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Transcript March 16, 2026 · 10:00 PM

Featured Session: Actionable Ikigai: Career Planning in the age of AI

Mike presents a career framework called 'Actionable Ikigai' for navigating work in the age of AI. He argues that modern workers feel small (social media comparison), slow (wealth inequality), and threatened (AI automation). The solution is refusing to compare yourself to others and instead aligning passion, prowess, purpose, and profit - ideally with AI tools helping rather than replacing you.

ikigai career planning ai impact social media comparison wealth inequality purpose passion vs profit venture capital technology consulting entrepreneurship
Key Takeaways
  1. 1Comparison is the thief of joy - the only fair competition is against your prior self, not imagined rivals amplified by social media.
  2. 2Modern professionals feel small (Dunbar's number overload), slow (economic redshift), and threatened (AI) - but these are perceptual traps, not destiny.
  3. 3Actionable Ikigai means deliberately aligning what you love, what you're good at, what the world needs, and what pays - ideally using AI as a tool to accelerate this alignment.
  4. 4Career paths are non-linear and filled with survivorship bias - the LinkedIn version omits failures, pivots, and health challenges that shape real trajectories.
  5. 5Use AI tools like the speaker's 'Actionable Ikigai' tool to explore career waypoints rather than fighting against technological change.
Full Transcript

The speaker opens by recalling Isaac Asimov's "Nightfall" - a story about people on a planet with six suns who've never known darkness. When they experience their first eclipse and see 30,000 stars, they go insane from realizing the vastness of the universe and their insignificance. This mirrors our modern condition in the age of information and AI.

In 1992, the speaker interpreted this as theology critique, like Galileo challenging geocentrism. The Catholic Church only apologized for Galileo's house arrest in 1992, 400 years later. But rereading it now, the story seems like a warning about the information age and social media.

In 1995, getting online meant hearing "You've got mail" and explaining the internet to mom as "a digital Gilligan's Island" - people with no business being in each other's business, suddenly connected. For the first ten years, it was glorious - unlimited collisions of unusual suspects.

Then social media changed everything. Anthropologist Robin Dunbar showed our hardware hasn't evolved - we're running the same biological firmware as 10,000 years ago. A Neolithic human had the same capacity for relationships: five intimate friends, 50 close friends, 150 meaningful connections maximum.

Social media blew up the denominator of loose connections. Suddenly Bob's in Mensa, Ted bought a Porsche, Frank's working out, Jane went vegan, Tony's into philanthropy. Our primate brain can't handle all those stars in the sky, so we conflate individual highlight reels into a single imagined nemesis better than us in every way. We feel small.

We also feel slow. Edwin Hubble discovered the universe is expanding and accelerating - the farther the star, the faster it's moving away. Economist Dalton Conley showed wealth works the same way. The rich accelerate faster thanks to compound interest, exclusive opportunities, and favorable tax rates - like Mario Kart leaders getting triple mushroom boosts instead of blue shells.

Philosopher Alain de Botton noted that the more you have, the worse you feel - because your reference group scales up. Making $40k, you're down $40k compared to friends. Making $200k, you're down $200k. Making $5 million, you know someone making $25 million. Economic redshift makes us feel perpetually behind.

The third horseman is AI. In a world of intelligent machines, it feels like an unfair race - we're competing against Joneses with jet packs while robots chase us down. The only winning move in this rigged game is not to play. You will never be a Jones, only Joneses can be Joneses, and even they aren't what they seem.

Teddy Roosevelt said "Comparison is the thief of joy." Moses warned against coveting in the tenth commandment. Buddha warned of the comparing mind that detaches you from enlightenment. The only fair comparison is to your prior self - am I better than yesterday?

The speaker shares his career story. In 1997, he had five majors (government, anthropology, economics, philosophy) but zero neckties and no clear path. A friend got hired by a consulting firm looking for "a certain kind of mind" not a certain major. The speaker positioned himself as a "smooth geek" - founder of a campus ska band about Commodore 64 computers who also learned accordion.

He joined Accenture in 1998 as a business doctor. The LinkedIn version: 12 years and 12 patents, became first global innovation director, CTO at a major education nonprofit, co-founded a venture capital firm, chief futurist at Deloitte, now adjunct professor and keynote speaker. But that version is engineered for survivorship bias and confirmation bias - it's not false, but not quite true either.

The real story: he cried the night before starting work, feeling like "a leaf blowing in somebody else's wind," crushed that his rainbow self would be reduced to "process analyst." After a year paying bills, he found Accenture Technology Labs - more fun, but less traditional career trajectory. He chose passion over profit initially.

His boss gave him "Learn Java in 21 Days" and said "you have 10." He learned enough, worked hard for 10 years, then got promoted to manage all the geeks. But he'd hit the Peter Principle - promoted exactly one level beyond competence. He was making money but not loving it or excelling at budget management.

A nonprofit he'd done pro bono work for asked him to be their CTO. He took the job, sat next to the future governor of Illinois on day one, and felt like he'd arrived. Then the next year and a half was just migrating legacy Windows systems - not the inspiring work with at-risk youth he'd imagined.

