31 Life Lessons on the Road to 31: A Collection of Musings on Life

Disclaimer: The following piece contains no life hacks or shortcuts – just 31 years of living distilled into 31 thoughts.

When I turned 30 last year, I had a lot to say. 28 and 29 which were sandwiched with twists, turns, highs, lows and more humbling events than I care to admit. By the end of my 20’s, I was ready to turn the page and start a new decade.

Previous Musings: 30 Life Lessons on the Road to 30

At 31, I have less to say. The past year has been more about integration of wisdom and life lessons than reading about them. 31 is less me and more you.

So, here we go. A collection of the 31 wisest things I read / listened to / learned and figured out over the past year.

1) “Never recline your seat on an airplane. In economics, we call this an externality.” – Ryan Holiday

Are there exceptions? Sure. But the more cognizant we are of how our self-interest affects our neighbour, the better off we’ll all be.

2) There’s no such thing as a “free lunch”.

We live in a world that prioritizes convenience and leads people to expect things for free. The advent of the online shopping revolution has brought with it a culture of “freebies”. Free delivery. Free return policies for life, no questions asked. Free lunch because someone else picked up the tab.

Nothing is free. There is always someone on the other end of “free”.

3) “Capitalism without bankruptcy is like Catholicism without hell. It appeals to me strongly. Markets work best when participants have a healthy fear of loss. It shouldn't be the role of the Fed or the government to eradicate it.” - Howard Marks

The financial markets of 2020 summed up in a single sentence.

4) “If more information was the answer, then we’d all be billionaires with perfect abs.” - Derek Sivers.

The modern world is a confusing place with far too much information and forms of media for our thousands-of-years-old brain to handle. Cal Newport has coined the concept of a “media diet” to ensure we stay grounded. The diet doesn’t always need to consist of the same media sources and mediums forever. But think of it like that really disciplined, fashionable friend who has a rule that if something new goes into their closet, something old comes out.

For example, my favorite University professor told me one of his favorite things to do is reading a physical copy of the Saturday morning Wall Street Journal. I put off doing this for a good 7 years and finally started getting a paper copy of The Globe & Mail delivered to my condo every Saturday morning (save the old man jokes – I’ve heard them all). I really enjoyed this at first but truth be told, reading the paper takes time and energy when my weekend’s of late have been about recharging the batteries after heavy work week’s.

Reading the paper brought me into the world of current events and quickly made me realize the more I know about the chaos of the world, the less I actually know. This Saturday morning ritual morphed into an anxiety inducing activity at a time when my weekend’s were to get away from the hustle & bustle of the week – to connect back in with myself, my friends, family and outdoor pursuits. The paper’s started piling up next to my couch, weekend after weekend. What started out as an idealistic notion became a source of anxiety. I’ve since cancelled the paper subscription and opted for digital instead. Sometimes, less is better.

5) “Modern day capitalism rewards single-minded sociopaths.” - Successful entrepreneur friend of mine.

The more I’ve learned from personal experience and reading about successful entrepreneurs, the more I’m convinced this is the case.

Honorable Mention: Nearly a year after the conversation referenced above, we were on a group call and this friend said something profound along the lines of “people think its the ‘podium’ moments that will define their life when in actuality, it’s often somewhat dark, isolated moments in time that have a weird unintended way of galvanizing your identity.” He then referenced traveling through a dark Polish train station at midnight many years ago and how it changed him forever…

This hit home. When I look back on my journey to date, very rarely is it the podium moments that stand out. It’s the stressful, sweat filled moments where I’m often alone fighting a battle no one else knows about. Those are the moments that forge a spine of steel.

6) “Finding the right tide (industry) and a good company is better than a great company in the wrong tide (industry).” - Scott Galloway

2020 has proven as such.

7) “Developing an attractive lifestyle is a long term (in duration) but worthy investment.” - Mark Manson

For me, this has rang very true, in addition to being far more expensive than I thought. Prior to COVID, I was on an airplane 40% of the time and personal hobbies took a backseat to work but when COVID hit, all of a sudden many of us had more control over our time and far fewer social situations to immerse ourselves in.

