40 Years, 40 Lessons (Maxims Only)

NOTE: This particular post is the MAXIMS ONLY version. It offers my thoughts in rapid fire style, but admittedly, without much (potentially helpful) context.

The FULL TEXT (~8000 words) version is for those who want to understand my perspective more completely via examples, qualifications, further reading suggestions, etc. For the FULL TEXT post, go HERE


Hi there true believers!

As I approached my 40th birthday, I wanted to share some things I’ve found helpful. In this article, you’ll find a hodgepodge of considerations, suggestions, and thinking tools for a better life. After 40 years of thinking, reading, testing, and living, I’m confident the thoughts below will bring you more joy/ fulfillment and less suffering/ disappointment.

No set of maxims can (or should!) shield you completely from adversity; your failures, struggles, and mishaps are what will sharpen the saw of your humanity. But as the saying goes “A smart person learns from their mistakes, a truly wise person learns from the mistakes from others.” 

Some of these thoughts represent a radical departure from what I would have said on the eve of my 30th birthday. I suspect after ten more years of life these will further evolve, as they should. But for now, consider these musings some of my “Notes From The Road (So Far).”

AND if you like this kind of stuff, I’m posting a daily 1-3 minute stories over on Instagram for all of 2020. (Follow me HERE.) Topics include business focused content like time management, leadership, and customer service, AND musings on learning theory, psychology, and practical philosophy.

New DECADE… let’s GO!!!!


1) No maxims are 100% correct in all contexts. 

Virtually all maxims (including all of these) have an implicit qualification: “But of course, there are obvious exceptions.” Or as the staticians say, “All models are wrong, some are useful.”

It is appropriate to observe where/ when the maxim/ principle doesn’t apply. But it’s probably more useful to identify the circumstances under which it would be correct.

2) When there’s something you want that you don’t have/ can’t get, there’s something you don’t know.

It’s unwise to bang your head against the wall trying to figure it all out on your own. It’s also unwise to bury your head in the sand, though this can be a common response when we’re struggling so much with a given topic that it’s painful. 

If you’re not happy with an area of your life, invest time, energy, and money in studying that area.

3) If you want to be successful in life and business, you’ve got to get the incentives right. 

This goes for you personally, for your team, for your clients/ customers, and for your society.

4) “The most important ability is dependability.” – Zig Ziglar

Being dependable has outsized impact on your success and doesn’t require talent. However it does require caring enough to develop some system for organizing your commitments and deadlines. 

Related:  “Self esteem is your reputation with yourself.” – Naval Ravikant

Yes, sometimes low self-esteem is a result of trauma, socialization, or something that requires the support of a clinician like a therapist.  But on balance, for most people, your self-esteem is a reflection of your reputation with yourself. Can you rely on yourself to do what you commit to do? 

If not, it’s a good place to start if you’d like to improve your self-esteem. 

5) Don’t care too much about what other people think. But it’s ok and ideal to care some. 

“Fuck the haters” is a silly philosophy. Sometimes haters make accurate (if painful) observations.

However, it is also silly to give your power away willy nilly. Because you’ll never please everyone. And if you have any level of success, you WILL have rocks thrown at you.

A related thought: 

6) Feedback is just data. 

When you receive feedback, it’s your job to consider it and decide if it’s true or not. 

Carefully considering the merit of feedback is superior to automatically dismissing it (because of poor delivery OR you dislike the messenger OR because it makes you upset OR etc. etc. etc.). 

However, carefully considering the merit of feedback is ALSO superior to taking all feedback to heart, being reactive, solving problems you don’t have, giving away your personal power, etc. etc. etc.

7) It’s particularly helpful to be able to learn from people that are not your cup of tea. 

People you don’t like and/or who dislike you are uniquely well positioned to help you discover things that aren’t obvious to you. It’s BECAUSE they’re unlike you that they hold so much value for you.


8) Be wary of cynics. 

Sometimes you can get helpful feedback from them (see 5, 6, and possibly 7). But people that fundamentally distrust the sincerity and integrity of most/ all humans have a warped frame. Keep this in mind.

9) Pretty much everybody could benefit from therapy of some kind. 

Unless you made it out of childhood and your adolescence without any wounds.

Not everyone needs therapy. But pretty much everyone would benefit. You’ll just suffer less. And that’s not purely a selfish consideration. When you suffer less, you’ll be a better version of you for the people you love and the world at large.

Also worth considering:

10) Work on yourself some. But not too much.

Too little focus on personal development and self-work and you won’t reach your potential.

But self-work can take up a disproportionate amount of resources past the point of diminishing returns. This can displace/ impede action-taking. At some point you have to engage with the world, with other people, and with society. 

Of course, it’s not either/ or. We want both. But there IS a balance to be struck.

11) “Your weaknesses are your strengths taken to their extremes.” – Ari Weinzweig of Zingerman’s Deli in Ann Arbor, MI.

