The Fail Project — try. fail. laugh. try again.
A protocol for trying things

try. fail. laugh. try again.

A small, slow rebellion against the version of you who plays it safe.

The Fail Project is a 13‑year experiment in building courage on purpose — and a home for the essays, tools, and 30‑day cohorts that came out of it. Watch the 3‑minute story below, then grab the field guide or join the list.

The story behind it

Most of us aren't blocked by failure. We're blocked by the fear of it.

Years ago, at the edge of a milestone birthday, I realized something quiet and uncomfortable: I'd built my life around not feeling failure. I ran one mile instead of ten. I added $1K to my income instead of 10x‑ing it. I made moves only the size I was sure would succeed.

And I was angry at myself for not hitting goals I'd never actually set.

So I gave myself a year to fail at things on purpose.

Trapeze. Ballroom dance. Salsa. Cold approaches. Restaurants I'd known about for years but never walked into. A list of things I was sure I'd flop at.

I failed at my goal. I succeeded at almost everything on my I‑will‑likely‑fail‑at‑this list.

Turns out I'd been cutting my own legs out from under me by assuming I'd fail at things I'd never even attempted. My comfort zone was smaller than my actual capability.

Try. Fail. Laugh. Try again. Try until trying is easy.

The Framework

The Fail‑Win Loop.

Every Fail Project tool — the field guide, the audio, the cohorts, the host kit — runs on the same daily loop. Four steps. One built to compound.

1

Risk

Take one small, intentional act of awkwardness. A Hat. A Haircut. A Tattoo. The size grows with the rep.

→
2

Process

Three light moves to lock the rep in before your brain rewrites it as "no big deal" or "that was dumb":

  • Reward — name what was hard, then mark the win.
  • Journal — write what surprised you in two lines.
  • Discuss — say it out loud to one person.
→
3

Rest

The nervous system stores the rep when you stop hammering at it. Sleep, a walk, distance from the moment — required, not optional.

→
4

Repeat

Tomorrow: a slightly bigger rep. The loop is the protocol. Run it daily and notice what becomes ordinary.

This is the engine. Everything else — the 30‑Day Fail Project, the Audio Companion, the cohorts, the host kit — is scaffolding for this one loop, run daily.

The two ways to start

Pick the door that fits.

Two offers wrap the protocol. Same field guide. One adds the audio that makes most dads finish.

The Field Guide

The 30‑Day Fail Project

Everything you need to run the 30 days on your own pace. The complete print‑ready protocol — 10+ files, lifetime access, instant download.

  • The Core Guide — 26 chapters
  • The Field Guide workbook
  • The 30‑Day Daily Calendar
  • 30‑Day Risk Tracker (interactive)
  • 70+ Hat Risk Idea Bank
  • Tattoo + Haircut Worksheets
  • Daily Debrief Sheet
  • Embarrassment Reset Card
  • Family Conversation Prompts
$27 one‑time
Get the field guide

No audio · Same 60‑day guarantee

Recommended · Most popular
The Complete Bundle

The 30‑Day Fail Project + Audio Companion

Everything on the left, plus the full audiobook narrated by Ryan and 30 daily 6 AM cues that make dads 3× more likely to finish.

  • Everything in The Field Guide
  • + Audiobook (narrated by Ryan)
  • + 30 Daily Audio Cues (6 AM)
  • + Private podcast feed
  • + Lifetime audio access
$44 one‑time · $17 more
Get the bundle — $44

Most dads pick this · Same 60‑day guarantee

Inside the protocol

The eleven pieces that make the 30 days work.

Each piece is its own file. All ten field‑guide pieces are included in both offers above. The Audio Companion is the difference between the two.

PDF
01 · Main Book

The Core Guide

26 chapters walking you through the science, the framework, and the daily practice. The book the whole protocol is built around. Beautifully designed, no fluff.

$37 valueIn both offers
PDF
02 · Workbook

The Field Guide

A consolidated 15‑page workbook with all 8 tools — fillable on screen, printable for the wall. The protocol's working surface.

$27 valueIn both offers
PDF
03 · Calendar

The 30‑Day Daily Calendar

Every day mapped out with its theme and suggested risk type. Tape it on the bathroom mirror so you never wake up not knowing what to try.

$17 valueIn both offers
PDF
04 · Tracker

30‑Day Risk Tracker

Type your daily risk and check it off. Tape it up or fill it in on your phone. 47 interactive fields covering all 30 days.