We no longer could just go out for drinks with friends to mindlessly take our minds off the crappy Wednesday we just had. Instead, we’re now ‘stuck’ with ourselves and whether we’ve realized we’re into mandala art, collecting wine or cycling, turns out the equipment adds up rather quick.

But once you get up and running, it gets fun and provides a foundation to anchor your lifestyle around.

8) “The target attracts the arrow, not the other way around” - Matthew McConaghey

Resonant body language -- this is something I’ve been very conscious of and worked on in 2020. In all elements of life, we can push our way into people / things or use more natural forces to “pull in” what we want to attract in life (ie. the right partner, the right profession, the type of friends you want to have). This is definitely a concept that requires playing the long game as the “pay-off” (if there is one) is at an indefinite point in the future.

This builds off the concept that developing an attractive lifestyle is a worthwhile but long-term investment. You don’t just start doing a new activity and all of a sudden people start gravitating towards you – it takes reps. Consistency. Letting luck find you as opposed to having to chase it down.

Matthew McConaghey introduced this concept to me in Green Lights and man it was refreshing. As a Type A guy, I’ve often felt the need to always be in a “hunter” like mentality which is great in its own way and can lead to successful outcomes but takes its toll after a while. For me, shifting to a “pull” mentality required tweaking my body language. Very subtle physical tweaks that to the naked eye are barely visible but have become a profound internal cue for how I want to show up every day.

9) For anyone trying to develop healthier, more productive habits, James Clear is a fountain of wisdom. He has developed too many foundational concepts / themes around habit building that it’s impossible to only share one.

• “The sweeter the initial satisfaction, likely the worse the long-term consequences are.” 
• “The consequences of bad habits are delayed but the reward is instant.” 
• “Are you making a choice for the present-you or future-you?”
• “The cost of your good habits are in the present, the cost of your bad habits are in the future.”
• “Incentives start a habit. Identity sustains a habit.”
• “The more immediately pleasurable something is, the more you should question whether it aligns with your long term goals.”
• “Habits don't add up. They compound.”
• “We optimize for what we measure. And if we choose the wrong measurement, we choose the wrong behavior.” - (Note to self: don't measure yourself against other people's posturing.)
• "It took me 200+ articles before I got a book deal. 250+ articles before I got major media coverage. 100+ interviews before my book hit the bestseller list. You need a lot of shots on goal. Not everything will work, but some of it will. Keep shooting."

10) “Everyone has a plan until they get punched in the face.” - Mike Tyson

I didn’t hear this quote for the first time this year but I think it hit home for a lot of people because of the unexpected pandemic. Physically speaking, I’ve only been punched in the face once without a helmet on. I’ll never forget the night it happened. However, metaphorically speaking, it felt like life punched me in the face many times as a 28 & 29 year old. Life cracked me open.

A quote of a similar vein that’s just as powerful, "sometimes you have to be beaten up a little bit to be tender enough to feel" - David Brooks.

Why do I reference this Mike Tyson quote?

Well, growing up, I naively used to admire perfection in people – almost put these people on a pedestal. Having now been punched in the face in more ways than one, I can spot someone posturing or putting out a ‘facade of perfection’ rather quickly as they often reek of insecurity and lack life experience.

As I’ve grown older, I’ve become far more attracted to people with interesting life experience and the scars to show for it rather than those who’ve towed the line on what the world has told them their ideal of ‘success’ should be. Scars show you’ve lived for and loved someone or something greater than yourself. Put something near and dear on the line and have the scars to prove it. I know I certainly do.

11) “Heal the boy and the man will appear.” - Tony Robbins

I grew up playing every physically demanding team sport a Canadian kid can imagine: hockey, lacrosse, football. Throughout that time, you end up playing with kids of all personality types and are exposed to a somewhat single-minded definition of what it means to be tough. I played with some physically tough guys along the way but my definition of tough has evolved as I’ve grown older.

