This Is 38
With every passing year, birthdays are increasingly strange, if not entirely chaotic. I turned 38yrs old this week, and no joke, in addition to working on my birthday my wife and I also spent the day juggling 3 dental appointments for myself and the kids, a vet appointment for our 3 cats, and a social group meeting for our son. (Don’t cry for me, though…my wife took me out for dinner and drinks.)
Despite the insanity - and quite possibly because of it - birthdays are a wonderful time to reflect on our lives and take stock of all the knowledge we’ve aggregated over the years. And so I did just that. In no particular order, here are 38 learnings - one for each year of my life - that I’ve internalized and tried to live out.
1) If You Feel It, Speak It
Good intentions are a wasted resource. Acts of kindness are great, as is quality time, touch, and gifts, but unless the people you care about are adroit in the art of telepathy - and I assure you they’re not - they won’t truly know how you feel about them unless and until you actually tell them. An introvert by nature, this is a shortcoming of mine, so I have to consciously work on this every day. Point being, if you feel it, speak it.
2) You Can Be You
Who you are is inherently interesting. There is quite literally no one else on this planet who looks, smells, feels, and believes just like you. This is great news because differentiation, I’ve learned, is a key component of success. So, as long as it doesn’t involve being amoral or unethical and it doesn’t lead you to engage in illegal acts, set yourself up for success - you can (and should) be you.
3) First, Tackle The Monkeys
Monkeys and Pedestals is a mental model that’s useful when attempting to solve complex problems. Essentially, it states that if you are trying to train a monkey to sing while standing on a pedestal, you have to both train the monkey to sing and build the pedestal. Both undertakings will compete for your money, time, and attention, so the question, then, becomes which task should you approach first - building the pedestal or training the monkey to sing? You’ll have to complete both if you want to succeed, but the trick is to start with the more challenging task, which in this case is training the monkey to sing while standing on the pedestal. What’s the point in spending the time and resources to build the pedestal if you can’t figure out how to train the monkey? Avoid unnecessary sunk costs - first, tackle the monkey.
4) Being Effective > Being Right
It doesn’t matter how correct you are (or think you are) if you can’t affect and ultimately shape a desired outcome. Be right, but for goodness sake be effective.
5) Say “I’m Sorry” (and mean it)
Saying “I’m sorry” and, more importantly, actually meaning it can be incredibly difficult, especially when the apology is met with pushback or a lack of generosity from the other party. There’s just no getting around it - genuine apologies require a willingness to be vulnerable, and vulnerability is hard. But that’s ok. We all screw up from time to time and hurt the ones we love; what’s important is that we articulate that we’re sorry and sincerely mean it.
6) Just Do It (Responsibly)
Life is short (I blinked and 38 years flew by!) If there’s something you want to experience or accomplish, don’t wait - do as Nike tells us to and “just do it.” ***Note, though, that this is not a license to be irresponsible. This one requires planning and prepping up front in order to create margin for error, which in this case means aggregating the necessary resources to support whatever it is that you want to do.
7) Confounding Compounding
In finance specifically and life more generally, compounding is a game changer. According to Einstein, “compound interest is the eighth wonder of the world. He who understands it, earns it. He who doesn’t, pays it.” The idea of compounding isn’t intuitive, but it’s an essential concept to understand and apply across multiple areas if you want a joy filled life. Whether it’s investing in finance, self-improvement, or in relationships, small, incremental investments early on can grow into something truly extraordinary, so start early and contribute often.
8) Make Friends, Form Allies
I love Scott Galloway’s take on relationships: “Greatness is in the agency of others.” A decent indicator of your future success will come down to how successful you are in developing deep and meaningful relationships. Want to be economically secure? Partner with someone who has similar financial values and goals. Want to transform an organization, institution, or market? Partner with others who share your vision and who offset your weaknesses. The Navy Seals put it well - “If you want to go fast, go alone. If you want to go far, go together.”
9) We are Antifragile
In their bestselling work The Coddling of the American Mind, Greg Lukianoff and Jonathan Haidt assert that children (and thus people) are antifragile, as opposed to fragile or resilient. Antifragility is a property of systems in which they increase in capability to thrive as a result of stressors, shocks, volatility, noise, mistakes, faults, attacks, or failures. Think of antifragility in terms of muscle development - muscles require resistance not just to grow, but to ensure that they don’t atrophy. Appropriate levels of stress and discomfort are not only acceptable, they’re necessary for adequate human development. So, get used to being challenged and become comfortable with discomfort. Remember, you are antifragile.