Two board members invited him to co-found a venture capital firm. Like Ghostbusters' "if somebody asks if you're a god, you say yes," he agreed despite knowing nothing about finance or VC. For a couple years it worked, then he realized understanding technology isn't the same as understanding business strategy. The firm fell apart during economic downturn.

Suddenly he was collecting $500/week unemployment after thinking he had it figured out. But it was an important reset - a chance to focus on teaching, which he loved. Through guest lectures, he became a part-time adjunct professor, which led to Deloitte. A senior leader wanted him for healthcare insurance work; he said "that's not what I do." The response: "sounds like you'd like to make less money."

They introduced him to emerging tech instead. He proposed calling himself "chief futurist" - they thought he was nuts but the world loved it. It was glorious, scratching the purpose itch of teaching while firing on all other cylinders. Best job ever - though he became Deloitte's most frequent flyer at 133 flights per year.

Then he was diagnosed with multiple sclerosis. He could burn brightly for 45 minutes but not all day, every day, 365 days a year. At SXSW two years ago, he met future agents who showed he could do more of what he loved, less of what depleted him, and earn as well or better. Last year he met his publisher; he just signed a major book deal.

This wasn't random - it was accidentally marrying up passion, prowess, purpose, and profit. Profitable doesn't mean "rich guy with monocle" - it means enough money to keep doing you at scale. The most engaged people fire on all four cylinders.

For eight years he's done an exercise with everyone from middle schoolers to MBA students to 30-somethings facing quarter-life crisis: make four lists (love, belief, skills, values), stick them in a drawer, forget about them, then assemble them into you. But why not get the robots to work for us instead of against us?

He built a free AI tool called Actionable Ikigai. Instead of manual reflection over weeks, you tell it your name, role, location (economics work differently in Topeka vs San Francisco), then answer questions about passion, prowess, purpose, and profit. It gives you a "true north" destination and three waypoint paths to get there.

Like sailboats tacking into the wind at 45-degree angles, you can't go directly to your goal. The tool suggests reasonable waypoints to visit en route to your treasure chest.

For passion: What are you pumped about? Where do you lose track of time? What have you done for free? The speaker was the world's most prolific unpaid writer and speaker for 20 years - first happy to help, then grumpy and undervalued, then realizing it was about finding the right monetization.

For prowess: What are you complimented on? What do people say about you behind your back, positively? No false modesty - if you light up a room or excel at quantitative analysis, own it. Express your quiet, hidden strengths.

For purpose: Resist ocean-boiling virtue signaling. Everyone wants to end cancer, hunger, and war. Think global, act local. One user said "I just wish the world were a little less cutthroat and a lot more chill" - the system did wonders with that.

For profit: This is where everyone falls off the cliff, shifting from self-actualization to "investment banking, pro sports, or YouTuber" because we're trained to believe interesting stuff and lucrative stuff don't meet. Don't brainstorm - have a frank conversation with yourself about your constraints.

Eminem and Kid Rock had similar origin stories - white male rappers from Detroit in the early 2000s. But Eminem was rags-to-riches, while Kid Rock was heir to luxury car dealership franchises. Kid Rock felt he had nothing to lose. If you're broke or rich, you go all-in. But most of us feel comfortable with a lot to lose and sunk cost.

Be honest about your ceiling - what does success look like? Some want generational wealth, others just want to retire at 60. Then define your floor - how low can you go? The speaker had middle-class suburban upbringing, so he could YOLO in his 30s and 40s.

The tool has a bonus Robert Frost question: conservative well-trodden paths, or spicy creative "go nuts" suggestions? And for entrepreneurs: option three skips jobs entirely - you're creating businesses, art, culture.

Is the tool perfect? No, it's the ultimate AI-coded thing. But is it useful? Yes - it gets you thinking about questions that matter and starts a conversation you can have with AI tools for the rest of your life. Work with this stuff, not against it. The best antidote to dread of digital Joneses and their jet packs and robots is to use your tools for your own purpose.

Finally, from the futurist: directionality matters, but timing is everything. Check in with yourself every couple months on how you feel about your rewards, pain, recognition, and results. Does it feel fair, or does it feel lost?

