The biggest career wins often come with risk. On our series, The Big Bet, Chief speaks with some of the most powerful members in our network about that single moment when they bet on themselves — and won.

“My path is very non-traditional, very non-linear,” says Chief Member Nneka Ukpai, Head of Financial Innovation at digital mortgage lender Better. “I have a mentor who used to say, ‘When you plan your life, make sure you do it in pencil.’ There's power in the pivot.”

Ukpai knows a little something about powerful pivots. During the pandemic, she realized that working in big law and "helping rich people get richer," as she describes it, wasn't feeding her soul, so she embarked on a quest to find an outlet for her innovative nature. She became the Co-Founder of CultureCrush, a popular social and dating app in Brazil, and Wellthi, a social finance app. “I found myself happier in tech support and fielding customer questions and complaints than focusing 10 to 12 hours on the practice of law,” she says, which prompted her to leave her job at “a big fancy law firm.”

The experience eventually helped her land an exec role at Better. “Being a serial entrepreneur rapidly taught me skills that would have taken years to learn on a more traditional corporate path. When you create a startup, you have to get good at everything, from strategic partnerships, marketing, and design, to financial models and product roadmaps, to IT support and customer service.” (Ukpai still remains invested in the success of the companies she founded and takes meetings with investors who are looking to support more Black women-led companies.)

In her current role, Ukpai advises Better on business, legal, and investment strategy, and new financial technology products. But these creative-leaning responsibilities weren’t part of her original duties. When she first got to Better, Ukpai held a hybrid role in business and legal affairs, because of her long-standing experience as a lawyer working with large corporations. Once she understood the ins and outs of how the business operated, Ukpai says, “I had bigger ideas for how the company could potentially monetize other areas, create new revenue streams, and lean into new verticals. That's what led me to promotions.”

In this edition of The Big Bet, Ukpai recounts how straying from the “risk-averse” path in big law — and gleaning from the advice of mentors, as well as becoming a mentor herself — has opened far more opportunities for her to grow professionally. “Being able to bet on yourself and say, I think I'd be really good at this and I'm not afraid of failure, and stepping out on faith to try is so powerful and freeing.”

On Stepping Outside of Your Comfort Zone

“I constantly take big bets on myself, but I wasn't always this way. I'm not a delusional human who thinks I can do everything. Instead, I'm a forever student. I take the approach that everything is learnable if you're willing to put in the time and effort. And I take the position that stretching might be uncomfortable, but there's no growth without the stretch.”

On Lifting Women Up From Behind You

“It’s imperative to pay it forward, to hold that door open and pull people behind us as we go. I co-founded a nonprofit that's focused on mentoring and improving outcomes for people of color in big law. We have a boot camp every summer where we go through substantive skills training, soft skills training, and all of the intangibles that you have to learn through hard knocks over time. If I had to stumble and step on landmines, let's make it so that the people coming behind us don't have to make those same mistakes. Taking time to mentor younger professionals, especially women in the profession, is my most valuable asset. There's no substitute for kindness. Kindness costs you nothing, and relationships are everything.”

On Prioritizing Your Well-Being

“Women have been conditioned to fear, what if you lose this opportunity? What if you lose this income? Those things don't concern me. There's no shortage of opportunities. What I'm concerned about is my bandwidth and my time. My dad used to always say that great service to many leads to greatness. When I think about how to serve many, I have apprehension about what that means for my personal wellness, my mental health, my personal life, and my time. That’s what scares me the most. Do I help the world at the expense of myself? It's something I think a lot of women grapple with because we're inclined to want to be problem solvers. But we also have to care for ourselves and to be unapologetic about being a little selfish sometimes.”

Fail early and often. If you are not failing on a regular basis, you're not trying hard enough.
Chief Member Nneka Ukpai, Head of Financial Innovation at Better

On Embracing Failures and Learning From Mistakes

“Don't be afraid to fail. Fail early and often. If you are not failing on a regular basis, you're not trying hard enough. Failure is not an indictment of you. It is an opportunity to learn. It is an opportunity to understand what works and what does not work, and most importantly, it's an opportunity to iterate and grow into the next best version of yourself. Carla Harris, the chairwoman of Morgan Stanley, always says, ‘When life shows up to teach you a lesson and you do not pass the test, you will repeat the course.’ It’s so powerful. Failure is a gift and you should treat it as such.”

On the Future of Women In Leadership

“My big bet is that the next-generation companies that are in their growth stages, the pre-IPO companies that are at their series Ds and Es and being led by millennials, are going to make a massive impact in getting more women and more minorities on corporate boards. I'm slightly biased because I'm in the space and I help growth-stage companies with this type of strategy, but I find that they are much more excited about the opportunity to play their role in shaping history. My big bet is that the next-gen companies that are being born out of innovation and out of necessity are going to usher in a new era of change.”

On Harnessing the Relationships at Chief

“We don't need allies, we need co-conspirators. We need people who are willing to get very intentional and mercenary about creating opportunities for each other. There’s a saying, ‘Surround yourself with women who are willing to scream your name in rooms full of opportunity.’ That is the Chief community on steroids. It is one of the most intentional and deliberate places where people know that we're in a space of collective excellence. Being in a room where you can be unapologetic and vocal about what you want, what you hope for, how you see yourself in your future and your trajectory, and having other women come up to you and say, ‘Hey, I've been there. This is how I did it. Hey, I'm going through that right now. I can help.’ It's almost like having thousands of mentors all in one place.