The traditional notion of what it means to be masculine or to be a man is to be physically tough, isn’t it? “The toughest guy on the team”. The guy no one would want to go toe-to-toe with. Call it old-school masculinity.

Let’s unpack what it means to be ‘masculine’ in a modern context. Surely, everyone’s definition will have its nuances but for most of the ‘toughest’ men I know, it has nothing to do with their physical toughness. Oftentimes, the ‘physically tough’ end up becoming a victim of their own ‘toughness’ later in life because they’ve bottled up so many things masked by their intimidating stature. Too tough to open up, have a real conversation, talk about their insecurities, talk about traumatizing events in their childhood. Whatever it may be.

Let’s set the record straight. The toughest thing a “man” can do, while not easy, is confront both his past and his insecurities so he can step into the man he wants to be, whether that’s for himself, his family or his partner. When he does so, that’s real toughness. True masculinity.

12) “A relationship that cannot tolerate a thoughtful conversation about needs, disappointments, and desires is not a healthy relationship.” - Tucker Max

I can’t recall if it was Esther Perel, Tom Bilyeu or Mark Manson (I think all three in some capacity) who spoke about the quality of a relationship can be judged by the quality of its “fights”. Learning to ‘fight well’ is a critical component of not only loving relationships but all trusting relationships.

Relationships where it is okay to openly and honestly discuss points of tension or conflict with one another. Often times, we learn (or don’t learn) how to have mature conversations without shi* hitting the fan watching our parents during our adolescent years. Unfortunately or fortunately, some of this is circumstantial and out of our control.

But what is in our control as Tom Bilyeu drives home so importantly is a) always maintaining respect for the person, even if you don’t agree or like the person in the moment, and b) most importantly, never using their weaknesses or insecurities against them in an argument. That is the key to ‘fighting well’.

13) "A bird sitting on a tree is never afraid of the branch breaking because her trust is not on the branch but on it's own wings" - Denzel Washington

I wrote about where to optimally root your confidence and habits in last year’s 30 for 30 but this is a never-ending process where rent is due everyday. It’s one thing to say, it’s another thing to actually do. I’ve tried to pay on time every time in the form of building strong, healthy habits.

14) Find things in life that don't have diminishing returns. Develop hobbies that are sustainable for life. Surround yourself with people who look to give than always take. People that fill your tank.

Find hobbies and outdoor pursuits that while physically draining fill up your tank in more ways than one. Find or create a job / career that you look forward to Monday’s.

Find the right mix of doing pleasurable things (short term gratification) and hard things (delayed gratification) that are difficult in the moment but will pay dividends over the long term. Play the long game. Develop skills that will allow you to create a body of meaningful work over time.

Tom Bilyeu has a great formula on the amount of time spent in the pain vs. pleasure zone. This is 100% worth the watch.

15) “The ratio of time you spend sweating vs. watching other people sweat is a forward-looking indicator of your happiness. I think spectator sports are the new cancer. Show me someone who watches ESPN 2-3 hours per night and their Sunday’s watching broadcast television sports and I’ll show you someone who has a history of failed relationships and anger in their life. Show me someone who does SoulCycle and CrossFit 2-3x per week and uses sports + spectator sports as a means of increasing intimacy with others and I’ll show you someone who’s good at life.” - Scott Galloway

There’s nothing wrong with watching your favorite sports team or some national news to stay in the loop but aimless, unabashed consumption of sports / news and the prescription drug, insurance and fast food commercials that come with it isn’t healthy long-term for any one.

16) “Think of money as ink in a pen. Does it really matter if you have the best pen in the world as long as you have enough to write your unhindered story with?” - Scott Galloway (Prof G)

Have you noticed I listen to a lot of The Dawg? Damn right I do. Whether he’s your cup of tea or not, I think Prof G is a wise man who’s been on both sides of the ledger many a’ times.

I remember 3-4 years ago being a cash poor entrepreneur but full of zest & energy. On paper, I was a cash poor entrepreneur running a coffee business but in reality, I was closer to the life I wanted to live than ever yet I was running on fumes financially speaking. However, I had enough ink to get by for that chapter of life.

