When Is Done Done?

On Founder Identity, Transition, and Letting Go

Dear FFF,

I am a fabulous female founder who, at least optically, has had the dream founder experience. I created a solution for comprehensive elder care, brought it to market, raised some capital, almost closed, found a buyer, and for the last two years have seen an infusion of capital into my idea. Every day, I know I am impacting lives.

But…I am done. Or at least, I think I’m done. I’m not done with the solution we deliver. But I’m done running to a standstill with the company’s new owners. For the last 8 months, I’ve been considering leaving and taking a “normal” job. It sounds so seductive, doesn't it? Just to show up and contribute and do a good job. Then, just go home and not wonder what I need to accomplish to keep the lights on another day. 

But am I really done? If I leave, it’s likely that my product will be shelved. What comes out of my mouth is that I’m okay with that. Part of my heart feels that too. But do I really? Or will watching it fail this way feel like my failure?

I am currently interviewing for a role that lights me up. While I know I’m getting ahead of myself (they haven’t offered me the job yet), I’m wondering what you recommend to help me think through the decision to accept or not in light of my founder’s journey. 

It’s easy to compare benefits, it’s another thing to think about walking away toward a new future.

Thank you! 

- Ready or Not

Dear Ready or Not, 

Congratulations! You’re way ahead of most founders who never get to see their dreams realized. Among those who do, you’re in good company with those who sell or merge, work for the new parent firm for a period of time, and then move on by choice or not, leaving their baby in someone else’s hands to morph or grow or shrink or die. 

It’s an emotional process, not unlike birthing, raising, and launching a child, then watching and marveling in amazement or dismay as they make their own choices and become the person they become, none of which can be construed as failure.

The big question is: Are you ready to let go and let the fate of your idea rest in others’ hands? 

***

Identity and Transition

Know it or not, you are in good company. Serial founder Ann Sacks created and sold her first tile company to Kohlers, stepped out 14 years later, and went on to launch another tile company, an eyewear company, and a non-profit animal rescue. Katie Poppe founded and sold Portland’s iconic Little Big Burger, then launched Blue Star Doughnuts. SK Lee started, grew, and sold a Shanghai-based education business, then took on a role as Head of BD/Strategy at a hyper growth venture-backed startup, then became an investor and executive coach. Mara Zepada simultaneously co-founded three non-profit organizations: Xcelerate (a support system for female entrepreneurs), Zebras Unite (an international movement), BBPDX (an alternative chamber of commerce), as well as a for-profit company, Switchboard, which merged with another female-founded company, Hearken, a couple of years ago. Mara transitioned all four to others and is now entrepreneur-in-residence at a small college in South Carolina. I could go on and on with examples like these.

Personally, I wasn’t planning to exit when I did, but after we sold our bike share company, I felt depleted and longed for time with my kids, plus my consulting firm co-founder and I had slid out of alignment. For weeks, with girlfriends, my husband, a CEO mastermind group, and an executive coach, I ruminated, much as you’re doing. I felt at a crossroads, like the classic Robert Frost poem, The Road Not Taken. 

Down one road: great staff and projects… and many more years of doing what I’d been doing. Down the other: a scary void, for who would I be without my firm, my mission, my field, which had defined me as I had defined it? If I left, would I be letting down my staff, particularly the women I’d been mentoring? Was I satisfied with my legacy? What would I do with my time? What would happen to my firm without me? Classic founder questions, wrapped in layers of emotion. 

Well, as you know, I did step out and take the road less traveled. And yes, as Frost wrote, “That has made all the difference,” for I’ve gotten to use my business skills to organize and lead a much-needed and thriving community organization (Eastside Jewish Commons); sit on corporate and non-profit boards; and serve as a coach, advisor, investor, mentor, and writer supporting founders like you. I don’t regret selling the bike share company; my partners and I were the right ones at the right time to get the ball rolling, but not the right ones to take it to the next level. My consulting firm is also in others’ hands now, evolving with the times.

See, that’s what founders do: Create, grow, lead, let go, rinse, and repeat.

Ready or Not, if you decide to move on, you won’t be walking away. You’ll be walking toward your next adventure, bringing with you the knowledge gained on this phase of your journey.

***

Write Your Story

My family and I love smooshing together on the couch and watching American Ninja Warrior, cheering on the athletes, applauding each and every one for their effort no matter how far they get. The ones who finish all say things like, “Believe in your dreams,” and “You can do anything you set your mind to.” But the truth is that we cannot always do the things we set our minds to, and sometimes our dreams and aspirations are not achievable, at least not in the ways we originally envisioned or conceived. This does not diminish the vision or effort. It is simply reality. We can try to bend the world toward our will. We can do everything in our power to plant, nurture, and grow seeds of beauty, and our plants may still refuse to flourish or thrive. We can only control what we can control.

You don’t know what will happen with your product. Maybe they will shelve it, maybe they will evolve it, maybe they will sell it. Maybe you will come back to it or maybe you will move on and do something else altogether that draws from the experience. We can only live life forward and reflect backward. 

Here’s what I suggest: Write your story from the vantage point of 10 years from now. Let’s say you are in Alaska on a cruise up the Northern Passage to see the Mendenhall Glacier. You spend the day marveling at the seals floating on icebergs and the shimmering greens, blues, and purples radiating from the ancient melting ice. At twilight, relaxed and drunk on scenery, you find yourself chatting with a stranger who asks about your career journey. What will you say?

Write your story with pride. Practice saying it out loud. Try different versions, one in which you take the job you describe, another where you stay where you are. Keep going, adding a third or fourth scenario where you draw from your experience as you create something different but equally fulfilling. Think of this as your next phase elevator speech, refined and massaged down to its core sentence or two. Which story do you want to tell your grandkids? 

***

Two Roads

Back to Robert Frost, here’s how I see it. Down one road: what you’ve been doing, your baby close by. Down the other: reinvention, letting go, a story not yet written.

Whatever decision you make will be the right one for now and won’t be forever. 

Speaking on behalf of the worldwide community of fabulous female founders, I applaud you for dreaming big, fulfilling your dream (even if it didn’t end up exactly how you envisioned it), learning incredible lessons, and continuing to contribute to making the world a better place. 

Wishing you all the best, 

- FFF