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It’s time to rethink your entire life plan - Dave Evans

Chris WilliamsonFebruary 21, 20261h 48m
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Dave Evans is co-founder of Stanford's Life Design Lab, a small operation in the design program applying design thinking innovation principles to designing life at and after university. Bill and Dave used design thinking at Stanford since 1963, at Apple early days, building Silicon Valley. They applied it to designing their own lives.

Design has two categories: craft/engineering design (precise, e.g., ergonomist, car designer, graphic designer, illustrator) and design thinking (innovation methodology for new ideas, past 50 years). People saying "design my life" mean engineering it—figuring out, solving, crafting. That's valid, but people get stuck finding their way.

Example: In 1970s, 19-year-old Dave at career center: "What do you want to do?" Hard part is figuring out what you want; getting it is easy.

Life Design Lab objective: Assist in forming conscious competency in life and vocational wayfinding. Life is an improv skit; they are improv trainers. Like orienteering for life direction. Distinction: navigation (know where you are/going, data on space, GPS optimizes straight path) vs. wayfinding (wicked problems, no data on future, empirical "try it" via prototyping—jagged pathway, learn forward, bouncy line is shortest for mortals).

GPS brain: Forgive yourself for wrong turns; GPS continually updates without judgment. No angry co-pilot even after repeated mistakes. A "move," not a mistake—you learn and adjust.

People seek impact (making a difference, changing world, mattering) or fulfillment (manifesting fullness of self, per Maslow's 1943 hierarchy apex of self-actualization). Both dead ends.

  • All contain more aliveness than one lifetime allows; can't fully manifest everything.
  • Impact out of control (others go off-script), short half-life ("What have you done for us lately?").

Example: Scottie Scheffler post-PGA Masters win (last year, green jacket): Fleeting, hollow; quickly back to diapers, trash, dinner. Michael Jordan's 1993 Hall of Fame speech called out insulters, little gratitude.

US Olympic Committee: Gold medalist syndrome—thrilling ascent, short drop to dumpster diving. Elite Meet: Volunteer group of former top gun pilots, Rangers, Green Berets, special forces retiring at 42 after 20 years (start at 22); world doesn't need them anymore.

Impact reframe: Don't put all eggs there (transactional world). Seek flow world (present moment, reality now, rich with meaning).

Fulfillment reframe: Can't be fulfilled, but be fully alive in present. Celebrate scandal of particularity (theological/philosophical: ultimate truth/beauty/justice/purity only in partial, temporary particularities; reality's nature).

Example: Amazing sunset, green flash—want more, falls short. Befriend longing: Participate in sincere reflection of perfection briefly, celebrate as good as it gets, try again tomorrow.

High performers lose impact and flow vehicle (e.g., gymnast, tennis player, neurosurgeon). Double whammy.

Dave stopped teaching undergrads 2018; now DCI (Distinguished Careers Institute) at Stanford: Gap year for 45-90 (mostly 55-75), second half-life transition from role to soul. Shift from role-based identity (good at impactful thing, in flow) to soul. Sticky; elective maturity move starts ~30 (neocortex ~27-28, later in men). Build ego to transcend it; make person in 20s-40s, then empty for transcendent experience.

Ancestrally, past 40 rare (death more frequent). Mismatched for modern longevity/environment. Few historical models for 50-60-70 transitions; window stretched/shifted from mid-30s/early-40s.

William Bridges' Transitions (1980s, based on Erikson): Changes (external) vs. transitions (internal: ending → neutral zone → new beginning). People double down on known (e.g., buddy John starting 12th company: "I'm good at it").

Crabs shed shell to grow; anorexic hermit crab refuses to eat to avoid outgrowing shell, skips neutral zone, stays "found."

Chip Connally (Modern Elder Academy): Midlife crystallis (good transformation) vs. crisis (badly). Life is change; being a person is becoming. Seasonal stage-like transitions.

