Draw My Career (Kinda)
An ode to my weird as f*ck career path
Success is messy as hell.
Pre 2014
I was a 17 year old who looked, acted, and dressed like a 40 year old (see actual evidence pictured to the left). I had to take life very seriously. The stakes were too high. One bad decision in high school could alter my life outcomes—and that’s not a dramatization. That was the reality of growing up in poverty. I had to succeed by any means necessary. I had to make it to college.
I was crystal clear about my vision. I knew exactly what I wanted to do: become a banker, hustle my way up the corporate ladder, and eventually become the CEO of JP Morgan Chase. Then, two important moments in college changed the trajectory of my 25 year plan—I took a finance class (got a C) and I discovered my youthful spirit. I happily dug a plot and buried that former dream.
I was definitely on my way to the sunken place if I stayed on that path.
2014 - 2016
I saved my internship earnings, bought a DSLR camera, bought a domain, and I began blogging in my dorm. I started a video campaign called Dear Black Girl, loved that. I snapped pictures of black women, loved that too. I became part of a blogging tribe, a micro community, of 5 bomb ass Black women, loved that 3000x. My new mission in life was to expand, humanize, and add depth to Black womens’ stories as a producer. I scored an internship at Viacom, in VH1, with two Black senior executives. I could see myself hustling up this corporate ladder.
I had seen the light. This was it.
2016 - 2017
My photography dramatically improved. I was the only student at my all business college who could take great event photos, even better than outsourced event photographers. Suddenly, I had a monopoly within several campus departments. Suddenly, my earnings rose rapidly and my clientele was growing into the Greater Boston area. Suddenly, fuck corporate became my new anthem. I applied to zero jobs. I graduated business school and I proudly moved back to NYC as an anti-corporate freelance photographer. I was confident I could earn as much if not more in New York. I was completely shocked by my bank account in Boston versus my bank account in New York. In Boston I had strong steady earnings. In New York I was chasing breadcrumbs in a market that was 1,000 times more competitive. As a matter of fact, I would make the occasional trip to Boston to pick up some work. Those hard core business lessons humbled me, and my relationship with photography fundamentally shifted. It was time to start applying for jobs.
I received a serendipitous call from Penguin Random House, where I previously interned—and overnight I became an executive assistant at Random House Children’s books. What was supposed to be a two-week fill-in, part-time was extended every week. One month. Two months. I learned my boss was inspired by my curiosity, energy, side-hustles, and willingness to try, so she relieved the other temps. In a flash, I was a full-time temp. At work I was intellectually stimulated, stumbling, learning, and code switching. Outside of work I was helping CRWN Mag, researching emerging artists on Instagram, connecting with emerging artists, and putting together events to showcase my favorite artists. A few more months later my former boss laid off her executive assistant and popped the big question, “Do you want the job?”
Around the same time I received a text that read something like,
“Hey Michelene, are you able to take photos at this partner event we have with this new space called The Wing on XX night?”
Unbeknownst to me, it was the photo job that would alter my career and life path. The Wing had been open very shortly, but when I stepped in, I knew it was somewhere I needed to be. I didn’t know what a startup was at the time, I just knew the energy and pace of the space was infectious. It felt fundamentally different than any other company I had ever experienced.
Actual footage of me shooting my shot to The Wing’s founder and former CEO. She responded.
2018-2020
I loved the publishing industry. I deeply admired my boss. I was doing good at work despite my extreme self criticism. But every fiber of my body knew that job was not for me: the fibers were anxiety attacks every day. (At the time I did not know I was anxious. I wouldn’t be diagnosed with anxiety until mid-2019, but I wouldn’t start to really understand how it affected my life until Fall 2020). That’s a different story for a different day). Do I choose my boss’s clear vision for me, or do I follow my gut and fuzzy vision? I made an impulsive jump, got some bruises, and eventually landed at The Wing.
My new dream became to fly up the ranks at The Wing—and I had long a way to fly—starting at front desk. Over time, like other women of color, I was practically transitioned to clean team. I was ashamed that I was cleaning in a predominately white space. How the fuck did I get in this situation? What kind of horrible cycle have I gotten myself into? God, will I ever have a real career? How the fuck am I ever going to get out of this? If my confidence was the stock market, it plummeted 1,000 points. I felt like a failure and a disappointment to those who invested so much in me. I was hiding behind smiles at work and in every realm of my life. In fact, I avoided telling my mother, my friends, my boo at the time, and my peers what exactly I did at work. After a year and a half of bringing my best self to every menial task, plus a deep depression caused by work and a health crisis, I made the transition to brand partnerships.
I was a star that combusted and mutated into a black hole.
For the first time in my life I was working in what seemed to be a dream job on a dream team. I was soaring and then—COVID. I survived a slaughterhouse layoff and transitioned to digital events in a massive company restructure. Then, The Wing’s wings were snipped in a great social media reckoning. It was the final cue that it was time to move on. The week before the great social media reckoning I finally cut all ties with my situationship of 2.5 years . The week after the great social media reckoning my father died. Three of the biggest chapters of my life closed in 3 weeks time, all before July 1st. Devastated was an understatement, but one thing I have learned about myself—when I go down, I rise again.
