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The 15 Best Life Lessons I’ve Ever Learned

A short collection of sage wisdom for living a longer, happier, healthier, wealthier life.

Oh, god. I’m going there. Look, you’ve read hundreds of lists like this. I know that. So, I’ma try and do this one a bit different.

Most comprehensive lists like this feature too much to do, that will take up too much of your time, and fly at too many different altitudes to be definitive. That shit’s not workable. You’re not a superhero.

And, by the way, there’s a pandemic out there, a civil rights movement worth focusing on, and an economic depression that’s so low on millibars that’s become a Category-4 economic hurricane. What you’re probably not gonna do is make your first million.

But, what I will do in this here dispatch, is give you the 15 greatest life lessons I’ve ever learned … and I’m going to float those sweet little doves into the wind, where they’ll sail across the boundless, beautiful sea of ones-and-zeroes directly onto your screen of choice, lapping against you like waves against your prefrontal cortex.

Shall we begin? Sure … beats ending, anyway. I’ve cited material where applicable.

Lesson №1: We still haven’t improved upon the Mediterranean diet.

I highly recommend reading the book Blue Zones. Author Dan Buettner studied five areas of the world where people live the longest — Ikaria (Greece), Sardinia (Italy), Loma Linda (California), Nicoya (Costa Rica), Okinawa (Japan) — and identified the key components of their longevity. And, while the research isn’t air-tight, it’s compelling nonetheless.

In addition to life purpose (keep reading), stress reduction (keep reading), spirituality (*crickets*), close family (keep reading) and close social bonds (keep reading), Buettner found diet to be highly correlated with enduring health.

The components of that diet include: “whole grains, fruits, vegetables, nuts, legumes, seeds, and spices, olive oil and occasional meats (mostly fish).” For three consecutive years, the Mediterranean diet’s led the US News & World Report rankings of the world’s best, while the Standard American Diet, Keto, Paleo, Atkins and Whole30 continue consistently bring up the rear.

Lesson №2: Give yourself something to look forward to.

Confession: I was pretty down on myself a little over a week ago. 2020’s been a disaster globally, torpedoing mental health (along with just about everything else, and killing over 250,000 people in the US alone) on a mass scale, so it’s no surprise it’s dragged me into various depressive and anxious episodes along with it. (I have a history, and no amount of ketamine — still by several light years the best pharmaceutical alleviator of mental health I’ve ever tried — could overcome this hellscape of a year.)

Then I remembered some advice from (the extraordinarily problematic) former Notre Dame football coach Lou Holtz: “you have to have something to do, someone to love, something to believe in, and something to look forward to.” Say what you will about his politics — and I’ve cussed his name often — that advice is pure gold. And, while I definitely have things to do (write, run, run a business), someone to love, and something to believe in … I didn’t have much to look forward to: I’m high-risk for severe COVID-19, haven’t seen anyone outside my partner in 250 days, haven’t traveled in 300, cancelled an international move, threw myself into survival mode, and the pandemic’s getting exponentially worse in the US — not better. There’s no real relief in sight.

So, after a call where a potential client wanted to sign me up to craft an automated LinkedIn retargeting campaign, I took a good, hard inventory of my professional life and thought, “I was not put on this Earth to do this,” and wrote him a Jerry Maguire-style manifesto communicating as much. At the same time, I reached out to a couple of moonshot dream clients, basically offering myself up them. I may not get them, but at the very least, it rejuvenated me. I’m now excited to check my email and hop on calls. I write with renewed vigor. There’s possibility, even if my ability to socialize, travel and make any major moves is just as compromised as my immune system.

This is consistent with past experience: The happiest years of my life (2000, 2002, 2008, 2010, 2015, 2018, 2019) were all years in which I had things to look forward to — professionally, socially, geographically.

Hope is more important than ever. By giving yourself something to look forward to — whether its applying to your dream job, scheduling travel, making plans, or even just buying something you really want — you boost your mood.

Lesson №3: You are the 15 people closest to you.

This one comes from the Quartz column, “Why We’re Better Off With Fewer Friends.” The money passage is as follows:

Nearly all the well-being benefits from relationships don’t come from the 500 Facebook friends, or even the 150 or the 50. They come from the 15. Quality time spent with your 15 closest friends and family will have a direct impact on your happiness, health and longevity (and theirs too).

