{"id":1345,"date":"2025-08-25T21:28:06","date_gmt":"2025-08-25T13:28:06","guid":{"rendered":"http:\/\/jointings.org\/eng\/?p=1345"},"modified":"2025-08-25T22:03:12","modified_gmt":"2025-08-25T14:03:12","slug":"flounder-mode%ef%bd%9ckevin-kelly-on-a-different-way-to-do-great-work","status":"publish","type":"post","link":"https:\/\/jointings.org\/eng\/archives\/1345","title":{"rendered":"Flounder Mode\uff5cKevin Kelly on a different way to do great work"},"content":{"rendered":"

Columnists<\/a>>\u00a0About Education<\/a><\/span><\/p>\n

By Brie Wolfson\uff0cColossus<\/a>\uff0cJune 2025<\/p>\n

\"\"<\/p>\n

Kevin Kelly isn\u2019t known for one \u201cbig thing,\u201d and doesn\u2019t aspire to be. He\u2019s as intelligent, hard-working, ambitious, and prescient as history\u2019s most iconic entrepreneurs\u2014only without any interest in building a unicorn himself. Instead, in his words, he works \u201cHollywood style\u201d\u2014in a series of creative projects. What follows is a sampling of his life\u2019s work.<\/p>\n

Kelly was an editor for the Whole Earth Catalog in the early 1980s, helped start WELL, one of the first online communities, in 1985, and co-founded WIRED magazine in 1993. He\u2019s written a dozen books and published hundreds of essays on topics from art to optimism, travel, religion, creativity, and AI (even before it was a thing). Kelly rode a bicycle across the United States in his 20s. He was Steven Spielberg\u2019s \u2018futurist advisor\u2019 on Minority Report, and the inspiration behind the famous \u201cDeath Clock\u201d on Futurama, after the show\u2019s creator Matt Groening caught wind of the Life Countdown Clock Kelly keeps on his computer desktop. He organizes tightly curated group walks across Asia and Europe, regularly covering ~100km in a week. He sculpts, draws, paints, and photographs. And he\u2019s a longtime friend and collaborator of Stewart Brand (whose famous line, \u201cStay hungry, stay foolish,\u201d Steve Jobs quoted in his iconic commencement address at Stanford).<\/p>\n

To encourage long-term thinking, Kelly is helping build a clock into a mountain in western Texas that will tick for 10,000 years. Brian Eno and Jeff Bezos are active collaborators. He\u2019s a born-again Christian. He\u2019s been married to his wife, Gia-Miin, for 38 years, and they have three children together. He was pivotal to a fringe-turned-mainstream movement to identify and catalog every living species on earth (now owned and operated by Smithsonian). He was early to think and write about the quantified self, which gave rise to products like Fitbit, Strava, Apple Watch, Eight Sleep, and the Oura Ring. Kelly\u2019s idea of \u201c1,000 true fans\u201d practically christened the creator economy with his 2008 insight that \u201cif 1,000 people will pay you $100 per year, you can gross $100k\u2014more than enough to live on for most.\u201d<\/p>\n

\u201c The people who become legendary in their interests never feel they have arrived.\u201d<\/span><\/h3>\n

Kevin Kelly<\/span><\/h3>\n

Naval Ravikant has called him a \u201cmodern-day Socrates,\u201d Marc Andreessen has said that \u201ceverything Kevin Kelly writes is worth reading,\u201d Eno called him \u201cone of the most consistently provocative thinkers about technology and culture,\u201d and Ray Kurzweil said that \u201cKevin Kelly understands the direction of technology better than almost anyone I know.\u201d<\/p>\n

Kelly\u2019s Hollywood style of working has always resonated with me; it\u2019s the way I aspire to work and largely have since starting my career. Yet now, 15 years in, I\u2019ve become self-conscious about it. Working in Silicon Valley will convince you that starting a company with its sights on unicorn status is the only possible way to make an impact, and the only work worthy of an ambitious individual.<\/p>\n

Kelly is a cheerful and enterprising repudiation of that path, and I didn\u2019t get very long into my interview preparations to realize that I wasn\u2019t only writing about a personal hero; I was seeking a way to make peace with my own professional choices. After a day together, I realized that my pilgrimage to meet the man in his element might also grant permission to others in our line of work who are interested in charting a different course to impact.<\/p>\n

