The Identity Shift After Selling Your Company

Nobody told me that a successful exit could feel this complicated.

The first time I felt like I was no longer running my own company, there was nothing for me to do. We had just sold Reaction Commerce to Mailchimp. That same week, there was a Mailchimp all-hands meeting on my calendar. I had nothing to prepare. No meeting to lead. All I had to do was join. The meeting was lovely. We were welcomed and celebrated.

It felt like a luxury. It also felt really odd. After years of being responsible for leading the all-hands, I could simply attend someone else’s. I was relieved. I wasn’t sure what to do with that relief.

I expected selling Reaction Commerce to feel like an accomplishment, and it was! We sold to Mailchimp, after all, which at the time was still an independent and hugely successful company, and it was a brand I admired. I had successfully landed the plane, as they say. My board was pleased. It was during the pandemic, so we toasted the acquisition over video calls.

I felt a weight lift off my shoulders. I also felt something I hadn’t expected: grief. Part of me even felt like I had failed because I didn’t stay independent. That was hard to reconcile with the celebration. We had achieved something worth celebrating, and I was mourning it. It took me time to understand that those feelings could coexist. I could be proud of the outcome, grateful for it, relieved by it, and still grieve what I had given up.

What I had actually sold

For years, I had been the founder, the chairperson, the CEO. What I did, what I was responsible for, and who I understood myself to be had become intertwined. The company shaped my days, my relationships, and the problems I went to sleep thinking about. Being its founder and CEO was one of the primary ways I knew who I was. Then the deal closed, and my role changed much faster than my understanding of myself did.

I was now a product executive being asked to present to the company executives. I remember thinking, “Hey, I used to be the person who made those decisions in those meetings.”

I still had a lot of responsibility. I still cared deeply about what happened. But I no longer had the final say. I had to learn how to keep caring without assuming that caring gave me the right to decide.

That became especially painful when Mailchimp decided to rebrand Reaction Commerce as Mailchimp Open Commerce. I struggled with that decision. We had worked so hard to build that name and brand, and now someone else could change it. I could disagree, but it still wasn’t my decision.

That was part of what we had sold: the right to decide what happened to the company. I understood that as a business transaction. Watching it happen to something I had helped create was different. When the Reaction Commerce domain stopped working, the loss became even more tangible. So much link rot! Links that once led to our work no longer went anywhere. Something we had spent years building was becoming harder to find.

It was harder to let go of the team, too. Some people got new managers. I went from leading all departments to leading product and design. There were good organizational reasons for those changes. They still changed relationships and responsibilities that had mattered to me for years.

I was also ecstatic to see my team grow and thrive in new and expanded roles. I was thrilled they were rewarded with compensation and retention packages far beyond what we could offer.

What I gained, too

It was a joyful day when I handed over full access to our accounting software. I was delighted to no longer have to worry about payroll, legal contracts, or HR. I didn’t miss carrying all of that. And once I could focus on product, I didn’t have to think about fundraising, runway, or burn in the same way. I could put my energy into building and successfully launching a new product line.

As VP of Product for our commerce initiatives, I got to work with a team that could act a bit like a startup inside a larger company. We could build and launch new products in short periods of time. There was room to enjoy work I loved without carrying the entire company along with it.

The things I was relieved to give up were telling me something, too. Some of the responsibilities I had treated as inseparable from being a founder were responsibilities I was happy to stop doing. Letting them go gave me more room for the work I wanted to keep.

Later, as CPO of Mailchimp, I led a large product organization and was responsible for the strategy of a product generating hundreds of millions in revenue, serving customers around the world. I had access to more research, product analytics, and support for strategy. By then, Intuit had acquired Mailchimp, so I was also learning to lead inside a much larger public company.

The scope of my work had grown again. My authority worked differently. I had to keep learning how to lead through influence: explain the direction, work across teams, understand other people’s priorities, and make a case for decisions I couldn’t make alone. Founding a company had required those things, too. But inside Mailchimp and then Intuit, I couldn’t fall back on being the founder and CEO. My leadership had to work within an organization I didn’t own.

I was still someone who could build, lead, and help people do good work. I was learning what that looked like without the company being mine.

Between identities

For a while, I knew what I wasn’t anymore before I knew what I was becoming. I had a new job, but that didn’t immediately give me a new understanding of myself. There was a period of being between identities. The old role was gone, and the next version of me was still taking shape.

I always say that transitions are sacred. This was a massive transition, and looking back, I wish I had been gentler with myself inside it. I didn’t need to turn every confusing feeling into a problem to solve. Some things needed time and attention.

Change is hard. It can be wonderful, and we can still say, “This is hard.” Sometimes we need space to grieve what’s ending, even when we chose it. We can take a minute to mourn what was before asking what could be.

I worked with my coach through the transition, and I’m so glad I had someone who understood acquisitions and the changes that come with them. There was room in those conversations for more than whether the deal had been successful. There was room for how I was actually doing.

That experience is part of what I bring to my own work as an executive coach. A change in someone’s role can reach much further into their life than the new title suggests.

Think about life after the deal

If I were approaching an acquisition again, I would spend more time thinking about the life I was agreeing to after it closed. Of course, many things were negotiated and known, like my role, title, and reporting structure, but you can only outline so much. The transaction understandably takes up so much attention. But alongside the terms, I would ask some very ordinary questions:

• Which decisions need to be made? Which will still be mine? Which will require someone else’s agreement?
• What will success look like in my new role?
• How long do I want to stay, and what do I want to learn while I’m there?
• What am I giving up that matters to me personally?
• What am I looking forward to putting down?

Discuss those questions with the people you’ll be working with. Make the expectations as concrete as you can. Then leave room for the possibility that knowing what will change won’t tell you exactly how it will feel.

A purchase agreement can describe your future role and title. It can’t tell you what it will be like to sit in a meeting and realize the decision belongs to someone else.

I would also make more room to notice what was happening along the way. I would journal more. I would make time for meditation, even if it was just a few quiet minutes to sit with what I was feeling. I would use affirmations to remind myself that my worth wasn’t tied to my title, and manifestation to imagine the life I wanted to create next. I would find a small group of founders to talk with regularly, people with whom I could be honest about both the celebration and the uncertainty. I would keep the conversations with my coach.

You deserve somewhere to say that a good outcome is also hard. If I could talk to myself in the week of the acquisition, I would tell her to enjoy the toast. We had done something worth celebrating. I would also tell her that she didn’t have to feel only one way about it.

You’re going to miss parts of this more than you expect. You’re going to be delighted to hand other parts over. Pay attention to both. What you grieve will tell you what mattered. What you’re relieved to give up will help you understand what you want your life to make room for next. And when that all-hands meeting appears on your calendar, it’s okay to just join. You don’t need to know who you are becoming yet.