I left Twitter in 2019 and Facebook in 2020, and those moves drastically reduced my social circles while minimizing my time frittered doom-scrolling. It’s helped me focus my energies on the people closest to me.

I’ve often said I don’t have a best friend, I have a Board of Directors — people I bounce my major life decisions off of, and people I try to text regularly. My partner, my dad, my sister, my three friends from my time in New York (none of us live in New York anymore), my good friend from college (who does live in New York), two friends in LA, a friend in Dallas, three friends in the Bay Area, four friends in Austin, and a five-person International delegation. Alright, that’s 22 — it’s a big board, but that’s plenty big enough.

Crucially, it’s important to cultivate and calibrate that group to be people who are high-character, optimistic, loads of fun, and — most importantly — actively cheering for you. I’ve had to kick a few folks off the board for not adding much in those departments. That might sound cold, but it’s nowhere near as cold as the chill you’ll feel spending your time slumming it with energy vampires.

Lesson №4: Always make (and keep) promises.

This one comes from The Atlantic. One of my favorite essays ever written, “Always Make Promises,” waxes poetic about a nouveau Golden Rule: “Make promises you can keep, but you don’t need to exceed them. Just do what you say you’ll do.”

This is probably the single greatest slice of prosocial advice ever put to print. Tell folks when you’ll show up, then show up at that time. Tell clients what you’ll deliver it, then deliver exactly that. You get points for integrity — because you made a promise and kept it — as well as generosity. You don’t earn bonus points for overdelivering, but you do earn extra points for keeping a promise, rather than merely offering something up.

The paragraph worth framing in the Smithsonian is the following:

Imagine you’re a kid with a cookie and a friend who has no cookie. What happens if you eat it all? Your friend will be upset. What happens if you give all of it away? Your friend will like you a lot. What if you give away half the cookie? Your friend will be just about as happy with you as if you gave him the whole thing. His satisfaction is a pretty flat line if you give anything more than half of the cookie. People judge actions that are on the selfish side of fairness. Maybe because we denigrate do-gooders, or because we’re skeptical of too much selflessness, the research shows that, as Epley put it, “It just doesn’t get any better than giving half of the cookie.”

Only make promises you can keep. Then, keep them. Always give half the cookie — no more, no less. That’s a great lesson in boundaries, too.

Lesson №5: There’s a trick to improving your mood, but you probably don’t want to do it.

This one comes from the eponymous Quartz column. It’s two minutes long, and I always send it to everyone who feels down in the dumps, because it almost always helps me, and I believe in its thesis so strongly.

The advice is the inverse of its opening paragraph: “Conventional wisdom holds … the better we feel and the more motivated we are, the more likely we are to act.” There’s an entire billion-dollar industry focused exclusively on cultivating a winning — depending on who you listen to, it goes by different names: growth, abundance, high-vibration — mindset. There’s value in that work, yet in a pinch, it’s much harder work than working backwards.

When you’re in a funk, talking shit to yourself, moping and struggling with motivation, sometimes the very best way to break yourself out of that slump is to just do something. Errands, the dishes, a small project, a long walk outside or a leisurely drive to nowhere in particular.

A few months back, I was spiraling mood-wise in front of my partner, and she asked me, “what’s the best way I can help you when I notice you doing that again?” I said, “tell me to ‘take a lap.’” For me, running — even for just 30 minutes — is the quickest (no pun intended) road to recovery. One of my guiding maxims is: “You’re always just 3 miles away from a better mood.”

One of my most popular essays — “12 Common Ways You’re Sabotaging Your Mood And Your Life” — is a literal mood troubleshooter. When I find myself down, if I can force myself to run through some of the basics of the list (e.g. drink water, tidy up, exercise, go outside), I can generally pull myself out of the clouds. It’s no guarantee, but it at least gives you a chance.

Lesson №6: True wealth is passive income minus burn.

This axiom stems from Scott Galloway’s The Algebra of Happiness. You’re rich if the money you make by doing no work at all — royalties, pension, dividends, interest, asset appreciation — exceeds the money you spend. I currently make about $1,000 a month doing no work at all: investments and my Medium back-catalog. I spend about $4,000 a month. The more I invest, and the more I add to the Medium machine, the closer I’ll get to my benchmark of $4,000 a month.