If you’re capable of creating extreme results, you likely have some extreme tendencies. Be mindful of how far you’re pushing your strengths. They can come out the back door and bite you in the ass.

12) To be fulfilled, focus on two things: being a Student and being a Servant.

When uncertain what to do with your morning/ day/ life, learning things and/or serving people will be a satisfying choice.

BONUS: The best and most foundational form of service is unconditional positive regard (acceptance, compassion, and sincere love). Hard to do, but a worthwhile goal.

A related thought:

13) It’s a trap to define your self-worth purely in terms of what you can do for other people.

You are more than simply your ability to DO stuff.

14) Happiness is best created by (spending time, energy, and money on) experiences and relationships, not things.

If choosing between buying an expensive designer luxury thingamaroo or going on a weekend vacation with a partner or dear friend, it’s usually best to choose the latter.

15) A disciplined gratitude practice is the most reliable intervention to improve your mental well-being.

You’ll still see negative things. That’s not only ok, it’s desirable; this can help spur action and identify opportunities for improvement (see 16).

But particularly if you overweight the negative and and rarely appreciate what’s going well, take some time each day to identify what you’re grateful for.

BONUS: When you feel gratitude towards a person, let them know. And tell them why. Perhaps in a handwritten card.

16) If you’re not sure what you want in a situation, ask yourself what you DON’T want. 

That will probably be more obvious. Then explore the opposite of what you DON’T want. 

BONUS STRATEGY: If you’re not sure how to get what you want, identify the OPPOSITE of what you want. Then identify how you’d need to behave to create the OPPOSITE of what you want. Then identify the opposite of those behaviors.

17) To increase your probability of achieving a goal, first decide on exactly what you want. Then track stuff. 

You’ll be best off tracking both inputs (behaviors, processes) and outputs (outcomes, results), though sometimes focusing on behaviors alone is sufficient.

NOTE: Clarity on your goals does not guarantee you will achieve them. However, NOT having any clear goals makes it very unlikely that you’ll accidentally stumble into the life of your dreams. You can find a simple visioning system with prompts HERE.

And now… a counter thought:

18) What gets measured gets managed. But you can’t always measure what matters.

Be mindful of “The Tyranny of the Quantifiable”: the sneaky impulse of your brain to prioritize goals that can be quantified over things that are actually more impactful for a good life. 

19) The best time management skill is the the ability to do one thing at a time without letting yourself get distracted. 

Manage external distractions by communicating boundaries with humans and blocking digital distractions.

Manage internal distractions by committing to a “Pomodoro” approach (25 dedicated, focused minutes of work, followed by a 5 minute break).

20) Good time management is about weaponizing (smart) laziness.

Even if it only takes me 60 seconds to do, I’ll happily spend 30 seconds to write an email to delegate the task.

Seconds make minutes make hours make days. And the days may be long, but the years are short.

A related observation/ inversion:

21) Few things will impede a successful life more than a tireless commitment to becoming world class at shit that doesn’t actually matter.

It’s helpful to be able to put your head down and get to work (see 19). But you will get nowhere fast unless you learn how to prioritize based on your long term goals and your personal values.

The essence of effective strategy is identifying what you’re NOT going to do. You will never get it all done. Particularly in today’s day and age. Eliminate the non-essential.

“Less but better.” – Dieter Rams

22) Conventional intelligence is just table stakes. Unless combined with the ability to consistently produce work AND emotional intelligence, it will not lead to success.

The world is filled with hyper-intelligent people who are personally and professionally unsuccessful. 

Brains alone are not enough. Commit to actually getting things done AND to life long learning about your emotional life and interpersonal skills.

23) Training, delegating, and managing other people are non-negotiable skills if you want to maximize your output and impact on the world. 

Otherwise your output and impact will always be limited by your personal time, energy, and skill capacity.

24) “Never attribute to malice what can adequately be explained by stupidity (or incompetence).” – Hanlon’s Razor

A related customer service mantra: “Better naivete than paranoia.”

Everyone’s doing the best they can from where they are. Even though that may objectively be shitty. 

Everyone’s fighting a battle. Be kind.

25) You can be a great human without being a great leader. But you can’t be a great leader without being a great human.

You have to be the kind of person that other high quality humans are willing to follow.

26) There is no such thing as a universally effective leader in all situations. And certainly not for all people.

Leadership is always contextual. 

This is why a leader can thrive in one business and be a bust in another. It’s also why the person who starts an organization isn’t always the one who can lead it through various stages of growth. 

27) Learn how to write and speak (sufficiently) well.

You don’t even need to be great. I’m an adequate writer at best. But I AM able to communicate quickly, concisely, warmly, and clearly. And without exaggeration, this “just good enough” skill is the parent of much of my professional success.

While writing matters in many contexts, at the risk of stating the stupidly obvious, much important communication will happen via conversation. Sales pitches, “sales” pitches (see 28), writing up a team member, having a difficult conversation with a loved one, giving a speech to a group of people, articulating your love for someone you adore… these are important skills.

