I'm a Big Tech executive. My journey here has felt like falling forward — painful stumbles and detours, yet still progress.

Wainwright Yu. Courtesy of Wainwright Yu Wainwright Yu's unexpected journey at a Magnificent 7 company led to a director role, despite setbacks. Not landing a return offer after an internship and unexpected team assignments were part of his journey. Yu said what he had to let go of was the perfect career path he had crafted in his head. The email came in on a Tuesday. It was an announcement that I had been promoted to director, an executive position at the Magnificent 7 company, where I had worked for eight years. Follow-up congratulatory emails started to pour in. I sent brief but genuine replies, "Thank you." A few weeks later, another email went out. My manager was leaving the team. Having just been promoted, I thought this was an obvious next step for me. That didn't happen. They were hiring someone else instead — another director from another team was coming in to take his place. My role and title stayed intact, but there was no scope expansion for me. I earned the title, but I didn't have what I thought it signified: readiness for more. From the outside, a career at a Magnificent 7 company looks like a straight line — competitive offer, steady promotions, increasing scope. From the inside, it rarely feels that way. Mine certainly didn't. What it felt like, more often than not, was a slow accumulation of near-misses, wrong fits, and closed doors — with just enough daylight between them to keep going. The door that barely opened This wasn't the first time I was passed over for an opportunity I wanted. In fact, my career at this company felt like one failure after another. When I was a first-year MBA student, I applied for a summer internship at the company where I now work. I was rejected. A few months later, I received an email that felt auto-generated. It was from the company, inviting me to apply for a full-time role. I was confident this was a mistake. They probably didn't filter out summer intern rejections from the target list they sourced from the school. I applied anyway and was accepted. I didn't understand why I wasn't cut out for an internship, but was good enough for a full-time job. I didn't ask. I was happy to have the role. The recruiter let me know that all full-time hires would be receiving introductions to three teams across the company to assess the best mutual fit. I received one introduction. While the role was called a product management role, the real job was to run the team's weekly business reviews. Not quite the product management job I had in mind, but I accepted it anyway. The team I would have never chosen That pseudo-product manager role eventually became a real product manager role. I was promoted to principal product manager with a small team just over three years later. Then, I made a leap to a startup team within the company. I was employee number three on a business that was no more than an idea sketched on a piece of paper. I thought the idea had potential and was excited to be on the ground level to build it. Three months, six hires, and several more papers later, the project was canceled. I was moved to a different team I would never have chosen to join, yet again, working on a product I thought would never find product-market fit. As it turns out, I was wrong. Instead of getting shuttered, the program has scaled tenfold. We expanded the product line from two to four. Customer adoption grew. I was wrong about the product and the team, not because what I saw wasn't real, but because the thing wasn't yet what it was going to be. I spent the next four years on that team. The dud I thought I had been exiled to was the same team that made me a director. What I learned from a career of closed doors There are moments when everyone around you seems to be headed for the exit. Those are often the moments worth staying for. I've learned to run toward fear, shame, and disappointment rather than away from them. What I find is that the people who stay through the hard times earn the trust to do and be more. We get anchored on what we think we should have. I did too, and almost missed what was actually being offered. The job that looks beneath you on paper — running the weekly business review — is often the one that makes you, if you let it. What I had to let go of People talk about resilience like it's armor — something that makes us impervious to pain. That's not how it felt to me. Every failure hurt, but what ultimately helped me get up after every fall wasn't a fancier title, a more glamorous product, or a larger team. It was having the opportunity to make things that people use and love. What I had to be willing to let go of is the path. The door into the company via a summer internship closed, the door into a real product role through post-MBA placement closed, the door to scaled impact through a startup product closed, but the goal remained the same: build things that matter. I was promoted to director six years ago. I now lead larger businesses with larger teams that make a bigger impact on customer lives. How did it feel getting here? About the same as always: like falling forward. Painful stumbles and many detours, but making forward progress nonetheless. Wainwright Yu is a technology executive, mindfulness teacher, and leadership coach who supports neurodivergent individuals as they discover and harness their (often hidden) strengths. Read the original article on Business Insider

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