The 30-Day Fail Project — How Dads Raise Brave Kids by Going First
A 30-Day Field Guide

Your Kids Don't Need You to Be Perfect. They Need to See You Try.

A 30-day protocol — built over 13 years and refined with hundreds of dads — that turns small, awkward failures into the courage your kids will quietly inherit.

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Introducing The 30-Day Fail Project

The fix isn't a lecture. It's a practice.

A guided 30-day protocol that uses James Clear's Hats, Haircuts & Tattoos framework to train courage the way an athlete trains a muscle — one small, awkward rep at a time.

Each day you do one small, intentionally awkward thing in front of your kids. Wear mismatched socks. Order in a new language. Sing the wrong words to a song on purpose. Strike up a conversation with a stranger. Post the imperfect video.

Nothing reckless. Nothing dangerous. Just consistent reps proving — to your nervous system and to your kids — that discomfort is survivable.

By Day 31, you don't just know something different about courage. You are someone different. And your kids saw the whole thing.

The 30-Day Fail Project — book and bonus stack
Watch — 3 Minutes

The Fail Project, in my own words.

The Conversation This Came From

"I don't want to look stupid in front of everybody."

That's what my friend Mark's son said the week of baseball tryouts. He'd practiced for months. He loved the game. Then, at the last minute, he refused to go.

Mark told me later that something in him went cold the moment his son said it.

He realized he hadn't taught his son a single thing about caution. He'd just modeled it — across years — in a thousand small avoidances his son had quietly catalogued.

I'm hearing my own voice coming from my son.

If that line lands the way it landed for him — keep reading.

3 Quiet Signs This Is Happening In Your House

You're Teaching Safety Instead of Courage If…

1

You avoid your own discomfort

You sidestep anything that might embarrass you — modeling withdrawal instead of resilience.

2

You intervene quickly

You step in at the first sign of struggle — robbing your kids of small wins won through effort and risk.

3

You say "be careful" before "go for it"

Your default advice is about guarding, not growing. So they hesitate instead of exploring.

What's Inside (10+ Files)

Everything You Need to Run the 30 Days

Main Book · PDF

The Core Guide

26 chapters walking you through the science, the framework, and the daily practice — beautifully designed, no fluff.

Workbook · Interactive PDF

The Field Guide

A consolidated 15-page workbook with all 8 tools — fillable on screen, printable for the wall.

Tracker · Fillable PDF

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.

Calendar · PDF

The 30-Day Daily Calendar

Every day mapped out with its theme and suggested risk. So you never wake up not knowing what to try.

Reference · PDF

70+ Hat Risk Idea Bank

Categorized prompts — wardrobe, food, conversation, online, in front of the kids. You'll never run out.

Worksheet · Fillable PDF

The Tattoo Framework

Three-part worksheet to name the big-scary-thing you've been ducking for years — and take the first real step.

Worksheet · Fillable PDF

Haircut Risk Worksheet

Mid-challenge stretch picker. Brainstorm candidates, test against criteria, commit to a first action.

Daily · Fillable PDF

The Daily Debrief Sheet

Two minutes a night. The three questions that turn experience into growth.

Card · PDF

Embarrassment Reset Card

Wallet-fold card with five tools for the bad days. Print, fold, carry.

Reference · PDF

Family Conversation Prompts

For the weekly Two-Way Debrief. Post on the fridge.

From the Author

I Love the Process of Building a Life and Businesses that Work

At 29 I realized my thirst for getting everything right was holding me back. I'd gotten bad at being bad at things, which steered me away from the real things I needed to try. So I started a quiet experiment — every day, do one small, awkward thing on purpose. Sing the wrong words. Wear the dumb hat. Say the thing in the meeting. Just to prove to my own nervous system that discomfort wasn't fatal.

That experiment became the spine of the next 13 years. It got me into the best shape of my life. It got me the nerve to help take a company from startup to IPO, then co-found my own tech startup. Today it's the engine behind the work I do — helping founders and operators change their brains, launch their ideas, and build the growth engines behind them.

I'm not the dad in the room. I'm the friend with 13 years of receipts on the method — and the outside eye that sees patterns the dad inside the house can't. When the dads in my life started telling me they could see their own avoidance showing up in their kids, they asked me to build them a version they could run with their family.

So I did.

— Ryan Holdeman

What 30 Days Can Look Like

The Version of You Your Kids Are Waiting For

Imagine a version of yourself who doesn't just talk about courage, but demonstrates it — sometimes awkwardly, always openly. The dad who tries new things, laughs off mistakes, and shrugs off embarrassment because each small failure is a step toward deeper connection and real confidence — for you and your kids.

This isn't theory. It's reps. And the next month will rewire not just your routines, but your relationship with your kids.