I would consider myself a conscious capitalist who works hard and appreciates the value of a dollar. But to me, money has never been about the number of zeros in my bank account. To me, the point of having money is to not have to think about money. It’s to be an enabler so you can live life on your own terms, within reason. While its fiscally responsible to keep an eye on your chequing account balance, you don’t want to go to sleep dreaming that you’ll have “made it” when a certain number of zeros appear or on the contrary, worry there’s not enough to put food on the table the next day. Neither constitutes financial freedom, one is literally a shackle. The other metaphorically speaking.

Side note: Scott Galloway has a great take on ‘what being rich actually is’ breaking down income vs. burn on episode 8 of his podcast, The Prof G Show. Scroll to 33:18 for the 3-minute closing clip.

17) “Eliminate the tiny risks so you can take the big ones.” - Tom Bilyeu

Tom has a concept of “building a liquid cash reserve so that if your regular income were to cease tomorrow, you could live your current lifestyle for 6 months with no additional cash flow (rent / mortgage payment included)”. This is certainly a balancing act but when I’ve noticed that when I’ve had the discipline to get myself into this place of financial stability, it has both consciously and subconsciously allowed me to live life on my toes, play from a position of strength, take more calculated risks and aggressively pursue life on my own terms. There’s no better feeling.

18) You can be in the middle of the desert with no one around you and feel the most connected to the world you ever have. Yet, you can be in a group of 100 people at a party and feel more lonely than you ever have. Choose wisely.

The most vivid memory I have of this was cooking dinner over a fire in the Australian Outback with a few fellow campers/strangers and not another soul in sight for hundreds of miles. No tent. Just a campfire, swag and most impressive astronomical display I’ve ever been privy to. Rarely have I felt more connected and filled up than in that moment.

19) Self care and self indulgence are fundamentally different things. Take the time to understand the difference and do the work.

Going for a weekly massage / yoga class / [insert your high-priced boutique wellness practice of choice] might seem indulgent to some but a necessity for others. Everyone has their ‘thing’. What I do know is that I’ve rarely regretted any investment made in my own health and well-being.

Living loose, feeling limber, having pep in your step with no tension in your neck / back / hips never gets old.

20) I was reading The Wisdom of Insecurity by Alan Watts on a remote beach on Vancouver Island and the book introduced the first distinction between joy and happiness that ever made sense to me. Whether this is what Alan was actually teaching or simply my interpretation, it goes something like this.

Happiness is a state of mind dependent on the future – it’s living for tomorrow – setting ourselves up for success. Joy is different. Joy is being able to turn off what may happen in the future, good or bad, for what is happening now. Joy is being able to experience the present moment for all its worth without any expectations on what may transpire in the future.

Culturally speaking, I think North Americans are tuned from a young age to live for tomorrow and seek happiness. As a result, we are typically very career driven people and often sacrifice the now for what’s to come tomorrow. As such, it might be wise for people to seek joy rather than happiness. We might realize we’re actually very good at being happy but it’s ‘joy’ we don’t understand or know how to experience.

Don’t believe me? Think of the people typing on their cellphones while at a nice gathering or party thinking about where they could be or should go next… We’re all guilty at some point or another.

21) "There is perhaps nothing worse than reaching the top of the ladder and discovering that you're on the wrong wall" - Joseph Campbell

I’m surprised that so few people take a second to look out the window in their careers along the way. I’ve done so and I didn’t like what I saw (more than once) so I pivoted. Those ‘pivots’ were painful as hell but I’d rather experience that pain in my 20’s than later in life when I’m locked into a mortgage with a family to feed.

22) Spend more time in small towns on the weekend. It’s good for the soul and spirit.

23) “Don't leave crumbs…” - Matthew McConaghey

The old adage “how you do one thing is how you do everything” applies. Matthew goes a little further to explain why it’s important to keep things tight, “Voluntary obligations -- the ones we make with ourselves, the ones you make with yourself. The ones that define our personal constitution. They are secrets with ourselves. Faith based responsibilities. Personal protocols. Private counsel in the court of our own conscience. While no one will give us a medal or throw us a party when we abide by them, no one will apprehend us when we don't because no one will know except us.”