I started my career at Google selling AdWords to small businesses, and finished my first quarter as the number three seller in North America. Professional opportunities immediately unfolded\u2014early nods for management, trips to global offices to present my \u201cbest practices,\u201d my face on slides next to impressive metrics, and attention from more senior leaders.<\/p>\n

It\u2019s hard to say why none of that seemed very interesting, but it didn\u2019t. What I did like was starting a campaign to rename the conference rooms and helping my coworker launch his internal content series, G-Chat with Charleton, in which he would interview Google executives while sitting with them in a two-person snuggie. I had earned myself a ticket to the fast career track at one of the coolest companies in Silicon Valley, but climbing the corporate ladder just wasn\u2019t for me.<\/p>\n

So I spent the next 10 years chasing what seemed most fun. After 14 months at Google, my work bestie, Jenny, and I left Google together to give the startup thing a try. We went to a mobile gaming company where I learned to make my way around spreadsheets, play Magic: The Gathering, and cash in on a blockbuster \u2018pet hotel\u2019 game. Eighteen months later, it was a six-person startup that was known as \u201cthe black sheep of Y Combinator.\u201d In my free time, I coached a JV high school soccer team, volunteered at Dandelion Chocolate (all that working on software made me want to make something with my hands), and finished writing a novel.<\/p>\n

My resume of under-two-year gigs spooked recruiters, except for one at Stripe. \u201cWe\u2019re impressed by how much ground you\u2019ve covered,\u201d was the backhanded compliment I got. I started on the Account Management team in early 2015.<\/p>\n

I spent nearly five years at Stripe, but the lily-padding continued\u2014only this time it was all under one roof. A year into my tenure, I was given the choice between management or a nebulous role focusing on projects that would impact company culture. Like evolving our tradition of work anniversary celebrations, standing up company planning, establishing Stripe as a carbon-neutral company, getting non-developers to participate in our annual hackathon, defining our version of the \u201cbar raiser\u201d interview, and printing and distributing a book (which eventually became Stripe Press). With very little pressing, I learned this nebulous role had emerged from the growing pile of projects that the former McKinsey consultants on the Business Operations team were avoiding.<\/p>\n

Guess which role my friends and parents thought I should choose? Guess which one I chose.<\/p>\n

Kelly would say it\u2019s good to have an \u201cillegible\u201d career path\u2014it means you\u2019re onto interesting stuff.<\/span><\/h3>\n

I started to take pride in this \u201ccool girl\u201d approach to work. I joked about having never been promoted, but could feel my scope, impact, and relationships with colleagues growing. I remember rejecting a (well-meaning) manager\u2019s suggestion to build out a five-year career plan. I scoffed at people who cared about titles, did things for money, and had professional headshots on their LinkedIn. I mocked MBAs, bragged about \u201cstaying off the org chart,\u201d and being good at \u201cgiving away my LEGOs.\u201d I became the person you asked to have a coffee with when you wanted to quit your job and do something weird. Once I mentioned \u201cenjoying working in the wings,\u201d and a (well-meaning) executive suggested I \u201ckeep that to myself if I wanted to be seen as a leader.\u201d I ignored the advice.<\/p>\n

And then, I\u2019m not sure when the switch flipped, but I started to have a sinking feeling that I had it all wrong the whole time. I looked around and felt I was being outpaced by my colleagues\u2014specifically by the MBAs and the people who chased titles, promotions, money, and building teams. And it wasn\u2019t just a vanity thing. They genuinely seemed to be focused on bigger, more interesting problems. And they were having more impact. They were mentoring young talent, influencing top lines and bottom lines, and had their fingerprints on all kinds of cool industry-recognized work. They seemed to always have invitations to exclusive gatherings and job offers in their inbox. Several started companies, and rumor had it that some had term sheets before investors even opened their decks. I didn\u2019t only feel jealous of their work; I felt unqualified to do it. That stung.<\/p>\n

I started to reflect on my own trajectory with fear that it didn\u2019t mirror my ambition, work ethic, or deep care about the role of work in a life. Had I pointed my ambition in the wrong direction? What did I have to show for all my effort? Had I made some irreversible, unforced error with my career? How much money had I left on the table? Would the people I respected respect me back for much longer? Despite working my butt off for a decade, I had no expertise and no line of sight into where I was going. I felt immature for placing such a high value on \u201cfun\u201d and \u201cbouncing around,\u201d and full of regret about not picking a lane (or even better, a ladder). It had become hard to explain what I was good at\u2014most importantly to myself. My sister had recently made partner at a prestigious law firm, and it seemed easier for my parents to be proud of her than of me. I couldn\u2019t really blame them.<\/p>\n

