Seeing Yourself As The Person You Could Be, If You Got Out Of Your Own Way

Last month, I started the process of raising venture capital for Boost. Mostly, this entails having lots of conversations with venture capitalists about the company you’re hoping to raise money for—why it’s a worthy investment, why it’s different, why it matters. On these topics, I’m well-versed; I’ve spent many hours working to identify Boost’s market fit, why Boost’s is a viable business model, and why now is the time for it to exist. I was confident in my ability to define all this when the time came. 

But so, too, you are asked in these convos to share things about yourself. This part of the pitch entails condensing a lifetime’s worth of experience into just two or three poignant, relevant, and compelling points that synthesize the whole of who you are and why you’re worthy of investment. I wracked my mind for the right things to say. Then I couldn’t think of anything. What about me was noteworthy? What about me actually made me worth investing in? Were the things I believed about myself—the answers I thought I should give—actually true? In an early conversation, I spiraled. I fumbled for an answer. I babbled. And the longer I went on, the less articulate I became. The VC on the other end of the Zoom nodded politely. Two days later, he passed and shared that he loved the idea, but I wasn’t the right person to build it. 

I knew as soon as I got off the call that I had to tighten my pitch. I knew, too, that I needed help. When I sat down with a pen and paper, the points I came up with felt inadequate and unimpressive, evidencing only my lack of experience and smarts. 

I reached out to my brother, who’s a killer marketer, has a long and notable list of logos under his name, and is well-versed in corporate speak. But after our conversation, I mostly felt inadequate in comparison to him.

Finally, I texted Lizzy, one of my advisors. “What’s compelling about me?” I asked her. “Help.” She suggested we hop on the phone. A 10-minute conversation turned into an hour and a half conversation, during which—unbeknownst to me—she took notes. While we were talking, she sent me an email, written from my perspective, about myself. 

It caught me in my tracks. She identified experiences and accomplishments that I’d known to be formative, but detailed how they’d bloomed into identity traits in a way I’m not sure I would have been able to articulate. “I’m a former Division 1 athlete,” she wrote. “On the field, I was the goalkeeper, the protector. I taught and I coached from the net. Later, I did the same thing in New Orleans, where I taught children from underserved communities. I only left the classroom because I realized I could teach, coach, and impact on a scale greater than just a single classroom. Rather, I could teach and coach organizations and nonprofits. So I started a consultancy firm to do exactly that. Now, I’m starting Boost to do the same thing but for a generation of...”

Lizzy was reading this aloud to me. When she finished, I was silent. I was shocked not only by Lizzy's insight into me—her ability to connect lines of logic I’d always felt, but had never connected myself—but the conviction with which she shared it. She sounded as if she truly believed these things about me. Her version of me was a different, more confident, better version. The version I could be, maybe, if I got out of my own way. 

I didn’t tell Lizzy this, but I started to cry. I’m not sure whether they were tears of joy, or gratitude. They weren’t tears of sadness. I was sort of just overwhelmed. It was one of the nicest things anyone had ever done for me. It was like a kind of recalibration, a reminder that the way I think of myself, particularly in moments of doubt, is not the way other people see me. 

Since then, I’ve spent a lot of time thinking about why it was so much easier for someone else to describe me—to tell me a bit about myself—than it is for me to talk about myself in the same way. To capture why I’m building Boost, and why I’m deserving of investment, in precisely the way I wanted to, subconsciously, but couldn’t. 

This is something that’s hard for most women. A recent study by Harvard Business Review revealed that men rate “their performance” at work “33% higher than equally performing women.” They also engage in more self-promotion. Why is this? Well, for one thing, when women do advocate for themselves and their accomplishments, they’re “judged more harshly than men,” as Joan Kuhl, author of "Dig Your Heels In" and "Misunderstood Millennial Talent”, wrote last year. That’s something Lean In calls “Likeability Bias,” an insidious societal trait “rooted in age-old expectations… We expect men to be assertive, so when they lead, it feels natural. We expect women to be kind and communal, so when they assert themselves, we like them less.”

All of which is to say, it’s not necessarily your fault if you, like me, have trouble advocating for yourself, personally, with conviction. The problem, of course, is self-promotion is important. That HBR study found that “Workers who rated their performance more highly...were more likely to be hired and offered higher pay.”

I’m not sure how to reverse Likeability Bias at scale, such that we can uproot what sociological factors work to hold women back—and make us more timid and penitent inherently—but I do know now that it’s something we need to be aware of, so that we can push back against it. 

Like everything else, speaking about yourself with confidence and conviction—being fully the person you think you are—is a matter of practice, a thing you get better at and that comes more easily the more you work on it. I’m lucky in the sense that, in advocating for Boost every day on calls with VCs, I’ve had ample opportunity to do precisely that. And I can report that it is getting easier. That I’ve begun to see and think of myself more clearly and more honestly the way Lizzy sees and thinks of me. I can tell you a bit about myself now, including why I’m deserving of investment—deserving of a chance—and, on a good day, I’ll believe every word.