In the midst of another torrential downpour in my life, the grounds were being watered to bloom a brand new beginning.
A few weeks before the house of cards fell at The Wing, I penned a think piece for their newsletter. That piece was circulated to 15,000 people—and one new fan in particular wanted to connect. That fan was Brianne Kimmel at Worklife Ventures.
Venture capital always peaked my curiosity, even when I was at Penguin Random House. Publishing, like other creative industries, has a lot of parallels to VC. In fact, Bertelsmann, the German parent company of Penguin Random House, has a venture capital arm that drew my interest during my executive assistant tenure. Like many, I was intimidated by the aura of tech bros speaking jargon, emitting braggadocio, and Silicon Valley culture. So I shied away. It didn’t feel like there was space for me as a young Black woman at that time. This time, however, I approached it differently. While I was at The Wing I was dreaming and noodling on business ideas. Stepping into vc now would provide me with an opportunity to conquer some fears, make some new connections, and begin to learn the industry. This time there was space for me—in a weirdly titled, new function called “platform.”
After several google searches and a few articles I grasped the concept of platform. In a nutshell, rather than solely handing founders a check and looking for their 100x return, investors are now trying to be more helpful and add value in other ways (because what founder wants a useless investor). How do they help? Founder education, mentoring, strategic introductions, talent networks, and more. But platform goes beyond building a support infrastructure for portfolio companies. It can span into brand, community, editorial, events, and operations—an ultra generalist function. It turns out my odd career stack was the perfect fit. I had touched all of this work, I’d just be applying it in a new context and industry. In a way, I was a unicorn parked in East Flatbush.
I flew the coup and joined the freelance life again later that summer. I was scared stepping into freelance again. I expected my earnings to plummet like before, but God had a different plan for me. I began freelancing in VC. I went from $16.00 an hour in 2018 to crossing the six-figure line for the first time by the end of 2020, at 26 years old. It was a pleasant plot twist. I never thought my earnings would rise amid the pandemic. To celebrate, I bought a $5.99 bottle of White Zinfandel from Stop & Shop and shed a few happy tears.
2021 - Now?
I’m having a blast working with Northzone Ventures, and outside I consult businesses think about their brands. This year I incorporated my consultancy, Michelene & Co. I cried paying my taxes (no happy tears there). I’m slowly brewing my own venture Dropt, for the second time. Dropt is a discovery platform where artists can release, showcase, and monetize their best creative projects. I’m making that big transition from contributor to a builder. It’s painful, but I’m sure it’ll be worthwhile.
Lastly and probably most importantly to me, I’m unashamedly doing important life things—redecorating my mom’s apartment, starting driving classes, talking with my godparents, loving the homies, cooking instead of ordering out, mustering up the courage to travel more, and getting challenged in therapy. In my own way I’ve blasted to the moon came back—and I’m understanding the magnificent beauty of the simplest moments of life.
A few big lessons I’ve learned along the way, in no particular order:
Work and money really aren’t everything. Create experiences with the people you love. I can earn more money, more status, and more rewards. Guess what? I can never hug my father again. I’d trade it all to take a walk with my father in Coney Island after dark, with Nathan’s hotdogs.
Sell your time wisely. The time you spend in that job, that gig, or with that client could also be spent in other deeply meaningful ways. Work smarter not harder. There are times we just need a dollar to pay the bills, that’s fine. But time is all we have, so don’t be afraid to ask for the raise, the bigger salary, or the bigger fee. I’m learning this.
You can only go as far as your manager allows you, so interview the hiring manager as much as they are interviewing you. A good manager will care about your professional development and general wellbeing. A great manager will stretch your skills, amplify your work, and take real bets on you (plus everything a good manager does). A bad manager will stagnant your growth long term or make you miserable, maybe even both.
The body knows the answer—trust your inner knowing and act accordingly. This especially applies to women, because so often we are conditioned to stop trusting our instincts. Instincts aren’t just feelings, they are a ton of physiological data points. #Learning
*This is for people of color: all skinfolk ain’t kinfolk. In my journey, some of my biggest, realest champions have looked nothing like me. Some of my biggest exploiters have looked just like me. Stay woke and watch if their actions live up to their marketing—regardless of what outer appearance.
Don’t suffer in silence and shame, run to your support system. Yup, don’t walk, run. Yes, you have to develop the skills to manage and cope on your own. However, communal support is critical to our ability to survive and thrive. My support system looks like my mom, my sister, my godparents, my therapist, my career coach, a few great mentors, and a few close friends. In my entrepreneurial journey, I have a lot of work to do in this area, but I’m learning.
It’s been a wild journey so far, but looking back I wouldn’t change any of it. I cannot wait to see where the next call—whether a tangible opportunity—or a deeper calling will lead me next.