then be grateful for the learnings and move on to the next thing.

• It’s likely that younger generations (myself included) are underestimating the sacrifices that are required to do great work. Somewhere along the way society coddled us and told us that we could have work life balance and a six figure starting salary. Scott Galloway often says “you can have it all, just not all at once. Expect to work very hard and make sacrifices if you want to achieve wealth and influence at a young age. The myth of work-life balance is unrealistic”. I think the useful takeaway here is to acknowledge that this will be hard and to make a choice: are you willing to make the necessary sacrifices that come along with the type of work you are pursuing?

• Everyone has blind spots. The surface area of what you know is likely much smaller than you think, this is especially true if you’re young. You can be smart and still have lots to learn. Make sure you are open to being wrong and learning from it. It’s great to have informed opinions and stand up for what you believe, but try to avoid dying on hills that you don’t fully understand.

• Geography matters (sorry). Before you get all defensive: I am MASSIVELY pro flexibility, but there is no substitute for human connection. Working from home is not sufficient. You can start there. You can work there sometimes. You can have a day off there. But at some point, you need to be in person with your team/customer/mentors/fellow solopreneurs/humans. This could be going to the office 5 days a week, a weekly meetup, a quarterly offsite, random coffee shop meetings, whatever works for you. Go find the people that you need to interact with and spend time with them, in person (this would be such an insanely obvious thing to say a few years ago).

• Expose yourself to as much information as possible, but use a good filter. It’s helpful to cast a wide net for information and get good at filtering, since you don’t know where the gems are going to be. I think early on you want to meet everyone, read everything, listen to every podcast, go to every event, and then filter out all the bullshit and take the learnings you can from each one.

• You should be slightly extreme. If you’re feeling it, give yourself the space to ride that wave. Clear your calendar. Stay up all night. Leave tomorrow morning on a week-long trip without your phone. Say no to everything and lock yourself inside for 3 days. Go out partying all weekend. Try and free yourself from what society tells you is normal, and focus on doing things that seem crazy but work for you.

• The journey is paramount. The biggest sin is to spend all your time focusing on a goal only to completely miss the actual life part. Yes, making sacrifices is necessary, but there’s more time in a day than most believe, and it’s up to you to make sure that time is spent being present. If you’re working, work insanely hard. But don’t use it as an excuse to not have dinner with your partner, or to act stressed out all the time, or to not enjoy the sunshine in the morning. Life is not that serious. It’s serious, but just not that serious. Enjoy the sunshine.

If you happen to be on your own quest, here are some things that have helped me:

• The Algebra of Wealth - Book by Scott Galloway

• How to Do Great Work - Essay by Paul Graham

• So Good They Can’t Ignore You - Book by Cal Newport

  

For so long, I wanted nothing more than for other people to respect me for being successful and not be seen as a failure. Through a series of hard conversations with a good friend and mentor, I learned what true failure is. Failure is living for something other than what the universe/your god/your intuition is telling you to do. This is a challenging truth for people to accept because listening to yourself and trusting that voice requires stepping far outside your comfort zone, embracing the unknown, and failing. It’s a long-term game.

Why willingly put yourself into this uncomfortable state when your life is fine (stable career, free time on weekends, generally happy life)? Personally, I couldn’t shake the feeling that there was more to my story. Not in the sense that I was ungrateful for what I had, but more that I was not listening to myself because it would be inconvenient. 

The truth is that choosing to pursue your unique path is hard but necessary. People will call you lucky when good things happen to you. They will talk behind your back and lose confidence when they see you fail. People are scared of this. I am scared of this, but experiencing failures means you are living, truly living. It’s real-time feedback that your life is underway. Pursuing your path is necessary for your evolution as a person, otherwise you become someone else.

So now I’m 28, unemployed, with no real plan for the future. Why? Because I finally listened to myself and trusted my intuition. The initial results are promising. More energy. Less worrying. More building. I’m meeting interesting people and they are eager to help in any way they can. I’ve stopped thinking about the life that could be and I’m just living it. I know this sounds cliche but it’s true. 

Once I started talking about it openly with others, I quickly realized I was not alone in feeling this way. There seems to be a shift among young people away from traditional paths. I believe this can be attributed to increased prosperity leading to more flexibility (more ways to make money, geographical flexibility, internet leverage) and to the fact that it feels harder than ever for young people to achieve the American Dream with a default path (high housing costs, rising cost of living, overreaching government). Either way, I’d argue that it’s a positive trend to see young people thinking differently about their life’s work. Imagine our world if more people pursued what they truly cared about.

So what would you tell your younger self standing at the crossroads? I would say enter the void. A well-lived life is nothing but the act of living intentionally in pursuit of your path, whatever that may be.

***

Some people will read this as “quit your job and you’ll be happy” - to be clear this is not what I’m saying (although, you might). My anecdote at this particular stage in my journey involved leaving my current job to explore my interests, yours may be entirely different.

By the way, my sister is an example of someone who has been relentlessly pursuing her path for as long as I can remember, and she also happens to be the happiest person I know.

