The entrepreneur and loss

A few days ago someone I know posted a note saying his father died.

He was unusually blunt in his assessment of the circumstances, and of watching his father suffer through hospital care when all he wanted was to go peacefully. 

Entrepreneurs tend to absorb a great deal of grief. This is true of all humans, but the risk undertaken building a company from scratch leads to a deeper emotional risk than most people are willing to take. 

It’s most frequently expressed by a conflicted relationship with winning and losing. We tend to punish ourselves for loss because we assume internally that we are strong enough to navigate all currents, if not direct or control them. 

A friend who works in / with startups wrote about that dynamic a few months ago… 

One of the things she asks is if there is a difference between winning and losing. While both are obviously self-defined by the individual, I suspect she’s right to wonder about that. 

But it is not grief that hurts us most, that prompts us to drown in work, alcohol, drugs, or unhealthy relationships. It is the absence of room to breathe, support, and the belief that we are worthy of and can take time to acknowledge loss.

That loss can take many forms: a relationship ending (personally or professionally), losing a customer that there was a deep connection with, feeling that you are not who / where you thought you would be.

Too often we wait for the bigger things, like losing a family member, failure of a company, or getting fired, before we dig deep, and by then we are so out of practice with loss that we fall apart completely. 

A framework for dealing with loss

Acknowledging the everyday griefs is critical to growing as an entrepreneur, and as a human. 

Here are a few questions that I use on a regular basis to dig deep, and to ensure that I’m building a life and company that I believe in: 

  • What is natural here, in this moment? - this is a difficult question, and it’s often necessary to ask a bunch of times, and in different settings.
  • What do I know and what do I simply have to accept? - constant practice with this question makes it easier to let go of what you don’t control anyway. 
  • The person that I want to be, how would they feel about / act in this situation?  - so often when we are critical (or not critical enough) it is through the lens of self-doubt, of believing something about ourselves that undermines the best action we could take.

In startups the mantra of “fail fast” is used so often that it feels meaningless. Perhaps a better approach is to lose with grace, and with acknowledgment.