Fully alive: Present moment, even with particularity's insufficiency. Practices for transactional world (performance) vs. flow world (now: behaviors, awareness, attention for deeper experience). More aliveness feels more meaningful, human.

Joseph Campbell: Is it meaning or "true rapture of being alive?"

Example: First can of new tonic—best so far; enjoy as is, don't blame for not being perfect.

At the end of the day, decide if the human person is fundamentally a production engine—I equal what I did—or a living being where I equal the life I lived. Decision about what it means to be a person is significant.

Meaning through evolutionary lens: depends on cosmology. As a theist, if evolution has trajectory energized by collaboration, community, persistence, then leaning deeply into personal and collective life sustains community and genome. Alignment of pro-social macronutrients, internal and kin-based, Dunbar number stuff.

People seeking more meaning want more aliveness, to feel more alive. Add aliveness to definition of meaning and provide tools to acquire it. Current food groups limited (e.g., impact); suggest five: impact, wonder, flow, coherence, community for more calories. Fulfillment breaks into component parts. Different aspects of humanity experienced, grown, expressed. Not comprehensive, low-hanging fruit book—zero to one approach.

Set bar low and clear it: provide doable, accessible tools for regular people. Life is long, incremental evolutionary process. Through design thinking lens, reframes and mindsets helpful; four areas—wonder, flow, coherency, formative community—readily available, accessible quickly. Design tools/practices/ideas to get them.

Life is largely a story we tell ourselves; neurophysiologically, we see what we're looking for. Lens and anticipation matter. Reframe: not trying to be fulfilled, but fully alive—changes everything.

Be transformed by the renewing of your mind.

Top-down vs. bottom-up: much is thinking problem, but move to embodied experiences. Flow not thought-based. Over time, start from experiences in the moment, noticing from body not brain.

Problem-solving world has narrow meaning. Model: transactional world vs. flow world. Neurologically, achieving brain vs. awakened brain (Lisa Miller at Columbia; Jill Bolte Taylor's Stroke of Insight, left brain loss). Integrate for fuller consciousness, richer life.

Flow world: give airtime to consciousness experiencing other reality aspects—free experiences wasted otherwise. Get more out of life you're in, not cram more in. Wrote two books on big changes, but don't forget to live current life.

Optimization or overoptimization can drain meaning. Happiness = delta between reality and expectations. Quality of life based on imaginal idea.

Good enough is... Good enough isn't... Both true—pick carefully when to apply.

High performance good (listen to Huberman, Chris Williamson), but if always narrowing gap, as soon as close, up game—never maximize productivity.

If we are altogether unduly absorbed with improving our lives, we may forget to live them. —Alan Watts

Provisional life, arrival fallacy—no done, no right, no 'it'. Memento mori: one day you'll die, inbox still accumulates emails; people email asking why no reply, call rude, unaware you're dead.

51-year support group (formed 1974), all ~73. At 50th anniversary (18 months ago), discuss becoming elders. Next milestone: death.

Father died by suicide at age 9; wife Claudia to cancer 5 years ago. Remarrying (Compassment woman). Marrying = moving to foreign country (John O'Donohue); no second marriages, only first the second time (Jerry's sister)—first marriage third time. Steep learning curve, terrific.

Death awareness popular, freeing. Finitude (burying people helps): 12-15 years left, productivity plummets after death. Area under curve last 6 months won't matter much—not mailing it in, but you're a person with life. Leave campground better (Boy Scout), but what's it for?

Your job is to be Chris. Each is gift from God/universe to unwrap before game over.

Dalí: parents said he was reincarnation of dead brother (born 20 months earlier, same name); took 20-month-old to gravesite. At 10, threw self down stairs—pain interesting, manipulates people. Walked anteater in Paris streets: "anteaters never in fashion." Pistol at talk, fired intermittently; deep-sea suit talk, suffocated, wrenched out. Refused forward through doorways (side/back)—habit destroys creativity patterns. Sued for dreaming about him: subconscious belongs to me. Buried under museum, people walk over body.

