Today I did a #givefirst call with someone introduced to me by an entrepreneur I liked. The person I spoke to is in her early 30’s and is in the middle of business school. She had noticed that I had pivoted a couple of times in my work life, and she wondered how I’d done that. For background, I left the legal profession at 33 and moved into tech. I then left the realm of full-time employment at age 46 to become a full-time executive coach and consultant.
When I speak publicly, I often mention this Steve Jobs quote:
You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.
I mention this quote because it feels so relevant to my career and these 90-degree pivots I made. What I shared with this woman today is that most of my big choices looked ridiculous when I made them. It’s just that looking now at my Linkedin page, it is possible to find a thread.
Here’s how I talk about that thread:
I knew I wanted to be a federal prosecutor in the Department of Justice Civil Rights Division when I was 11. That happened in my late 20s. I felt I had the best legal job on the planet, but some aspect of my creativity wasn’t being sufficiently tapped. So at night, as a moonlighting endeavor, I started an e-commerce business at the dawn of the consumer internet. I realized I loved selling and the dynamics of the web, and I decided to leave law to work in business.
I applied for two jobs and I got one of them, in part because one of the execs who interviewed me at Discovery Channel was an ex-lawyer. So, I sold my little company for $20,000 to a friend and I became a digital business development person. For the 20 years after that, I founded and ran a series of internet companies.
Ten years ago, a coach came to my company, and she showed me that I could work more effectively and with less personal suffering. I kept working with her, discovered conscious leadership, brought that work to the companies I ran and mentored, and eventually, I decided I could work with more companies and have more fun if I worked for myself. I gave up the notion of being a full-time operator, and jumped in with both feet to my current life. In there somewhere, I leveraged my startup and mentoring experience to co-found an investment fund focused on companies with at least one woman in leadership.
When I lay out my journey like that, it sounds almost wise, doesn’t it? It wasn’t. This story lives at the nexus of two factors:
- Although my path looks risky, I hedged every bet I made. My first internet company was backed with a $10,000 loan from my best friend, and I kept working as a lawyer while I lived that experiment. I didn’t actually complete the transition into business until Discovery gave me a really attractive full-time job with benefits. I got to learn that having a job is no guarantee of anything when the dot-com bubble burst; I was one of very few people at Discovery.com who stayed on, finding a role in the consumer products division of the company. That honestly was pure luck. During my migration to being a coach and consultant, I always knew I could get a job if I needed one. I pared down expenses. I got a few early clients. I offered to coach over coffee for $65. Eventually things came together in a sustainable way.
- I did what I wanted to do next. I believed that I could create a life that I wanted. I believed I was allowed to make choices that felt aligned in the moment. Part of that is luck. If things fell apart, I could have lived with my mom. Part of it was conviction and a belief that I could engineer my own next reality.
The person on this call felt grateful. She said that in business school, they keep bringing in what she called “Hollywood stories” about giant risk and huge, successful outcomes. Although we both surmised that her program heads must think this is inspiring, for her (and me) it has a chilling effect. If I thought my options were my current life or a unicorn outcome, I’d probably get a secure job that covered me but didn’t meet my ambitions. I’d count myself out of the likely huge win, and I’d be right based on the odds. There is a giant middle of the failure-to-success continuum that should be part of her curriculum and our mindsets. If we ignore it, we do students and ourselves a disservice.
The myth of success is that “success” is narrow, newsworthy, and “Hollywood.” For me, success is alignment with what I most want and can achieve, through trial and often error. Success is reflected in the stories of winners you may never hear about. This caller was relieved to hear my story, and I thought you might be as well.