Some conversations really stick with you.
I had been working at a private equity firm in San Francisco for a year and a half. The investment thesis aligned so well with my engineering background and interests. We looked for bootstrapped businesses that we could optimize “go-to-market” for and then double and triple growth numbers in a formulaic way. The team was bright and driven. But something wasn’t quite right.
One of the soon-to-be partners met with me to chat about my future there. That conversation made it clear for the first time that my interests in operations and sales weren’t aligned with my current deal sourcing role.
Around that same time, I met one of our senior investment contacts for lunch. Have you ever noticed how CEOs and founders — often exceptionally bright —really know how to dig in below the surface? The work of digging into the motivation behind our actions can teach so much.
Adrianna knew exactly what dim sum she wanted. I was following her lead in ordering and in the conversation.
“What are your superpowers?” she asked me.
She also shared that in answering I should think about what others told me I was great at, not to reply with how I thought I was best.
Some career feedback sticks with you, and some feedback takes years to sink in. That review back in my Wall Street analyst trading days that said I was tough to manage, for instance. I’m sure that was true, but I was also trying so hard to demonstrate that I was capable as a young woman in a man’s world that I developed characteristics that were “off-putting”to my managers. I was also bright, they’d say.
Looking back on it, I have realized that intelligence is important, but without coupling it with patience and strategy, it’s not enough
I let Adrianna’s question sink in. I spent some time thinking about my past careers, roles, and accomplishments. The answer was an easy one— sales and people
“Your ideal role is where your superpowers and interests overlap,” she tells me. “If you can nail this, then you’re unstoppable.”
The conversation then switched to my role at the investment firm. It was clear to me then that my role wasn’t in alignment with my superpowers.
I’ve thought about this conversation with Adrianna numerous times since. Her words really hit home and I’m so thankful for that thoughtful feedback and the path that it put me on.
I left the private equity firm within a few months and went through some major life changes following the loss of my mother to suicide.
You don’t recover a few weeks or even a few months after a loss like that. I sold my pristine condo in the Mission District of San Francisco and drove to Colorado where I’d been fantasizing a move for years. I had best friends living there locally and the community mattered more than anything.
Jumping back into work as I continued to prioritize healing from the loss meant I was only going to work on things that truly aligned.
I started work on “She’s Independent, a mission-driven impact business that gave back to women, a business that my mom would have loved. I shared career lessons, guided professional skill development, and offered mentorship. I wanted to create a space that acknowledged the challenges for hard-working, intelligent young women in the workplace and provided guidance and community in addressing those challenges.
Working on that business was a start but my professional career still mattered deeply. Going back to Adrianna’s earlier advice, I started crafting my ideal career trajectory, taking into account my superpowers and focusing on the overlap with my interests.
I’ve since stepped into numerous sales leadership and advisory roles. I’ve also increased my activity in early-stage investing through small angel checks, which has been fun. It’s less execution and more strategy, but squarely focused on sales and people. I’ve continued execution where my superpowers are needed, but continue to find ways to scale myself and my skills now that I have a more strategic approach to my career and more clarity around what I want.
I may still lack the confidence and experience to order my perfect dim sum meal but I can happily say that I feel much better today about how I’m executing against my career goals and knowing what will be fulfilling and aligned. Plus, I can still look forward to the adventure of uncovering my perfect bite.
Natalie Levy is the founder and lead at mentor at She’s Independent.
Passionate about pushing boundaries and being independent from a young age, she holds a BSE of Industrial Engineering and minor in Mathematics graduating Magna Cum Laude from the University of Michigan. She has held roles in derivatives trading at Citigroup, enterprise data sales and operations at numerous technology businesses including Bloomberg and early stage ventures. She led business development efforts for private equity investor Turn/River Capital which was focused around SaaS and go-to-market optimizations. She currently resides in Boulder with her loving rescue pup Bina and operates in a fractional executive capacity alongside staying active in early stage growth businesses as an investor and advisor.
Following the loss of her mother to suicide in January 2019, Natalie launched She’s Independent while she transitioned from corporate roles to a more entrepreneurial and balanced lifestyle. She grew through the loss and continues on her healing journey to discover what is authentically aligned and enjoys tapping into her professional superpowers that also highlight self-awareness and personal growth. Through She’s Independent, Natalie offers coaching and mentorship from professional confidence and salary negotiation to business strategy, including go-to-market and fundraising.
Thanks to my loving cousins Ari Fink and Leah Fink for reviewing this post!