10) The Hedonic Treadmill (As It Pertains To Stuff)
The Hedonic Treadmill is a metaphor for the human tendency to pursue one pleasure after another. In his debut book The Psychology of Money, Morgan Housel asserts the following: “Be nicer and less flashy. No one is impressed with your possessions as much as you are.” This isn’t to say that nice things are bad, nor is it necessarily a call to be frugal. By all means spend money, just do it for the right reasons. Focus less on acquiring stuff that you think will make you impressive to others (news flash: it won’t) and channel those resources into 1) time and experiences with the people you love and 2) things that truly give you joy.
11) Rich Vs. Wealthy
Most people who say “I’d love to have a million dollars” are full of it. What they really mean is they’d love to spend a million dollars. Drawing again from Morgan Housel in The Psychology of Money, “…the truth is that wealth is what you don’t see. Wealth is the nice cars not purchased. The diamonds not bought. The watches not worn, the clothes forgone and the first-class upgrade declined. Wealth is financial assets that haven’t yet been converted into the stuff you see.” Rich, as Housel puts it, is what you see; wealth is what you don’t see. There’s a reason 90% of my wardrobe consists of black t-shirts, jeans, and Tom’s; I made a conscious decision to get off the Hedonic Treadmill, to stop keeping up with the Joneses (not to mention the Kardashians) and instead focus on reducing economic stress my family and me.
12) Positive Outcomes Can Come From Negative Sources
One of my favorite holiday movies is Netflix’s Klaus. The story’s protagonist, a spoiled postal student named Jesper, finds himself banished to Smeerensburg, a frozen and far away place above the Arctic Circle, where he is commissioned to establish a thriving postal program. What begins as a selfish and dishonest campaign to hit a delivery threshold for the sole purpose of returning home and back into the lap of luxury ultimately ends up transforming both Jesper and the Smeerensburg community for the better. What Klaus demonstrates is that positive outcomes can come from negative sources. Whether it’s an illness, an ex, or a loss of employment, ask yourself how might this negative scenario also serve as a catalyst for positive transformation.
13) Addition By Subtraction
More doesn’t always mean more. What, or possibly who, could you cut out of your life that would ultimately have a net positive affect?
14) Ask For Help
The late, great Mr. Rogers once famously said, “When I was a boy and I would see scary things in the news, my mother would say to me, "Look for the helpers. You will always find people who are helping.” We are never alone, and most people appreciate the opportunity to offer assistance to others in times of need. Whether it’s a parent, a sibling, a friend, a teacher, or even a complete stranger, don’t be afraid to ask for help - you’ll be surprised just how often you’ll receive it.
15) It’s Not Your Fault
So much of our successes and our failures are out of our control. This is good news, because once we recognize this truth it allows us to practice humility when we’re killing it and compassion for ourselves and others when nothing seems to be working out.
16) The Balance Fallacy
Nearly 50yrs ago, the phrase “work-life balance” began making its way into the American zeitgeist as a way of describing the idea of balancing work with other areas of life, such as family, friends, hobbies, and health. Though it may be well intended, the idea of a “work-life balance” is a fallacy. Some people are certainly more successful than others in structuring a life that seems to resemble a balanced state, but the reality is that the so-called work-life balance is really just a series of trade-offs. This is an important and sobering truth. If you want more “me time” at home and with friends - which is latin for a 40hr work week - and you want less responsibility and stress professionally, the tradeoff is that you’re likely going to be more insecure financially. Conversely, if you’re ambitious and want to advance quickly in your career, you’re likely going to sacrifice at the alter of your job a lot of what would otherwise be discretionary time that could be spent with your kids and friends or pursuing hobbies. Neither path is necessarily right or wrong, and there are ways to somewhat thread the needle; I work most of the time I’m not sleeping, but I’m able to do this is because 1) I work with my spouse, 2) my children are directory or indirectly involved in much of my work, and 3) I’ve found a way to intertwine many of my hobbies and passions into what I do professionally. Not everyone can do this, nor would everyone would want to. What’s important is to recognize that you can have and do anything, you just can’t have and do everything, especially not simultaneously.
17) Hang Up and Hang Out
Get off your phone or device of choice and spend quality time with the people you love. Full stop.
18) Two Things Can Be True At The Same Time
Binary, black-and-white thinking often yields little in the way of progress. The world is a complex and nuanced place; the earlier you understand this and embrace the notion that two things can be (and often are) true at the same time, the more equipped you’ll be for the beautiful mess that is life.
19) Keep The Flag Flying
For better or worse, we’re all a part of someone else’s legacy. If you’re fortunate and come from a family or tribe who loved and made sacrifices for you, honor them in both word and deed. Keep the flag flying.
20) Cry More
Crying is cathartic, plain and simple. It doesn’t mean that you’re soft, nor is it a sign of weakness; crying is simply an output for complex and at times overwhelming emotions. Remember, “It’s alright. Crying is good. It lets the boo-hoo’s out.” - Freddie Prinze Jr. from Friends.