Source: stt · Language: en · Model: anthropic/claude-sonnet-4-5
Speaker 1 00:00 Pleasure of working with future smart sectors these past few years for South by Southwest sessions, and while the topics have changed year over year, there have been some there's been a through line in all this presentation. He has presented big ideas about the future with a level of intimacy where he finished the presentation knowing a bit more about evolving in technology and also humanity's place. With that evolution, it's a breath of fresh air in the timeline where we are constantly bombarded by AI hyper scaling and doom and glitter. This year, He zoomed the lens in a bit those of us that are young, ish people planning their careers out in this rapidly changing world. Please help me welcome Mike to the stage who Unknown Speaker 00:59 identifies as youngish. Speaker 2 01:05 Deeply grateful that you've all come and you've got a lot to get to you, a lot of dots to connect. So connect. So when Speaker 3 01:14 I was in high school, I read a story Unknown Speaker 01:19 by Isaac Asimov called nightfall. The and it was written in 1941 Speaker 2 01:28 the story about these folks who live on a planet that was in a solar system with six suns, and so these cats Unknown Speaker 01:35 had never known darkness, Speaker 2 01:38 that is, until the present day, because they were preparing for their first eclipse that would hit their civilization and all recorded history. Well, as the folks were nervously and fearfully preparing Speaker 4 01:58 for nightfall, for their first taste of darkness. None of them were remotely Unknown Speaker 02:05 prepared for the actual reservation 30,000 stars blooming in the night sky. None of them were Speaker 2 02:20 even remote. Remotely prepared for the sudden realization of the vastness of the universe or their relative insignificance. In light of that vastness, Unknown Speaker 02:35 they promptly go insane and then it state the end. Thank you for coming to my talk. Unknown Speaker 02:48 But that really is the end, and the story is wild. We need to spread. It spread. Unknown Speaker 02:56 When I first read that story Unknown Speaker 02:59 was the early 90s. It was 1992 Speaker 2 03:02 and I took it to be a theology critique, right? I figured this was like indirectly Asimov, sort of channeling Galileo. Now, part of the reason I was thinking Galileo in 92 was because Indigo Girls had just dropped a banner about Galileo. How many people here know Indigo Girls? World. What was his crime? Why was his head on the block? Because Galileo was pushing this idea, from the predecessor to Nicholas Copernicus, that the earth wasn't, in fact, the center of the universe had this has been a heat of centricity, that is that the Earth orders the sun, not the other way around, and the church wasn't hammering it. Speaker 3 03:52 And so Galileo ends up in house arrest for the rest of his life. Now, by sheer coincidence, 1992 was also the year that Pope John Paul the second formally apologized on behalf of the Catholic Church for that little bus stop Unknown Speaker 04:07 400 years earlier. When I reread this story this year, Speaker 2 04:16 it occurred to me that what Asimov may have actually been writing about wasn't the opportunity at all when he might have been writing about was an ahead of its time, warning Speaker 3 04:29 about the perils and struggles of the information age of social Media and the coming intelligence age, that his day out. Now before we jump forward, as I do, and I believe futurists are closeted historians, so we're going to hop into the Wayback Machine. I want everybody to channel your inner 1995 Unknown Speaker 05:00 anybody remember Unknown Speaker 05:12 what says Speaker 3 05:18 next? You've got mail. Look at this. I remember when I hop online, those few times when my mom would pick up the phone first, she would say, What are you doing up Unknown Speaker 05:41 there? And I'd say, No, Mom, I'm live. She said, Speaker 3 05:47 what is that? And I'm reaching. I'm reaching for analogies, which is what I want to do to make sense of it for mom. Speaker 2 05:55 And I'm like, you remember? You remember? And she goes, yeah. I go, well, the internet, it's like a digital Gilligan's Island. Speaker 3 06:04 And she says, What do you mean? And I says, Well, you know, it's like, you know, Speaker 2 06:11 Gilligan and the skipper, The Millionaire and his wife, the professor, and Mary Ann, these people have no business being in each other's business. Speaker 3 06:21 But because of the shipwreck on the three hour tour, they rubbing each other business, and it makes some great times. And it turns out the internet, Mom, it's like a digital Milligan title, where all these people with no business being each other's business. They're not in my basement, and they're all chitter chattering and not me. I met a model from Norway. Unknown Speaker 06:45 I met a Nigerian prince Speaker 3 06:50 and a whole constellation of characters. And to be honest with you, for the first 10 years of the internet, right, for those who remember, or those who've heard of this dusty dog, it was glorious. It was great. It was mercifully great. It was an unlimited set of collisions of unusual suspects, and then all of a sudden, Unknown Speaker 07:15 my degree, what happened? What Unknown Speaker 07:22 happened? I say, anthropology. Back in college, we learned about this guy, Dr Robin Dunbar. He's a sociologist. Speaker 2 07:30 Actually, he's a behavioral biological anthropologist, and he had this idea called Dunbar's number, and it works like this, his argument was, society progresses linearly in its own squirrely way. Technology progresses in a hockey stick exponential Moore's Law kind of fashion. But our hardware, our firmware, the chips that power home savings, Speaker 3 07:59 they don't really evolve that fast at all. In fact, we're still running on the same hardware that we were running on 10,000 Unknown Speaker 08:07 years ago. Let's consider the Neolithic period. Speaker 3 08:14 Now this handsome gentleman might have different grooming standards in a different fashion sense than us, but from a biological Evolutionary Anthropology perspective, he's exactly us, right? He enjoys a warm fire, he enjoys the company of his family, he enjoys the love of his children. And for this AI rider, he really sinks into that guy they Speaker 2 08:37 don't understand. Do. Especially the thing he is we, biologically, speaking, five close friends is about right. And while the costumes change, the hardware doesn't all right. 