Poor, signed uncashable checks, doodled—illustration worth more than check.

Notices fullness of self; patterns container to hold life, not be it. Transcends patterns. Moral commitment: press edge lest less than could be—monastic. Da Vinci didn't do Dalí, Michelangelo didn't—world less without fullness. Cosmic karmic duty: do what only you can.

Wonder equation: curiosity + mystery = wonder (lean into high-availability mystery).

Wonder/awe/positive overwhelm: Dacher Keltner (UC Berkeley) book on awe, 8 forms across cultures/spiritual traditions. Makes feel more alive, more self, part of great thing (e.g., concert, sunset, sleeping baby at 3AM—universality breaks through).

The moment one gives close attention to anything, even a blade of grass, it becomes a mysterious, awesome, indescribably magnificent world in itself. I have tried this experiment a thousand times and have never been disappointed. —Henry Miller

Habit of wonder moves beyond self (late Maslow: self-transcendence > self-actualization, not hierarchical—anyone, anytime via love, selflessness, compassion, beauty overwhelm).

Scott Barry Kaufman, Transcend.

Put on your wonder glasses:

  • Scan situation/room with normal (transactional) glasses: brain makes to-do list (e.g., blue lights, mic, water plant)—thank it, note list for later.
  • Scan again: anything interesting/curious? (e.g., plant, cameras, angles).
  • Wonder glasses: lean into curious for mystery (e.g., plastic plant—homage to life amid digital/electronic; reminders of life everywhere).

In 1-2 minutes, reopen to indescribably mysterious/wonderful right in front. Takes practice.

Reliable ways: natural world (sunsets); identify what naturally works; notice existence of the

The natural world is your friend. Identify things naturally working for you. Allow yourself to notice the flow world, where wonder is available, by dropping into the present moment. Exercise: Flip the Switch—in a boring staff meeting while the budget is hacked apart, say "flip the switch." Notice: What's happening in the flow world? Observe people like how Chris is feeling, a tree turning colors out the window. This takes 3-4 seconds, building the habit of returning to the present, aware of being a living person. Feel the cushion on your buttocks while sitting and talking, aware of the room. These awarenesses engage the right brain's attentiveness. Play little games to stay in the game.

Coherence: Align consciously who you are, what you're doing, and what you believe in. Have a story about who you are, things you care about, and current actions—do they align? With calculated compromise, experience coherency as an integrated, authentic person, living purposefully. The book risks not focusing much on purpose and mission because people are overmissioned, stuck in the transactional world, deferring hopefulness to coherency. If aware of values and actions, moving toward alignment (coherency), you'll do good things. Most people have great values; let them lead for a better world. No need to preach. Coherency sightings: Catch yourself being integrated and coherent—gratifying, e.g., "I'm talking in your studio about living meaningfully; this is exactly what I want to do."

Incoherence Example

Inverted: Out of coherence looks like a successful Hong Kong finance executive's 26-year-old Stanford economics grad son with a master's in computer science, excelling in investment banking, getting A's like at Stanford. Suddenly bored, wants to quit, travel, find himself. Neocortex forming around 27 (he's ahead), growing and winning motivation fades. Awakens as incoherent. Tries convincing himself success is its own reward but can't. Needs to recalibrate values and priorities. Right to transition. Others re-up incoherence for money, fear, or status—soul-sucking, be careful.

Coherence outperforms balance. Never had balance as a goal; never seen a balanced person where time/energy allocation perfectly reflects values. Instead, check your life dashboard or current portfolio mix. Balance is resource allocation; decide priorities. Example: Older sister ran graduate school of education at small private college for 15 years, then pursued PhD full-time while working full-time. Calculated six unscheduled hours in next five years; told friends they didn't make the cut for her time. Radically imbalanced but highly coherent and right for her. Balance is lovely if coherent life permits, but prioritize being alive, accepting compromises.

