How Owning My Sexuality Transformed My Career
Originally posted in SELF Magazine.
April 23, 2019
My career in the tech world started to take off a few years after I began building my first company, an accounting software for growing businesses called inDinero. I was closing more sales deals, nailing my speaking engagements, and getting feedback that I was positively impacting others on my team. When people asked me what I was doing differently, I would lie, saying something like, “Oh, I started meditating. Totally life-changing.”
The truth was that I was finally having the sex I wanted. My career transformation was the bonus cherry on top.
Taking control of my sex life was a long process. Although I was an early bloomer in some ways—I went to college at 16 and started building inDinero at 20—I was raised in a conservative environment that left me in the dark when it came to my own body and sexuality. I was 24 before I felt comfortable enough to look at my own genitals.
Around that time, I committed to learning about my body, leaning into my identity as a sexual being, and making time for pleasure. The results were powerful. Exploring my sexuality helped me unlearn a lot of harmful thought patterns about bodies and desire, and it helped give me both the sex life and career I’d dreamed about.
Now, I’m the founder and CEO of O.school, a welcoming online resource aiming to educate people on all things sex and sexuality. So, these days my career is obviously influenced by the subject of sex and sexuality—it's what we do at O.school! But aside from that—and even well before that—I found that tapping into my sexual energy led to enormous growth in my career. Here are a few ways that getting in touch with my sexuality spilled over into my professional calling.
1. I learned to listen to my intuition.
I used to be really uncomfortable even trying to think about my own pleasure. In bed, I was often completely focused on the other person. I would shut down when a partner would say, “Let’s make you feel good. What do you like?” I didn’t know because I didn’t have much sexual intuition, which I view as a connection to what makes me feel good.
Making time for pleasure helped me strengthen this sexual intuition. One thing that really got me there was orgasmic meditation. “OM,” as it’s often called, is primarily focused on exploring where you like to be touched on your clitoris. OM is about being present in how you’re feeling in one precise moment: One day you might like one kind of touch, and another day it could be something different. The key is being willing to listen to your own body, which helped me flex that mental muscle of knowing what feels good and right. This kind of gut instinct became a guiding compass for me at work, too.
In the span of a week, 20 smart investors can recommend I take my business in 20 different directions. I listen to everyone’s advice, but then I listen most to what feels right in my body. I know something is right for me—in sex or at work—when I feel curious, connected, and attentive. I feel calm and can see the pros and cons. When something is a bad fit, I notice that I feel fearful, anxious, and have a lot of spiraling thoughts. Listening to my intuition, no matter the situation, has rarely steered me wrong.
2. I practiced asking for what I want.
I know it seems obvious, but it’s so true that I have to emphasize it: People can only meet your needs if you make what you want clear. Sex has become a safe space for me to practice asking for what I want in a relatively low-stakes situation.
Once, right after taking a shower, a partner asked me to sit down and spontaneously started to blow dry my hair. It was one of the sweetest and, surprisingly, most pleasurable gestures I had ever experienced. I could have kept this quirky delight a secret from other partners, but I’ve chosen to talk about it with various people since then. While a few have declined to engage in this hair-focused foreplay, pretty much all of them have made a beeline for the blow dryer. This has reinforced that being open about what makes me feel good usually leads to me feeling, well, reallygood.
Experimenting with clear communication in bed built up my confidence to do the same in a professional environment. I’ve learned to be incredibly specific when it comes to asking for what I want at work. In the past, when I’ve expected people to decide on their own to give me what I “deserve,” I’ve been constantly disappointed.
For example, when I worked as a venture partner at a venture capital fund, I learned that a male coworker who joined the exact same week as I did was given a raise. I didn’t wait around hoping to have a commensurate raise land in my lap. Instead, I went to my boss and asked not just for a raise, but also for more travel opportunities to our global offices, introductions to people who could provide me with paid speaking appearances, and the ability to start making investments in international markets. I got all of it. That probably won’t happen every time, but it definitely wouldn’t have happened if I hadn’t asked.
3. I realized that connecting with my body clears my mind.
When I’m feeling too uptight, that usually means I haven’t made time for self-care. My sexuality plays a big role in renewing my energy. When I’m more connected to my body, I think more clearly, get more done, and make better decisions. I’m funnier, more powerful, and more relaxed on stage at speaking events. I can tell people read me as more confident and interact with me differently.
Feeling connected to my body is not limited to sex. Sometimes it’s a massage. Sometimes it’s hanging out with my friends and holding their hands while we drink wine, kiss, hug, and flirt.
Restoring myself in this way has become so important that I actually put self-caretime on my color-coded calendar. (It gets the honor of being purple.) Self-care is in the mix with my meetings and appointments because it’s just as—if not more—important. If I look at my week ahead and see no purple blocks, I make it a point to change that.
4. I learned to establish firm boundaries.
From a young age, I was taught that my body didn’t fully belong to me. (As are many of us.) Sometimes I had to kiss and hug relatives when I didn’t want to. On the playground, little boys would grab at me, and adults would say, “That’s how you know they like you.” I felt resigned to the fact that others could do what they wanted to my body, and I should stay quiet to avoid “making a fuss.”
This thinking persisted for years. One day in college, a guy in class with me started rubbing my leg under the table. I couldn’t move or say anything because I still didn’t feel in charge of my own body.
I started to unlearn these lessons through kink and role playing. A Kink 101 class taught me that nothing sexual should happen without discussing boundaries and consent. I also realized that “bottoms” (submissive people) are often viewed as the ones actually “in charge” because they can slow down or completely stop a situation with a safeword.
Meditating on these concepts helped me see how much of my sex life was spent going along with other people’s desires, following scripts I saw in movies and porn, and how little I was focusing on what I wanted. It took years of practice and overcoming occasional discomfort, but now I only have the sex that I want to have, and I stop sex that doesn’t feel good.
This sense of control transferred to my career. I’ve realized that, ultimately, I get to choose how I spend my time. (Granted, this is a privilege that I have due to my being an entrepreneur.) I swiftly decline opportunities that aren’t aligned with my goals, often leave draining events or meetings to take care of myself, and generally feel more empowered and less complacent about how I spend my time and energy.
5. I stopped caring about looking stupid.
Sex is a great chance to practice getting out of your head and seeing what happens when you do something “silly” without judging yourself. When I first tried to explore dirty talk and role play, I struggled with this big time. I wasn’t naturally excited about trying to say sexy things or pretend to be someone else, so I felt dumb when I tried. Then I decided to view it as a game of improv. That got me out of my “this is dumb” thought patterns, and I found myself surprisingly turned on.
That same fear of appearing stupid used to block the creativity my career needs in order to thrive. I’d get an idea in a meeting and hesitate to speak up, only to kick myself when someone else said the exact same thing. Sex helped me realize how freeing it can be to leave that fear of judgment behind, so I started to let go of it at work, too.
To experiment with bringing that mindset into my work life even more, I once hired an amazing business coach who was an ex-clown. She made me mime my talks with really exaggerated gestures. It felt horribly uncomfortable. But the next time I was on stage, I was more aware of my body and felt so much more dynamic. It’s all because I was no longer holding back due to fear.
It might sound unconventional, but for me, sex and work are intimately connected in a way that’s made my life so much better. Having good sex is worth celebrating all on its own. Being able to apply lessons I’ve learned through my sexual experiences to my career is even better.