The One Big Thing Calendar
Schedule one defining challenge each year before routine crowds it out
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 6
- Confidence
- 94%
Established routines make novelty increasingly unlikely: work, home and family obligations repeat unless something interrupts them. The One Big Thing Calendar creates that interruption deliberately. Start with a lifetime experience that has remained undone, select one substantial challenge for the year, and reserve its dates before waiting for a perfect opening. Then clear competing obligations and invite people who will enrich the experience. The mechanism is commitment through scheduling: a wish becomes a bounded project, and the fixed project forces practical decisions about time, preparation and companions. Success is not limited to speed or records. The challenge should create newness, relationships and memories as well as a finish line, so the process improves life even when execution stays flexible.
Origin
Jesse Itzler said he had followed the philosophy for years after making a lifetime list in 2006. Riding across the United States remained on it until he and a friend decided there was no better time, carved out two weeks and assembled a group.
Core principles
- 01New experiences rarely happen by accident in an established life
- 02A calendar commitment turns a distant wish into a real project
- 03A meaningful challenge can combine growth, friendship and enjoyment
- 04The right time often has to be created rather than found
How to run it
- 1
Revisit the lifetime list
Identify an experience that has mattered for years but keeps losing to ordinary obligations.
Pro tip Choose something you would still value even without public recognition.
Watch out Do not confuse a fashionable stunt with a personally meaningful goal.
- 2
Choose this year's big thing
Select one challenge substantial enough to create genuine newness and define the year's adventure.
Pro tip Look for a challenge that combines several values, such as endurance, friendship and exploration.
Watch out Avoid stacking several major challenges that compete for the same time and recovery.
- 3
Put it on the calendar
Reserve a real time window instead of waiting for life to become quiet on its own.
Pro tip Work backwards from the fixed dates to expose preparation and logistics early.
Watch out A goal without protected dates can remain a wish indefinitely.
- 4
Clear the slate
Treat the challenge as the primary job during its window by resolving or delegating competing work beforehand.
Pro tip Discuss the commitment early with the people affected by your absence.
Watch out Entering with unresolved obligations divides attention and weakens the experience.
- 5
Build the right group
Invite people with compatible values and enough capability to contribute safely, not merely the most impressive résumés.
Pro tip Optimise for support, shared curiosity and group chemistry.
Watch out One ego-driven participant can damage the experience for everyone.
- 6
Design the whole experience
Include recovery, friendship and memorable rituals rather than reducing the event to a performance metric.
Pro tip Decide what stories and relationships you want to carry home.
Watch out Do not let tracking or external proof replace the reason for doing it.
In the wild
A coast-to-coast bicycle ride had remained on Jesse's lifetime list since 2006. He and Chris reserved two weeks, recruited friends, cleared their schedules and built the trip around camping, recovery and time together as well as covering 3,000 miles.
→ A long-delayed wish became a scheduled shared adventure with a defined start and finish.
A founder chooses a three-day guided trek as the year's big thing, reserves the dates six months ahead, arranges business cover and invites two close friends. Training becomes manageable because the commitment is fixed.
→ The founder creates novelty and connection without waiting for an empty calendar.
Common mistakes
Waiting for the right time
Work and family routines rarely create a clean opening by themselves. The framework works because the experience is scheduled first and the opening is deliberately made.
Making metrics the whole point
External proof, rankings or tracking can crowd out friendship and exploration. Define the experience more broadly than the number achieved.
Choosing companions by ability alone
Technical strength cannot compensate for poor group chemistry on a demanding shared trip. Select for values and support as well as competence.
Is it for you?
Best for
Busy adults who want adventure and growth but need a concrete commitment to make them happen.
Not ideal for
People whose health, finances or essential responsibilities cannot safely accommodate a major challenge yet.
From the transcript
“every year I try to put something big on my calendar”
“as you get older to create newness is really hard like where does newness come from you have to schedule it”
“this is about newness it's about the if it's not the unknown like how do we plan it”
From the episode
Episode 237: All Day Running Co.: The Mindset, Lessons, and Benefits Of Biking 3,000 Miles Across America
All Day Running Co.