How an Ex–Pro Tennis Player Pivoted From Banking to Startups w/ Her Personal Brand

How Vitoria Okuyama left banking, rebuilt her identity, and used LinkedIn to open new doors

If you’re reading this, you’re probably ambitious, but a little restless.

You’ve done “the right things” — consulting, finance, Big Tech, other corporate jobs — and now you’re wondering: Is this it? What’s next?

Sharing roles you can apply to and my own advice is great, but you need to hear directly from different people who have navigated career transitions, rebuilt their identities, and rediscovered passions.

So I’m trying something new with my newsletter. I’m talking to people who are actually in transition — rebuilding identity, finding meaning, and creating work that feels purposeful again.

To kick this off, I spoke with Vitoria Okuyama — a former pro tennis player who went into investment banking, and then used her personal brand to pivot into the startup world.

(Fun fact: we met through posting on LinkedIn, grabbed coffee in NYC, and have kept crossing paths since. She inspires me a lot — and honestly, I wish I’d had the courage to do what she’s doing right after banking.)

Her path is anything but linear, which is exactly why I wanted to share her story.

I hope this helps if you’re feeling stuck or scared to make a change. If you like this format — or if you have your own story to share — I’d love to hear from you and make this a regular thing.

🎥 Watch the video, or read the summarized conversation below.

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Tennis to investment banking to startups

Hannah: For people who don’t know you, how would you describe your career journey so far?

Vitoria: It’s been intense. I started playing tennis when I was ten, competing in tournaments across Brazil. By twelve, I was already traveling by myself. When I was fifteen, I left my hometown to train at a bigger club that had more structure. I practiced six hours a day and spent five to seven months a year traveling around the world for tournaments.

At my peak, I was ranked 118 in the world. I played the U.S. Open, and colleges started recruiting me to play D1 tennis in the U.S. After college, I went straight into investment banking. So overall, definitely an intense and nonlinear career path.

Hannah: When you think about that path — from tennis to banking to startups — what connects those experiences for you?

Vitoria: Curiosity and adaptability. I’ve always been curious. The reason I started playing tennis wasn’t necessarily because I loved it — it was because I wanted to travel and see the world. Tennis was my best chance to leave the countryside.

Then I went into banking for financial freedom — I wanted to have the flexibility to explore my curiosities. Adaptability came in every time I had to reinvent myself: from athlete to banker, and now to entrepreneur.

Why she joined and left investment banking

Hannah: You initially joined banking because you wanted financial freedom and professional experience. What was that experience actually like for you?

Vitoria: It had a lot of ups and downs, but overall it was a huge learning experience — about myself and about skills I could use later on. The first year was brutal. I was working 80–100 hours a week. After about three months of 4 a.m.–2 a.m. days, I had my first burnout — just nine months into the job.

From that moment, I knew I wanted to leave banking, but I didn’t know what to do next. The last two years I spent there, I was just trying to figure out what was next.

Hannah: What ultimately made you want to leave? Was it the hours or something deeper?

Vitoria: It was a combination. Banking is so structured and hierarchical — as an analyst, you’re just told what to do and how to do it. There’s not much room for creativity. And I started realizing that the better I got, the worse my life became. The reward for doing well was… more work.

My quality of life dropped — I barely saw friends, I barely saw my wife. And I was still recovering from burnout. It all made me realize: this isn’t sustainable. This isn’t the career for me.

Hannah: Does the term “golden handcuffs” resonate with you?

Vitoria: Oh, absolutely. Especially when you come from a place where you didn’t have money before. I went from being a broke college student on a scholarship to suddenly making more than I’d ever seen. That comfort is hard to give up.

What helped me was realizing I’d saved enough to have a year of runway. Once I had that cushion, chasing money didn’t make sense anymore. I had a window to take a risk — and that’s what pushed me to actually leave.

Hannah: Once you decided you were ready, how did you prepare for that transition?

Vitoria: It was hard. I started doing tons of coffee chats and going to networking events. I spent almost two years collecting information, trying to figure out what I wanted. But eventually I realized — you’re never going to feel ready. You’ll never have enough information to make the perfect decision. Things only start to click when you move.

Hannah: What did that in-between phase feel like — knowing you didn’t want to stay, but not yet having the next thing?

Vitoria: Honestly, it was miserable. I wasn’t performing well at work because I’d already mentally left. But I was too exhausted to explore new paths after long nights. So I was stuck in limbo — not fully in banking, not fully in exploration mode.

Emotionally, it was really tough. I didn’t know who I was without that job. It felt like an identity crisis: if I’m not a banker, then who am I? What do I even like?

Rediscovering her identity and interests

Hannah: How did you carve out time to start exploring while still working those hours?

Vitoria: I started small. I created an Instagram account and began posting after work. Every night when I got home, I’d spend at least an hour making content. At lunch, I’d look up jobs or watch YouTube videos about other careers. I also started going to networking events — sometimes I’d tell work I had a doctor’s appointment just to make time.

Hannah: You’ve mentioned that period as an identity crisis. How did you start rebuilding a sense of who you were and what you wanted?

Vitoria: Around the one-year mark in banking, I knew I didn’t want to stay — but I also had no idea what else I wanted to do. As an international student, I couldn’t just quit and hope for the best, but I didn’t want to jump into something random either.

So I started asking: What do I actually want to do? What do I like? And I didn’t know the answer. That was the hardest part. I truly felt like I didn’t know who I was or what I enjoyed anymore.

I had to start paying attention — what kinds of events I wanted to go to, what kinds of conversations I got hooked in. Over time, that became a map of myself: Okay, I think I like this. I’m interested in that.

