CHAPTERS
- 0:00 – 4:10
2020: A Year of Perspective and Uncertainty
Bartlett opens by framing 2020 as one of the craziest and most perspective-shifting years in recent history. He describes the losses people around him have suffered—loved ones, health, businesses—and explains how crises teach us far more than times when life feels predictable and comfortable.
- •2020 forced a collective reflection on the past year and hopes for 2021.
- •Many people experienced severe losses: death, long-term health issues, and destroyed livelihoods.
- •We learn little when life is easy and predictable; disruption accelerates learning.
- •The foundations we thought were stable—jobs, health, routines—suddenly felt unreliable.
- •This shock created a new, less complacent perspective focused on what and who actually matter.
- 4:10 – 8:40
Black Swan Events, Social Media, and Fragile Certainty
He introduces the idea of 2020 as a ‘black swan’ event for a generation that has never known true hardship in adulthood. Bartlett criticizes the spread of conspiracy theories as a symptom of people’s inability to accept that bad, chaotic things can simply happen without a grand plot.
- •Defines black swan events as unpredictable events with severe, widespread consequences.
- •Lists historical examples: the Great Depression, Spanish flu, World Wars, dotcom bubble.
- •Argues younger adults haven’t faced such events before, and it shows in their disbelief.
- •Links social media-era conspiracies (5G, Bill Gates, Illuminati) to discomfort with randomness.
- •Speculates how much worse misinformation would have been during the 1918 Spanish flu with Facebook.
- 8:40 – 12:00
Mortality, Fragility, and the Call to Truly Live
Bartlett distills 2020’s core lesson: nothing is guaranteed—not health, jobs, dreams, or relationships—and we are all mortal. Rather than succumbing to pessimism, he argues that this realization should trigger optimism, urgency, and gratitude, pushing us to stop procrastinating and live fully.
- •Life and society are fragile; chaos is certain even if specifics are unpredictable.
- •Awareness of mortality can be misread as pessimism, but he frames it as empowering.
- •If nothing is guaranteed, the rational response is to start living now, not ‘one day.’
- •He calls out procrastination, self-doubt, fear, and ego as illusions from a mind that thinks time is infinite.
- •Reduces what ultimately matters to a few essentials: your health, your happiness, and the wellbeing of loved ones.
- 12:00 – 15:50
Personal Confessions: Fear, Ego, and Misplaced Priorities
In a candid section, Bartlett admits that despite outward success, he has often held himself back. He recounts moments of fear, pettiness, and superficial focus, recognizing how foolish those behaviors look when contrasted with the finite nature of life.
- •Even as a young, ‘successful’ entrepreneur, he admits he hasn’t fully lived.
- •Examples: not speaking up, failing to express love, letting fear make decisions, procrastinating.
- •He allowed Twitter trolls, superficial validation, and ego to dictate his emotional energy.
- •He has hurt people who loved him and avoided responsibility in some areas.
- •The new perspective of fragility makes grudges, superficiality, and ego-driven decisions look profoundly stupid.
- 15:50 – 20:40
Life Milestones, Aging, and the Realization of Time Passing
A close friend’s pregnancy, a late-night walk to the gym, and even a questionable haircut trigger Bartlett to confront his own aging and mortality. He unpacks diary prompts like ‘Hurtling towards death’ and ‘Why are we half-living?’ to explore how life stages can jolt us awake.
- •Friend’s baby news feels like his own life advancing into a new phase.
- •He writes diary prompts while walking: ‘Hurtling towards death,’ ‘Receding hairline,’ etc.
- •We rarely notice aging because it’s gradual and we age alongside peers.
- •Significant life events—friends’ babies, parents aging, hairlines receding—make time’s passage undeniable.
- •He argues most decisions are made as if we’ll live forever, which is a core mistake.
- 20:40 – 25:00
What the Hell Is Everyone Doing? Half-Living and Wasted Time
Seeing a man slumped at a bus stop sparks a raw internal question: ‘What the fuck is everyone doing?’ Bartlett clarifies he knows not everyone has full choice, but he uses the moment to highlight how absurd it is to squander time if you truly believe life is finite.
- •He visualizes himself and others as ‘on a clock,’ represented by a sand timer he keeps nearby.
- •When you genuinely feel time is limited, wasting it on the wrong people or jobs looks insane.
- •He acknowledges structural constraints but still urges deep self-audit of where time goes.
- •He links understanding mortality with making better decisions through a completely different perspective.
- •Frames ‘How dare you?’ as a rebuke to himself and others for not respecting the preciousness of time.
- 25:00 – 31:40
Create Memories and Choose the Right Buckets
Bartlett shifts to the importance of memories and how aging changes how we value them. He introduces the ‘buckets’ metaphor to describe where we invest our limited caring capacity, arguing that pandemics and crises reveal which buckets are truly worth our time.
- •Lockdowns robbed many people of chances to create meaningful memories in 2020.
- •He notes that as we age, we typically spend less time with friends and extended family.
- •His friendship group is collectively realizing that money is best spent on unforgettable shared experiences.
- •A friend’s impending fatherhood may limit spontaneous travel, increasing the value of current memories.
