I feel very fortunate to have had the personal freedom this year to work and create for myself. Across the board it’s helped me focus on the commitments, projects and relationships that mean the most to me. Many don’t get to have that independence, which speaks to some very fundamental problems with how we collectively allocate and value human potential.

And, as you might have guessed, one of the reasons I haven’t posted much this year is because I’m trying to get sh*t done, including:

  • Launching Brightest in beta – a discovery engine for finding ways to make you, your community and the world better (a lot more on that very soon)
  • Mentoring a 9 year old in my neighborhood through a wonderful Brooklyn organization called Children of Promise
  • Co-launching The Museum of Pizza, an announcement which has already generated international joy and been featured everywhere from Eater and Food & Wine to the Wall Street Journal and Italy’s Repubblica. Growing up family pizza night at Regina Pizzeria (1 cheese, 1 supreme) was a weekly tradition, and it’s been awesome to collaborate with some really impressive emerging artists (yes, it’s an actual, pop-up contemporary art museum), eat lots of pizza (mostly), not to mention already fund thousands of meals for New Yorkers in need through our non-profit partners
  • Producing a foundations of Strategy 101 class for Skillshare, which I got to road show at WeWork this summer and teach some classes in person, which was cool

And it’s still June so my year’s not over yet 🙂

But 2018’s been about a lot more than getting things off my to-do list. It’s also been about thinking about the broader world, its biggest problems, the future we can (need to?) all build together, and how I can contribute.

I’ve spent 10 years now working in “tech.” But I’ve spent more than 30 as a person on Earth, a span where I’ve seen a fair bit of success, but also experienced plenty of failures, negativity, and disappointment.

So rather than focusing on a particular personal or professional topic, I thought I’d change things up and try to focus on the most important topic: the topic of life and what I feel like I’ve learned so far. Here are some of my best and most important personal insights I’ve tried to condense and summarize, and I’d like to share them here in case they’re helpful for you.

1. Life = ((People + Places + Projects) * Meaning) * Time

I wrote this as a formula, but the long of it is that life is a journey through places, projects and relationships – and, most importantly of all, your relationship with yourself — in search of meaning, multiplied by however long you get in this world.

The earlier you create and discover meaningful relationships and projects in life, the more leverage you get on both your happiness and your impact. And this momentum feeds itself. The key isn’t that you have to find it early – it’s a difficult task, most of us don’t, and there are thousands of examples of people ranging from Van Gogh and Thelonious Monk to J.K. Rowling and Mark Twain who hit their stride late in life — the key is to actively go out and look for it (and look inside too).

One of my favorite hobbies is music (listening to it, studying it, occasionally composing it), and one of the things I’ve noticed is a lot of the hardest-working and happiest people are musicians and other artists who truly love their craft. Just Blaze, the iconic hip-hop producer responsible for shaping Jay-Z’s sound and catapulting hip-hop music into the commercial mainstream in the early 2000’s is, today, 40 years old and a multi-millionaire. He could be on a beach right now; he doesn’t need to work. Yet Just still regularly spends 16 hour days making music, often until 3 or 4am in the studio — because music isn’t work to him, it’s meaning.

Paul McCartney, Prince, Bach, Vivaldi, Schubert and many other great artists are the same way — they produce so much over their careers because as soon as they get their initial creative momentum every day, hour, minute and second is lit by the fire of purpose.

There was a great account I heard recently of an elderly classical composer who was asked to do a press interview.

“I’m sorry, he won’t be able to do the interview,” his assistant said, apologizing to the journalist.

“Well, would he be available another time?” the reporter asked.

“Unfortunately no. He only has time for his music and his family,” came the reply.

Find the most fulfilling way(s) to spend your time, spend time with people who matter, and do whatever it takes to focus and cut out distractions. There’s no better recipe for maximizing your personal well-being and making the most of your time.

And yes, it might be a privileged thing to say “work on finding the work that doesn’t feel like work,” some of us truly can’t, but nearly everyone can carve out some hobby, side-hustle or social time to get the mental nutrition they need. And if you already love your 9-to-5 and that’s your art, awesome — even better.

2. Life’s priorities are zero sum

Extending on from my first point, I find it (personally) helpful to think about life in terms of four areas or territories:

  1. Career – how earn a living and do meaningful work
  2. Art – what you create or bring into this world you find personally meaningful (and may want to share more broadly or treat as an artifact to leave behind)
  3. Health – your personal health and fitness (sleep, nutrition, exercise, self-care)
  4. Relationships – family, your personal connections, and your network

Again, when I’m at my best, happiest and most productive — or when I observe others really making strides — it’s typically when these four areas are reasonably well-balanced and at least some attention and investment is happening across all of them.

BUT, time is precious and limited, and prioritization is pretty zero sum. As much as I’d love to create galleries full of art, grow a dozen successful companies, exercise regularly, spend lots of time with friends and family, and sleep ten hours a day, I can’t. You can’t either — even with wealth and a team. People like Elon, Lin-Manuel Miranda and Kanye still fall short here. It’s impossible. The time just doesn’t exist to do it all.

