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He’s as 77 intelligent, hard-working, ambitious, and prescient as history’s most iconic 78 entrepreneurs—only without any interest in building a unicorn himself. Instead, 79 in his words, he works “Hollywood style”—in a series of creative projects. What 80 follows is a sampling of his life’s work. 81 82 Kelly was an editor for the Whole Earth Catalog in the early 1980s, helped 83 start WELL, one of the first online communities, in 1985, and co-founded WIRED 84 magazine in 1993. He’s written a dozen books and published hundreds of essays 85 on topics from art to optimism, travel, religion, creativity, and AI (even 86 before it was a thing). Kelly rode a bicycle across the United States in his 87 20s. He was Steven Spielberg’s ‘futurist advisor’ on Minority Report, and the 88 inspiration behind the famous “Death Clock” on Futurama, after the show’s 89 creator Matt Groening caught wind of the Life Countdown Clock Kelly keeps on 90 his computer desktop. He organizes tightly curated group walks across Asia and 91 Europe, regularly covering ~100km in a week. He sculpts, draws, paints, and 92 photographs. And he’s a longtime friend and collaborator of Stewart Brand 93 (whose famous line, “Stay hungry, stay foolish,” Steve Jobs quoted in his 94 iconic commencement address at Stanford). 95 96 To encourage long-term thinking, Kelly is helping build a clock into a mountain 97 in western Texas that will tick for 10,000 years. Brian Eno and Jeff Bezos are 98 active collaborators. He’s a born-again Christian. He’s been married to his 99 wife, Gia-Miin, for 38 years, and they have three children together. He was 100 pivotal to a fringe-turned-mainstream movement to identify and catalog every 101 living species on earth (now owned and operated by Smithsonian). He was early 102 to think and write about the quantified self, which gave rise to products like 103 Fitbit, Strava, Apple Watch, Eight Sleep, and the Oura Ring. Kelly’s idea of 104 “1,000 true fans” practically christened the creator economy with his 2008 105 insight that “if 1,000 people will pay you $100 per year, you can gross 106 $100k—more than enough to live on for most.” 107 108 The people who become legendary in their interests never feel they have 109 arrived. 110 111 Kevin Kelly 112 113 Naval Ravikant has called him a “modern-day Socrates,” Marc Andreessen has said 114 that “everything Kevin Kelly writes is worth reading,” Eno called him “one of 115 the most consistently provocative thinkers about technology and culture,” and 116 Ray Kurzweil said that “Kevin Kelly understands the direction of technology 117 better than almost anyone I know.” 118 119 Kelly’s Hollywood style of working has always resonated with me; it’s the way I 120 aspire to work and largely have since starting my career. Yet now, 15 years in, 121 I’ve become self-conscious about it. Working in Silicon Valley will convince 122 you that starting a company with its sights on unicorn status is the only 123 possible way to make an impact, and the only work worthy of an ambitious 124 individual. 125 126 Kelly is a cheerful and enterprising repudiation of that path, and I didn’t get 127 very long into my interview preparations to realize that I wasn’t only writing 128 about a personal hero; I was seeking a way to make peace with my own 129 professional choices. After a day together, I realized that my pilgrimage to 130 meet the man in his element might also grant permission to others in our line 131 of work who are interested in charting a different course to impact. 132 133 [009_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 134 [015_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 135 136 I started my career at Google selling AdWords to small businesses, and finished 137 my first quarter as the number three seller in North America. Professional 138 opportunities immediately unfolded—early nods for management, trips to global 139 offices to present my “best practices,” my face on slides next to impressive 140 metrics, and attention from more senior leaders. 