So You Think You’ve Failed? What a Joke—You’re an Amateur
I’ve been failing since before you could walk. For example, early in our marriage, my job required me to write a lot of 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 an English-to-English translator. One day Mary, who had consulted as a technical writing expert for a major Swedish global 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 was embarrassing. I thought I was being brilliant, but Mary’s feedback showed me I was just being confusing. I was a communicator who couldn’t communicate. 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 evolved. 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 kept making mistakes, but they were better mistakes. And eventually, something I was totally unprepared for happened. 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 moment, the scene in the ballroom where a street peasant is suddenly transformed in the eyes of high society as royalty. It was the moment when the world finally recognized the capability you always hoped was deep inside you. I didn’t become a different person. I simply learned how to communicate the person I truly was. So why am I telling you all this? Because writing wasn’t the only area where I failed consistently. I failed the second grade—I believed in getting an early start. I failed at money for 40 years—the ultimate slow learner. I failed at two businesses—one wasn’t enough. I had to make a point. My first, a retail business, failed after four years of relentless struggle. I’ll never forget the day I realized I wouldn’t have enough cash to make it to the end of the month. That pit in my stomach is a pain I’ll never forget. Standing in that empty space, surrounded by inventory I couldn’t sell, inventory that once looked beautiful, now looked painfully ugly, the weight of what I’d put my family through hit me like a physical blow. I thought I was smarter with my second business, but I hadn’t yet learned the absolute necessity of a critical lesson. Within five months, the writing was on the wall and I shut it down. I failed as an employee—proof is being fired after 18 years with the same company. I failed trying to learn to play the piano—my poor piano teacher deserves an award for patience even when there is no hint of talent or even slight progress. I failed at spelling—I have made this one a life mission, spellcheck was like a personal gift to me. 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 the foundation for my book, One-Page Wealth Compass: Fired at 63, Nearly Broke, Safely a Millionaire by 69. It is the exact tool that helped me go from financially lost to a secure, seven-figure portfolio in just six years. 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: Correct. Refine. Repeat. Grow. Failure wasn’t holding me back. Failure was my teacher. When I reached financial freedom at sixty-nine, I realized that those 40 years of making every money mistake in the book were actually my greatest asset. They showed me the traps most people fall into and the simple, “Set it and Forget it” approach that actually holds up when life gets messy. 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 expands in a simple, step-by-step way on the same ideas I used to rebuild after failing financially. It’s there as a resource if you need a clearer path or want to safely accelerate your journey to your own seven-figure destination. Buy Book