28) We are ALL in sales. We are all “Agents of Influence.”

Every human has desires that require “selling” other people on a shared vision and parting with resources (time, money, energy). You may be “selling” your child on finishing their homework. Or “selling” your mom on recycling. Or “selling” your boss on giving you a bigger raise.

The key to doing it with integrity (and frankly, to doing it well) is: 

1) Genuinely care about the individual you’re influencing. 

2) Sincerely believe your proposed plan of action is actually in their long term best interest. 

3) A deep respect for their autonomy in making their own decisions.

29) Intellectual humility – coupled with the right dose of introspection – is the foundation to continued personal and professional growth.

“The first principle is you must not fool yourself – and you are the easiest person to fool.” – Richard Feynman

30)Seek first to understand.” Particularly when mad, hurt, confused, offended, etc. 

A curious, open mind is always a good look. It’s particularly valuable when emotions are involved. 

31) Emotions are vital, helpful, and often slightly flawed tools for understanding our preferences and driving decision making. 

We don’t want to deny or ignore our emotions. And we should be realistic that total conscious control isn’t possible, or frankly, desirable. But we also don’t want to assume our emotions always lead to good decisions without at least some oversight. 

Your heart matters AND your brain matters. As is often the case, we want both.

32) An addiction to being “right” often prevents people from getting what they really want.

Everytime you feel your ego flare up during a disagreement, you’re slipping into an unhelpful place; it’s a warning sign you’re about to start arguing why you’re “right” and trying to “win.” 

You’ll stop seeking to understand and an opportunity to learn will be lost. And more than likely the quality of the relationship is going to take a hit.

When you find yourself in conflict with someone else (which is normal and generally valuable, see 34), zoom out and make sure you’re clear on what you actually want most. 

33) Be cautious when you have strong opinions about topics you don’t actually know much about. 

Strong and forcefully held opinions – with no knowledge base or track record of results in a given domain – are the source of much human suffering. 

34) Healthy conflict is the secret sauce to leveraging the power of groups. When you do this right, two plus two will equal five.

Without conflict/ debate/ disagreement, there’s no growth. In any community/ organization/ society, the quality of thinking improves by marrying different perspectives and ironing out the conflict. To do this well, see 30.

“When two people in business always agree, one is unnecessary.”

35) The Law of Attraction may or may not actually be true. Regardless, it’s a good way to approach your life and work.

Are there actually esoteric metaphysical currents of energy stirring the cosmic soup in the direction of your thoughts/ feelings? No idea. 

But it’s logically a useful strategy to focus on what you DO want. To greet your day like a happy warrior, confidently and boldly moving in the direction of your dreams. 

Also:  “When you pray, move your feet.”

36) Authenticity is poorly understood, and possibly overrated.

This is not to say it’s good to be fake, forced, disingenuous, conniving, etc. 

It’s simply acknowledging that “authenticity” is a nebulous concept since it implies there’s a true you. And in fact… you “contain multitudes.” And you’re forever in the process of (re)creating yourself.

(I concede advice to “be authentic” is well-intentioned and can be helpful in some situations. Particularly when it refers to exploring what you really want, what you really feel, what you really think, etc.)

37) We are ALL practical moral philosophers.

By being a human and having any opinion whatsoever on – or taking part in –  a business, a community, marriage/ romantic relationships, family, parenting, politics, social justice, the government, the law, power dynamics, etc.… you DO have ethical intuitions.

And if we’re apart of any of the above systems, as we all are, we’re making choices every single day. So although it may seem strange, we are all practitioners of moral philosophy.

And that’s why I think it’s good to spend at least some time thinking about it.

38) Choosing the right people to build a life with will do much to mitigate suboptimal decision making and bad luck. 

Conversely, you can do almost everything “correct” to create the life you want, and yet have your happiness totally thwarted by poor choices of spouse, business partner(s), teammates, etc.

39) Health really is the first wealth.

There is LOTS of debate about the best way to pursue health and fitness. As most readers will know, my other business is devoted entirely to helping people find the path that works for them. But at the risk of being totally reductionistic, some non-controversial guidelines:

  • Eat a reasonable amount of mostly non-processed, perishable single-ingredient foods that you actually like. Emphasize plants.
  • Get in some kind of physical activity that you actually like at least several times a week, ideally every day.
  • Take sleep hygiene seriously. Strive for 7-8 hours a night.
  • Cultivate self care rituals that nourish you: walks in nature, meditation, prayer, reading, etc.
  • Find work you genuinely enjoy/ love. If that’s not possible, find work you don’t hate.
  • Spend time every with people you love and who love you back.

Final thought: always remember you are robust. During a season of career focus (or young children!), you may not nail all of the above. Do your best. Accept it won’t be perfect. 

But also be honest about the difference between a temporary disruption and an indefinite lifestyle that needs an intervention.

40) Memento Mori. 

Remember you will die.

“The goal of personal growth should be deathbed clarity while your life is still happening so you can actually do something about it.” – WaitBuyWhy.com