I’d like to also add “work that doesn’t feel like work” to the passive income bucket. That work is my Medium work, and my super-fun creative work (not all of it is super-fun, but some of it definitely is) The hours I spend on it are some of the most rewarding hours of my day. I’m not someone who writes essays or stories when I don’t feel like writing. So, all additional money I make per month is still, technically, not money I worked to earn.

On average, that’s an additional $2,000 per month, meaning I’m about $12,000 per year away from being rich. I’m not there yet. I still have to work for the rest, and in this economy, that work hasn’t been guaranteed. (I make about 50% less as an entrepreneur in Year One than I did at my last corporate job.)

On the other end of the ledger, I used to spend $6,000 per month. I spent a solid week in July ruthlessly slashing my budget just to get down to $4,000. That’s an easier way to lower your wealth threshold, although its not exactly fun. Given an unlimited budget — which in 2015 through 2019, I basically had, as I averaged about $100K in income — I’d probably spend $7K monthly. I’d need $85K in passive wealth to have truly won capitalism (which is, I might add, a bullshit, unjust and wholly inequitable game) and not feel compelled to obsessively check my balance.

In Galloway’s book, he tells the tale of his friends who make multiple millions of dollars per year, but are still overleveraged because they live well outside their means. They, he posits, are poor. You, on the other hand, don’t have to be. Find out what your target burn rate is and do the work you need to get there.

Lesson №7: When faced with a difficult decision, err on the side of risk. (Most of the time.)

I’m paraphrasing, but the Bhagavad Gita says: “We are kept from our goal, not by obstacles, but by a clear path to a lesser goal.” Now, living in the United States, with our the rigid social hierarchy — wealthy white dudes at the top and everyone else fighting for distant second place — taught me that yes, obstacles can absolutely keep you from your goals, but within the context of preexisting limits and injustices, the mantra holds about a half-bucket of truth.

Most of us don’t fulfill potential — actually, who fully does? — because of decisions we make that reinforce limiting behaviors and beliefs. Our brains are wired to seek out comfort and familiarity. We go to regular bars, we develop fairly intractable habits and beliefs, and we tend to err on the side of caution with respect to our relationships, our careers, and our desires. That tends to work against us.

To butcher a Mark Twain aphorism: “We regret the things in life we didn’t do more than the things we did.” So, when faced with decisions or potential courses of action, if we’re struggling with the decision, its generally better to choose the path with the higher upside. Succinctly: to choose in the affirmative. This does a few things: It gives you something exciting to look forward to, it snaps you out of whatever lull you’re in, and it expands your catalogue of experiences. All three of those benefits last whether or not you actually succeed in what you decide to do. (And, of course, you might not.)

Scared money don’t make money, and if you’re not willing to invest your time and energy into something that scares you and forces you to change, you’ll never see just how far you can go. As T.S. Eliot said, “Only those who risk going too far can possibly find out how far they can go.” My cousin passed me a card with that quote on it during my last meal with them before I packed up my life and moved from Buffalo to Austin. That was, by far, the greatest decision I’ve ever made, and I still have that card.

Lesson №8: Do more things that make you put down your phone.

I forget who said this originally, and the Internet isn’t much help — unless “Pinterest” qualifies as a person — but this one’s pretty self-explanatory.

Our phones are making us miserable. (Shoutout to Niklas Göke.) Between doom-scrolling and endless Insta-comparison, there’s a sprawling body of research correlating excessive smartphone usage with increased depression, anxiety and existential dread. In 2020, that phenomenon’s been placed into sharp relief.

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Prior to the pandemic closing Earth for business, the solutions for these were pretty obvious — meet with people in real life, go to concerts and museums, put your phone away when out with them, travel and explore — but COVID’s rendered those options extraordinarily difficult.

Still, the outdoors are available. It’s still a good time to take up a craft. The less you can spend time staring at the “nightmare rectangle,” the better you’ll feel.

Lesson №9: Everything’s great in moderation, including moderation.

The most successful people in the world are highly unbalanced. Chances are, you don’t want to be one of the most successful people in the world. Still, to accomplish anything great, it requires a bit of maniacal commitment to the cause.

The most well-adjusted people in the world are, by contrast, extraordinarily well balanced. They earn B+ across the board in their careers, relationships, finances, health, learning, and passion pursuits. If you want my opinion, there isn’t much good in aiming for straight-A’s. You’ll drive yourself nuts in your pursuit of perfection, likely alienating people in the process.