Flow world: Place of present moment where flow occurs, distinct from flow state (Mihaly Csikszentmihalyi's term from Flow: The Psychology of Optimal Experience, 1990). Flow state: fully engaged, time stands still, fully present. Flow channel: Task demands match skill set—neither bored (overskilled) nor anxious (underskilled), like zone of proximal development. Apex flow: Ragged edge of capability; task demands all capacity, delegating engagement to task quality (task's job to make you present).

Simple flow: Choose full attention even if overskilled, e.g., chopping onions for soup ahead of dinner guests—fully engage, appreciate knife, feel the experience. Calmly detached, more alive. Even on hard tasks, drop elective anxiety by accepting mistakes. Mental discipline expands flow channel. Multitasking example: Chopping onions while listening to Chris Williamson YouTube—possible but lower flow; go all-in on onions for 10 minutes in zen way.

Multitasking degrades flow; humans task-switch, not parallel process. Task-switching is performance optimization for productivity (more done, higher pay), but flow requires full presence—time elongates/disappears. Multitasking and flow are different states; high-performance multitasking gratifying but not true flow if only game played. Meta-thinking (thinking about thinking) prevents flow when juggling. Example: Running nightclub front door—messaging about flyers, managing queue, tills, DJ—multifaceted but linear, cohesive (all about the event), peripheral awareness enables flow. Opposite: Preparing podcast with Slack open, other thoughts—too disparate. Adam Lane Smith: Life needs simplicity, not ease—humans handle intensity but not complexity/complication. Front-of-room multitasking like all colors on one palette (cohesive) vs. painting while jogging.

Example: Friend Steve ran large high-end catering company (presidents, Beyoncé's birthday, thousand-plate events), now lives in Redwood forest near Santa Cruz. Excellent host/waiter: Scans seven tables, knows needs (water, soothe conversation, hunger), routes effortlessly, selfless—cohesive context, high complexity/intensity, low complication, one fabric, enables flow.

Pay attention. Mindset design choice: Choose how to be in situations. Live in this day/moment. Bill's morning practice (out loud while shaving): 1. "I live in the best of all possible worlds"—biases attention to positive, increases catching good things. 2. "Everything I do today, I choose to do"—owns agency, outs victimhood (e.g., chose the meeting, DMV delay). Most important: Daily mindset practice for flow-rich life.

Examples: Stack calls on "get it done" days (Wednesday/Thursday)—cohesive, necessary work. Reframe: From "[__] Thursday" to Ubermensch Day—turns experience inside out, crushing it. Trash run becomes "trash mission."

Book structure: Reframe meaning, think like a designer (five mindsets), four areas (natural flow, flow world, coherence, flow). Killer mindsets: radical acceptance and availability.

  • Radical acceptance: Design works only in reality; be present to win. Accept things as they are (ice storm, power out)—neutral fact, not good/bad.
  • Availability: Lean in, wonder what's wonderful here.

Reframe "[__] Thursday" (unwanted crap) to Ubermensch: Accept reality (trash, taxes must happen), own efficiency, pat self on back.

Other mindsets:

  • Wondrous mindset: High availability to wonder.
  • Fully engaged, calmly detached: Fully present, bring best, alive experience; no control over outcomes, drop expectations.
  • Create your world: Create your story.

Suddenly getting expectations leads to anxiety. Aim to be fully engaged, care deeply, bring your best self, while recognizing little control over outcomes. This allows simultaneous engagement and detachment, which is freeing. Detach from outcomes while fully participating in the moment.

Transactionalists focus on outcomes as primary agents. Flowists are participants, with energy in the present moment, improving outcome probability. Becoming flow-oriented doesn't sacrifice transactional success; it eliminates wasted energy.

High achievers tie meaning to outcomes, leading to endless pursuit rabbit holes. They correlate decision-making with outcomes. After failure, most ask, "What did I do wrong?" This question assumes: (1) doing everything right guarantees success, (2) the mistake was yours—both egotistical and false.

