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BONUS | No One Is Coming to Give You Permission

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Feb 5, 2026

Guest

Brent Underwood

Brent Underwood, owner of Cerro Gordo and author known for Ghost Town Living, shares how waiting for permission and perfect conditions becomes procrastination. They cover deadlines vs open projects, using accountability and consequences to finish work, fear that success will overload future bandwidth, and practical habits like one hour a day and iterating early.

39:31

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ANECDOTE

Publisher Ultimatum Forced Completion

Brent delayed his book multiple times until the publisher threatened to cancel the contract.
That external ultimatum suddenly produced the work and finished the manuscript.

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ADVICE

Use External Accountability

Use accountability partners or contractual consequences to force progress on projects.
External pressure can convert chronic procrastination into finished work quickly.

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ADVICE

Make Failure Painful

Make failure costly to yourself by using public deadlines or financial stakes to motivate completion.
Tools like escrow penalties or public commitments change incentives and reduce procrastination.

Get the Snipd Podcast app to discover more snips from this episode

Why Brent hesitates to start open projects

02:57 • 3min

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Deadlines, perfectionism, and approval

06:05 • 2min

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Using accountability and consequences to finish work

Practical advice: one hour a day

14:40 • 3min

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Seneca on always getting ready

17:45 • 4min

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Fear of future bandwidth and success

21:50 • 4min

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Start the clock: iterate and learn

Small tasks, big procrastination cost

30:53 • 2min

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Avoid all-or-nothing and write daily

32:30 • 4min

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The myth of writing retreats and environments

36:30 • 4min

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Set commitments and begin now

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If your New Year motivation didn’t make it to February, this episode is for you. Ryan and his business partner and longtime friend, Brent Underwood, talk about how waiting for permission, perfect conditions, or external validation quietly turns into procrastination, even for high performers. They discuss why open-ended ambitions are harder than deadlines, how success can actually make starting new things scarier, and the trap of telling yourself, “I’ll get to it later.”

Let’s not write the year off just yet. The Daily Stoic New Year New You challenge is opening back up for a limited time. Learn more and sign up today at dailystoic.com/challenge.

👉 Get The Daily Stoic New Year New You & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life

Brent Underwood is the owner of Cerro Gordo, an original boomtown silver mine, established in 1865. Check out Brent's book Ghost Town Living: Mining for Purpose and Chasing Dreams at the Edge of Death Valley at The Painted Porch.

Youtube: @GhostTownLiving

IG: @BrentWUnderwood

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