If this resonates, grab your keys and go for a drive. I hope you hit some Green Lights on the way.

24) “What you were taught is healthy growing up probably is not.” - Mark Manson / Ryan Holiday (can’t remember – perhaps both).

The more I learn and immerse myself in the commercial food industry, the more this is strikingly apparent. I plan to unpack some of my thoughts in Food for Thought: Season II.

25) "Real freedom is not so much the absence of restrictions. It's finding the right ones." - Tim Keller

The above is a quote from David Brooks, The Second Mountain. The next one I can’t remember where I heard it but is just as relevant. “Young people define happiness in terms of excitement. Old people define happiness in terms of peacefulness and contentment.” - Unknown

When you find inner peace, everything else is gravy.

26) “Vices create as many problems as they solve. Hallucinogens are to insight what Oxy is to pain relief. Band Aid relief. Solutions come from doing hard things.” - (I think it was Ryan Holiday who made an Instagram post about this).

None of us are immune to our vices and I try to refrain from being judgmental to those more experimental with theirs. However, I’m a bit wary of people who glean too much wisdom from their time ‘on’ their vices. Quarter and mid-life crises are very real things (admittedly I had one, if not two of them prior to 30) but they shouldn’t happen every year, nor always require a vice to illuminate one’s path forward.

27) Whenever I’m caught up in the rigours of corporate life and less than ideal health habits, I often listen to a Laird Hamilton interview as a way to tap back into my mind body connection. Laird is one of the ultimate extreme sport athletes to ever live and believes in a very natural way of building your body up and resting to let it down.

One of my favorite insights gleaned is learning to use swelling in your body as an effective feedback loop rather than medicating it away. Swelling is an important feedback loop and our body's way of telling us when the physical activity we did was overdone, not done with correct posture or sub-par mechanics. There’s nothing wrong with utilizing pharmaceuticals to control inflammation as a means of recovery but it should be used strategically rather than as an immediate numbing agent (interview on XPT Life podcast: start at 12:45 - 24:15).

28) Pain and pleasure are two sides of the same coin. You can’t cancel out pain with pleasure – they’re interrelated at a physiological level. To free yourself of suffering, there are two avenues in my experience 1) lean into the discomfort, sit with it, be humbled, let your ego (but not your soul) surrender and then grind like hell (hint: this will take weeks / months / years and likely require lots of exercise / meditation / reflection and/or seeing a therapist) or 2) start living for someone or something greater than yourself to free your mind. The latter isn’t necessarily a long-term solution but will help get you out of your own head and do some good along the way.

29) “In emptiness, find abundance. Abundance of solitude, stillness and space to think which as a whole contribute to a fuller, more fulfilled life.”

This is an affirmation I developed and read aloud everyday in the early days of COVID. Something I still think about it as we’re physically distant from the people we care about most.

30) “Change is hard because it involves loss. Even if that change is better, it involves the loss of the familiar. The loss of your comfort zone.” Lori Gottlieb.

Lori is a fountain of knowledge when it comes to doing ‘your’ work.

31) Earn the right to be the hero in your own journey.

This is the greatest honor you can bestow upon yourself – to play big in the moment and step into the person who flies high in your dreams. Don’t outsource this honor to anyone other than yourself. Earn it.

---------------------------------------------------------------------------------------------------------------

Thanks for reading. If any of this resonated, I’d love to hear which points hit home most for you. 

While I glean inspiration and wisdom from many, below are the individuals who’ve had the greatest impact on me from afar.

Mark Manson

Tom Bilyeu

Scott Galloway

Ryan Holiday

Cal Newport

Tim Ferriss 

James Clear

Esther Perel

Gabby Reece

David Goggins

Stephanie Ruhle

Jerry Colonna

Matthew McConaghey

Previous Musings: 30 Life Lessons on the Road to 30