I had a great talk today with a dear friend about the demise of his business that he had invested heart and soul in, and about the rise and fall of Critical Path (where I was co-founder during Web 1.0 boom and bust). People tend to talk a lot about what circumstances or decisions cause a business to fail, but not much about how it feels.

I know from experience how awful this is: if I had to pick the most poignant day in my career, it would be a toss-up between (a) the day I had to lay off 10 close friends from the company they’d helped me take public, and (b) the day the news broke that last quarter’s earnings were falsified, and the stock plummeted to under $1. (It wasn’t the money that bugged me, although that was awful too; it was the shame of having the company I’d helped to create tarnished by underhanded business dealings.)


Originally uploaded by Erik Charlton

As an entrepreneur, you are probably spending more hours a day on your business than you would with your significant other, and maybe even your child. You’re pouring so much energy into it that you end up identifying with it, as if it is a part of you. Every time you pass out a business card for your new venture, you’re essentially saying “this is me; this is my dream! come join me! the world will be a better place when it has this thing!” After months and months of doing that, the business name might as well be your last name… And you pretty much *have* to be this crazy, this passionate, and this committed, to have a chance as making something work.

When your business doesn’t work out, or when you get forced out, what do you do?

If you lost your partner, you would grieve, nonstop, for weeks or sometimes even months. No one would ask you “so, will you be registering on match.com?”  So when you lose your business, why do people think it’s OK to say “wow, tough luck”, and then in the next breath, to ask cheerfully “so, what’s next for you?” as if there is no emotional content to having a business fail whatsoever?

My guess is that people are uncomfortable with grief, and maybe don’t understand what a big deal it is to have your startup collapse. I’m all about helping people have more success, more happiness, and more joy in their work and their lives. But if you’ve just been through a dramatic business failure, you will likely be consumed by that experience, and you won’t be able to pull through to the other side until you’ve dealt with it. And, if you don’t deal with it, stuff will pop up at inopportune times. You get to do it now, or do it later. Might as well tackle it while it’s fresh…

Take some time to be sad. The five stages of grief will apply:

Denial – “I feel fine.”; “This can’t be happening, not to me.”

Anger – “Why me? It’s not fair!”; “How can this happen to me?”; “Who is to blame?”

Bargaining – “I’ll do anything if it will make my business go”; “I will give my life savings if…”

Depression – “Why bother with anything?”; “What’s the point?”; “Business just sucks”

Acceptance – “It’s going to be okay.”; “There is something else out there for me.”

You might have to give your close friends some cues so they know where you’re at, and how to support you. You might want to lay low for a while, but don’t do it for too long. If you’re supporting a friend who lost this business, you can always ask what would be most helpful. Just having someone to talk to that doesn’t have any agenda is a great starting point.

It’s only when you get to Acceptance that you will have the energy and perspective to choose something new that isn’t a reaction to what just happened. Just like when you break up with a partner, you might think “I’m unloveable” or “I’ll never meet another person as perfect for me as so-and-so”. Then with time and perspective, they get to see that they learned some valuable lessons, had some fun times, had some hard times, and they’re ready for something new.

In hindsight, you’re going to get to say exactly the same thing about a business failure: you learned some valuable lessons, you had some fun times, you had some hard times, and now, the person you became by doing all those things is ready for something new.

Thanks for sticking with this; it’s a hard topic, but seemed worth an entry, since it’s rarely talked about.