I Took the Leap from Wall Street to Join a Tech Startup in Silicon Valley

After four years in the financial industry, I was ready for a change. Here’s why and how I ended my career on Wall Street to be the first employee at a tech startup in Silicon Valley.

Photo credit: Quinnton Harris

As a first-generation college graduate, I was determined to be a trailblazer. I aspired to be the CEO at a financial institution. I fantasized about climbing through the corporate ranks. I was driven to spark new ideas, ready to be a catalyst for change, and excited to infuse the corporate culture with creativity. At 22, I entered the world of Wall Street with a mapped future. By 26, I was in a position of influence and on a clear path to success:

• I was the Global Head of People Agenda and Communications in the Finance and Business Management sector. My job was to build the sector’s internal community across 42 countries. I developed and managed employee programs that were inclusive of learning, career development, philanthropy, networking, diversity & inclusion, wellness, and communications.
• I had a seat at the table. I was a Black, millennial woman whose opinions were greatly valued by employees of all levels — from Analysts to Managing Directors. I was in a position to make changes to the corporate culture, while being the voice of employees my age.
• I had exceptional managers — all four years. Starting with my rotational program right out of school to my position as a global lead, my managers were determined to set me up for success. They taught me, they believed in me, and they provided me with opportunities to develop.
• I built long-lasting, solid relationships in the workplace. I was the girl who would tell you good morning (whether I knew you or not), the girl who would stop and ask how you are doing on my way to kitchen, and the girl who had a genuine interest in learning about your life in and out of the workplace. Through these interactions, I built solid friendships that I cherish to this day.
• I received support for my outside venture. This was a plus for me. I didn’t know of many people on Wall Street who had side gigs that didn’t relate directly to their full-time jobs. In 2015 I launched Gym Hooky, a wellness brand helping women incorporate healthy habits into their busy schedules. I had endless support from my colleagues.

After four years, I realized that this shiny, coveted role on Wall Street was not for me. I was not happy. I was not fulfilled. I dreaded coming into work.

The Push To the Ledge

I was deeply unfulfilled. I wasn’t enjoying my work, I felt like I wasn’t using my full potential, and I longed to wake up feeling like my work was making a difference to someone or something. Where were these feelings coming from? I loved what I was doing in my role, so what led to my change of heart? Well, the environment, in my opinion, was toxic.

Here are some things that I learned about the corporate culture during my four years on Wall Street:

• It’s difficult to make significant changes in the workplace. The corporate structure is relatively solid, so it’s common for people to be comfortable with the way things are. I found myself fighting to propose a culture of innovation. As time went on, my creative ambition was crushed. I longed to be in an environment where I was challenged to think outside the box, encouraged to build, and pushed to take risks.
• Colleagues walked on eggshells daily. When I looked around me, I saw fear everywhere. Fear that disagreeing with someone of a higher level will cost you a promotion. Fear that leaving the office at 5:30pm will deem you as “less hardworking”. Fear that providing honest feedback on company surveys would bite you in the ass. This fear soon impacted my experience in the workplace to the point where I felt like I had to talk and dress certain ways to fit with the corporate culture. I no longer felt like I could be myself.
• There was a desire to have power. Titles in the workplace held a lot of weight. Conversations with colleagues highlighted the impression that the higher your level, the more money you make, the more you are valued, and the more your opinions will matter. Many are on a mission to get that promotion. The corporate world really is a rat race and people will do anything to get to the finish. Of everything, this bothered me the most. I witnessed colleagues fight to have someone report to them just because being a manager looked good and checked off a box on promotion requirements — there was no desire to develop an employee or a team. I witnessed colleagues take credit for other people’s work or throw their counterparts under the bus for their own advantage. I witnessed colleagues ‘volunteer’ to get involved in employee resource groups — not because they were genuinely interested, but because it was required to get to the next level.

This hunger for power was just something I couldn’t relate to. I wanted to make a real impact. I wanted to be an influencer in my community.

• Burnout runs rampant. I was mentally drained and became physically sick. Burnout is REAL and I admittedly ignored all the signs. Late nights in college prepared me for working long hours (and throwing back some coffee if I was feeling tired), but this particular case was different. My lack of self-care was coupled with my dissatisfaction with my job. One day my body just gave up on me. I woke up one morning barely knowing where I was. I couldn’t think, stand or walk. My body and mind were tired. And it was about time I acknowledge what was happening to me — my career, my life, and my happiness.

On the Ledge

I wanted out. I wanted to escape from corporate’s cubicle chains.

So many questions swarmed my mind. What was I going to do next? Was I going to move internally? Perhaps, look for a similar role at another financial institution? Leave the industry?

I was already on my way to making a transition and didn’t even know it. I realized that much of my downtime was already spent reading about innovative solutions and technology startups. I was amazed at the amount of creative energy bouncing around, amplified by peers my age. I had the desire to learn more about this new space and was compelled to take a risk. I started attending tech meetups and events after work. I met people who left the corporate world to work at startups. I met founders of cool products. I met SO many people who were driven to make an imprint in the tech industry. I was inspired.

But I quickly found that attending events wasn’t enough.

While at these events, I met many people who were in the same boat. People stuck in one reality, cautiously dipping their toes into a pool of possibilities, but never fully jumping in.