Once you recognize this — and particularly when you start trying to time-manage around it — you’ll likely realize:

  • You can do one of these four things great or world-class (the best you can possibly do it with your full, personal investment)
  • You can do a second one pretty well
  • You can probably at best juggle the other two ok-ish and keep them in maintenance mode

This just always inevitably ends up true for me. The times when I’ve been most professionally or financially successful usually come at a cost to my personal health or relationships. If I’m investing a lot in others, that has trade-offs as well.

Keep this in mind and decide where and how you want to focus — and what feels most important to you.

BUT (x2), here’s the real life hack: you get the most leverage when more than one of those things is the same.

  • Your career = your art (filmmaker, writer, chef, teacher, philanthropist, innovator, first-responder, etc.)
  • Your relationships = your art (great mother/father/brother/sister/son/daughter/partner/etc, uniter and enabler, community-builder, activist, etc.)
  • Your art = your health/wellness (yoga teacher, physical therapist, athlete, etc.)

Really thinking about and understanding these two insights has led to some of the most important and radical changes I’ve made in my own life (virtually all of them for the better).

Or consider for example, the stated priorities of one of the most economically influential and materially wealthy people on the planet:

As one of the few people in the world who can do pretty much anything, it carries a lot of weight that — recognizing that possibility — he’s made his picks.

3. There is a formula for happiness and it’s mostly about expectations (and meaning)

Ok, you’ve read this far. Congratulations. And now for your reward, here it is, the actual formula for happiness:

happiness formula

Oh? You never pursued that PhD in physics?

No worries, I can help explain this one too.

What researchers at University College London discovered studying thousands of people’s brain patterns and responses is happiness doesn’t come from getting rewards, happiness principally comes from how the rewards you earn compare to your expectations.

If you have low expectations, psychologically, you can never be disappointed (sound familiar?).

But moreover, the positive expectations you have about something — like going to your favorite restaurant with a friend — is a major contributor to your happiness. Arguably the defining contributor.

A lot of proverbs and famous quotes are well-known and developed around this insight (“it’s not the destination, it’s the journey…”) that research shows are essentially correct and true.

And this is yet another reason why my first point about life as a journey in search of meaning becomes so important: if you think of life as a linear narrative guided by the pursuit, discovery and sharing of meaningful moments, experiences and accomplishments, then meaning logically becomes the north star that helps guide and set our expectations.

The person who’s found meaning will always be happier because that meaning frames the balance between their mission, their expectations, and the path they take to pursue it. There is no one reward, there are infinite rewards along the way. And passion will always be the most important guiding light in a world of infinite choice and possibilities.

This is also why, in my view, a lot of rich people end up very unhappy: they see wealth as the last level, get there, then don’t know how to play the rest of the game.  I’m now old enough — and worked in tech long enough — to personally know multiple people in their 30s and 40s who can be considered rich by any conventional standard, and can honestly tell you (without naming any names) many of them have demons or aren’t particularly happy.

The happiest guy I know? He’s a millionaire many times over and seems to spend most of his time playing with his kid, being a good dad, reading, and tinkering on side projects he believes in.

4. Personal vs. professional you is an arbitrary and unhelpful distinction

I remember being in my 20’s just starting out in my career when I used to think there was a professional me (how I was at work: serious, disciplined, data-driven, looking and carrying myself a certain way, trying to be cool) and a personal me (how I am when I’m alone or with friends and family: playful, more of an open communicator, more varied in my interests or “creative,” as much as I dislike framing around that term, genuinely not that cool) and that the two were often — or could be — incompatible.

Maybe I’d come off as unprofessional to my team. Or my friends might mistakenly get the impression I’m a boring workaholic. Maybe I should have a different voice and tone on LinkedIn vs. Instagram…

But honestly, the older I get the more I realize this distinction is mostly bullshit. You are who you are, and the more you can be a single, unified you the happier, healthier and more successful you’re going to be, and others will recognize and be drawn to your authenticity. Of course, please don’t hold up this essay as carte blanche to do whatever you want at any time (particularly if it infringes on the rights, identity, happiness, productivity and purpose of others) — be the good, balanced, and empathetic version of yourself. Just be cool.

Unless you’re a true celebrity (and even most of the time when you are) there’s a strong, inverse relationship between how happy you are and how much time you spend trying to perfect and position your personal brand. It’s so clear.

Don’t fight a perception battle; shape and guide the you that exists in reality. (Most) people want that and anyone who doesn’t whotf cares?

5. Productivity = (Focus + Delegation + Unblocking ) * Automation

The two most radical productivity improvements I’ve seen for myself and others (or blockers for people who aren’t as productive and impactful as they should be given their talents) come from:

  1. Delegation – knowing when you aren’t the right person to do something or be the expert and recognizing X needs to be handed off (I like the 80% rule – if you can delegate something to someone else and they can do 80% as good a job as you while you’re 100% on something else, pass the baton ASAP. If they can’t do it 80% as well, either (a) you need to go 100% on getting them to 80% or (b) they’re not the right person to be doing it in the first place and you have other things to course-correct). Again, time is precious and even the most talented individuals pale in comparison to a focused, well-orchestrated team that understands how to parallel-path.
  2. Unblocking – being able to recognize what dependencies or impediments are preventing others from doing their 100%, and figuring out ways to remove those obstacles.

