Five years ago this summer, I took a leap. I quit my job in the investment industry. It wasn’t a long-planned decision. In fact, I was surprised how quickly I came to it with the utmost confidence and clarity. But I had done the research.
And the research was on me.
I was clear on my values. What I was uniquely good at. What inspired me, grounded me, made me genuinely happy. It wasn’t about what those answers should be. It was about the truth. My truth. So when my work environment changed around me, it was as if a decision had been made for me.
I sat down with a piece of paper and drew three concentric circles. I labeled them leadership, girls education and global investing. I wanted to work at the intersection of my three big passions. I listed things I wanted to do: write, travel, be more impactful with money. I scribbled down some of my key words–among them were connector, growth, and global. My early website name came from that list.
The first thing I did was spend a month at a girls’ secondary school in rural Kenya. As expected, it rocked my world. Upon my return, I dove into learning about impact investing and philanthropy. Eventually, I set up a company to advise impactful organizations, coach mid-career professionals, and lead transformational trips to thriving economies in Africa and Asia. I continue to enjoy the journey.
I’m frequently asked about my story, lessons learned and advice for making a transition. So in celebration of this five-year anniversary, I’m sharing five learnings.
1. Figure Out What To Call It
I’ve never been one for titles. I avoid labels because I hate being labeled. But when I described to people my three circle concept, I’d get blank stares. And then questions.
- “Would you ever return to the investment industry?” (I don’t know)
- “Are you wanting to work for a non-profit?” (I don’t know)
- “How were you able to retire?” (I am not retired. And please, let’s retire that word)
I realized I was to blame for the questions. What I was describing was novel; the questions were people simply seeking to understand. I came across the term Portfolio Career. I adopted it as my descriptor. It was a play on my earlier investment career. Like any good portfolio, my next-stage had consistent themes. But my holdings—what I’m doing, who with, percentage of time spent—continually change.
If I had to do it over, I’d title my new stage from the beginning. For example, I’ve seen people simply say “I’m on sabbatical” and the listener nod in understanding. It allows the storyteller to control the conversation and their activity going forward.
2. Say Yes & Find Your Partners
I don’t recommend most people quit their job the minute they feel out of alignment. But you do need to trust that feeling. And act on it.
I remember beginning to feel lonely in the investment industry and at my company. Outside of work, my friends naturally included many from financial services; most were near my age.
While still committed to my job, I sought out new circles. I worked with professional coaches who pushed me outside my comfort zone. I got to know employees and fellow supporters of literacy non-profit Room to Read. Through the International Women’s Forum (IWF) Northern California, I satisfied my craving to learn from women leaders across different industries—especially those decades older and wiser.
When I made my professional leap, I said yes to coffee dates, dinners and conferences with friends in new circles. I hosted events and leaders in my home. I flew across the U.S. and the world to immerse in investment and philanthropic experiences.
As my circle grew, I became more clear on what I needed to see in a partner—for profit, non-profit, or individual (Your Due Diligence). When I find a partner, I’m all in. I invest in their company, take on advisory assignments, make introductions, and simply enjoy their friendship. They know little about what I used to do; we are fully immersed in our present efforts. My favorite part is our diversity. With completely different backgrounds and often a decade or more in age between us (20’s to 70’s) I’m continually peeling the onion on their stories.
3. Say No
When you’re a classic Enneagram 7 Enthusiast, focus is always the challenge. I consider myself fairly focused and good at saying no. But in this new career stage, I had to up my game. The only way to have the capacity to say “yes” was to become better at saying “no.”
I looked to my favorite leaders like Jacki Zehner to see how they tackled the challenge (Hell Yes! Yes! No. Have Too). Reading Greg McKeown’s book Essentialism, I became a self-declared essentialist. I flipped my mindset from “what do I have to give up?” to “what do I want to go big on?”
Even with my existing partners, I re-assessed my role. Perhaps there was someone else better suited for my advisory role. Maybe a mentee had grown out of needing me as a mentor. Some friendships dropped when I realized they were based more on a past history than a connected present. With practice, letting go became easier.
I changed little things. If someone suggests a meeting, I sometimes reframe the request. An article, book, or different person might prove more useful; a 30-minute call may make more sense than an hour coffee date. I no longer feel guilty about not finishing a book or leaving an event early if I’m not into it. And I don’t have business cards—it allows me to control the follow-up, which I do immediately with those I want to connect to.
I pause before accepting small requests or new roles. The more clear I become on what I need, am good at, and choose to go big on, the easier it is to articulate my conditions for a “yes” or why I’m saying “no.” One day, a coach I admire, Barbara Waxman, said “I heard you are really good at saying no.” I paused, letting the initial pinch of the statement fade before privately congratulating myself.
4. Start With Why
After viewing Simon Sinek’s famed TED Talk Start With Why, I became obsessed. His premise? We spend the majority of our time explaining the what and how of what we do instead of why we do it.
I thought back to my earlier career. About the successes and failures we had in promoting various investment strategies. About candidates I had interviewed for jobs. About roles I had interviewed for. We had been brainwashed in one formula for success. Our pitchbooks and LinkedIn profiles were full of what‘s and how‘s while completely lacking in why.
I read Simon’s books; I did his exercises. I realized that although my career focus was global investing, it wasn’t my why.
My why is connecting people & ideas so that we maximize our impact. What do I do? I’m an advisor to impactful organizations, a success coach, a trip curator, and an investor, writer, and speaker. How do I go about doing this? I harness my personal strengths and story to help individuals and teams define and live their own why.
You likely don’t care about what I do unless you know why I do it. It’s one reason I write blog posts. Likewise, I realize the people and organizations I am most pulled to all have a very strong why.
This is powerful. I wish I would have realized it decades ago.
5. Maximize Your Capital
Money is one of the most powerful tools we have to express our values. When I made the decision to be more purposeful and impactful with my money, the hardest part was getting clear on what impact means to me. Being the good student, I felt I had to have it all figured out before I started. It was another outdated rule to throw out the window.
On the investing side, I started with a single private investment. I’d learn more, test my assumptions, meet new people, gain additional ideas, make further investments, and continue to define what impact means to me. It was an Investing Circle that continually widened.
I did the same with my philanthropy. Girls’ education and empowerment in emerging countries is actually a massive space. I made small commitments to test a few non-profit partners, reassessed as I learned more, eventually Doubling Down. A 10-year commitment to sponsor 1000 girls in one year of school through Room to Read is one result.
Along with it, I now invite people to join me in Venture Travel. Because capital isn’t just monetary. My social capital—voice, advocacy, connections, time, travel—is potentially more powerful than my monetary capital. Through Venture Travel, I pull together my original three concentric circles—conscious leadership, girls education, global investing. In connecting individuals to new people and ideas, I watch them begin to think differently and find ways to further their own impact. The gifts that I’ve received from this work are unimaginable.
I share these stories and lessons because my story is your story.
Success is how you define it. You don’t need a job change or anniversary to get clear on it. Nor do you have to have the destination all mapped out. Just make sure you’re on the journey.
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