141 142 It’s hard to say why none of that seemed very interesting, but it didn’t. What 143 I did like was starting a campaign to rename the conference rooms and helping 144 my coworker launch his internal content series, G-Chat with Charleton, in which 145 he would interview Google executives while sitting with them in a two-person 146 snuggie. I had earned myself a ticket to the fast career track at one of the 147 coolest companies in Silicon Valley, but climbing the corporate ladder just 148 wasn’t for me. 149 150 So I spent the next 10 years chasing what seemed most fun. After 14 months at 151 Google, my work bestie, Jenny, and I left Google together to give the startup 152 thing a try. We went to a mobile gaming company where I learned to make my way 153 around spreadsheets, play Magic: The Gathering, and cash in on a blockbuster 154 ‘pet hotel’ game. Eighteen months later, it was a six-person startup that was 155 known as “the black sheep of Y Combinator.” In my free time, I coached a JV 156 high school soccer team, volunteered at Dandelion Chocolate (all that working 157 on software made me want to make something with my hands), and finished writing 158 a novel. 159 160 My resume of under-two-year gigs spooked recruiters, except for one at Stripe. 161 “We’re impressed by how much ground you’ve covered,” was the backhanded 162 compliment I got. I started on the Account Management team in early 2015. 163 164 I spent nearly five years at Stripe, but the lily-padding continued—only this 165 time it was all under one roof. A year into my tenure, I was given the choice 166 between management or a nebulous role focusing on projects that would impact 167 company culture. Like evolving our tradition of work anniversary celebrations, 168 standing up company planning, establishing Stripe as a carbon-neutral company, 169 getting non-developers to participate in our annual hackathon, defining our 170 version of the “bar raiser” interview, and printing and distributing a book 171 (which eventually became Stripe Press). With very little pressing, I learned 172 this nebulous role had emerged from the growing pile of projects that the 173 former McKinsey consultants on the Business Operations team were avoiding. 174 175 Guess which role my friends and parents thought I should choose? Guess which 176 one I chose. 177 178 Kelly would say it’s good to have an “illegible” career path—it means 179 you’re onto interesting stuff. 180 181 I started to take pride in this “cool girl” approach to work. I joked about 182 having never been promoted, but could feel my scope, impact, and relationships 183 with colleagues growing. I remember rejecting a (well-meaning) manager’s 184 suggestion to build out a five-year career plan. I scoffed at people who cared 185 about titles, did things for money, and had professional headshots on their 186 LinkedIn. I mocked MBAs, bragged about “staying off the org chart,” and being 187 good at “giving away my LEGOs.” I became the person you asked to have a coffee 188 with when you wanted to quit your job and do something weird. Once I mentioned 189 “enjoying working in the wings,” and a (well-meaning) executive suggested I 190 “keep that to myself if I wanted to be seen as a leader.” I ignored the advice. 191 192 And then, I’m not sure when the switch flipped, but I started to have a sinking 193 feeling that I had it all wrong the whole time. I looked around and felt I was 194 being outpaced by my colleagues—specifically by the MBAs and the people who 195 chased titles, promotions, money, and building teams. And it wasn’t just a 196 vanity thing. They genuinely seemed to be focused on bigger, more interesting 197 problems. And they were having more impact. They were mentoring young talent, 198 influencing top lines and bottom lines, and had their fingerprints on all kinds 199 of cool industry-recognized work. They seemed to always have invitations to 200 exclusive gatherings and job offers in their inbox. Several started companies, 201 and rumor had it that some had term sheets before investors even opened their 202 decks. I didn’t only feel jealous of their work; I felt unqualified to do it. 203 That stung. 204 205 I started to reflect on my own trajectory with fear that it didn’t mirror my 206 ambition, work ethic, or deep care about the role of work in a life. Had I 207 pointed my ambition in the wrong direction? What did I have to show for all my 208 effort? Had I made some irreversible, unforced error with my career? How much 209 money had I left on the table? Would the people I respected respect me back for 210 much longer? Despite working my butt off for a decade, I had no expertise and 211 no line of sight into where I was going. I felt immature for placing such a 212 high value on “fun” and “bouncing around,” and full of regret about not picking 213 a lane (or even better, a ladder). It had become hard to explain what I was 214 good at—most importantly to myself. My sister had recently made partner at a 215 prestigious law firm, and it seemed easier for my parents to be proud of her 216 than of me. I couldn’t really blame them. 217 218 Kevin Kelly would say it’s good to have an “illegible” career path—it means 219 you’re onto interesting stuff. But I wasn’t so sure anymore. 