I also started talking to my parents and close friends to see how they saw me. Sometimes they noticed things I didn’t. Over time, through all of that reflection and curiosity, I started to rebuild a sense of who I was. I’m still working on that — I think it’s a lifelong process.

Hannah: What did that early “map” of yourself look like?

Vitoria: It was messy at first. I started just by looking through Luma events and seeing which ones interested me. I found myself signing up for content creator events, CEO events, startup panels — and realized, Okay, I’m drawn to creators and founders.

At events, I’d pay attention to what I asked people. I was always asking: What brings you fulfillment? Are you happy? Do you like your job? Those were the themes that stood out.

In the beginning, it was all just fragments — unconnected information. But as I kept exploring, those pieces started forming a clearer picture.

How she built her personal brand

Hannah: When did you start sharing that process publicly?

Vitoria: My first attempt was on Instagram. I was scared to post on LinkedIn and didn’t want to show my face, so I posted random pictures with long captions every day for about three months. It didn’t go anywhere. My designs were terrible, my writing was long — I just wasn’t getting traction.

After a short leave of absence, I decided to rethink everything. I realized I loved writing and that LinkedIn felt more natural to me. Plus, I was two months away from finishing my contract, so I stopped caring what coworkers thought. That’s when I finally started posting on LinkedIn.

Hannah: What kind of posts first gained traction for you?

Vitoria: The first one that really took off was about how I was ranked 118 in the world but didn’t love playing tennis. Hundreds of people reached out the same day. It went viral.

I think it resonated because not everyone grows up with the privilege to “follow your passion.” Many of us have to use the skills we have to build the life we want. That’s what I did — and that message landed with people.

Hannah: How did you keep that momentum going?

Vitoria: I focused on writing for my past self. I wrote what I wished I had when I was figuring things out. Early on, I shared resources for breaking into investment banking. Then I started writing about burnout — because no one at the bank talked about it, and I felt so alone going through it.

Later, I shifted to reflections on career transitions. I posted around three times a week, but prioritized quality over quantity.

Hannah: What kinds of opportunities has your personal brand opened for you?

Vitoria: So many. I’ve met incredible people all over the world, received job offers almost weekly, and I’m now part of a fellowship with Andrew Yeung at Five, where I get to connect with top founders in New York and learn directly from him. I was also featured by Business Insider.

All of that came from simply sharing my story online.

Hannah: If you were starting from scratch today, what would you do differently?

Vitoria: I’d start on the platform that really fits me. I always knew LinkedIn made sense for me, but I was scared. So I’d skip Instagram and start where I actually enjoy showing up.

Hannah: What’s something people misunderstand about building a personal brand?

Vitoria: That it’s just about posting. It’s really about storytelling. A lot of content is purely tactical, but stories are what connect people. Every idea you share should be embedded in a story.

Hannah: How do you think about storytelling in your own writing?

Vitoria: I usually start by asking: What’s the lesson here? Then I find the experience that taught it. Or sometimes it’s the other way around — I start with an experience and pull out the lesson. Either way, there needs to be both.

Life lessons from pro tennis

Hannah: What did you learn from playing tennis at that level that you still carry with you?

Vitoria: Adaptability. When you’re traveling five to seven months a year as a teenager, every week you’re in a different country — new altitude, new courts, new partners, new everything. You learn to adjust fast. That experience gave me the ability to reinvent myself and learn quickly in any environment.

Hannah: What didn’t tennis prepare you for?

Vitoria: Mental limits. In sports, your physical limits are clear — you know when your body’s done. But in banking, I didn’t recognize my mental limits. I didn’t understand when stress was too much or when anxiety was crossing a line. I had to learn that the hard way.

Redefining success, contrarian advice for “nonlinears”

Hannah: How do you define success and freedom now compared to when you were in banking?

Vitoria: I define success through my daily life now. I have five core values, and every night when I journal, I ask: Did I live them today? If the answer is yes, that’s a successful day.

It’s still hard to let go of outcome-driven patterns. I’m learning to enjoy the process — to have fun even when things don’t go as planned. Instead of getting frustrated, I try to see every “wrong” turn as getting closer to the right one.

Hannah: What’s one belief you hold about career or ambition that most people would disagree with?

Vitoria: That “follow your passion” is terrible advice. Unless you come from privilege, you need to build leverage first.

I didn’t love tennis, but it was my best option. I didn’t love banking either, but it gave me the financial base to explore what lights me up now. You can’t always start with passion — sometimes you have to earn your way to it.

Hannah: For someone thinking about their own pivot, what would you tell them?

Vitoria: Two things.
First, you’ll never have all the answers. You won’t have 100% of the information — maybe 50 or 60%, and that’s enough. Point your boat toward your North Star and jump. You’ll pivot again later, and that’s fine. Staying stuck is the worst thing you can do.

Second, put yourself out there. Whatever platform fits you — LinkedIn, Instagram, TikTok, YouTube — start sharing your journey. It’s life-changing. So many of the opportunities I’ve had came from doing exactly that.

Hannah: What’s next for you — what are you excited about right now?

Vitoria: Building my business. When I left a structured environment, I lost my habits and routine and felt really lost. I want to create something to solve that — to help high performers who are navigating “what’s next” build new systems and direction for themselves.

Follow Vitoria on Linkedin

You can follow Vitoria Okuyama on LinkedIn for reflections on career transitions, personal growth, and entrepreneurship; and her personal Instagram.

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If you liked this interview — or if you’ve navigated your own pivot — reply and tell me. I’d love to feature more stories like this in future posts.