I want to talk today about something that I don't hear discussed very often, especially among women in leadership. I want to talk about what happens when your career looks successful on paper, but you still don't feel like you've arrived. I don't mean this as a dramatic confession, and I don't mean it as a complaint. I mean it as an honest observation that many of us quietly carry. We work hard, we gain experience, we take on responsibility, we build credibility, and yet there is no clear moment when everything suddenly feels settled or complete. For a long time, I assumed that this feeling meant I was maybe doing something wrong, because early in our careers, we absorb a fairly clear promise, even if it's never stated directly. We're taught that if we work hard enough, make good decisions and keep moving forward, there will eventually be a moment where we arrive right. That arrival is supposed to feel like confidence and certainty. It's supposed to feel like standing on solid ground that moment has never really happened for me. What has happened instead is growth. So over time, I have gained experience perspective and responsibility. I have learned how to navigate change and how to build things in uncertain environments. However, the feeling of being finished, fully settled or permanently secure has never appeared when I was earlier in my career. I have very specific expectations about what this stage would look like. I assumed that by now I would feel more certain about my direction and more confident that I was exactly where I was supposed to be. Instead, I have continued to feel curious. I have continued to feel pulled toward learning, building and trying new things. I have changed industries more than once. I have changed roles, responsibilities and environments. I have worked at early stage startups, large media companies and established organizations. I've also worked independently and built my own businesses and podcasts. From the outside, that kind of career path, it can look intentional and even strategic, and a lot of times it is, but from the inside, sometimes it felt like I was becoming something new again and again, every time I thought I was approaching a sense of arrival, something shifted. The company changed. The market changed. My priorities changed. I changed for a long time that unsettled me, because we're taught that uncertainty is something you eventually grow out of. We're taught that confidence is something you eventually lock in. So over time, I started to wonder if some careers are not designed to end uncertainty, right early career, and the first taste of uncertainty is like when I think about where this pattern really started for me, I go back to the very beginning of my career, even though I did not recognize it as the beginning at the time, I'll take you back. I had moved to San Francisco in the late 1990s I was young. I'm still young. Okay, it was newly married, and I was going to school at San Francisco, San Francisco State University for film Go Gators. I did not have a long term career plan, and I was not trying to build a career in technology at that point, the Internet didn't feel like an industry with a future. It just felt kind of unstable, experimental, temporary, slightly unreal. My husband had accepted a job at a startup called listen.com I was working part time and going to school, and eventually I transitioned into working full time there while still finishing my degree. So this was during the.com boom, which meant that everything felt exciting and unstable at the same time. There was energy, amazing energy everywhere. There was money flowing in ways that did not always make sense. There was also a constant underlying question of whether any of it would last. So what stands out to me now looking back is how little anyone really knew what they were doing. People were building companies, products and roles at real time. There were no established playbooks. There were no long term guarantees. Everyone was improvising, whether they admitted it or not at the time, I assumed that this uncertainty was temporary. I thought, Oh, I'll eventually move into something more traditional, something more stable. I didn't realize that I was learning how to operate in. Ambiguity, how to build while learning and how to tolerate not having clear answers. So that environment shaped me more than I understood at the time. It would, it's it worked. It would change me quickly. It taught me that titles were often fluid. It taught me that competence did not come from certainty, but from adaptability. So then when the.com bust came, oh, it was brutal. Companies folded, jobs disappeared, people who had been celebrated as visiting visionaries just months earlier was suddenly scrambling. I actually volunteered to be laid off because the situation had become unsustainable. That moment really stayed with me. I fully understood that careers do not move in straight lines, and that no role is immune to external forces. I did not know then that this lesson would repeat itself many times over the next two decades. So one of the tensions I have wrestled with for most of my career is the difference between ambition and restlessness. From the outside, these two things can look very similar. Both involve movement, both involve change, both can involve dissatisfaction with the status quo. Internally, though they feel very different. For a long time, I worry that my desire to keep learning and evolving meant that I was never satisfied. I worry that it meant I lacked focus or commitment. I worry that it would eventually be interpreted as instability. The concern is not unfounded, especially for women, there is an unspoken expectation that at a certain point we should settle. We should pick a lane, we should pick the stop, you know, pick a lane and not change our minds as much we should become predictable. So ambition is celebrated when it looks linear. It's celebrated when it follows like a recognizable arc. It becomes suspect when it does not so. There were moments when I questioned whether my continued curiosity was a liability. I wondered whether wanting to try something new meant that I was failing to appreciate why I already had I wondered whether growth was supposed to feel more calm than it did over time, I started to understand this difference. This