$17 valueIn both offers
PDF
05 · Reference

70+ Hat Risk Idea Bank

Categorized prompts — wardrobe, food, conversation, online, in front of the kids. The first place to look on a day when you can't think of anything.

$17 valueIn both offers
PDF
06 · Worksheet

The Tattoo Framework

Three‑part worksheet to name the big‑scary‑thing you've been ducking for years — and take the first real step. The "big" version of the protocol.

$17 valueIn both offers
PDF
07 · Worksheet

Haircut Risk Worksheet

The mid‑challenge stretch picker. Brainstorm candidates, test against criteria, commit to a first action. For the bigger moves in the middle of the month.

$12 valueIn both offers
PDF
08 · Daily

The Daily Debrief Sheet

Two minutes a night. The three questions that turn experience into growth. The single most under‑rated tool in the protocol.

$9 valueIn both offers
PDF
09 · Card

Embarrassment Reset Card

Wallet‑fold card with five tools for the bad days. Print, fold, carry. Pull it out when you flop and your nervous system needs help recovering.

$9 valueIn both offers
PDF
10 · Reference

Family Conversation Prompts

For the weekly Two‑Way Debrief. Post on the fridge. Turn the whole month into a household conversation instead of a solo experiment.

$9 valueIn both offers
AUDIO
11 · Bonus

The Audio Companion

The full book narrated by Ryan plus 30 short daily cues that drop in your podcast app every morning at 6 AM. Dads who add this finish the 30 days at 3× the rate of dads who don't.

$47 value Bundle only
Combined value of all eleven pieces
$218 · You pay $27 or $44
See the offers
The Audio Companion

Why most dads add the audio.

Reading the book is one thing. Hearing it from me, in your earbuds, while you're walking the dog or driving to work — that's when the practice actually sticks.

Dads who add the audio finish the 30 days at 3× the rate of dads who don't.
From the 200+ person cohort that ran the protocol in 2024–25.
  • 📖
    Full Audiobook (~2.5 hrs)Every chapter, narrated personally by Ryan. MP3 download + private podcast feed.
  • ⏰
    30 Daily Cues (~2 min each)A short audio dropped at 6 AM every morning. Names the day's risk type and pushes you to take it.
  • ∞
    Lifetime accessYours forever. No subscription. No second checkout.
🎧

The book in my voice + a 6 AM nudge.

Paste the private feed URL into Apple Podcasts, Overcast, or Spotify. One new episode at 6 AM each morning for 30 days.

Included in the $44 bundle
More ways to engage

If you're not ready for the 30 days, start somewhere else.

The Fail Project is bigger than one product. The essay started it, the newsletter feeds it, the cohorts test it together, and the host kit lets you run it with friends.

Free essay + guide

The Fail Project Essay

The 2,500‑word piece that started the whole thing — plus the Quick Start guide that walks you through naming what you actually want.

Read in 12 min · Free PDF
Read & download Cohort · Coming soon

Run the 30 Days With Friends

A live, time‑boxed cohort. Daily prompts, a weekly call, and 30 days of doing this alongside other people who are sick of playing small.

Next cohort · TBD · Join the waitlist
Join the waitlist For leaders

Host Your Own Cohort

Run the Fail Project with your team, church group, or friends. White‑labelable kit, facilitator guide, and the protocol used with 20 coworkers at a time.

For teams of 8+ · Roadmap pricing
See the host kit Writing

Notes & Essays

Short‑form writing on courage, identity, the internal battle, and building a life that works. Updated on ryanholdeman.com/reps.

Free · Updated weekly‑ish
Read the blog Newsletter

Try. Fail. Try Again.

A short note in your inbox most weeks. One idea, one prompt, one thing to try. The cheapest way to stay in the project.

Free · 1 email / week
Subscribe Flagship · $27 – $44

The 30‑Day Fail Project

The complete protocol — book, workbook, calendar, worksheets, prompts. Optional Audio Companion for the bundle. Where most people start.

10+ files · Instant download
See the offers
About Ryan

I'm the friend in the room who kept hearing it.

I'm Ryan Holdeman. I run operations at an influencer marketing company and I do fractional growth work for founders. But the work I'm proudest of is the quiet protocol I've been running on myself and the people around me for 13 years.

I'm not a coach. I'm not a guru. I'm a systems guy who got tired of his own avoidance — and noticed that almost everyone I love was carrying a version of the same thing. The Fail Project is what came out of that.

More about me at ryanholdeman.com →