220 221 [041_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 222 [047_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 223 224 I pull up to Kelly’s Pacifica, California studio—the last house at the very 225 edge of Vallemar off Route 1. It’s a big, barn-looking structure pressed up 226 against a steep hill, which is covered in wild flowers and towering trees. It 227 was overcast and smelled like the ocean and eucalyptus. The only way I knew I’d 228 come to the right place was the very small sign on the door that read “kk.org,” 229 on which I’ve spent dozens of hours over the years. 230 231 Stepping inside, I felt like I’d time-traveled back to the early 1990s and 232 entered my little brother’s dream bedroom. There were huge LEGO towers, K’nex 233 sculptures hanging from the ceiling, and a massive wall of books spanning two 234 floors. Most of the books were faded from use or sunlight, the dust jackets 235 bent, and they were all stacked and tilted in a way that suggested they’d 236 actually been read. There were knickknacks piled up everywhere, and even more 237 haphazardly tucked into bins or captured in jars. 238 239 It was hardly the image of a futurist’s office, and in sharp contrast to the 240 Japandi workspaces you see going viral on X. Yet despite the sheer amount of 241 stuff lying around in Kelly’s haven, nothing appeared like junk. Every object 242 seemed to vibrate with meaning, begging you to ask, “What’s this for?” or 243 “Where’d you get that?” 244 245 As I was scanning the lower rungs of the bookshelf, Kelly materialized on the 246 indoor balcony and invited me upstairs to talk. He was wearing socks that were 247 way too big—the spaces where his toes should have been were empty and flopped 248 around in front of him—and his pants were stained from actual paint (i.e., not 249 in the Rag & Bone way). 250 251 As I walked up the stairs, I asked him what the oldest object in the studio 252 was, but he immediately deflected. No interest in nostalgia from the futurist, 253 I guessed. 254 255 I slowed down as I walked by the second-floor wall of knickknacks and started 256 scanning. Kelly caught me doing so, pulled some leather doohickey about the 257 size of my hand off the shelf, and handed it to me. 258 259 “What do you think this is?” he asked. I twirled it around and desperately 260 wanted to answer correctly, but figured that wasn’t the point. Still, I fumbled 261 around nervously and couldn’t even eke out a guess. Probably sensing my 262 anxiety, Kelly jumped in. “It’s a leather cap for an eagle.” He got it in 263 Mongolia where there’s a tradition of using eagles to hunt, he explained. Now 264 things were feeling looser. I got the feeling I could pull this thread about 265 the Mongolian eagles or get another story. Kelly made my decision for me when 266 he directed my attention to a small jar containing a little creature’s bones. 267 “This is from a bird that flew into that window,” he said, pointing to a window 268 over his desk. I nodded along with enthusiasm. “I freeze-dried them!” he said 269 proudly. 270 271 We strolled over to his desk, where he asked me to try to lift a small but 272 dense ball that was sitting on the floor next to it. I could barely get it 273 above my ankle. Kelly told me it was made out of tungsten. “It has a similar 274 density to gold,” he continued. “Now every time you see a criminal in the 275 movies running away with a bag of tungsten, you’ll know how unrealistic it is.” 276 277 Greatness is overrated. It’s a form of extremism, and it comes with extreme 278 vices that I have no interest in. 279 280 Kevin Kelly 281 282 It was so much fun connecting with Kelly over these random little objects—I 283 felt I was learning something about him I couldn’t through his books and blog 284 posts; like I was getting to the real spirit he brings to his life and work. 285 But before I could think too much, we were onto the next. 286 287 There was a train track running along the wall, just below the ceiling, and I 288 asked if it worked. I half-expected him to yell, “Alexa, start your engines!” 