ama #5 - 10 years of perspective in 1 analogy

a note to someone turning 20 as i turn 30

h/t midjourney + runwayml

“🏇 learn how to ride the horse in the direction it’s moving.”

this was an analogy first used by a 72 year old developmental psychologist over dinner with humans in their 30s in san francisco. as i begin into this decade, it’s something that piqued my interest as focus is an emerging theme for me.

while reflecting on this for myself, i shared this with an ambitious 20 year old also starting a new decade ahead. i realized that this is not specific to a particular decade. it’s worthwhile at any point in time when evaluating personal alignment between desires, choices, and actions.

my intentions: this is not advice

when reading online reflections, i find some lists of insights feel contextless as they are made generic for an entire online following. without context, it’s hard to personally discern relevance.

this kind of reflection can be more bland than someone else eating your birthday cake every year for the next ten and then trying to describe it bite by bite to you over a zoom call.

the intention of this piece is to be closer of a menu of stories paired with a narrative for you to find what resonates with you right now. resonance is a proxy for what you’re curious about right now.

there’s also an actionable practice that helps take the overall idea and apply it to seek personal insights.

starting my 20s, i sought perspective

when i entered my 20s, the main thing i was hungry for was perspective.

i was curious to hear what others had to say, like this stanford professor writing a letter to her son, or biographies like steve jobs by walter isaccson, and even this history of western philosophy over millenia. 

for me, the first book revealed the cultural differences common on the east coast (traditional, linear, and conventional) v. west coast (embracing uncertainty, being more audacious, and intentional).

the last book highlighted engrained differences in eastern philosophies (collective, nondual, and seasoned over millenia of developmental practices) with western philosophies (individual, bunch of sky gods, and seemingly still emerging).

those books were fun to read and find what resonated with my curiosity at the time, but they were limited in their pragmatism.

as i leave my 20s, if i could tell myself one thing it would be: embrace your 20s as they will be. it is fully yours. perspective and data from other smart people can help with guiding insight, but ultimately it’s up to you to actively write in the pages of your life daily and annually what will be the decade ahead.

it’s a simple grounding insight, but it’s profound as many people share their textual memories without admitting to the limiting factor that the world keeps changing, and so what is captured in their perspective is limited.

the world, where it was ten years ago, is different from where it is today. in the last ten years alone, we went through a century making global pandemic complete with total shutdowns, starting to see the climate crisis heat things up, generative content explode with llms, and challenging macro economic conditions that challenge outlooks for investment.

the person you are reading this in the moment is different than the one you were 10 years ago. and in the next 10 years.

you and the world will continue to evolve, shift, and change. embrace the rich and dynamic exchange between them.

this is a decade long analogy

more sweetly phrased by a developmental psychologist over dinner: “🏇 learn how to ride the horse in the direction it moves.” 

• horse = life. it’s a bit wild and some times has it’s own way.

• rider = your choices, decisions, and actions.

• direction it’s moving = the way all the things in life come together.

in your 20s, you may try to kick right, scream left, or even ride it backwards. i know i did.

sometimes you may even fall off and have to find a way to get back up. or maybe there are times you don’t even realize what has the ability to move. in extending metaphors, i digress. 

the main point is to embrace the journey as it comes in the direction life is coming to meet you. one way to practice this in reflection is keep a list between what you want (ideal outcome) on the left and what actually happened (real outcomes).

i dont think the psychologist who inspires this uses #FFA500 poppins for his list, but he should consider it. 

explore the gaps, especially when they don’t align. these will be important for being honest with yourself.

for example, one for me recently: 

what i wanted (age 29): work with founders directly with a focus on human development and coaching for startup progress. i piloted a 3 month incubator program for pre-seed stage founders building across synethtically engineered algae, large salt cavern storage, and more. all interesting startups, that i’d bet on if i was investing.

what actually happens: a 24hr long public hackathon in the middle led to more inner joy than 12 weeks of the program.

how i’m currently closing that gap: explore an earlier stage of people’s journey for my next accelerator. this summer, i piloted a 2 week sprint for college aged students in climate tech.

both had interesting opportunities to build a program from first principles and work with driven people on big problems. the difference? the education focused one sparked more curiosity for me. this may seem subtle, but for me was a signal for what has personal longevity.

i’ve embraced year to year hypotheses in my 20s, and am just starting to feel the transition as i kickstart my 30s that i’m ready to focus for the next 10+ years. i don’t think that has to coincide with decades, as i think in 10s or 20s or even later in life people can continue to explore and re-explore.

that’s one one way to live many life times in one: explore, focus skill building, figure out where to apply it, then, if you so choose, switch it up in a 7 year cycle. the fly hitting the edge of a bottle to get out. the bee flying in a straight line is an apt analogy. 

it’s an ongoing process of figuring.

intentional, directional goals, reflection, and preparedness go a long way in examining a life well lived, and yet there is still more to fully embrace through experiencing in it’s fullness. i guess the stories we tell ourselves can be tricky to navigate. 

and for the sole point of continuing the metaphor to see what else may resonate, below are example of times where i felt i was riding the proverbial horse:

• backwards - these are things i actively avoid

• sideways - not far off from my personal center, but easily knocked off

• forwards - alignment in things that have continued and are meaningful throughout the last decade

note, this was only obvious in hindsight. in the moment, it was the best decision i felt my past self could have made.