“What do you do?” I would ask. “I work in X, but what I really want to do is Y” was the common response. Sometimes I would challenge their response, asking “So what are you doing about it?” This was often met with shrugs, blank stares, indecision, and helplessness. And that’s when I had my epiphany: I had to be all in or nothing. If I was going to turn my ideals into reality, I had to dive headfirst into unfamiliar territory, without looking back.

But first, I had to consider the logistics. I was intrigued by everything tech, but how was I going get into the space with a finance industry background? What type of roles could I apply for? Which of my skill sets were transferable? Do I look for opportunities in large organizations or do I join a startup? Was I prepared for a potential pay cut?

Here are some of the steps I took to prepare for my transition:

1. I lived lean. My rent was inexpensive. Even though I could have afforded something much nicer on my corporate salary, I resisted the urge. If you’re interested in taking the leap to join a startup, be sure to avoid “lifestyle creep,” because you have no way of knowing what your compensation package is going to be once you say goodbye to your corporate salary. Your best bet is to keep your fixed costs (like rent) very low, abide by a budget, and save as much as you can.
2. I did my research. The first thing I learned was that tech companies actually need people who don’t code. As talented as the company’s coders are, they’re not going to be happy if their founder asks, “Hey, would you mind jumping on a sales call for me?” or “Sorry to interrupt your programming, but I really need you to file our taxes”. But this stuff does need to get done. And every great technology product the company delivers only increases that workload. So it should come as no surprise that tech firms employ 3x as many non-technical staffers as coders. I discovered that there were plenty of non-technical roles and functions at tech companies, including people operations, marketing, sales, business development, finance, and analytics. I quickly learned that the skill sets I acquired on Wall Street could be applied to these non-technical roles.
3. I knew what I wanted in my next job. The best way to find any job is through people, but people can only help you if you know what you’re looking for. “I want to join a startup” isn’t enough — many people want to join a startup. Your best bet is to be as specific as possible because it will help people you meet to recall founders and companies who are hiring for those types of roles. When I was job searching, I had very specific criteria when it came to the role I was seeking and the culture I was looking for. I was, in turn, referred to a lot of great people and companies. Sometimes people think that being specific will limit their choices. It won’t.
4. I asked myself important questions about my current work situation:

• Am I passionate about working in the finance industry?
• Am I excited to go to work every day?
• Will staying here another year get me closer to my dream life?
• If I had a year to live, would I still be working here?
• When I look back on my life, what will I regret more, staying or leaving?

I wanted to feel at peace about my final decision. Once I answered these questions (all of which the answers were ‘No’ or ‘staying’), it became extremely evident that the biggest mistake I could make would be to stay and do nothing. I started my six month search for a new job.

I Leaped

I took a risk. Along with this risk came great support from my amazing fiance, friends, family, and colleagues. Along with this risk also came doubt from the people who thought I was crazy to leave a “boss job” and a high paying salary. People who thought that leaving Wall Street will divert me from a path to success. But I made a vow to do what was best for my career. It was no easy feat, BUT it was a memorable journey.

I landed a job as the first employee and Program Director at /dev/color, an amazing non-profit working to advance the careers of Black software engineers. I landed a “boss job”.

I moved from New York to San Francisco. I left a 250,000 person organization to be the first employee at a startup. I ditched the corporate salary to do something I love — making an impact in my community. And it was one of the best decisions I‘ve made. My learned lesson from this experience:

You Don’t Have To Settle.

No one loves their job all the time.

It’s like a relationship. There are good times and there are not-so-good times. Sometimes you have to ask if what you are going through is simply a lull, or if either of you have anything left to give to each other anymore.

It may be hard to recognize, but sometimes a job is too far gone beyond repair. It’s not a reflection of you, your abilities or level of success. And most importantly, it’s not an admission of failure. It’s just a matter of circumstance and your place in life. Some people may be perfectly content doing the same exact job for the next 15 to 30 years. But for others, the thought is unbearable.

I’ve had many conversations with friends and old colleagues about making that switch. From these conversations I’ve learned that many (not all) people accept being unhappy in their jobs because they’re afraid of the struggle it takes to figure out how to do what they really love. I encountered this fear almost every day, especially among my high-achieving peers. They are funneled into jobs as consultants, investment bankers, and analysts. They stay for the required two years or more, even when they realized that cubicle life wasn’t for them. They dreamed of inspiring their community, of impacting policy, of building an empire, of making their mark. Instead, they chase that promotion (because its next logical step), keep crunching numbers (because that what their degree trained them to do), or hold off on making that career switch (because everyone will think they’ve gone crazy).

Sound familiar?

If you are truly unhappy in your job, you owe it to yourself to make a change.

It takes a lot of courage to admit that you don’t have the perfect professional job. It takes even more guts to do something about it. You can do it! The happiness and fulfillment you have been longing are waiting for you to make a move. I know that jumping from a corporation to join a startup may not be for you. I know that student loans suck and you have to make that monthly payment. I know that you may be a provider for your family so taking a risk of this nature is not an option. I know that your family may give you shit if you ‘throw away your degree’. I get it. And I am in no way telling you to walk into your boss’ office and hand over a resignation letter.

I am, however, encouraging you to think about where you are in your career. Define your vision for success. Ask yourself if this is the direction you want to go and if you are on a the path to a meaningful career trajectory. Set SMART career goals and measure your happiness against them. Never settle and constantly sniff out opportunities that will move you closer to what you can uniquely offer.

I challenge you to own your career. After all, you never know what new trail you may uncover.

Thank you for reading! If you were inspired by my story, please recommend and share. Feel free to connect with me on on twitter.