- •He describes ‘good’ buckets (career, family, meaningful relationships) and ‘toxic’ buckets (materialism, social media validation, fear).
- •Caring is costly; a better life requires caring deeply about fewer, more important things.
- •Quotes Marcus Aurelius about giving attention in proportion to worth and avoiding lesser distractions.
- 31:40 – 34:30
Resolve to Live Boldly: Love, Risk, and Cutting Dead Weight
Before transitioning to productivity, Bartlett offers a call to action for 2021: do not let fear win. Using Stoic quotes as a backdrop, he lists concrete behaviors that embody living urgently—taking risks, expressing love, learning, and cutting toxic ties.
- •Reinforces Stoic advice: stop being distracted; live as if you were dying now.
- •Encourages spontaneity: book flights, apply for opportunities, start businesses, learn new skills.
- •Advocates saying ‘I love you’ more, even when ego resists.
- •Pushes for blocking people from the past who drag you backwards.
- •Ties urgency to conquering procrastination and making 2021 meaningfully different from 2020.
- 34:30 – 39:00
From To-Do Lists to Time Blocking: A Productivity Shift
Bartlett transitions into a concrete productivity strategy born from the unstructured nature of remote work in 2020. He critiques traditional to-do lists and explains how moving tasks into time-blocked calendar slots transformed his output.
- •Lockdown removed his usual structure of full meeting calendars and travel.
- •To-do lists feel good but lack urgency, time constraints, and consequences; tasks expand and get delayed.
- •He continues to use to-do lists only as a capture system, not an execution system.
- •The key change: transfer each to-do into a specific time slot in a calendar.
- •He built a custom app, Timeblock, combining a to-do list with a visual calendar, but notes any calendar will work.
- •Time blocking creates urgency, clarifies priorities, and reduces the chance of aimless YouTube or social media binges.
- 39:00 – 41:30
Designing for Future You: Empathetic Scheduling
He shares mistakes from his early time-blocking attempts and the insight that you must be realistic and compassionate toward your future self. By scheduling breaks and leisure as deliberately as work, he makes time blocking sustainable and effective.
- •Initial mistake: scheduling relentless 7 AM–midnight days that future Steve could never realistically follow.
- •Distinguishes between ‘planner you’ (now) and ‘executor you’ (future), who must live the schedule.
- •Builds empathy for future self by adding rest periods and unstructured downtime into the calendar.
- •Literally schedules ‘do nothing’ time, social media, and watching Manchester United.
- •Warns that without kindness and realism, time-block systems will be abandoned.
- 41:30 – 43:00
Sponsor Interlude: Huel and Health as a Foundation
Bartlett briefly promotes Huel, tying the product into his broader themes of health, convenience, and consistency. He emphasizes his genuine use and belief in the product while noting the creative freedom Huel gives him as a sponsor.
- •Credits Huel for helping him reach the best physical and mental shape of his life.
- •Highlights the convenience and nutritional completeness of Huel, especially amid a busy life.
- •Emphasizes authenticity: he drinks it daily and is not scripted by the sponsor.
- •Encourages listeners who skip meals or struggle with diet to try it.
- •Signals he will share a personal story related to Huel in part two.
- 43:00 – 49:40
Parkinson’s Law and the Power of Urgency
Returning to a thematic throughline, Bartlett doubles down on urgency as a central lesson from 2020 and his entrepreneurial journey. He explains Parkinson’s Law and illustrates how compressing timelines can radically change outcomes in both business and personal life.
- •Defines Parkinson’s Law: work expands to fill the time allocated.
- •Examples: a paper given two weeks will take two weeks; a full-day house clean will fill the day.
- •Clarifies that urgency is not about burnout or busyness, but about fast-tracking what truly matters.
- •Describes a failed internal project that dragged on for months due to lack of deadlines and accountability.
- •When he personally applied urgency—building a tool with a freelancer over one weekend—it succeeded and proved his hypothesis.
- •That tool, Likewise, generated thousands of inquiries and made the company millions over years.
- •He formed a small WhatsApp group ‘Move Fast and Make Things’ with a strict two-week deadline for any project.
- •Short deadlines forced creativity, dismantled excuses, and showed how much is possible in compressed time windows.
- 49:40
Memento Mori: Stoic Urgency and a Life Without Regret
In the closing section, Bartlett ties urgency back to Stoic philosophy and his own changing relationship with death. He argues that remembering we can ‘leave life right now’ should generate clarity, gratitude, and decisive action, not paralysis.
- •Explains the Stoic concept of memento mori: remembering your own mortality as a guiding principle.
- •Quotes Marcus Aurelius: ‘You can leave life right now; let that determine what you do and say and think.’
- •Frames death not as something to fear but as a tool for priority-setting and gratitude.
- •Shares that once he became agnostic rather than religious, his fear of death diminished.
- •Notes 2020 was saturated with loss—millions of deaths and everyone knowing someone affected.
- •Urges listeners to treat urgency as proof they understand life’s preciousness and to declutter their lives of what doesn’t matter.
- •Reiterates his own goal for 2021: to become even more urgent, despite others already seeing him that way.
- •Closes the diary, invites subscriptions and reviews, and tees up part two for early January.