🏇backwards (ie. lessons i now avoid): ignoring basic needs making harder things harder. i had a friend who reflected this back to me once: “you like doing hard things. that’s cool. but make sure you don’t make the hard things harder on yourself.” some ways in which that was truly backwards: 

• working 2x as much in the day, stealing time from sleep,  to fulfill curiosity of exploring different things. through 20-25 i didn’t really get to sleep until 2a or later because i would spend 1/3 of my day on learning in school, ⅓ on startups, and 1/3 meeting awesome people. it took the last 5 years to undo that bad habit. while the night holds the illusion of the infinite, early mornings always feel better. and aligning more long term, sleep helps with the marathon ambition pushes for v. the sprint that desires short term results. 

• financial risks. i paid for grad school out of pocket because the university didn’t have formal support, meaning a lot of debt. i hustled to make it work and got generous private scholarships along the way, but if i could have helped my past self i would have found an alternative ambitious path that was financially more sound so that it didn’t weigh into future decisions of what to do post grad. 

• enjoying long round about paths between two points, rather than the shortest. in building culinary ai, my co-founder and i focused on building whatever we could imagine just to see if it could work. it felt like the kitchen as a living lab, shipping 8 different neural nets as cooking experiments with hundreds of algorthmic recipes. that makes for a fun research project and oddly delicious dinners, but made for a bad businessl. because startups are so hard, where even luck plays a role, it’s better to keep things simple. i appreciate that more now than before seeing in places it’s failed as well as seeing different successes.

all of these have pushing personal boundaries in common. i think many things can and should be pushed to their limits, but it’s not wise to sustain that intensity to the point of sinking or slowing down one’s hull of their ship, to use scott kaufman’s metaphor of the basic needs from maslow. ie. the above didn’t make sense.

🏇 sideways (ie. not far off, but not centered either): in my early 20s, each project was a chance to work with a new team and really challenge what was possible. the reason i finished architecture school was each term was a chance to explore something from a systems perspective: nuclear waste, aging population in poland, and more.

in side projects, it included art museum saas projects, social mobile apps, sustainable building materials, and hackathons as a service.

i chose speed in collaborating with someone who had major leverage in projects v. steady development in personal skillset training to check what was needed for longevity. 

for example, some of those projects required every founding team member or nothing would have gotten done, either due to a lack of intrinsic motivation, personal alignment, or inability to build. 

looking back, i wish i had explored what was possible first and fill in with skillsets that were necessary to continue on. while it was fun to explore sideways, it was not forwardly personally aligned, making it fragile long term.

• the first social mobile app i was a ux/ui designer on stopped as soon as the back end engineer graduated. i also realized i didn’t want to solely do ux/ui design.

• the art museum saas project kept no one’s interest. the founding team took higher paying full time jobs stopping that after the first pilot. while i learned skills in customer discovery, i realized i wanted to be in the accelerator space and not in the product space.

• the sustainable materials project was based on grant funding. as soon as the grant dried up, the lab stopped working on the project.

forward (ie. felt like accelerated flow): being authentic and honest with myself has gone a long way. these are little things that turned into bigger things. 

• hosting experiences for groups of people, usually over dinner. what started as a curiosity in undergrad as young people had unintentional ways of gathering, ended in an odd series of dinners. undergrads didn’t want to sit still for 2-3 hours for longer conversation. i also was learning how to cook and host, so we had some awkward initial gatherings. fast forward, the food got better, the groups of people did too, and the experiences are some of the richest moments of my last decade: cooking weekly for a group of people. 

• finding place to live where there’s belonging and growth. being close to my twin, having other ambitious people, and finding a city i feel personal belonging to has all felt like an important thing to figure out in my 20s. i travelled to 50+ cities across 15+ countries to see where i really wanted to be. first it was cambridge > ithaca, then it was sf > boston. those were each step gap improvements in quality of life, quality of growth, and places near and dear to me. pg has it right that each city has a currency. you want to make sure your personal currency (what you value) is also in the ether around you. note, it does not have to be city wide, could be what you activate + build too with where it makes sense for you. also, for many, it may be a different model, like a hub and spoke or more nomadic.

these last two points connect to discovering what is important for me: quality time with interesting people usually over a dinner and an environment i feel i can grow within.

these were not obvious insights at the start. they became more obvious over time because they stuck. i didn’t cook 1 week, 1 month, or 1 year of dinners. it’s been 10 years and 350+ dinners later.

one way to find things that stick is to get the reps in. the first 5-10 times may be intentional exploration. my challenge to you is scale that up to 100 reps to see if you actually care about that thing. that could be:

• getting to record your 100th podcast or write your 100th blog post

• spending 100hrs learning how to code

• meet 100 people to practice interesting conversations

in cal newport’s so good they can’t ignore you, he shares that “follow your passion,” can be abysmally vague advice because passions do not appear out of thin air. they take time to develop and usually are a consequence of getting the reps in and getting better.

t/y to zayn and sofi for reading drafts of this post and to barry for hosting the initial dinner bringing together such an insightful conversation across decades.

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^ if you have questions, post below in comments of DM me on linkedin. i write these to discuss ideas. these are starting points.