The messy side of building a dream… and the magic that came from every single “fail.” -

Thursday, February 29, 2024

Introduction:

In honor of my ten-year coaching anniversary (say whaaaat!?), I decided to share ten stories of epic fails and major disappointments that ultimately led to powerful lessons.

At first, I wondered if I could even name ten. Now that I’ve been brainstorming, skimming old journals, and writing, I can say with absolute certainty: the hard part wasn’t finding ten… it was choosing only ten. You’ll see I didn’t stop at ten.

I forgot how many times I wanted to quit and walk away. This work is beautiful, meaningful, transformational—and also really hard. Then, just when I felt discouraged, something magical would happen: a client breakthrough, a fresh idea, or the thought of putting on shoes and leaving the house. Suddenly the spark would return.

Here’s the happy, cheery, ignorance-is-bliss face of me earning my first (of many) coaching certificates in Los Angeles on March 9, 2014. Mary Morrissey of the Life Mastery Institute trained, coached, and mentored us. Her framework beautifully dovetailed with my 17-year background in teaching and counseling.

1. When the Failures Felt Heavier Than the Wins

The moment I realized my disappointments were shaping me more than my victories.

It’s easy to love an epic success story—the underdog rising, the triumphant comeback. But when I sat down to write my own “top ten fails,” I felt a pit of sadness.

On paper, it looked like the disappointments outweighed the wins. Money spent on experts with very little return. Programs that didn’t launch the way I dreamed. Giant opportunities that quietly faded away.

Feeling too ashamed, I shared only one story.

Recently, I decided it’s time to let go of the coulda-shoulda-woulda beliefs. There is no such thing as failure. It’s all feedback. If this series had a name, it might be Three Feet From Gold—but I prefer I Didn’t Come This Far to Only Come This Far.

Lessons:

💥 We are all a work in progress; there is no finish line.

💥 It’s okay to cringe on the way to loving your whole story.

💥 Vulnerability is a powerful form of bravery.

2. My First Digital Course Flop

Eighteen months of work. Two sales. Ouch.

My first digital course took about 18 months to create and launch. I surveyed my email list, gathered their struggles, organized the top themes, and built a 5-session course around their needs. I offered it live many times—at my dining room table, adult ed programs, yoga studios, wellness centers, even rented conference rooms. Eventually, I had it professionally filmed and edited.

I was so excited. This was going to be my passive-income golden ticket.

I sold… two copies. One to a college friend. One to my aunt who felt bad for me.

The course has long since been retired and does not appear in the dynamic digital library I offer today.

Lessons:

💥 There’s no such thing as an overnight success.

💥 Success leaves clues—notice what actually worked.

💥 “The first draft of anything is shit.” —Ernest Hemingway

3. The Card Deck That Didn’t Save the Course

Surely the deck would lead people back to the course… right?

Since the digital course wasn’t selling, I created a 26-card deck using questions from the five sessions. My logic: anyone who bought the deck would want the course to go with it.

Nope. Not true.

Lessons:

💥 Expectation is resentment waiting to happen.

💥 Wishful thinking isn’t a marketing strategy.

💥 Creative problem-solving is a gift (and I love the deck!).

4. The Cards That Didn’t Fit… and the Cat That Finished Them Off

Manufacturing mistakes, launch panic, and a very unhelpful cat.

I ordered 500 of each card (13,500 total), and my friends and I spent hours collating them perfectly. Only then did I realize the stack was too thick for the cute tin I bought. My launch party at a local gift store was two days away.

Cue panic.

I rushed to package them in wedding favor bags instead, then ordered new, thinner cards that actually fit the tins.

And then—the cat sprayed half the 500 bagged decks. They were soaked in feline stench. Into the trash they went.

Lessons:

💥 Ask better questions.

💥 Get the details before you invest—clarify and verify.

💥 Shift attention from problems to solutions; energy grows where it goes.

💥 Be a dog person.

5. The TJX Almost-Big Break

4,800+ stores. One massive “maybe.” And one very real fear.

A serendipitous connection got my deck onto the TJX buyers’ table (TJ Maxx, Marshalls, HomeGoods, etc.). The initial response was positive, but the book buyers would make the final decision.

They told me the deck would sell for $3.99…and if they said yes, I needed to ship 10,000 units immediately.

I had zero manufacturing knowledge and was terrified. If they said no, I pictured my basement filled with decks for years.

I froze. The opportunity passed.

Lessons:
💥 Find the experts and model their success.
💥 Get a mentor who’s learned it and earned it.
💥 Fear doesn’t mean you can’t—it just means you haven’t (yet).