differently. I realized that what I was responding to is not boredom or dissatisfaction, but alignment. When I stayed in roles and no longer fit, even though they looked good on paper, I felt constrained when I moved toward work that challenged me or stretched me. I felt energized even when it was harder. So that distinction mattered. It helped me understand that ambition does not always point upward. Sometimes it points inward, sometimes it points sideways, sometimes it points toward sustainability rather than scale. Once I reframed ambition this way, I stopped judging myself for not wanting to arrive. I stopped assuming that the desire to keep becoming meant I was a problem to be solved. Instead, I began to see it as a form of self trust. There have been several moments in my career where I made choices that did not look impressive from the outside. In some cases, those choices involve taking pay cuts. In other cases, they involve turning down opportunities that would have come with more prestige or visibility. I made those choices because I had learned what certain environments required of me. I had learned how much sustained stress I could carry. I had learned how burnout showed up in my body and my thinking. These decisions were not driven by fear or a lack of ambition. They were driven by clarity. It takes a surprising amount of confidence to choose Fit over optics. It requires trusting that your value is not dependent on constant upward motion. It requires believing that stepping away from something does not erase everything you have already built. There is a strong cultural narrative that frames these choices as opting out. That narrative suggests that if you slow down or choose differently you're no longer serious about your career. That framing does not reflect the reality that I experienced in many cases. Choosing fit allowed me to do my best work. It allowed me to show up with energy, creativity and perspective, rather than exhaustion. It also forced me to let go of the idea that my career needed to look a certain way in order to be valid. Even with that clarity, there were still moments of doubt. There were moments when I wondered whether I should be further along by now, or whether I was making things harder than they needed to be. So those questions never fully. Appear, at least not for me, what changes is how much power they have over your decisions. So another lesson that reshaped My thinking is the myth of stability. I have lived through enough market cycles to know that stability is often something we recognize only in hindsight. I started my career During the.com boom, and I experienced the best. I volunteered to be laid off. I have had contracts end. I was furloughed during covid. None of these experiences were unique, but each one reinforced the same lesson, companies are systems. They're not families. When circumstances change, systems protect themselves. This does not make companies immoral. It makes them predictable. Understanding this changed how I relate to work. It made me more intentional about boundaries. It made me less willing to sacrifice my health or personal life, for a sense of loyalty that would not be returned. It also made me more compassionate with myself. During periods of transition, I stopped interpreting disruption as failure and started seeing it as part of the cycle. So early in my career, I believe that leaders knew what they were doing like all the time, all the leaders. I assume that leadership came with certainty and confidence. I believe that once you reached a certain level, the doubts would quiet down. And what I have learned instead is that leadership often involves making decisions without complete information and moving forward anyway. Some of the most capable leaders I know are still figuring things out in real time. They simply do not wait for certainty before acting. They understand that clarity often comes after movement, not before. I also learned that leadership does not require direct reports. It does not require performance, permanence or a specific title. Some of the most meaningful influence I have had came from expertise, perspective and trust, rather than hierarchy. Leadership for me has become less about position and more about how I show up when things are unclear. There is one part of this story that still feels slightly vulnerable to say out loud, but I am not where I thought I would be at this point in my life. I don't say that with regret. I say it honestly. I might never feel as if I have arrived and I am starting to believe that this is not a problem that needs to be solved. There is always something new that I want to learn, understand or build right for a long time, I wonder that this meant I was restless or dissatisfied. Now, I think it means that I am still engaged with my own curiosity, and it's a pretty good place to be, because that curiosity, it shaped my career far more than any single role or title. So if you're listening to this and thinking that you thought you would feel more settled by now, I want you to know that you're not behind, you're not late, you're not failing to figure something out that everyone else has already mastered. Some careers are not meant to arrive at a final destination. They are meant to unfold over time with twists, pauses, recalibrations and second acts, third. Acts, four, Act Four. Acts, five. Acts, right. The pressure to arrive is real, and I get it, especially for women, and it shows up in subtle ways. It shows up in expectations about age, experience and expertise. It shows up in the idea that by a certain point we should have everything figured out. But I no longer believe that story. I believe that becoming is not a phase you out grow. It's a way of moving through your work and your life with honesty and agency. That belief is at the heart of why this podcast exists. Clover is a place for stories that reflect how leadership actually unfolds, not how we are told that it should. If this episode resonated with you. I hope it offered you permission, rather than solid answers, and that permission would be to trust your own timing, permission to choose Fit over optics, permission to keep becoming even if arrival never comes, that is not a failure, it is a form of leadership. Thanks for joining me this week, and I'll see you next time on clover. You.