You Think You’ve Failed a Lot? What a Joke—You’re an Amateur at Failure.
I’ve been failing for a long time.
Failed early in our marriage, my job required me to write business memos. I could speak well, I could hold a room, present ideas, and connect with people—but writing? Writing was a different story. Anyone reading my documents needed both patience and a translator.
One day Mary, who had consulted as a technical writing expert for a major Swedish corporation, read one of my drafts and said gently, “You can’t send this the way it’s written.”
She wasn’t being cruel, just honest.
She took my document and rewrote it. Same ideas, same message, but suddenly everything was clear. It felt like hearing your own voice played back and realizing it sounds nothing like you thought.
From then on, she edited everything I wrote.
And I studied her changes the way Eliza Doolittle studied pronunciation—slowly, painfully, but determined.
Little by little, my writing transformed.
I’ll never forget sitting in a meeting with an Ivy League MBA consultant. We were deciding who should draft a key document, and he said:
“David should write it. His ideas are always so clearly articulated.”
For a moment, I felt proud.
Then I remembered: he wasn’t complimenting me—he was complimenting Mary. I felt like an imposter.
Because honestly, I was.
But I didn’t quit.
I practiced.
I learned.
I failed forward.
And eventually, the day came.
I handed Mary a complex document. Later, she returned it to me with no markings.
A little frustrated, I said, ‘Honey, you need to edit this document. I need to send it out first thing in the morning. We don’t have much time.”
“No edits,” she said. “It’s excellent.”
“Are you kidding?” I said cautiously.
Then I could tell by her expression she was serious.
That was my Eliza Doolittle ballroom moment, the moment when the world finally sees the capability you always hoped was inside you.
I didn’t become a different person.
I simply learned how to communicate the person I had always been.
So why am I telling you all this?
Because writing wasn’t the only area where I failed early and often.
I failed at money.
I failed at two businesses.
I failed as an employee.
I failed trying to learn to play the piano.
I failed at spelling and still do regularly.
Honestly, if failure had a loyalty program, I’d have earned Platinum status.
But every failure taught me something (except spelling).
Every attempt added a little clarity.
And over time, the lessons started to form a pattern.
A simple framework.
A “compass.”
Something that helped me just like Mary’s editing did— showing me where I stood, what needed fixing, and what the next step was.
That framework eventually became my One-Page Wealth Compass—
the same tool that helped me go from financially lost to financially free.
It wasn’t genius.
It wasn’t luck.
It wasn’t a gift from the success fairy.
It was the same process that transformed my writing:
Repeat.
Refine.
Correct.
Grow.
Failure wasn’t holding me back.
Failure was my teacher.
And if you’ve stumbled financially, fallen off track, or felt stuck…
you’re not behind.
You’re just in training.
If this makes sense to you, I have a suggestion. I regularly share short, practical posts to help people who either got a late start, or want to get an early start, turn discouraging money stories into hopeful ones. You’re welcome to keep reading along and use any tools and tips you find helpful.
And if you ever feel ready for something more structured, my book, OnePage Wealth Compass, expands in a simple, stepbystep way on the same ideas I used to rebuild after failing financially—going from nearly broke at 63 to a secure sevenfigure portfolio by 69. It’s there as a resource if you need a clearer path or want to safely accelerate your journey.
David