That said, striving for excellence in a couple key areas will help you find a nice mix between success and balance. If you can become the Top-1% in any skill — doesn’t matter which — and moderately prodigious in maintaining good health, good friends and a job you don’t hate, you’ll reap more than enough rewards to feel content with your lot.

Or, as I put it in “How To Lose 44 Pounds,” eat healthy about 80% of the time. Because life without chocolate chip cookies is stupid. Indulge every now and again — whether it’s in mowing down a plate of wings, writing a magnum opus over the course of a weekend, or a 24-hour sexcapade.

Lesson №10: Satisfaction = Experience — A(Expectations)

Satisfaction is one of two life goals shared by all humans. (Belonging is the other. Again, see the “You Are the 15 People Closest To You” above.) The above equation is how I calculate satisfaction. It’s the quality of the experience, minus your expectations.

You can see here, clearly, that the higher your expectations for something — a relationship, an election, a meal, a concert — the lower your satisfaction. And, if your expectations are higher than what you actually experienced, then you end up with a net-negative satisfaction. Disappointment.

The “A” outside the expectations is what I call the “attachment coefficient.” That’s the weight you assign to your expectations, and it has a multiplying effect. If you focus intently on what you expect, you’re increasing the value of expectations and setting yourself up for greater disappointment down the road should things not quite level up.

We are only guaranteed the present, and so to focus more generally on how you plan to spend your time, vs what you hope to gain out of it, can help prevent you from inevitable disappointment.

Lesson №11: Plan your time, or someone else will.

You could sum this up as “be proactive,” but I wanted to be a bit more specific. Your time is the only resource you can’t get back once its gone. (Yes, specific people can’t be replaced, but there’s also a metric hellaton [eight billion] of people available at any given moment.)

I love my mom, but I like to use her as an example of someone who’s been pretty miserable most of her life. (Counterpoint: She does not like me using her as an example.) She’s miserable because she does not actively grab the bull by the horns, take responsibility for her own happiness, or plan her time and fill her calendar with things she wants to do.

Instead, she complains about the same half-dozen or so things, consistently, repeatedly. (In some order: I wish I could see you guys [her kids] more often, I’m lonely, my boss is an asshole, I wish I could travel, I think I’m sick/dying/injured [to be fair, she had a brutal stretch this summer where she got diagnosed with a broken elbow, COVID-19, bursitis and arthritis in less than 90 days].) She’s a pushover, doesn’t advocate on her own behalf, and constantly thinks up new reasons why she “can’t” or “won’t”. This is a great way to guarantee your own misery.

When it comes to your time, there’s nothing more valuable. If you can stuff happiness, meaning, learning, kindness, and important decisions into that time, you can change your fortunes, change your mood and change your life.

If you choose not to plan — whether that’s your day, week, month or year — outside forces will make those plans for you. Your boss will drag you into another meeting that should be an email, or set you up with an unreasonable deadline. The energy vampires you surround yourself with will demand your attention. You’ll spend an entire decade talking about how you want to see Paris, when it could take you just $400 and ten minutes to book yourself a flight and — again — give yourself something to look forward to. (And I get, again, that in this economy most of us don’t have $400 or the vacation days. But if you do? Pick a place you’ve always wanted to go and just buy the ticket.)

Lesson №12: Assume other people are more interesting than you.

This is probably the most niche lesson on the list, but I think it’s the most important. If you go through life thinking you’re the most interesting person in the room — no matter the room — you won’t endear yourself to anyone, and you won’t learn anything.

Everyone has a story. Everyone has dreams. Everyone has areas of expertise. Everyone has beliefs (even shitty beliefs are beliefs). They can entertain you, teach you things and leave you better than they found you. Learn how to ask great questions that reveal the depth of one’s soul. Talk to everyone (within reason). Make great conversation and help people along if you’re able to.

The more interesting you find others, the more interesting they’ll find you. That sounds a bit backwards, but the most fascinating people I’ve met are the most humble, curious and empathetic. They listen well, share vulnerably, and ultimately mirror back the energy you give them.

Lesson №13: Diversify, diversify, diversify.