21) Start With One
There is a massive gulf between credentialing and competency. In most fields you don’t need to be credentialed with a degree from a top tier school; you simply need to demonstrate competency. (There are, of course, obvious exceptions to this rule - think medicine, law, and aeronautical engineering.) Point of fact: the development of so many extraordinary technologies that are also relatively low in cost have made the barriers of entry to developing competency relatively low. And you don’t need to have it all figured out in order to get begin. Start learning, growing, workshopping, and then “ship the work” as Seth Godin likes to say. Rob Bell articulates this point well in his book How To Be Here when he says,“Far too often, we don't start because we can't get our minds around the entire thing. We don't take the first step because we can't figure out the seventeenth step. But you don't have to know the seventeenth step. You only have to know the first step. Because the first number is always 1.” No more excuses; take that first step.
22) If You Can, Buy Yourself Time
There are a lot of big trees surrounding our house, so hiring a lawn-care company to take care of our yardwork was one of the best gifts I ever gave myself. The fact that I was physically able to mow, edge, and bag leaves made this feel like a frivolous purchase, but every weekend during the fall it would take me all day Saturday and the better part of Sunday to get everything manicured and cleaned up. What’s worse, by Monday it would look like I’d accomplished nothing - see above, a lot of big trees. The lawn-care company cost $180 a month, which at the time was a lot of money for us, but in the grand scheme of things it was ultimately an IQ Test. For what amounted to $45 a week I was able to purchase and reallocate no fewer than 8 days back into my schedule every month. Time is the most precious, finite resource there is - if you can afford it, buy yourself more of it.
23) Your Kids Will Surprise You
My wife and I have 3 children: two are my step-kids and one is my biological child. We went through an incredibly painful period that lasted about 3yrs where we didn’t see much of our oldest, and when we did she was exceptionally challenging. She was angry and confused - for the most part justifiably - and this often resulted in hostile, disrespectful, and self-destructive behavior when she was in our care. Come to find out years later, she had a literal hit-list of one with the only person on that list being yours truly. Fast forward a few years; we have dinner, take trips, and celebrate holidays together. We laugh about the hit-list. Despite the odds, we have grown quite close. Are we the exception or the rule? Hell if I know, but what I can tell you is that you should never give up on your kids. They will surprise you to no end, so keep an open mind and good things can happen.
24) Where You Stand Vs. Where You Sit
One of the wisest sayings I’ve ever come across as it relates to leadership is “where a person stands on any given issue depends on where that person sits.” It’s easy armchair quarterback and offer opinions from the cheap seats, but the person who’s in charge and thus ultimately responsible for the outcome of a decision is likely going to scenario plan and evaluate things much more thoroughly, diplomatically, and sensibly than anyone who isn’t. Bearing that in mind, interpret decisions you may not agree with or like with generosity; who knows just how many complex inputs went into the simplified output.
25) Interests Over Positions
When in a disagreement or negotiation, especially with a partner or friend, frame things in terms of interests rather than positions. Disagreeing or negotiating with a framework that’s “interests” oriented sets you up to find common ground, whereas doing so from a “positions” oriented framework sets you up to conquer and capture uncommon ground. Relationships are complex, and complexity often leads to disagreement, so by all means fight, but fight well and with good intentions.
26) Balance Grit With Quit
There’s no denying the importance of grit in a capitalist society. Grit is a wonderful character attribute, one that should be celebrated; however, the other side of the grit coin is quit, which is equally as important yet often overlooked. In her appropriately titled book Quit: The Power Of Knowing When To Walk Away, Annie Duke says, “That’s the funny thing about grit. While grit can get you to stick to hard things that are worthwhile, grit can also get you to stick to hard things that are no longer worthwhile. The trick is in figuring out the difference.” It bears repeating - life is short. Everything we decide to pursue results in opportunity costs, so whenever you decide to start or continue on pursuing something make sure the juice is worth the proverbial squeeze.
27) Call Your Shots
That’s right, Babe Ruth that shit. Think about what you want in life, reverse engineer it to a reasonable starting point (see above #21, Start With One), announce what you’re setting out to accomplish, and then swing for the fences. Of critical importance is making the announcement; calling your shots puts skin in the game because it introduces an element of risk, specifically the risk of public failure. The Babe broke the record of most home runs in a season (60), but he also struck out more than any other player (89). Success requires risk, and risk means skin in the game. Call your shots.