289 Instead, Kelly walked over to his desk and picked up a controller and turned it 290 on. Nothing happened. He replaced the batteries, gave the controller a smack 291 like it was a Nintendo 64 cartridge, and tried again. The train, looking like 292 something my dad might have built at the model shop down the street in the 60s, 293 immediately started choo-chooing around the room. Kelly stood and smiled 294 proudly again as he watched it go. Eventually we took our seats next to his 295 desk to talk. 296 297 I started off by asking him whether there is a unifying theme to his seemingly 298 diffuse life’s work, which has included old-school magazines and books, 299 bleeding-edge technology, conservationism, photographing Asia, and teaching. 300 “Following my interests,” he said simply. 301 302 It sounded awfully cutesy for someone so accomplished. I said that there is an 303 idiosyncratic magic to the way he follows his interests, which is that they’re 304 not just an input; Kelly turns his interests into an output that he can share 305 with others. When I asked if I was onto something, I learned that Kelly doesn’t 306 think in outputs. For him, doing is part of learning. “I don’t really pursue a 307 destination,” he said. “I pursue a direction.” 308 309 I asked him the difference between “following your interests” and being 310 scatterbrained or having shiny object syndrome, like I sometimes worry I do. 311 “The people who become legendary in their interests never feel they have 312 arrived,” he said. When he talked about the power of passion and obsession in 313 that process, I asked him if passion is enough. “Enough for what?” he asked, 314 somewhat rhetorically. He had an impression of what I meant. “I think one of 315 the least interesting reasons to be interested in something is money,” he said, 316 and cited Walt Disney. “We don’t make movies to make money. We make money to 317 make more movies.” 318 319 Money isn’t actually what I meant, but I appreciated that he took the 320 conversation there. I let the silence hang for a minute before he continued. 321 “What I’m talking about is taking your interests seriously enough to have the 322 courage to stay moving. You can give stuff away. You can abandon things. You 323 can tolerate failure because you know that tomorrow there is more.” 324 325 I asked Kelly about the tradeoffs of focusing on a single thing if you want to 326 be great (which is what I had been getting at before). “Greatness is 327 overrated,” he said, and I perked up. “It’s a form of extremism, and it comes 328 with extreme vices that I have no interest in. Steve Jobs was a jerk. Bob Dylan 329 is a jerk.” 330 331 The way Kelly approaches work differently was starting to come into focus. 332 333 [051_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 334 [011_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 335 336 Accounts of people pursuing their life’s work often include phrases like 337 “maniacal focus” or “relentless pursuit.” I hear investors say they’re looking 338 for founders with “a chip on their shoulder.” Facebook’s iconic “Little Red 339 Book” from 2012, which still serves as a pillar for peak tech culture, features 340 a full-page spread that says “Greatness and comfort rarely coexist.” 341 342 A recent xeet from Reid Hoffman reads, “If a founder brags about having ‘a 343 balanced life,’ I assume they’re not serious about winning.” Jensen Huang says 344 he wants to “torture people into greatness.” When I was on the job hunt many 345 years ago, an investor was pitching one of his portfolio companies by saying, 346 with a wink, that the founder would do “whatever it takes to win.” I genuinely 347 didn’t know what he meant by that, but it sent a shudder down my spine. Once I 348 heard a serial founder say he started his second company “out of chaos and 349 revenge.” I heard about another prominent CEO that looks in the mirror every 350 morning and asks himself, “Why do you suck so much?” I read a biography of Elon 351 Musk; he seems tortured. There’s some rumor floating around about how Sam 352 Altman was so focused on building his first startup that he only ate ramen and 353 got scurvy. [96]According to Altman, “I never got tested but I think (I had 354 it). I had extreme lethargy, sore legs, and bleeding gums.” 355 356 Compared to this, Kelly’s version of doing his life’s work seems so joyful, so 357 buoyant. So much less … angsty. There’s no suffering or ego. It’s not about 358 finding a hole in the market or a path to global domination. The yard stick 359 isn’t based on net worth or shareholder value or number of users or employees. 