1700s Same deal. 1920s same basic deal, 1980s same basic deal. Software Unknown Speaker 09:14 changes, Speaker 3 09:21 network changes, but the hardware can change much. And what Dunbar figured out was that the hardware can support five intimate relationships, the hardware can support 16 close friends. The hardware can support 50 Canada friends. And then here's the big kind of headline number we can support 150 meaningful contexts, Speaker 2 09:46 that's about it. And corporations know this right, departmental design and division design in universities and businesses that this is a novel because at about 150 we feel a sense of call it, Speaker 3 10:03 pardon me, that was shock. It's not getting way. Down at 150 we feel a sense of place. We feel a sense of belonging, and a sense Unknown Speaker 10:13 of this guy feels pretty good. But 10 years after digital growth revived, we introduced social media Speaker 3 10:26 into the universe by blowing up the denominator of acquaintances and loose connections online friends. What happened was we started to feel a whole lot smaller, Unknown Speaker 10:38 a whole lot we all live this. Speaker 2 10:45 This is our time, right? Because our home was taking his brain, right? Our primate brains when we're introduced to the idea that Bob was just admitted to Mensa and Ted bought a Porsche and bought a Porsche, Speaker 3 11:02 and Frank has been working out, and Jane has gone vegan, and Tony is now super into philanthropy. You can't handle all those stars in our sky. Speaker 2 11:20 It's too much, and so what is our software doing to compensate? We conflate. We build this, this collage, this, this conflated pastiche of an imagined friend who's better than us in every way. Now, what's really going on right Speaker 3 11:44 individual highlight reels, but our mammal brain turns it into a single Nemesis that may feel smaller than and lesser than and it's nightfall. Well, Speaker 2 12:03 it. One of the most inspirational figures in history. The coach at my alma mater, Kurt, plays his end boy, Lou Holtz, one of the most inspirational speakers ever. He was getting his players ready for a huge game against another team, and he said, he said, Boy, you know, the other teams are bigger than us, and they're stronger than us, and we might be small. Both Speaker 3 12:31 are also slow. We're gonna save the pick me up for about five minutes later. Because here's the thing, not just small relative to the information you need. Information Edwin Hall building on the work of Christian Doppler. Everybody know the Doppler effect, like when an ambulance comes at you. Speaker 4 12:55 Why is it happening? Because when the sound waves are coming action, they're compressed, so it's a higher frequency, and when it drives away from you, they're stretched out. So it's a lower frequency, the length of that too. It's called red sheet. And what Hubble figured out was that the stars that are changing the galaxy are redder than the stars shows about Speaker 3 13:20 and when he put together the scientific community, he said, not only is the universe expanding, but the people, the stars, the galaxy is furthest from us, they're speeding up. Unknown Speaker 13:32 The further the star, the faster it's going. Whoa. What's that have to do with this? Speaker 3 13:38 Well, the sociologist by the name of Dalton Conley. He wrote a book called elsewhere USA. Head around 2008 he said, you know, economics works like this too, Unknown Speaker 13:52 right? As people accrue more wealth, Speaker 3 13:57 the speed at which they continue to accrue more wealth speeds up, and it makes us feel like we're further and further behind, like you're in a race where people in front of you have flipping jet packs. How many y'all are Mario Kart players? A shocking percentage of the room. Let's hear it for defender of America. Okay, in Mario Kart, the lead car, right? If they get a big lead, anybody want to shout out, what happens to the car who gets way too far disadvantage the blue shell, right? The leader is reined in by the fearsome progressive tax of the laggards. Blue Shell. In the real world, the leaders, thanks to the triple mushroom boost of compound interest, exclusive private accredited investor opportunities and favorable long term capital gains rates, is rewarded with more mushrooms. Unknown Speaker 15:01 I'm so proud of that monocle. The punchline is this, there's a psychological component to it too. Speaker 3 15:12 Because it's one thing to be objectively behind. It's another thing to feel like, despite your best efforts, you're falling further behind. Right? This fella, Alan de baton, an English, Swiss philosopher, he said wildly, the more you have the Saturn feel, because if you're making 40 grand, you hang out with 20 grand and 80 grand folks, you're down by 40 grand. You're making 200 grand. You hang out with 104 100 grand folks. You're down by 200 grand. You make five mil. You know a guy who makes 25 mil, and you're really near the about it. Unknown Speaker 15:47 Anybody ever see this 80s classic poltergeist? What Oh, Speaker 3 16:16 it's good. So we feel small in the modern world because of social media, we feel slow in the modern world because of wealth inequality, Gini coefficients, right and economic redshift. Unknown Speaker 16:32 Can anybody guess the third Horseman of this apocalypse? Unknown Speaker 16:35 It starts with an A Yes. Speaker 3 16:46 Last year, for Aiden's gracious introduction, I spoke about a completely different topic. The topic was that in a world of increasing intelligent machines, humans are going to thrive through breath over depth by that connecting, but it didn't allay the feeling that we all continue to have, which is that, good Lord, is if everything I just shared weren't enough of an existential threat, now we're dealing with the rise of the robots. Speaker 4 17:15 Now we're dealing with an AI. This quote from Gary Castro wasn't plenty of AI talking short over the past six days in this conference, but I'll tell you, Speaker 3 17:40 the rise of the robot here So many of you are, in