Pivot to Pirouette
My bumpy career transition
Continuing my “Bank to the Ranks” series of transitioning from social entrepreneur to senior management. The first 3 episodes were:
1. Knowing When to Walk Away: How to know when to step down as a founder-CEO
2. 28 Lessons from 10 Years as a Social Entrepreneur: Pretty much exactly that
3. Borrowing Against Retirement: On the value of taking a sabbatical
Something I’m Learning
"When you pour your life into building something, and then you change course, you almost have to redefine yourself.” - Sasha Orloff
How terrifying, or exciting, or both, is the blank page? The new chapter in life? The vast expanse of open ocean?
When I stepped down as a founder-CEO with no settled next move or even a clear idea of what direction to go in, I had to confront the emptiness of my calendar and the removal of professional responsibility. It was both liberating and intimidating. And while changing jobs or career paths is not all that unusual, there does seem to be something different about an entrepreneur doing so, something more at the level of one’s identity or personal mission.
Getting Stuck
The only thing I knew for certain when I turned to my own blank page was that this next chapter of my life would happen in the United States, which was for personal not professional reasons. Yet I felt pretty bullish about my prospects. After all, I had just built a profitable global social enterprise across 3 continents. I have two degrees from leading American universities, including the one ‘in Boston’. I was moving to Washington, DC, a major hub for nonprofit and development organizations. I’m a catch, I thought. How hard could it be to get a new job? I was so confident I didn’t think about my next job at all during the 8 months of my sabbatical.
It did not turn out to be so easy.
Starting the job search meant entering the desolate wilderness that is our utterly broken job hunting/recruitment system (more on that in a later post). After more than 20 rejections, and feeling the dejection of failure and the pressure to start generating income, I changed strategy towards a consulting-first approach. I identified climate change and philanthropy as the two fields in which I wanted to build up my portfolio and began calling everyone I knew in those two fields, offering myself for short-term projects. Meanwhile, I continued to keep an eye out for opportunities in my third area of interest - working at scale in a large organization.
Getting Going
At first I accepted everything that came my way. My first two gigs were to plan a conference and to ghost-write for a thought leader. Neither was particularly future-forward but they allowed me to launch my portfolio of philanthropy clients - and to get paid. Both those gigs came from friends, and I’ll always be grateful to them for getting me going.
The consulting work (and income) not only kept me moving towards the type of work I was interested in, but also created the option to decline offers from organizations that would not take me in new directions. I also learned that while I could build a consulting practice, I prefer helping build institutions, as opposed to offering recommendations and moving on. No disrespect to consultants but, at least in this stage of my career, it ain’t me babe.
Helpful Thought Experiments
Because pivoting, i.e., going from a career in which you were an expert to breaking into an entirely new one, is just really tough to do, I found these thought experiments helpful in getting unstuck and leaning towards possibility:
1. On Reframing a Career Narrative:
After several rejections, I was advised that, if I was going to pivot, then I somehow needed to connect my new field to what I had done before. While I never would have considered myself a ‘fellowship expert’, it was true that I’d worked in the fellowships industry for more than 20 years. Re-framing my background from social entrepreneur to fellowship expert helped land my most consequential consulting role, the one that set the stage for everything that’s come after.
2. On Linking Between Life Chapters:
A blog post (I can’t find it now) asked the question: how do we show up when we’re in between major chapters in our lives? It posed three questions: 1) What from the last chapter should be left behind? 2) What do I want to bring with me into the next chapter? 3) What new and different things do I want to introduce? Writing down my answers to each question allowed me to move forward in a way that was both reflective and forward-looking.
3. On Identifying a ‘Leadership Value Proposition’:
What specifically, regardless of type of job or industry, can I bring to the table in terms of my leadership potential? I developed this ‘leadership value proposition’ frame while preparing for interviews with people not familiar with my past jobs/organizations. Having that on hand helped me feel a lot more confident and grounded going in to the interviews. (If you want to develop your own, just hit reply, and I can share mine as an example.)
Landing the Pirouette
It was a full year – to the day! – between when my sabbatical ended and my next full-time job began; twelve whole months to make that career transition from CEO to going back to the ranks. And yet, despite the humbling lows of rejections, it was still a wonderful year. In addition to building a consulting practice for climate-related philanthropies, I also became a university professor and a published author, travelled the country for speaking engagements, and joined the board of one of the largest NGOs in the world. It turned out there were many unexpected benefits to not finding my next gig right away, that you can turn a pivot into a pirouette if you’re lucky.
Something to Consider
Some humor on career transitions, courtesy the India Development Review: Entering the Social Sector: Expectation vs Reality (PS: it’s even better if you know the actor)
Something to Quote
Total confidence at the beginning of a new phase of life means we are misinformed…that we think we know what is about to occur and who we are about to become.
- David Whyte, Consolations