Though I didn’t know it at the time, a partner at Bain Consulting gave my 24 year old self what is still the best piece of career advice I’ve ever received: change your role, or change industries, but never both. The underlying logic is that new roles and new industries have steep learning curves, and you’re better off climbing one learning curve at a time, while leaning on competence in the other to be a contributing and valued member of a team. I got this advice on my way out of Bain, after my search for an operational role at a cleantech startup didn’t bring the opportunities I had hoped. The companies I applied to recognized what I did not, that I had neither the operational experience nor the cleantech expertise to deliver enough immediate value.
After the wisdom of this advice took to heart, I joined Village Ventures, where I could immediately take advantage of the business skills I had learned at Bain, while being thrown into the deep end of this new and unfamiliar startup ecosystem. I had comically little understanding of the VC-startup dynamic, the various flavors of startup wisdom that I now take as given, and perhaps most importantly no knowledge of, or certainly connections to, the influential thinkers and doers in the NYC startup world. However, what I could do was quickly and competently boil down the dynamics of a business or market, prepare a professional and compelling presentation, and chew through and make sense of mountains of data and information. While I was a startup baby, I relied on these abilities to make a place for myself on the Village Ventures team.
Through four years at Village Ventures, and with the generous mentorship of so many, Bo Peabody and Matt Harris particularly, I was able to move from a baby to an adolescent in my knowledge of the startup ecosystem and dynamics, and perhaps even young adulthood in a few markets, digital media and advertising technology particularly. With whatever startup and industry acumen I’ve been able to develop, I found myself with a far more exciting opportunity than the operational roles I had lunged for at 24 when I was lucky enough to join SimpleReach as President.
Again the same dynamic played out, though in reverse of Village, in which I struggled mightily, and continue to struggle, up the learning curve of my new role, while using my knowledge of digital media and venture capital to immediately contribute to the team. As SimpleReach CEO Eddie Kim will attest, I wasn’t much of a salesman when I joined, but I quickly added to the strategic, market, and fundraising thinking.
I’m cognizant of the way in which this highly practical and seemingly conservative advice contradicts the ‘you can do anything’, ‘find your passion’ ethos we often rightly celebrate in the startup ecosystem. However, I’ve found that by tackling steep learning curves one at a time, you maximize the value of your past experience and knowledge while placing yourself well outside your comfort level and forcing yourself to learn and adapt. This approach also keeps you from the grass-is-greener phenomenon we are all vulnerable to, in which ignorance of a job or industry makes it seem more attractive than it truly is. You can only be so uninformed about roles in your industry or functional area.
This approach marries two core, shared human dynamics: we want our efforts to have meaning, and we learn best when pushed to the limit. By combining our strengths and weaknesses in new opportunities, we balance the need to learn with the need to matter. And there’s nothing contradictory about that.