28) It’s Not A Party If It Happens Every Night
Isn’t that a great lyric?! I wish I’d written it (although, probably not considering the meaning behind it). This line from The Postal Service song “This Place is a Prison” is about struggling with alcoholism. Whatever your poison is - and let’s be clear about two of things: 1) drugs and alcohol are all various forms of poison, and 2) mine is alcohol - it isn’t a party if it happens every night. If substances are getting in the way of your goals or inhibiting your health, it’s time to reevaluate your relationship with them.
29) We Teach Who We Are
This is the single best piece of parenting and teaching advice I’ve received, and it’s credited to Laura Shoffner. Of course, the message matters, but the medium matters more.
30) Find Your Medium
Speaking of mediums, of critical importance in terms of personal and professional relationships is finding a medium you’re good at and become OUTSTANDING at it. I’m a good writer and a decent, dare I say “good” photographer, so my mediums are some combination of long and short form text-based platforms that allow me to integrate visual imagery to support my claims. Maybe you’re a gifted orator and a fantastic public speaker, or perhaps you’re a talented stop-motion artist who leverages video-based platforms. Whatever your medium is, lean into it and use it as leverage.
31) Cynicism & Hope
Cynicism and hope are both contagious, so ask yourself which you want to be known for. Pick your infection wisely.
32) Good and On Time > Great and Unreliable
For the first 10 or so years of my professional life I was a working musician. Don’t get me wrong - I have some talent, especially as a vocalist, but there are certainly any number of people who can do what I do and are, in my opinion, better at it. My key point of differentiation? Musicians specifically and creative types in general are notoriously flaky, so in an industry full of infinitely more talented creatives than me, I differentiated myself by being responsive, reliable, and on time. I found that people would much rather hire someone who’s good and dependable than someone who’s remarkable and a flake.
33) Context Creates Value
Let’s stick with music. I made a good living (and what felt like a small fortune at the time) performing sets in grocery stores, airport bars, Chinese restaurants, bus stations, coffee shops, and bookstore cafes. Did I also play upscale bars, festivals, and high-end private events - you know, the kinds of gigs musicians aspire to play? Of course. Without question, though, the majority of my income from music as well as my most meaningful gig experiences came from these unexpected venues. The takeaway, here, is that it’s context, not talent, that ultimately creates and drives value. Your skills are going to be worth more to some people, institutions, organizations, and industries than others; the trick is keep an open mind and use that to your advantage as leverage.
34) Entrances and Exits
In work and in life, people will notice how you arrive and they’ll appreciate how you handle yourself while you’re there, but what they’ll ultimately remember you by is how you make your exit. Consider the following Warren Buffet quote: “It takes 20 years to build a reputation and five minutes to ruin it.” Regardless of the circumstances, leave well.
35) Drink It ALL Up
It may be a morbid thought, but as far as I know the mortality rate for people is still 100%. No one gets out alive, and while it’s probably unhealthy to full-on ruminate about death, as someone who increasingly struggles with social anxiety I’ve found it helpful, dare I say liberating, to casually remind myself that I and everyone I know will all be dead in 100 years. Put fear of failure and regret in their proper places and do as Alfred, Lord Tennyson directs us to in poem, Ulysses - “drink life to the lees.” We’re all going to be dead sooner than we think - drink it ALL up.
36) Attach To Something Real
For all the good that our modern tools do with regards to productivity and efficiency, the other side of the trade is that we’re increasingly isolated and disconnected from the real world and, consequently, real people. Humans are mammals, and mammals are inherently social beings. Whether it’s a religious organization, a non-profit, an educational institution, an investing club, or a Bridge group, the key is to attach to something, and thus someone, that’s real.
37) Never Stop Dating…
Especially if you’re married or in a committed relationship with a partner. Most romantic relationships go off the rails when one or both parties decide that they no longer need to make an effort to impress their partner. This isn’t to say you should strive to artificially manufacture the romantic whirlwind that often accompanies the beginning of relationships. As relationships evolve, other priorities will inevitably arise - i.e. saving for a home, investing for retirement, having children, etc. - which will ultimately make the original dating dynamic unsustainable. This is an explanation for why couples stop dating, but it serves as a poor excuse. Rightly or wrongly, your partner will absolutely make inferences about how you feel not just by what you say and do, but also by what you don’t say and do. It doesn’t take much - a compliment here, a thoughtful gift there, maybe dinner and a movie (do people other than me still appreciate going to the movies?). And for goodness sake, dress up every now and then. Never stop dating, especially your partner.
38) Say, “I Love You”
These are without question the three most powerful words a human can utter. When loaded with sincerity, there’s little they can’t fix and their potential to bring about a positive impact is infinite in its enormity. It can be tempting to take shortcuts, but “love ya” and heart emojis simply don’t cut it. And so, we end where we began; if you feel it, speak it…all of it - “I love you.”