When you (or you and your team) is focused, priorities and tasks are clearly communicated then delegated, and the roadblocks are cleared — progress happens fast. Then layer on smart automation (or repetition, templating, etc.) to really get leverage on your output.

6. Most evil is dull, unfeeling and administrative.

For the most part, I’ve tried to keep this essay positive. But the reality is there are bad acts and actors out in the world, and sometimes it’s important to recognize that.

What I’ve increasingly realized, particularly over the past several years, is that our archetype of evil is the cinematic or Marvel comic book villain — the bad guy who shows up and says “I’m going to take over the world,” then launches a sinister plot to do it.

And that archetype is completely, spectacularly wrong.

The reality is a lot of “evil” in the real world is actually very banal, bureaucratic and administrative. It’s boring, it turns a blind eye to itself, and that’s why in an attention economy our media glosses over it and we tend to miss it until it’s too late.

This is the type of evil that doesn’t necessarily set out to be evil, but ends up becoming evil by virtue of callous, distanced decisions that carry malicious consequences. When the bystander effect manifests itself in social policy set by people with jaundiced values.

To briefly get very partisan (because I feel it’s absolutely necessary at this point in history), the following actions are evil:

  • The Trump administration and our Republican-led Congress’s efforts to sabotage and end the Affordable Care Act, depriving millions of people with affordable medical care, rather than trying to constructively reform and improve its shortcomings
  • E.P.A administrator and Koch Brothers’ lackey Scott Pruitt’s efforts to undercut consumer safety by rolling back protections for people and the environment which will cause lasting harm for every future generation
  • ICE, DHS and CBP’s ongoing separation and detention of thousands of immigrant, migrant and border-crossing families and children.

There’s no need to equivocate; these acts are beyond wrong. They’re evil. But they’re an evil subtly manifested and engineered through our existing legal, social, and economic system — less intended murder, and more abstract manslaughter.

Someone makes a decision with far-off consequences where people are reduced to numbers.

Someone’s just following orders.

Writing about the trial of Adolph Eichmann, the Nazi operative responsible for organizing the transportation of millions of Jews and others to various concentration camps in support of the Nazi’s “final solution,” the philosopher Hannah Arendt comments in her notable book (aside: re-reading Arendt and Jean Baudrillard this year has, for me, been incredibly constructive in thinking about the state of the world today in context), Eichmann in Jerusalem: A Report on the Banality of Evil:

“I was struck by the manifest shallowness in the doer [i.e. Eichmann] which made it impossible to trace the uncontestable evil of his deeds to any deeper level of roots or motives. The deeds were monstrous, but the doer – at least the very effective one now on trial – was quite ordinary, commonplace, and neither demonic nor monstrous.”

That’s the evil we face most in the world today; the toxic, boring, profiteering evil that warps and exploits vulnerabilities in the system or people within it who never think to question it. Know it, recognize it, try to give a shit, and work on fixing broken systems and moving hearts and minds in ways that help eliminate it or keep it out of power.

7. We are most limited by our own reality distortion

The more any of us work on one thing, stay in one place, or repeat the same motions, the more it frames and shrinks our perspective. Focus confines worldviews and creates simulated value equivalence when it proceeds uninterrupted.

It’s that feeling when something seems so important — so life-or-death — in the moment, and a few days later you couldn’t care less and barely remember it even happened.

I’ve spent a lot of work days or weeks in the past where I get to the end of it and realize I haven’t talked to anyone close to me, looked at the news, or considered anything from a different perspective.

Seek variety, change things up, step away for a while and spend time on the big picture: we plant a lot of false flags in our own minds. Hamlet (ok, Shakespeare) and Milton were right all along.

Our biggest limit is usually not giving ourselves the time, perspective or context to see life for what it really is. Or assuming our world is X-sized when it could easily be opened up to be X ^ Nth bigger (shit, more math, sorry).

Life’s always going to happen, but sometimes just remembering that is exactly what you need to break the cycle and pull back or reset unproductive filters.

8. True art (and the joy that comes from it) is about finding commonality in what makes us human.

I had the pleasure of meeting Shantell Martin at a Kickstarter event a few weeks ago in Brooklyn, and she shared one of my favorite things I’ve heard anyone say about the definition of art and the role of an artist.

Art, Life and Meaning - Shantell Martin

To paraphrase:

“An artist projects out their full public, vulnerable identity to recognize their real self. In doing so, they help their audience recognize those same human qualities in them.”

I thought that was awesome. I still think it’s awesome.

Art (and really all successful communication) is about knowing yourself, and projecting that knowledge, those insights — that realness — out into the world to break down barriers, connect with other people and help them learn about themselves.

And if I did my job right here, hopefully I did a little bit of that for you or someone you know here.

That’s what I’ve learned so far.

Be you, be real, be happy, value time, fight evil, and go find and make whatever your true art is — however you define that.

In the words of Cai Guo-Qiang:

“The sound of the fire was beautiful.”
Art & Purpose - Sky Ladder
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