Better question: "What happened?" or "Why did this happen?" Radical acceptance first. Analysis may reveal personal shortcomings (e.g., unpreparedness), but often prior self did the best possible. High performers believe they can cause outcomes every time, getting stuck in this mindset.

This stems from radical responsibility and high agency, a slippery slope. Leaning into agency creates impact but patterns rewarded professionally hurt personally. Rational analysis feels disempowering, risking victimhood narratives.

Take full responsibility for your finitude while growing. You're getting better, meaning you were worse before. No regrets because policy is to accept life fully; of course you'd do things differently now—otherwise, not paying attention. Like not picking different lottery numbers knowing outcomes.

Allocate finite, growing but decliningly available resource (yourself) across life aspects. Decide between unhappiness/suffering or joy en route. "Heaven all the way to heaven and hell all the way to hell."

Dave's wake-up: In 30s, workaholic in high-tech startups (70-80 hours/week, 3-4 hours sleep). Saturday morning, 3-year-old son Robbie asks mom, "Can we play with dad today or is he just going to fall asleep in the chair again?" Heart sank—didn't have a dad because he died (suicide at age 9); Robbie doesn't because dad asleep. Killing it at work but work killing him. Took 6 years to fix via radical change, learning to decelerate.

Tradeoffs exist: no solutions, best, right, done, max. Just choices. > "If I'm worth anything later, I am worth something now. For wheat is wheat, even if people think it is grass in the beginning." (Van Gogh)

"If you can't find enlightenment here, where are you going to find it? If you can't be happy with a coffee, you won't be happy on a yacht."

Objectively successful but subjectively miserable: achieved the thing, but doesn't feel like it. May have lost the why (Simon Sinek). Winning for winning's sake feels like dust. Post-achievement depression common among elites from overcommitting to performance, losing why.

Strive without missing life: Striving requires delayed gratification and future planning, pulling from present. But planning/training is an activity—enjoy it fully. Observer can notice present experience vs. outcome fixation. Even sacrifices (e.g., early gym) can be present (enjoy new reps/body feedback).

Risk: Insecure overachievers turn everything into performance, including meaning (practice-to-performance trap). Mindfulness gets transactionalized (e.g., streaks, shortening sits). Achieiving brain loves control. Invitation: Develop your practice for accessing meaning, permission to be happy.

Community is everything (Harvard Study, Bob Waldinger). Formative community (term from book): Three gathering types:

  • Social: Have good time.
  • Collaborative: Get something done (startups, military).
  • Formative: Become better together—intent on mutual becoming, not content/transaction/problem-solving.

In Stanford DCI program (10th cohort, 35-45 people 35-45yo), participants form deepest relationships ever, despite existing networks/families. Not random; enables resonance—you being you helps me be me. Impossible to hear yourself alone; social animals need places to be heard for growth.

Pushback on solopreneur/lone wolf: Seductive for building ego/self-trust early (first half of life), but temporary. Later, join something bigger. Co-working with similar trajectory accelerates (go faster together via shared fuel). Can be selfish about work goals but not live selfishly—find becoming conversations ("How's it going? Next question to grow into?") without goal problem-solving.

Signals in career conversations: thousands had with people.

People notice the work has left them rather than deciding to leave. Signals of change feel like an outside-in experience: going into the office and nothing happens in what used to be enlivening. It's like noticing the soundtrack has stopped and the movie might be over.

There's an awareness of your experience of something is shifting.

Bill, my partner, on Highway 280 driving into Apple, suddenly realized, "Oh, I'm done." He spent another year setting up how to quit, but the job left him right there. Leading up to that, stuff didn't feel as bright as it used to. Awarenesses can be sudden or grow over time.

This boils down to the Socratic idea: the unexamined life is not worth living. In an unexamined life, awareness comes slow and has to be dramatic.

High achievers are good at shutting up emotions and pushing through boredom, discomfort, low engagement, lack of aliveness—treating it as mere resistance to move through. The hypertrophied "move through it" muscle delays realizing it's not a right fit.