360 It’s based on an internal satisfaction meter, but not in a self-indulgent way. 361 He certainly seeks resonance and wants to make an impact, but more in the way 362 of a teacher. He breathes life into products or ideas, not out of a desire to 363 win, but out of a desire to advance our collective thinking or action. His work 364 and its impact unfold slowly, rather than by sheer force of will. Ideas or 365 projects seem to tug at him, rather than reveal themselves on the other end of 366 an internal cattle prod. His range is wide, but all his work somehow rhymes. It 367 clearly comes very naturally for him to work this way, but it’s certainly not 368 the norm. 369 370 If this is a way of living and working that’s available to all of us, why do we 371 fetishize the white-knuckling and pain? 372 373 I know I’m not the first person to have the brilliant idea that we can do 374 better work when we like it. I know that the whole “find your passion” movement 375 fell flat in its naivete. But I think somewhere along the way, the message 376 about what it feels like to be great has become a bit perverted. 377 378 A few years ago, I forced myself to try and write down a professional goal. 379 After several hours of forced meditation on the topic, all I could muster was 380 “have a good day, most days.” And don’t get me wrong, by “good day” I don’t 381 mean sitting by a pool drinking an Aperol Spritz. I feel alive when I launch 382 something exciting, close a big deal, or build an elegant model. I enjoy the 383 feeling of caring so much about something that it wakes me up in the middle of 384 the night (it happened multiple times writing this piece). And yet, I imagined 385 sharing my ambition to “have a good day, most days” in a job interview—and 386 decided to keep it to myself, because it probably doesn’t speak well of me. 387 388 But there I was, in front of a personal hero, whose most striking quality is 389 that he seems to be having a nice day, most days. Why can’t we work and enjoy 390 it? And I don’t mean in the masochistic sense. 391 392 I thought I was here to go deep on working Hollywood style, but as I sat there 393 with Kelly in a room of what are best described as his toys, I realized that 394 the most interesting thing about him is that he seems happy. At ease in the 395 world and in his skin. I wasn’t there with Kelly for permission to work 396 Hollywood style. I was there for permission to work with both ambition and joy. 397 398 If this is a way of living and working that’s available to all of us, why 399 do we fetishize the white-knuckling and pain? 400 401 This shouldn’t make us defensive or self-conscious, but it does. I, like many 402 others, want to be great. I want to feel commitment and camaraderie and work 403 hard and be my best and impact top and bottom lines. But I don’t want to also 404 feel tormented or be tortured into greatness or look in the mirror and wonder 405 why I suck. But what does that say about me? 406 407 I want more role models like Kevin Kelly. People that proudly whistle while 408 they work. Who have boundless energy and healthy gums. Whose enthusiasm is 409 contagious. Who are well-adjusted and emotionally regulated. Who have solid 410 relationships and happy families. Who are hungry and impactful and care deeply, 411 without being jerks. And I want more people to talk about these qualities with 412 respect and reverence. 413 414 I have never been a billionaire or built a unicorn, so I can’t speak with any 415 conviction about what it requires. I won’t be eulogized anywhere important and 416 no one 300 years from now will talk about what great things I did. But I want 417 to live in a world where you can have an impact and be happy. Maybe that’s 418 naive, but I’m sticking to it. 419 420 All of this occurs naturally to Kelly, and he doesn’t have complicated feelings 421 about it. I’m hoping to get there myself by channeling him more. “The more you 422 pursue interests,” he told me on the good day we spent together, “the more you 423 realize that the well is bottomless.” 424 425 [003_KevinKelly041725_Colossus_photobyAndriaLo-scaled] 426 427 Brie Wolfson is the chief marketing officer of Colossus and Positive Sum. 428 429 Back to top 430 431 Subscribe to Colossus 432 433 Colossus is the premier publication for definitive accounts of investors, 434 founders, companies, and the people & ideas that inspire them. 435 436 Subscription includes immediate access to our private audio feed and the print 437 edition delivered to your door at the end of each quarter. 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