Mapping your entrepreneurial journey
A few weeks ago, my friend, Dr. Angela Jackson, asked me to give a guest lecture in her class at Harvard. The course, “Entrepreneurship in the Education Marketplace,” has about 60 students in it who are emerging founders. Angela felt it would help them to hear about my entrepreneurial journey.
I gave my lecture last week and it was easily the hardest talk I’ve ever had to give because the focus was on me - and on my work. I was really nervous. I felt very quite vulnerable walking into a full lecture hall and opening up to a bunch of strangers about my windy career path and all of my decisions along the way, but I’m glad I did it.
The process of going back in time and mapping my journey from educator to intrapreneur to entrepreneur was actually rather eyeopening. I consider myself to be a deeply reflective person and yet I learned something new about myself from the experience.
I realized I’ve always been entrepreneurial.
Looking back, I was an innovator as early as my sophomore year in high school. I remember feeling disgruntled that my school was so sports-focused. I wrote a proposal, got support, and founded Arts Week in order to elevate the Arts and artists who were underrepresented. I am pretty sure that Arts Week continues to be an annual tradition there.
In college, despite having a billion majors to pick from at UPENN, I decided to design my own major in Environmental Science and Writing. As an inner city teacher, I designed an entirely new curriculum leveraging the City of Philadelphia as my classroom. As an educational leader, I led a community arts project as a guerilla marketing campaign for a small school in Beacon Hill; the project was on display at the Charles MGH Train station for 10+ years.
I didn’t even know the word “entrepreneur” existed until I ended up at MIT, in my mid-thirties, launching what later became the MIT Communication Lab.
During my third year at MIT, I got involved with the Sandbox Innovation Program and I was blown away that there were entrepreneurship frameworks and words to talk about all of the things that I thought about all of the time. I remember reading every single book produced by IDEO and feeling more seen than I’ve ever felt before - like their human-centered design process was describing my own brain to me.
Looking back, I see that I have been entrepreneurial my whole life - even if I only became a “capital E” entrepreneur a bit later in life.
The experience of being asked to map my entrepreneurial journey was a huge confidence booster because I saw so clearly that being an innovator is in my DNA. It’s how I think and operate. I have, actually, always been this way. It makes me feel like, even when I don’t know how to solve the next challenge I’m facing, it’s quite comforting to remember all of the previous ways I’ve identified problems, used data to create a hypothesis, and used creativity to create and scale lasting solutions.
This exercise also convinced me that my 13 year old son is absolutely definitely going to be an entrepreneur. That kid is 100% a capitalist and weekly has new ideas to make money. I can’t wait to be able to do this backwards mapping with him when he gets older and remind him about his various business ventures from upselling consignment Nikes to trading up basketball cards at trade shows (“Mom, wait outside. I’ll get better deals if I go by myself.)
So maybe, if you’re having a little bit of imposter syndrome, open up some old photos and spend an hour looking back at your roots as an entrepreneur. Make a visual of your journey and keep that document somewhere safe to look back upon when you’re having a hard day at your startup.
Here’s a link to my talk if you’re interested in looking at a model to help you map your own journey.