fact, young ish and because it feels like an unfair race, a race that's better Speaker 4 17:47 than the front and it feels like it's not just keeping up with the Joneses anymore. It feels like there's more Joneses than ever. The Joneses in front of us have jet packs and Speaker 2 18:01 we're being chased down. I'm ready for a happy new old school. Speaker 3 18:11 Well, channeling more early 80s nostalgia, I'll tell you, the only winning way out of this game is to refuse to play. The only winning move war games 1983 is not to play because it's a hell of a joke. You are and will never be a Jones only the Joneses can be the Joneses, and even the Joneses, for all their carefully manicured social media and bank accounts aren't even a fraction of the way they're portrayed in our distorted beyond our primate brain way of handling you. Unknown Speaker 19:04 To hell with the Jones. Teddy Roosevelt, Unknown Speaker 19:08 he totally did not say that. Unknown Speaker 19:12 What he did say was, he said, Comparison is the thief of joy. Speaker 3 19:19 That's a goose bumper. Comparison is the thief of joy, and that wasn't the 26 presidents. Insight first, right? If you go through the whole of the human tradition, Western and Eastern, 3300, years ago, Moses, right, in the Abrahamic religious traditions, comes down from Mount Sinai with these sort of 10 rules of the road for Western culture, and 10 of 10, last but not least is Thou shalt not covet. I don't Don't be envious. Don't be jealous. Don't compare your house to their house. Your wife to their wife, your cow to their cow. I should have re thought that scene. You about in the Eastern tradition, Siddhartha, batama, the Buddha, 600 years after Moses, warns of the comparing mind, that it detracts and detaches you from the path to enlightenment because you're spending your time in an imaginary competition against people who aren't your competitors in an imaginary competition, worse against your own imagined alternate skills Speaker 3 20:30 team. The only comparison we're making is to our prior self, because we're the only people who have ever started with that same inimitable mix of initial conditions. And so it's the only fair fight worth waging is, am I better than I was yesterday? Am I trending in a better direction than I was yesterday? And so what I want to share with you Unknown Speaker 20:56 for a sort of second act is a story about my prior selves. In 1997 Speaker 3 21:07 I was a handful. That's me at a hub in London, doing my best to sort of, I don't know, portray the opposite of the word photogenic. I I had five majors, not really. I was government, in anthropology, with a minor in econ and philosophy, but, you know, four fields of study, I probably had zero neckties, which killed me, because my friends were starting to get jobs. My buddy mark is coming back from a job interview, and Mark says that it went pretty well. And I say, Well, what are you talking about? Your majors are as weird as mine, your theology and biology with like a masochistic pension for taking classes like Space Systems Analysis, just to say it did? Unknown Speaker 22:01 He says, Yeah, well, it was a consulting firm. They say Speaker 3 22:07 they're not looking for a certain kind of major they're looking for a certain kind of mind. I think, well, I too have a certain kind of mind. And so I promptly began the process of cutting my hair and selling out to the man. And I remember those job interviews at the time, 1998 with Anderson Consulting the artist, presently known as Accenture. As far as I could tell, they were looking for extroverted engineers, charismatic computer scientists, or, as I call it, smooth geeks. And so I thought, like, okay, my mission is to show that I'm the smoothest Geek on campus. And so I literally, in the interview, I was like, Well, you know, Chad, after, you know, I founded a successful campus ska band called skaaholics. And Chad's thinking this guy's smooth. I'm like, which played songs about the Commodore 64 home computer. It's like, wow, this guy's a geek. Well, fast forward, I said, Well, I also learned to play the accordion. Wow, that's really geeky too. Impressed. My Polish American girlfriend's family, to my surprise and delight, but mostly surprise, I end up getting the job. And look at that, double breasted. Speaker 3 23:39 The job was painted as a sort of business doctor, right? You show up, you diagnose a sick company, you figure out what's wrong with them, and then, you know, you treat the patient. And from there, the rest was history. I mean, here's my, here's my, my CV. Let's do, let's do the version of me that shows up on LinkedIn, joining Accenture in 1998 one began his career with accentuate records 12 years and 12 US patents later, he was named that firm's first global innovation director. He then served as Chief Technology Officer at the ounce of prevention, the nation's foremost philanthropy committed to equitable early childhood education. In 2013 Mike co founded and led ringleader ventures, a venture capital firm investing in early stage startups. In 20 he became chief futurist for Deloitte, founding and directing a global research team advising the boards of leading organizations around the world today. Mike serves as an adjunct professor teaching corporate innovation at the University of Notre Dame, and is a sought after keynote speaker with his rare mix of technology, business and charisma. Unknown Speaker 24:53 What's wrong with that story? I Speaker 4 25:00 speaking to highlight for you, it's not false, but handy little bit, I'll tell you, it ain't quite true either. Max is telling the tale that is engineered to create this response and Speaker 2 25:22 and on a place like big dead I can see why. That's pretty appropriate, Speaker 3 25:28 but in a more holistic manner, the problem with that telling the tale is it's rife with two of the biggest biases around survivorship bias you only hear from the scene on the stage and retroactively take his preferred connect the dot back to the origin, and in doing so, confirmation bias, like big Crosby said, you accentuate the positives, you eliminate the negative, you don't even touch messages in Unknown Speaker 25:56 between. That is not teachable moment, and that for those of you looked in your bullshit. Unknown Speaker 