"Day 1 felt ridiculous. I wore mismatched socks and I expected my kids to roast me at breakfast (they didn't). By the end of the month, my son was telling me about something he was scared to try at school (girl stuff). That conversation doesn't happen if I'm still pretending I'm above embarrassment."
— Matt R. · Dad of 2 · Denver, CO
"This helped me become the kind of dad I kept telling my kids to be. I've said 'go for it' a hundred times. But for 30 days, they saw me go first. That changed the tone of our home."
— Michael S. · Dad of 3 · San Diego, CA
"I thought this would be cheesy. It wasn't. It gave me a simple way to show my kids that courage isn't a speech — it's a rep. We laughed more in 30 days than we had in months."
— Chris M. · Dad of 3 · Boulder, CO
"The biggest surprise was how quickly my kids started paying attention. I didn't have to announce some huge parenting lesson. They just watched me do awkward things, recover, and keep going. That landed way more than another lecture about confidence."
— Jason T. · Dad of 2 · Fort Collins, CO
"I didn't realize how casually I was teaching my kids to avoid discomfort until I started practicing not avoiding it myself. The 30 days gave us a shared language: 'Was that a hat risk or a haircut risk?' Now we talk about bravery like it's normal."
— Ben H. · Dad of 2 · Colorado Springs, CO
"My daughter has always been hard on herself when she makes mistakes. Watching me mess up on purpose — and laugh about it — softened something in her. She started trying again faster. That alone was worth it."
— Andrew K. · Dad of 1 · Lafayette, CO
"The daily risks were small enough that I actually did them, but uncomfortable enough that they mattered. By week four, I wasn't just checking off a tracker. I was becoming less fragile in front of my kids."
— David L. · Dad of 2 · Los Angeles, CA
Get Started Tonight

The 30-Day Fail Project

Instant download. Start tonight. Run for 30 days. Watch what happens to your kids.

The 30-Day Fail Project — book and bonus stack

Here's everything you get

Delivered instantly to your inbox

  • The 30-Day Fail Project Core Guide (26 chapters)$37 value
  • The Field Guide consolidated workbook$27 value
  • The 30-Day Risk Tracker (interactive)$17 value
  • The 30-Day Daily Calendar$17 value
  • 70+ Hat Risk Idea Bank$17 value
  • The Tattoo Framework Worksheet (3-part)$17 value
  • The Haircut Risk Worksheet$12 value
  • The Daily Debrief Sheet$9 value
  • The Embarrassment Reset Card (wallet-fold)$9 value
  • The Family Conversation Prompts$9 value
    • Total value$171
$67 $27 One-time payment · Instant access · 30-day guarantee
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Secure checkout · No subscription · Audio Companion add-on at checkout

The "It Didn't Move You" Guarantee

Run the 30 days. Show up daily. If by the end you and your family aren't seeing real shifts — more laughter, more attempts, more conversations — email me. I'll refund every cent. The risk is mine, not yours. (That's kind of the whole point.)

Questions Other Dads Ask

FAQ

You're not a dad. Why should I trust you?

Fair question. I'm not coming at this as a parenting expert. I'm coming at it as the friend who's been running this protocol for 13 years on myself and on a couple hundred other people — including 20 of my coworkers as a single 30-day cohort. The dads I'm closest to asked me to formalize what we'd been doing in our conversations. So I did. The method works on courage in general. I adapted it for the specific job of modeling for kids — because that's what my friends needed.

I'm not a "weird" guy. Will this feel forced?

The first few days might. That's the point. Discomfort is the signal you're rewiring something. The exercises start small — small enough that you'll only feel a flicker. The reps stack from there.

What if my spouse thinks this is dumb?

There's a whole section in the FAQ on this. Short version: don't sell it. Just do it. Most spouses come around quickly when they see the change in you and in your kids.

My kids are little. Does this still work?

Yes. Younger kids absorb modeling even more intensely than older kids. The book includes age-appropriate adjustments for 5-12, which is the sweet spot — but it works for any age.

What if I miss a day?

You will. Pick up where you left off. The 30 days are a path, not a prison.

What format is the product?

Beautifully designed PDFs — book, workbook, and 7 separate bonus artifacts. Most of the workbook fields are interactive so you can fill them out on your phone or tablet. Print anything you want. Delivered instantly to your inbox.

What's the refund policy?

30 days. Run the challenge. If it didn't move you, I'll refund every cent. No hard feelings.

One More Thing

A note from Ryan.

Your kids are watching either way.

The only question is: what are they learning from you this month?

Start The 30-Day Fail Project — $27

"Children learn more from what you are than what you teach." — W.E.B. Du Bois

The 30-Day Fail Project
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