In typical male fashion, I’ve spent the first 27 years of my life in somewhat of an emotional fortress. What do I mean by that? I rarely engaged with myself or others in dialogue related to my “feelings”. If this sounds familiar, that’s because it’s extremely common for men to act this way. I think there are many reasons why this is the case.

For one, a lot of guys can get a surprising amount of “emotional support” without actually needing to sit around with their friends, talk about how they’re feeling, and cry about it. Something as simple as exercising together or engaging in thoughtful debate can be an effective way for guys to bond and feel supported. It might sound weird but the experience of doing something challenging together can be a way of saying “I know that you are fighting your own battles, and I’m here for you” without actually needing to say it. This is a good example of how actions can speak louder than words.

The second reason worth mentioning is that growing up, men are taught to be men, and being a man meant sucking it up and showing strength. The narrative was that emotions are a sign of weakness, and young men will do anything in their power to avoid that. I think this narrative is changing in Western culture, but I don’t spend enough time with young people to really know.

The final reason is that everyone is on their own journey, and for a lot of people that journey has not yet led them to a place where they are able to provide emotional support to other people because they have not yet truly faced themselves. By that I mean they are still living in their “emotional fortress”, likely out of perceived necessity.

The problem with the emotional fortress is that it places limits on your interactions with the world. There comes a point where you can make a difference in other people’s lives and in the world by explicitly showing up for people. This can be as simple as you saying to someone, hey, I am here for you if/when you need me. The only way you can reliably do this for other people is to first show up for yourself and explore outside the fortress.

To heal is to repair and strengthen the mind and spirit. But this act of healing is not actually about you. It’s about what you’re able to put back out into the world for others. It’s engaging in hard conversations with yourself so that you can eventually be a better friend/husband/family member/father. Yes, to some extent you eventually need to heal in order for you to live a life of joy, but where this act of healing becomes most powerful is when it allows you to be there for other people.

So maybe being a man is actually healing yourself (not just emotionally but physically, spiritually, etc.) so that you can have the strength, courage, and resources required to show up for the people in your life. You can quite literally make the world better by healing yourself. As a guy who has had a challenging time engaging with and attempting to understand my emotions, this has been one of the single most effective changes in perspective.

Through a combination of growth and conversations with a friend, my perspectives on work and play dramatically shifted. What once seemed fun but ultimately useless to me now seems integral to living a meaningful life. The example I’ll use comes from surfing in Canada’s icy cold water.

Surfing at its core is a useless activity, especially in Canada where it’s also dangerously cold and incredibly inconvenient to get to. My aforementioned friend’s “useless” activity is climbing (rocks). What initially inspired me was the way he spoke about climbing. Throughout conversations about our professional lives (work), he kept coming back to examples of how a given work challenge was not unlike a challenge he faced while climbing (play). The boundary between these two modes was removed, and experiences, learnings, and synergies flowed freely between worlds.

The more I thought about this, the harder it became to ignore the significance of my time spent surfing or doing other seemingly useless activities. I’m starting to see examples of this in my own life as I increasingly blur the lines between work and play.

Paddling out

Surfing in Canada is a daunting challenge. I’d argue that standing on the shore of Lawrencetown in the dead of winter staring at a relentless onslaught of 8ft waves and choosing to get in the water and paddle out is one of the more challenging activities people engage in. Add to this the reality that unless you’re an experienced surfer, you’re probably looking at less than five good rides before you die of hypothermia, and you’ll almost certainly find yourself wondering why you put yourself in this position. That is until you catch your first wave. The moment you stand up and ride down the face of an unbroken wave, you suddenly forget you can’t feel your fingers and remember why you’re here. You’re here because the challenge is what makes it meaningful, and without paddling out, there’s no chance of catching a wave. Surfing is teaching me to paddle out (do uncomfortable things) more. I occasionally get knocked off (failure), but I also put myself in a position to catch more waves (opportunities).

Sets, patience, and staying calm

For the less ocean-literate (people from Ontario), this is how waves/surfing works: waves are created by energy passing through water, causing it to move in a circular motion. The waves that make it to a surf break usually come in “sets” of a few waves at a time. This might be 3-4 larger waves, followed by a period of no (or smaller) waves. To catch a wave, a surfer tries to be as close to the “take-off zone” (the first area where the wave is about to break) as possible. The main issue with sitting in this zone is the bigger the wave, the further out it breaks, so you run the risk of larger waves breaking before they get to you and, well, that’s no fun. So what do you do? Well at first you’ll probably panic, get knocked off your board, and curse yourself for sitting in the wrong location, but over time you start to remember that the waves are coming in sets. Sure enough, right as you’re thinking “I can’t dive under another wave or my brain will literally freeze”, you come up for air and see the sun reflecting peacefully off miles of calm water. You get back up on your board, catch your breath, and before you know it you’re riding a perfect wave from the next set. Surfing is teaching me to remain calm during a big set of waves breaking before they reach me (life’s challenges) and to have the patience to wait for a wave (good times) in the next set.

Joy

Lastly, and most importantly, I’ve learned that surfing brings me joy and that’s enough. Taming the desire to justify every action, every decision, and every hour of time spent has helped me start to live more freely and has made previously “useless” activities some of the most beautiful and meaningful experiences of my life.