26:06 That's why most career advice takes Speaker 3 26:09 his people, sit back, look back, presume this poorly, tenacious mix of correlation causality, and call it a guide in truth. What you have to do is you have to deconstruct it and figure out what constructive and figure out. When I started as a business doctor with Speaker 2 26:38 my fierce fit, I was looking I remember literally crying on my way home from my girlfriend's house to my house the night before I started work, the night before I put on that get up and I remember journaling. I found the journal I said, I feel like a leaf blowing in somebody else's name. Speaker 3 26:56 I feel like all the rainbow of stuff that's made me me is now going to be reduced into this monochromatic single pain called process analyst, Speaker 4 27:09 and it crushed me, but straight talk, it paid the bills, Speaker 2 27:18 and for a year, I did what I had to do because I needed to work and I needed to make money and I needed to make a doorbell I didn't Speaker 3 27:29 Well, I'm interviewing, I'm looking for other gigs, and I find this other group within Accenture called Accenture Technology Labs, and these cats seem to Have all the fun. I mean, this is 1999 this guy's, as far as I can tell, the prototype for the Apple vision club. And I'm thinking, Man, I would really like to work in that group, because they also seem to have bottlenecks and very cool art in the hallways. Speaker 2 27:58 And so when I talked to those cats, it was, getting clear, like you can work here. You can be in general, Speaker 3 28:05 but you won't have quite the same career trajectory. You'll be foregoing profit in search of your passion. Well, at the time, coming up with a year of Unknown Speaker 28:17 profit and compassion. I said, Let's go. Speaker 2 28:20 You. And as you can tell, I was pretty stoked, but I was also sort of a hollow chunk of money. And by that I mean my broken Catholic, Irish Catholic faith tradition, like invited in eastern money was just air. That was me. I was just there because I didn't yet have the skill. I didn't have the prowess. Unknown Speaker 28:47 I remember my boss puts that book at my desk. He goes, Unknown Speaker 28:52 here's how you learn Java and become relevant to this group. The book is, learn job in 21 days. You have 10. Speaker 2 29:02 You know if I learned the 10, but I learned it, and I got good enough, and not because it's magic. It was 10 years of great memories and hard work and blood sweat and tears in the whole nine yards. But the money came. The money came. And, in fact, after about 12 years, they did, they gave me a raising a promotion, and says, Congratulations, you're not in charge of all the geeks. And I thought that's super cool, but, but anybody ever been? Everybody ever hear the term the Peter Principle? Speaker 3 29:38 Peter Principle is the idea that the reason that everybody in corporate America is incompetent is because they've all been promoted exactly one level of what they used to be for, that I'm like, Man, I'm making money, but I'm not. I'm not loving it, and I don't know that I'm good at managing budgets, necessarily. Speaker 2 30:01 And it was around that time that this national not for profit, who we did pro bono work for. They said, Do you remember that technology strategy you did for us? It was great. I thought, yeah. And they said, Do you remember step seven of 10? And I go, No, it was to hire a cheap technology watch. Unknown Speaker 30:21 And feeling itchy on this side and wanted on that side. Speaker 2 30:24 I said it was pretty great. My first day at work, first day at work, I was sitting next to my boss's husband, who's about to become the governor of Speaker 3 30:45 Illinois, and this other guy was a textual hotel chain or something, and 10 years later, would become the next Governor Speaker 4 30:51 of Illinois. And I felt fancy, and I felt like I arrived. I'm going to do good and do well, and this is the best job ever. And then every day after that, the next year and a half, was minding, Speaker 3 31:06 legacy technology, and it wasn't stuff I was talking about. I love working in interstate schools of at risk youth. That's what I thought it would be. But I didn't think it would be my greatest service off Windows, so I thought, Hey, man, let's get back to the other news. And I had an opportunity through two board members at the philanthropy they said, Hey, we're looking, we're looking to build a venture capital firm, but we need something to inoculate us against snake oil and bologna. Can you be that guy? Maybe ever see Ghostbusters Ray? If somebody asks you if you're a god, you say yes. So I go, Sure. I can be that guy. I would love to do it. I don't know anything about finance. I don't know anything about venture capital, but I'll run a venture capital firm, and for a couple of years, it was back to fired on three cylinders. Then I realized that understanding how technology works isn't the same as understanding how business world strategy works. And then I started falling out of love with it. And the next thing you know, business started falling out of love with sounding economics. Unknown Speaker 32:22 So then stuff got really, really Unknown Speaker 32:27 nothing like collecting $500 a week after you Unknown Speaker 32:31 think that you've got it all figured out. But it Speaker 3 32:35 was an important reset, because what I found was it was a chance to focus on something I really love, even if I was making a bucket for a guest lecture and I was teaching. And then through a mutual friend and colleague, I found an opportunity to actually kick it from volunteer guest lectures to part time adjunct at the university meeting. Unknown Speaker 32:59 And it was through that opportunity that I fell into Deloitte, the senior leader there, says, What Speaker 3 33:07 do you say about joining me is my right hand at our large healthcare insurance plan? I said, That's not what I do. I work on what's new and next in tech. He literally, his literal response. He goes, sounds like you'd like to make less money. And he introduces me to the emerging tech people, and they say, We're doing Verizon three technology sensing and scanning. And I said, I don't know what that is, but let's call it chief futurist. And they said, You're nuts. The world loved it and I loved