What do I mean by “diversify?” The better question is “what don’t I mean?” Whether its building a more inclusive workforce, seeking out a variety of perspectives, opening up multiple streams of income, learning new languages and skills, or traveling to more places — diversity, in the broadest possible context, is the key to enrichment.

Have a friend group that’s not all people exactly like you: people who don’t look like you, talk like you, think like you, live near you. The same goes for a Board of Directors, an Executive Leadership Team, or any professional or extracurricular organization. You avoid groupthink, you learn infinitely more.

Read a few credible news sources from different parts of the world and from different perspectives. I don’t mean if you subscribe to The Atlantic that you should also comb the pages of NewsMax. I mean read Washington Post, The Guardian, Quartz, FT and South China Morning Post. Or, hell, even Medium. (Please do, and become a member.)

Also, get as close to the original data as you can. Read academic journals and published reports from reputable think tanks. (There’s plenty of garbage there, too, but at least it’s closer to raw data, if you know where to look.)

Try new foods. Learn a second language. Go to a mixer where you feel out of place. Find ways to make money that don’t directly correlate with you exchanging your time for it. (I almost wrote “exchanging time for money is a losing bet, as one of the 15, but I covered that in far greater depth here.)

Lesson №14: Build the best sandcastle.

This dreamy twist of phrase comes courtesy of Donald Glover, from one of the most fascinating profile pieces ever to grace the pages of The New Yorker — or anywhere, really.

The lessons here are three-fold:

  1. Whatever you do will most likely be forgotten, and therefore not worth getting too attached to the outcome.
  2. Whatever you do will most likely not be the last thing you do, and therefore continue to evolve and try new things.
  3. Even though the above are both true, still make whatever you’re building — an awesome day, a work of art, a business, a relationship — the best it can be, because you’re always going to be building something. Plus, high quality increases the odds that your work will be remembered, valued, and open the doors to future opportunities for you.

Lesson №15: Life is jazz.

I went to Paris in August 2018. Actually, I went to 10 cities over the course of a month, but my first stop in Europe was Paris. I went on the trip with zero itinerary beyond a couple basic “must do”s in each city. I had a flight from New York to Paris, and then another one a few weeks later from London to Austin.

In short, I had a lot of flexibility. I budgeted 2–4 nights in each locale, and $5K for the whole excursion. I booked my hotels upon arriving in each place. That would make a ton of people anxious, but not me.

I boarded a red-eye from JFK to CDG, and sat next to a charming Argentine woman about my age. We talked the entire flight, aside from a couple hours of much-needed sleep. We rolled into downtown Paris together, and then decided we’d spend an evening out. At the recommendation of a friend in Portland who used to live in Paris, we went to one of the Momma joints in Montmartre for pasta, and then to Cafe H for jazz. (This is very on-brand for me.)

Turns out: Cafe H discontinued their jazz the week before, and so instead we sat outside a cafe across the street, sharing long stories — I know this is difficult to wrap your mind around, yet she can spin better, longer yarns than I can — and plentiful laughs under the Paris moonlight. If that sounds romantic, well … it was.

After we parted ways — I had eight more cities on the hit-list — we kept in touch, and she became one of the 22 people I mentioned above. We’ve had two more dinners since, in two different cities. Had I been inflexible in my itinerary, or rigid in my scheduling, it would’ve never went down the way it did. That evening was one of my favorite of what was also one of my favorite months roaming this rock. (August 21 — September 20, 2018 is matched only by February 26, 2019 — March 25, 2019; September 4, 2019 — October 3, 2019; February 15, 2020 — March 14, 2020.)

Many people divide folks into “Type-A” and “Type-B,” but I find that delineation to be less colorful and helpful than the way I’m about to divide people for you: There’s two types of people in this world — “pop” people and “jazz” people. Pop people are rigid, exacting and need every detail mapped out. They seek the familiar, the proven and the expected. By contrast, jazz people flexible, adventurous, fluid and plan in rough sketches rather than note-for-note compositions.

I’m a jazz person. Just give me a key, a style, a tempo, and I can work alchemy within those basic constraints. Life is constantly throwing constraints and curveballs at us, the easier you can adapt to them and play within the context of them, the more you’ll get out of it.

I think we could use more jazz players among us.

Written by

Essayist and storyteller on life, liberty and the battle for happiness. Several million served. Words at Human Parts, Forge and PS I Love You. IG: heygorman

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