Kevin Kelly would say it\u2019s good to have an \u201cillegible\u201d career path\u2014it means you\u2019re onto interesting stuff. But I wasn\u2019t so sure anymore.<\/p>\n

I pull up to Kelly\u2019s Pacifica, California studio\u2014the last house at the very edge of Vallemar off Route 1. It\u2019s a big, barn-looking structure pressed up against a steep hill, which is covered in wild flowers and towering trees. It was overcast and smelled like the ocean and eucalyptus. The only way I knew I\u2019d come to the right place was the very small sign on the door that read \u201ckk.org,\u201d on which I\u2019ve spent dozens of hours over the years.<\/p>\n

Stepping inside, I felt like I\u2019d time-traveled back to the early 1990s and entered my little brother\u2019s dream bedroom. There were huge LEGO towers, K\u2019nex sculptures hanging from the ceiling, and a massive wall of books spanning two floors. Most of the books were faded from use or sunlight, the dust jackets bent, and they were all stacked and tilted in a way that suggested they\u2019d actually been read. There were knickknacks piled up everywhere, and even more haphazardly tucked into bins or captured in jars.<\/p>\n

It was hardly the image of a futurist\u2019s office, and in sharp contrast to the Japandi workspaces you see going viral on X. Yet despite the sheer amount of stuff lying around in Kelly\u2019s haven, nothing appeared like junk. Every object seemed to vibrate with meaning, begging you to ask, \u201cWhat\u2019s this for?\u201d or \u201cWhere\u2019d you get that?\u201d<\/p>\n

As I was scanning the lower rungs of the bookshelf, Kelly materialized on the indoor balcony and invited me upstairs to talk. He was wearing socks that were way too big\u2014the spaces where his toes should have been were empty and flopped around in front of him\u2014and his pants were stained from actual paint (i.e., not in the Rag & Bone way).<\/p>\n

As I walked up the stairs, I asked him what the oldest object in the studio was, but he immediately deflected. No interest in nostalgia from the futurist, I guessed.<\/p>\n

I slowed down as I walked by the second-floor wall of knickknacks and started scanning. Kelly caught me doing so, pulled some leather doohickey about the size of my hand off the shelf, and handed it to me.<\/p>\n

\u201cWhat do you think this is?\u201d he asked. I twirled it around and desperately wanted to answer correctly, but figured that wasn\u2019t the point. Still, I fumbled around nervously and couldn\u2019t even eke out a guess. Probably sensing my anxiety, Kelly jumped in. \u201cIt\u2019s a leather cap for an eagle.\u201d He got it in Mongolia where there\u2019s a tradition of using eagles to hunt, he explained. Now things were feeling looser. I got the feeling I could pull this thread about the Mongolian eagles or get another story. Kelly made my decision for me when he directed my attention to a small jar containing a little creature\u2019s bones. \u201cThis is from a bird that flew into that window,\u201d he said, pointing to a window over his desk. I nodded along with enthusiasm. \u201cI freeze-dried them!\u201d he said proudly.<\/p>\n

We strolled over to his desk, where he asked me to try to lift a small but dense ball that was sitting on the floor next to it. I could barely get it above my ankle. Kelly told me it was made out of tungsten. \u201cIt has a similar density to gold,\u201d he continued. \u201cNow every time you see a criminal in the movies running away with a bag of tungsten, you\u2019ll know how unrealistic it is.\u201d<\/p>\n

\u201cGreatness is overrated. It\u2019s a form of extremism, and it comes with extreme vices that I have no interest in.\u201d<\/span><\/h3>\n

Kevin Kelly<\/span><\/h3>\n

It was so much fun connecting with Kelly over these random little objects\u2014I felt I was learning something about him I couldn\u2019t through his books and blog posts; like I was getting to the real spirit he brings to his life and work. But before I could think too much, we were onto the next.<\/p>\n

There was a train track running along the wall, just below the ceiling, and I asked if it worked. I half-expected him to yell, \u201cAlexa, start your engines!\u201d Instead, Kelly walked over to his desk and picked up a controller and turned it on. Nothing happened. He replaced the batteries, gave the controller a smack like it was a Nintendo 64 cartridge, and tried again. The train, looking like something my dad might have built at the model shop down the street in the 60s, immediately started choo-chooing around the room. Kelly stood and smiled proudly again as he watched it go. Eventually we took our seats next to his desk to talk.<\/p>\n

