Founders’ Heartbreak, A Weight Many Carry
Sadness.
It’s perhaps the hardest emotion to express if you have a pattern of “playing strong”. Not sure if you play strong? Ask yourself what you did the last time something sad happened in your family, what did you do? Even in the presence of your loved ones, how did you feel about shedding tears? Were you embarrassed, did you do your best to hide them?
How about the work context? How is it different? Can you name it that you’re sad so-and-so left the company or layoffs were required or a beloved product feature got cut or sales were a miss again this quarter? Or is it easier to be angry about it instead? Anger is a way of covering up deeper emotions that might be more vulnerable to share.
The pattern I sometimes see at work is:
- something upsetting happens,
- people are upset, angry, frustrated, or annoyed about it and
- that might or might or might not get expressed, but
- the underlying emotion never gets acknowledged.
No one gets really gets complete with what happened because the feelings around it get half-processed.
I met with a founder yesterday who has been in his business for more than a decade. It’s had big ups and downs, and now it has come to a landing spot as a lifestyle business, growing linearly and throwing off some cash for the founder after expenses. It might have been a win except that the founder took VC money and had a plan to swing big but until it didn’t work out that way. His investors have failure (and in VC terms it is one) built into their model, but this founder didn’t. Even now that he’s into his second business and it’s going well, there is a lingering heartbreak over what happened with the previous company.
He’s not alone.
Given the number of startups that fail, there is a lot of heartbreak out there for founders, and most of it still has yet to be processed. Take another founder, one who has a thriving business, also his second startup. I asked him if he’d ever thought more about how failing to take the feedback about the design of the product even though it was consistent. Other products in the market later addressed that consistent feedback and while the quality of those products was not as high, they were more successful. Because it has been almost 10 years since that startup wound up, he surprised me by saying without a pause, “I think about that all the time.” The tone was sorrowful reflection, and we let the moment linger, clearly something close to his heart.
Another founder who sold his company a year and a half ago was generous with his time about what happened at the company, but there was a lot of sadness around things he would have done differently and choices he would have made differently that would have prevented confusion, stress and pain for others. Both founders have done a lot of reflecting around their previous companies, and the pain is still just under the surface even after years. Heartbreak is the only word I have for it.
So what is a founder to do?
Having a company that doesn’t work out, or doesn’t go like you planned is something to grieve. A wisdom teacher called Baal Shem Tov taught that there are three ways to grieve: tears, silence and singing. They are all such human traditions of working with and moving through the pain of what has occurred. It is up to us to be open to how that grief most wants to be expressed. To not do so is to let it continue to weigh on our souls. For many founders it also might require being in community with those who bare similar pain or in some cases anger. Letting go could be the same as getting complete, which borrowing from conscious leadership might be an integrity inventory of all the unsaids, unfelts, unkepts and unowns around what happened. That is the acknowledgement of the agreements that were not kept, your part in it, the feelings that arise from it, and the things that were not said around it. And if you really want to move past it, once that inventory is done, have the conversations, even (and especially) the truly uncomfortable ones with the people most impacted. This is emotional weight you can carry or shed, and it is possible to feel lighter by doing the work. It is always available to you to live with more integrity and perhaps happiness.