Seen in every industry: people outstay their aliveness by decades due to super hypertrophied delayed gratification (world champions at the marshmallow test) or lack of self-reflection to feel it.

Most people's besetting sin is not shadow dark side evil, but the overfunctioning strength.

There is absolutely too much of a good thing.

I'm too helpful. I'm too efficient. I'm too committed.

Stoics say moderation in all things: recognition that a good thing overexperienced—like productivity—is not good. Human experience is a mixed, hopefully balanced thing allowing capacity to be present and enjoying what is occurring.

Maxing out is important for a while. Advocate obsession, which recently changed opinion on—wrote an essay about it. Obsession is fleeting: confluence of desire, life situation, environment, meaning, motivation, skill set. Temporary.

Much of what looks like discipline now is the cooled aftermath of a past obsession. Started gym at 18 obsessed with bodybuilding forums, protein shakes, getting strong—two decades later still trains, but as a neutron star cooled from past obsession.

Serial obsessives justify going extreme, letting it consume. Strongest at 18-20s; now can poke nose above water line, look around—nice trajectory.

Rich, successful, happy people have survivorship bias. Model the rise, not the result: ask what they did at your stage. Even balanced people say family is most important, but at 25 they took a flamethrower to the candle. Would do the same, but sleep 6 hours not 4 to avoid health damage like atherosclerosis.

Reframe obsession as celebrating the scandal of particularity: suddenly obsessed with something means infatuated experience, which is temporary and lovely—go through it, make the most.

Most alive way is to be incredibly out of balance, going bat nuts about workouts, clearly identifying it's not the new norm to pull back later. Honeymoon phase for new experience.

Particularities include you and each day. Opportunities to be obsessed don't happen every day—have stoic relationship: most don't get worthwhile obsessions (politics, porn, ex). Life-giving, generative obsession with energy inflow/outflow.

Some go entire lives without obsessing over anything worth it—only lasts short time.

People cling to old obsessions like anorexic hermit crab in small shell for goal (Apple, EA). Like a relationship past its course: every minute spent is a minute not in the right one. No room for new obsession holding dwindling fire of last. Let it cool; some things from 20s no longer in life, others cooled to balanced version.

Grief year after wife Claudia died: leaned way in, obsessed with grieving well—killed it. People said first year hardest; on day 366 not transformed. But leaning in all way led to dream-state experience: Olympic marathon, last lap tunnel, crowd roars "Well done, Dave. You're done."

Part wanted to stop for loss of years 2-5 intensity. Now carries permanent befriended grief. New partner FR (soon wife) said: "I'm sorry I didn't meet Claudia, but look forward to getting to know her—the three of us will spend time together."

Missed that intense grief aliveness.

The addiction, the compulsion, the seductiveness of even negative emotions sufficiently intense that they make us feel alive.

Humans really like aliveness: rather be in pain and feel it than mundanity and feel nothing.

Befriend the longing: never get there, so if paying attention, stays interesting all the way.

Claudia's last words hours before dying: sits up, "Oh, it's so interesting," falls back—one foot on dock, one on boat pulling out, seeing stuff never seen.

Arie (real name Ronald, in Atlanta but really San Francisco, artist, died at 91). Days before dying—wheelchair, thin, teeth out, leaning on desk with blanket—says "David, read poetry to me. Get the Schwab on second floor." Read 18th-century romantic English poetry; he sighs, "Oh, it's so beautiful." Almost nothing left, but directed toward that.

We decide what to do with this life, how to allocate energies. Let them be what they can until they can't, then move on. Rein in obsession healthfully while it deserves, then move on.

Website: designingyour.life—takes to lots of places. Newsletter: Fully Alive by Design, weekly in mailbox. Book out a week from recording: How to Live a Meaningful Life: Using Design Thinking to Unlock Joy, Flow, Purpose, Flow, and Joy Every Day.

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