it. Everybody loved it, and it was glorious, because I was scratching the purpose edge of the teaching. I was scratching the other three with Deloitte. It was the best job I've ever had. It's probably the best job ever. Unknown Speaker 33:44 But it was around that time that I was diagnosed with multiple sclerosis, Speaker 3 33:52 and as fulfilled as I was being deloitte's most frequent global flyer for two years in a row, 133 Unknown Speaker 33:58 genomes a year, I must missed the team wouldn't happen, Speaker 3 34:05 because I can burn brightly. I can hang with y'all for 45 minutes, but I can't, I can't do it. Can't do it all day, all night, 365 and so it was on the back of that recognition that I realized, what do I really what do I really like to do? I like to be with y'all pray brightly, because please. It was in this room two years ago that I met the folks who are not my agents, who says, Listen, you can do more of what you do and less of it and have as good or better of a living. And it was in this room one year that I met my publisher, and I'm happy to tell you all news, just signed a major deal with Henry, ran in house for a major book that'll be dropping soon, and if you're interested, I'll get you the link. But super pumped to thank yourself. Speaker 4 35:00 This concludes the fishing for compliments portion of today's presentation, but much sciences. It wasn't that. It was that, Speaker 3 35:17 but that's not a random walk. That was a guy who was accidentally trying to marry up his passions, his prowess, his purpose, and to do so profitably. And for me, profitably doesn't mean rich guy, right? It doesn't mean Toad with a monocle. Profit means enough money to keep doing you at scale, right? Because how many people do it over the tire and then they're super sad? The most engaged people are firing on the other three cylinders, but they have enough dough to keep firing. Unknown Speaker 35:54 So when the youngish among you, what I want to Speaker 3 35:58 create together is we're going to take you one better than accidental ikigai. Ikigai, by the way, the Japanese 13th century term for reason for being in French. But the punchline is, it's been a little bit corrupted like it was never meant to be comparative advice for 21st Century professionals, right? But the popularized DKI, this idea of these four cylinders that you can go for before you're cooking, I've lived that, and I think we can do better than accidentally meandering into it. And so for the last probably eight years or so, I would do this exercise with everybody, from middle schoolers to MBA students to 30 somethings on my team facing a quarter life crisis, I'd say, I want you to make four lists. I want you to write down what you love, and then, and then stick it in a drawer and forget about it. And then you write down what, what you believe. You stick to the drawer, you forget about it. You do it for the other two categories. And then, and then you do an exercise where you assemble them into you. I can no longer own the whistles Unknown Speaker 37:08 simultaneously because of the existence, but it was quite something. I do love being Unknown Speaker 37:17 part history. I haven't figured out you. A certain buck. Speaker 4 37:23 The punch line is, y'all could do this with a sheet of paper, a cup of coffee and a couple of weeks reflection. But that's when it hit the team, Unknown Speaker 37:36 what if we got these stinking robots to work for us Speaker 3 37:40 instead of against us. What if we were being chased by robots? What if we were being lifted by robots? Speaker 2 37:48 And so what I went ahead and did, and I built this, just for you, free, is a tool that I've called actionable EBI. It's an AI Speaker 3 38:02 tool. And that your phones are going up in droves is warming to my art you got to create. And everybody Speaker 2 38:10 says, because it's amazing. But the idea is this, don't worry, it's not going away. That QR code will stay there for the next few minutes. The idea works like this. What if we can count on the combinatorial power of an AI to build the dead wood sandwich for us? Speaker 3 38:34 What if our job is to thoughtfully express ourselves, our roles, our goals, our hopes, our dreams, our constraints, our missions, and let the machine play the bike ride game to figure out what's in the middle, what's inside, what's worthy of your time and what's less. Speaker 2 38:52 The metaphor that I've built because it's fun, and by the way, permission to multitask, if everybody's eyes go down, if that's a feature, not a bug, and enjoy your straight time, but still listen. The idea is to say enough. You're going to tell it your name, you're going to tell it your role, option one talk where you live, because super straight talk are too big hits around the numbers work differently in Topeka than they do in Samar. But then what you do is, after you get those answers, on purpose, passion, profit, it's going to give you two things. It's going to give you a true north, a treasure chest. I think I've got it configured to be all right now to give you three, like three like three options. Here's three Unknown Speaker 39:48 potential. Best thing you learn Unknown Speaker 39:51 early on you can't go directly Speaker 2 39:59 into the window, physically impossible. So what again, you got to take these 45 degree angles. It's called leading into the wind attacking. Speaker 3 40:10 And so the tool is going to do one better. It's going to say, here's your shining city on a hill, and here's a reasonable set of waypoints to visit on route Unknown Speaker 40:18 to that treasure chest. You treasure chest. Now, usually when you talk easy guys, well, what do you love? Speaker 3 40:28 And that's so vague. And so what I've learned in doing this for five, eight years with people on paper, but it certainly matters with the tool too, is you just say, Well, I don't know what actually, sure. What are you pumped about? But what do you lose track of Unknown Speaker 40:45 time? Cliches are cliches for a reason. Speaker 4 40:49 And so time flies when you're having fun, where time flies, that is passion. Speaker 2 40:57 And then thing too. What have you done for free? And what you can do is for free because you have free. I was the world's most prolific unpaid writer and speaker for 20 years, and