6. The TEDx Talk That Didn’t Change Everything

I thought life would explode. Instead, I walked the dog.

I was convinced my TEDx talk would put me on the radar for bigger stages. After the event, I expected invitations, opportunities, momentum.

Instead, I drove home, peeled off my Spanx, and took Tootsie for a walk.

Lessons:
💥 Celebrate immediately after an achievement.
💥 The experience is often more important than the outcome.
💥 Don’t wait for invitations—initiate opportunities.

7. The iHeartMedia Buzz… and the Two-Year Follow-Up with Crickets

A huge moment. A huge invitation. Then—nothing.

iHeartMedia hired me for a pep-rally workshop when their advertising team had been crushed by COVID. It was a massive success, and they immediately wanted me to present in as many markets as possible.

I kept showing up, reaching out, adding value… for two years.

Crickets.

Lessons:
💥 Leverage your resources—who else can open the right doors?
💥 If it’s not working, stop. Pivot. Try again.
💥 Serve at the highest level and offer value without expectation.

8. My First Membership Burnout

“More” was not better. Not even close.

My first membership, Midlife Redefine, followed all the “right” steps for launching. I was enthusiastic—maybe too enthusiastic. I over-delivered: more lessons, more worksheets, more calls, more everything.

We all hit burnout.

After agonizing, I closed and rebranded. Five years later, it now exists in its third (and best!) iteration.

Lessons:
💥 Stay results-oriented, not activity-focused.
💥 More is not better.
💥 Use the recipe for success—and add your own flair.

9.The Big Corporate Connections That Slipped Away

KFC. New York Life. Dartmouth. All “almost.” All heartbreaking.

In a long airport line, I connected with an incredible woman—a high-ranking leader at KFC. She loved what I did and wanted to hire me for her management teams.

We kept in touch for a while. Then… I kept in touch a lot longer.

The same thing happened with a powerhouse at New York Life. And again at Dartmouth College.

It’s hard to watch big opportunities slip away. Scaling is so much easier with “same act, different audience” inside large organizations.

Lessons:
💥 Relationships matter—nurture them consistently.
💥 Every experience brings you closer to what you desire.
💥 “Rejection is God’s protection.” —Jamie Kern Lima

10. That Time I Sh*t the Bed on Stage

Yes, really. And yes, the video still exists.

Watch it here: https://www.youtube.com/watch?v=4KSZkUkVo6Q

Lessons:
💥 Ask for help.
💥 Be authentic.
💥 Other people’s opinions are none of your business.

11. When My Part Got Cut from Matthew McConaughey’s Program

Alright, alright, alright… or maybe not.

In 2023, I was invited to participate in the rough cut of Matthew McConaughey’s new coaching program. About a dozen of us beta-tested the course, filmed our responses, and provided raw, relatable footage.

It would’ve been super fun to leverage the connection.

Aaaaaand… our part got cut.

Lessons:
💥 Other people’s decisions don’t reflect your worth.
💥 The experience was exhilarating—nothing can take that away.
💥 Seeing behind the scenes adds depth to every polished product.

12. The Ads Team, the Sales Funk, and a Real Humbling

Loving the work. Struggling with the selling.

I hired a digital ads and marketing team to create a scalable system for one of my programs. The Art of Alignment is the culmination of ten years of best practices. The content, community, delivery… it’s my crowning achievement (so far!).

And the people in the program are incredible—engaged, reflective, taking action, creating momentum.

But when it comes to sales? I get shy. Wicked awkward. I let potential members quietly drift away.

I love coaching, community-building, speaking, and raising the collective consciousness. Sales? Not my jam. And it shows.

Lessons:
💥 You can’t be good at everything.
💥 Grow toward the light—lean into your strengths and delegate the rest.
💥 Let go of those who aren’t ideal and over-deliver to those who are.

13. THE GOLD BENEATH IT ALL

It was never about failure. It was about who I became.

There is no such thing as failure—it’s all feedback.

It’s not the big names, the status symbols, or the money that create self-worth, confidence, or success. Those things are external.

It’s your inner world that matters: the deep knowing that you have a calling, a mission, a purpose. It’s showing up consistently, serving without expectation, asking better questions, taking aligned action, and appreciating every step that brought you here.

I used to ask, “When does this get easy?”

Now I ask, “How can I appreciate the magic and miracles that got me here even more right now?”

It’s a much better question.

It’s been a wild ten years. I wouldn’t trade a moment of it.

Lessons:
💥 Life isn’t fair. Fear and pain are part of the human experience.
💥 “Comparison is the thief of joy.” —Theodore Roosevelt
💥 Your history does not dictate your future unless you drag it along with you.
💥 Thanks for reading. I love you.