--- title: "Success Stories Are the Hardest Ones to Tell" description: "We can talk about other people's wins all day. But our own? That's where things get hard. Success is so difficult to see from the inside." doc_version: "1.0" last_updated: "2026-05-05" --- # Success Stories Are the Hardest Ones to Tell I was on a podcast last month talking about how to build trust with your audience and the importance of storytelling. Before we signed off, the host asked me, “Is there a story you still struggle to tell?” Yes. Of course there is. The stories I still struggle to tell are my success stories. I can tell you my clients’ success stories all day long. I will wax poetically about the improvements they’ve made, the way they’ve evolved, the outcomes they got. That is easy. But tell a story about my own success? No ma’am. No sir. I don’t want to. And sometimes I’ll just say, eh, I’m not that successful, and leave it there. I had to unpack why. Why am I so bad at this? Why do my clients struggle with it? Because they do. A lot of people do. If you can tell your success stories all day, every day, today’s email isn’t for you. If you struggle to put words to your successes, or even to name things as successes in the first place, read on. Why We Struggle I have some theories, built from years of talking to genuinely successful people, trying to get them to articulate what they’ve done, and from my own experience with it. We don’t want to feel like we are bragging. We feel like our successes are nothing in comparison to someone else’s. Our brain or our guts may understand our success, but never both at once. But the big one? After a certain point in life, success stops being a destination. Success becomes an ever-moving target, an amorphous philosophical quest. After you graduate from college, there is almost never a moment where you stand in a room and have someone formally declare that you have succeeded at something. Even the moments that are designed to feel that way often don’t. I have two clients who rang the bell on Wall Street. That’s about as close as startup life gets to a real graduation, with the pomp and circumstance and champagne and speeches to match. And neither of them felt the success. One said he felt hollow. He left moments later and walked all the way uptown trying to figure out why, and ultimately what he landed on was that it meant nothing because he felt like he had lost his company. The other said she couldn’t celebrate the moment or look back on it as a success because all it meant to her was more and more and more work, with more and more and more stakeholders to serve. The thing is, we live inside our stories. We don’t read them from the outside. From the outside, we may have the trappings of success, the markers, the metrics, the benchmarks. But on the inside, we’re grinding. Sure, the stock price is fantastic, but tomorrow is another workday and we have to keep going. I ran a speaking series for 12 years in San Francisco and New York City. Hundreds of salons, thousands of talks, countless new speakers on stage, many for the first time, doing great. An audience that packed bars every month to listen to history stories. People outside looking in thought it was a success. To those of us running it, it felt like the thing we did with our friends. It felt like an endless march of production: technical errors and slide decks coming in late, managing extremely tight budgets and high expectations, and keeping a community engaged through economic booms and a pandemic. We didn’t have distinct markers that told us when success happened, so we missed it while we were standing in the middle of it. Success is amorphous and therefore hard to see from the inside. So we need to figure out how to see it as if we are on the outside. The Exercise Here’s what I want you to do. Write down everything that is true about what you’re doing and have done. The milestones, years of dedication, the revenue, the pivots, the challenges, the moments you wanted to quit, the number of employees, the number of people whose lives you’ve changed or whose work you’ve touched. Write all of it down. Now pretend this list belongs to a dear friend. Someone you love. Someone you’ve watched strive and struggle and overcome. Look at the list and highlight milestones. Highlight the triumph over challenges. Highlight success. Okay, pick one. Write out the stepping stones. The moments, good and bad, that got you there. The challenges and the pivots. The people, ideas, and mindset shifts that built it. Articulate not just the structure of the success but the texture of it. This is how you shift success from amorphous to tangible. This is how you see your own success. And when you can do that — when you can witness your success and tell the story of how you got there — you have a powerful tool. For building investor relationships. For helping your team understand that they have done improbable things before, and they can do them again. And for growing your confidence. I’m trying to get better at this. I hope you will too. If you take the time to do this exercise, tell me how it goes. Tell me about your successes, big or small, and how you got there. I want to hear it. Enjoyed this? I write about storytelling, public speaking, and experimenting to grow your skill in Permission to Experiment — a free newsletter, twice a month. Join here → ## Sitemap - [Home](https://trebalchowsky.com/index.md) - [About](https://trebalchowsky.com/about.md) - [Services](https://trebalchowsky.com/services.md) - [Pick Up the Mic](https://trebalchowsky.com/pick-up-the-mic.md) - [Let's Talk](https://trebalchowsky.com/lets-talk.md) - [Glossary](https://trebalchowsky.com/glossary.md) - [Newsletter](https://trebalchowsky.com/permission-to-experiment.md)