I felt originally I was just like, I'm happy to help because I'm Midwestern. And then graduate was like, I'm grumpy and I'm being undervalued. And then you realize, no, no, it's just about Speaker 2 41:35 monetizing for prowess. What are you complimenting? It's what do people say about you, behind your back, positively, what do they say to you, right, to your face, positively. And this is no room for false modesty, right? He lights up her room. I light up her room, right? She's really good at quantitative analysis, they say that to math, it Unknown Speaker 42:06 doesn't just have to meet the label Speaker 2 42:09 express your quiet, hidden strengths too. I know I'm great at XYZ. The key to that one is don't be overly humble. You. For group three, for purpose, hold my advice, resist ocean boiling, virtue signaling. I too would prefer a wound without cancer, hunger or war, and that's what we do. She Speaker 2 42:42 hears of course we do, but think global Admiral, right? I would love my community to be more financially literate. My son has used this tool successfully with this entire fraternity house, which is called Wild image. But one of the things that he said on this one, he's like, Yeah, I just wish the world were a little less cutthroat and a lot more chill, and the system did wonders with that business. It was great to Unknown Speaker 43:15 see nonprofit. This is the one where everybody falls off us. This is Speaker 3 43:21 where it usually goes back into handbags, because when you ask people this question, their posture changes, their brain changes, and go from like, self actualization to like, I don't know, like investment banking, pro sports or like YouTuber or something Speaker 4 43:43 because we're trained to believe that the interesting stuff and the lucrative stuff don't meet. Speaker 3 43:52 And so the big aha that I have here is don't brainstorm at all. Rather, Unknown Speaker 44:01 have a frank thought about your insurance. Here's what that means. Can anybody identify these two individuals? Eminem is to me it looks like Brett Michaels from poison, but it's supposed to be Kid Rock, Unknown Speaker 44:30 eminently. Kid Rock on the surface had a very similar story, Speaker 2 44:36 Caucasian male rappers achieving success from Detroit in the early 2000s they're the same thing, but Speaker 3 44:49 they're not the same. Turns out, everybody knows Eminem story because it was popularized in the movie eight mile panic, pop culture, Rags to Riches, the heroic Horatio elder tale of somebody who had literally nothing Louisiana rap his way out entrepreneurship yellow. Unknown Speaker 45:08 Lot of people don't know Kid Rock's story, Speaker 3 45:11 because Kid Rock was the heir to several luxury parking room shifts. Speaker 2 45:17 He was more than comfortable. He's literally on the family Apple working one day besides running automobile companies just seems tiresome. Now. Speaker 4 45:31 Why does this matter? Because here's why this matters. Kid Rock feels like he has figuratively, nothing to lose. Speaker 2 45:38 And what I've learned over the years is that if you're broke or you're right, Speaker 4 45:44 you're gonna be all up, you go nuts. Definitely hair all in because you only go so far here, and you've got plenty of cushion over here. But most of us, most of us, feel comfortable. Most of us, feel like we have a lot to lose, like we have a whole hell of a lot of sunk cost, and Speaker 3 46:11 I don't want to mess anything up, because I've come a long way, and I've busted my butt, and I don't want to wreck Unknown Speaker 46:19 it on a whim. Now, that's not bad. That's weird. Speaker 3 46:22 And if I learned anything as a venture capitalist who had no business being in that business in my early 30s, is that you need to have an honest conversation with yourself about your ceiling. What does success look like to you? Something literally, somebody in this room. You don't have to help yourself. Somebody's just like, billion or bust generational wealth. People younger than me are super interventional, great, good job. Other people are just like, I just want to make enough to retire when I'm 60 days. But then there's the four, right? How low can you go? I had a middle class, suburban family Unknown Speaker 47:04 feed so I lived within YOLO in my 30s and 40s. Now I can, because I've been more honest with myself. Speaker 3 47:16 You feed that into the machine, and then you do one more bonus question that I've added to the grins and giggles, and that is the Robert Frost question, do you want the machine to encourage conservatism, well known paths that the past muster with mother? Or do you want to kick up the spiciness and have it do now, give me some really crazy hair, very creative stuff. Go nuts, get clever, Speaker 4 47:43 because we're here at South by and we've got some entrepreneurs. I built a surprising third question. Namely, Speaker 3 47:57 like some of you, I don't want a job. Where we're going, we don't need jobs. We're creating businesses. We're creating art. We're creating culture. You pick option three Speaker 4 48:12 now, is the tool perfect? No, because it's like the ultimate bi coded thing. Speaker 3 48:17 But is it useful? Yeah, because it gets you thinking about the questions that matter, and it starts a conversation that you can have with the tools of your choice for the rest of your life. But if I learned anything, it's that you want to work with this stuff, not against this stuff. And the best antidote for the dread of digital Joneses and their jet packs and the robots is to get in there and use your tools to your own avail against your own purpose. Speaker 4 48:44 The final thing I'll get you over Speaker 3 48:51 take it from the futurist. Directionality is one thing, but timing Speaker 4 48:57 was everything entirely. The number of times I've been asked When did blockchain asked, How does blockchain Unknown Speaker 49:09 Here's a screen, there is a dashboard, there is a cockpit tool, Speaker 4 49:18 and from a note taking perspective, Here's what they are. The first is check in with yourself every couple of months. How do you feel about your rewards, your pain, your recognition and your results? Does it feel fair, or does it feel a little lost? Two you.

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