I started off by asking him whether there is a unifying theme to his seemingly diffuse life\u2019s work, which has included old-school magazines and books, bleeding-edge technology, conservationism, photographing Asia, and teaching. \u201cFollowing my interests,\u201d he said simply.<\/p>\n

It sounded awfully cutesy for someone so accomplished. I said that there is an idiosyncratic magic to the way he follows his interests, which is that they\u2019re not just an input; Kelly turns his interests into an output that he can share with others. When I asked if I was onto something, I learned that Kelly doesn\u2019t think in outputs. For him, doing is part of learning. \u201cI don\u2019t really pursue a destination,\u201d he said. \u201cI pursue a direction.\u201d<\/p>\n

I asked him the difference between \u201cfollowing your interests\u201d and being scatterbrained or having shiny object syndrome, like I sometimes worry I do. \u201cThe people who become legendary in their interests never feel they have arrived,\u201d he said. When he talked about the power of passion and obsession in that process, I asked him if passion is enough. \u201cEnough for what?\u201d he asked, somewhat rhetorically. He had an impression of what I meant. \u201cI think one of the least interesting reasons to be interested in something is money,\u201d he said, and cited Walt Disney. \u201cWe don\u2019t make movies to make money. We make money to make more movies.\u201d<\/p>\n

Money isn\u2019t actually what I meant, but I appreciated that he took the conversation there. I let the silence hang for a minute before he continued. \u201cWhat I\u2019m talking about is taking your interests seriously enough to have the courage to stay moving. You can give stuff away. You can abandon things. You can tolerate failure because you know that tomorrow there is more.\u201d<\/p>\n

I asked Kelly about the tradeoffs of focusing on a single thing if you want to be great (which is what I had been getting at before). \u201cGreatness is overrated,\u201d he said, and I perked up. \u201cIt\u2019s a form of extremism, and it comes with extreme vices that I have no interest in. Steve Jobs was a jerk. Bob Dylan is a jerk.\u201d<\/p>\n

The way Kelly approaches work differently was starting to come into focus.<\/p>\n

Accounts of people pursuing their life\u2019s work often include phrases like \u201cmaniacal focus\u201d or \u201crelentless pursuit.\u201d I hear investors say they\u2019re looking for founders with \u201ca chip on their shoulder.\u201d Facebook\u2019s iconic \u201cLittle Red Book\u201d from 2012, which still serves as a pillar for peak tech culture, features a full-page spread that says \u201cGreatness and comfort rarely coexist.\u201d<\/p>\n

A recent xeet from Reid Hoffman reads, \u201cIf a founder brags about having \u2018a balanced life,\u2019 I assume they\u2019re not serious about winning.\u201d Jensen Huang says he wants to \u201ctorture people into greatness.\u201d When I was on the job hunt many years ago, an investor was pitching one of his portfolio companies by saying, with a wink, that the founder would do \u201cwhatever it takes to win.\u201d I genuinely didn\u2019t know what he meant by that, but it sent a shudder down my spine. Once I heard a serial founder say he started his second company \u201cout of chaos and revenge.\u201d I heard about another prominent CEO that looks in the mirror every morning and asks himself, \u201cWhy do you suck so much?\u201d I read a biography of Elon Musk; he seems tortured. There\u2019s some rumor floating around about how Sam Altman was so focused on building his first startup that he only ate ramen and got scurvy. According to Altman, \u201cI never got tested but I think (I had it). I had extreme lethargy, sore legs, and bleeding gums.\u201d<\/p>\n

Compared to this, Kelly\u2019s version of doing his life\u2019s work seems so joyful, so buoyant. So much less \u2026 angsty. There\u2019s no suffering or ego. It\u2019s not about finding a hole in the market or a path to global domination. The yard stick isn\u2019t based on net worth or shareholder value or number of users or employees. It\u2019s based on an internal satisfaction meter, but not in a self-indulgent way. He certainly seeks resonance and wants to make an impact, but more in the way of a teacher. He breathes life into products or ideas, not out of a desire to win, but out of a desire to advance our collective thinking or action. His work and its impact unfold slowly, rather than by sheer force of will. Ideas or projects seem to tug at him, rather than reveal themselves on the other end of an internal cattle prod. His range is wide, but all his work somehow rhymes. It clearly comes very naturally for him to work this way, but it\u2019s certainly not the norm.<\/p>\n

If this is a way of living and working that\u2019s available to all of us, why do we fetishize the white-knuckling and pain?<\/span><\/h3>\n

I know I\u2019m not the first person to have the brilliant idea that we can do better work when we like it. I know that the whole \u201cfind your passion\u201d movement fell flat in its naivete. But I think somewhere along the way, the message about what it feels like to be great has become a bit perverted.<\/p>\n

A few years ago, I forced myself to try and write down a professional goal. After several hours of forced meditation on the topic, all I could muster was \u201chave a good day, most days.\u201d And don\u2019t get me wrong, by \u201cgood day\u201d I don\u2019t mean sitting by a pool drinking an Aperol Spritz. I feel alive when I launch something exciting, close a big deal, or build an elegant model. I enjoy the feeling of caring so much about something that it wakes me up in the middle of the night (it happened multiple times writing this piece). And yet, I imagined sharing my ambition to \u201chave a good day, most days\u201d in a job interview\u2014and decided to keep it to myself, because it probably doesn\u2019t speak well of me.<\/p>\n

But there I was, in front of a personal hero, whose most striking quality is that he seems to be having a nice day, most days. Why can\u2019t we work and enjoy it? And I don\u2019t mean in the masochistic sense.<\/p>\n

I thought I was here to go deep on working Hollywood style, but as I sat there with Kelly in a room of what are best described as his toys, I realized that the most interesting thing about him is that he seems happy. At ease in the world and in his skin. I wasn\u2019t there with Kelly for permission to work Hollywood style. I was there for permission to work with both ambition and joy.<\/p>\n

If this is a way of living and working that\u2019s available to all of us, why do we fetishize the white-knuckling and pain?<\/p>\n

This shouldn\u2019t make us defensive or self-conscious, but it does. I, like many others, want to be great. I want to feel commitment and camaraderie and work hard and be my best and impact top and bottom lines. But I don\u2019t want to also feel tormented or be tortured into greatness or look in the mirror and wonder why I suck. But what does that say about me?<\/p>\n

I want more role models like Kevin Kelly. People that proudly whistle while they work. Who have boundless energy and healthy gums. Whose enthusiasm is contagious. Who are well-adjusted and emotionally regulated. Who have solid relationships and happy families. Who are hungry and impactful and care deeply, without being jerks. And I want more people to talk about these qualities with respect and reverence.<\/p>\n

I have never been a billionaire or built a unicorn, so I can\u2019t speak with any conviction about what it requires. I won\u2019t be eulogized anywhere important and no one 300 years from now will talk about what great things I did. But I want to live in a world where you can have an impact and be happy. Maybe that\u2019s naive, but I\u2019m sticking to it.<\/p>\n

All of this occurs naturally to Kelly, and he doesn\u2019t have complicated feelings about it. I\u2019m hoping to get there myself by channeling him more. \u201cThe more you pursue interests,\u201d he told me on the good day we spent together, \u201cthe more you realize that the well is bottomless.\u201d<\/p>\n

Brie Wolfson <\/strong>is the chief marketing officer of Colossus and Positive Sum.<\/span><\/address>\n
<\/address>\n
\u4e2d\u6587\u8bd1\u6587<\/a><\/span><\/address>\n

<\/a><\/span>Edited by Jas<\/span><\/em><\/p>\n

\n

Related:<\/h3>\n

Kevin Kelly<\/a><\/h3>\n

Kevin Kelly\u2019s TED Talks<\/a><\/h3>\n<\/address>\n","protected":false},"excerpt":{"rendered":"

Columnists>\u00a0About Education By Brie Wolfson\uff0cColossus\uff0cJune 2025 Kevin Kelly isn\u2019t known for one \u201cbig thing,\u201d and doesn\u2019t aspire to be. He\u2019s as intelligent, hard-working, ambitious, and prescient as history\u2019s most iconic entrepreneurs\u2014only without any interest in building a unicorn himself. Instead, in his words, he works \u201cHollywood style\u201d\u2014in a series of creative projects. What follows is […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[31,8],"tags":[],"class_list":["post-1345","post","type-post","status-publish","format-standard","hentry","category-education-and-development","category-insight"],"_links":{"self":[{"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/posts\/1345","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/comments?post=1345"}],"version-history":[{"count":3,"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/posts\/1345\/revisions"}],"predecessor-version":[{"id":1347,"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/posts\/1345\/revisions\/1347"}],"wp:attachment":[{"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/media?parent=1345"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/categories?post=1345"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/jointings.org\/eng\/wp-json\/wp\/v2\/tags?post=1345"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}