The Trough of Sorrows and How to Climb Out

I have been in the deep trough of sorrows with a startup or two. Oh yes I have. I’ve got the battle wounds to prove it. So why keep going on? What’s the upside to such a very, very bad downside? Are we all just gamblers?

Previously published on Starting from Zero

The Trough of Sorrows

I live at a marina in a one bedroom apartment that I at times can barely afford. I love it here, because I have sailboats right outside my living room window. I watch the masts slowly pass by as they head out to the bay for the day. I really, really want a sailboat and have been promising myself one for the last 3 years. But instead, I start companies.

I recently did a salary check on and discovered just how much money I could be making if I were working at a big corporation, dutifully doing as I’m told and not thinking too hard about the future. It was a shock. Let’s just say, I wouldn’t be in an apartment if I’d taken the more traditional route. I’d be in a house. A very big houre. And one of those sailboats would be mine. In fact, instead of sitting on the couch writing this post this Saturday morning, I’d be out on my sailboat. Because I wouldn’t have a startup sucking up every hour of every day.

First Level of Sorrow – Limbo

This, my friends, is one of the higher ledges in the trough of sorrows: realizing you’ve probably lost out on hundreds of thousands of dollars over your lifetime by founding companies instead of working in companies. That realization sucks.

Limbo is where you are most of the time when you start a company. You’re working insanely, you never think of anything but your enterprise, and you still have no idea if anything good will come of it. You also don’t have any money, because you’re putting everything back into the company and you’re not paying yourself a living wage. Houses, sailboats and vacations to Hawaii are all out. 401ks are out. Going out to dinner is out. Limbo sucks.

If your startup begins to get traction, you rise out of the first circle and move up into the heavens where success on a small-to-grand scale await. This is what we’re all hoping for. But if you don’t get traction, then the trough begins to suck you down…

Second & Third Levels of Sorrow – Slow Death

Lower ledges in the trough are where you begin to have an inkling that your business model is just not viable. The suspicion that your baby will be stillborn after years of incubation. That one sucks too.

Even lower in the trough is where you’re out of money and you have to fire you sister and your friends. For which they will never forgive you, or even speak to you again. Then you start to wonder if this mother-f*ing startup is actually going to destroy every relationship in your life, leaving you cold and alone. The serious fear of ending up a homeless person wakes you up at 4:00am every morning. That is a low ledge, indeed.

Bottom of the Trough

But the very bottom of the trough is where you doubt your very sanity. You start to suspect that you’re one of those crazy people who think they’ve cured cancer, or invented time travel. People who tinker in their basement until they’re 88 and die of a heart attack having spent their lives impoverished and never succeeding at anything. Did I mention the Dementors live at the very bottom of the trough? This is soul-suckage time.

This is when you know every decision you have ever made was wrong. It’s when you lie on the living room floor and go through each point of your life and realize that you should have made the other choice. You should have married early and had kids, skipped graduate school (and law school? what were you thinking?) stayed in New York, stayed at CNN even though you had a sh*t job and your boss was misogynist.

You should have started on the bottom rung and climbed sloooowly to the top, instead of jumping from ladder to ladder to ladder. You should have certainly never started this stupid company and you’re pretty sure you can blame that all on a certain friend that kept calling you brilliant. And you fell for that flattery.

And on and on the tape goes. This is the bottom of the trough, and now you have to climb out.

Climbing Out of the Trough

Climbing out is not that easy. I know, because I’ve had to do it, several times. It requires turning off the tape, refusing to listen to your list of failures from others or from yourself.

It requires major repair to your self esteem, and that means getting far, far away from the people who take this opportunity to point out your shortcomings so they can feel superior to you. Walk away from them. If they are your “friends” drop them. (They are not really your friends.) If they are your relatives, put a moratorium on those toxic relationships. Keep all the Dementors out of your life, at least until you’re out of the trough and can deal with them again.

Write the Story of Your Startup

Then do a little PR work. You need to write the story of your venture so it makes sense to you and to others. You have to spin it the right way, not the soulless, bottom of the trough, no-self-esteem way. Anyone who has started more than one company knows the risks and won’t see your failed startup as a personal failure. You shouldn’t see it that way either.

So write the narrative you tell the world (and yourself at 4am). Here’s an example:

I started a company based on an awesome technology I invented. I raised nearly a million dollars and hired a great team that worked like crazy. We got the tech working great, but unfortunately our business model never caught on. We ran out of money a few weeks back, and I finally had to make the decision to close the company down. Startups fail all the time. It’s sad, but it happens. Now on to the next big thing.

That’s your new narrative. Customize it for your circumstance. Here’s one for the startup on hold:

We got the tech working great, but unfortunately our business model never caught on. We ran out of money a few weeks back, so I’m putting the business on the back burner while I work on one of my other ideas.

That one came from a friend of mine who is a serial startup founder. Putting things “on hold” or “on the back burner” is very common in this valley. Anyone who has done more than one startup knows about the back burner, where past projects go to either simmer to a boiling point, or die a slow, quiet death.

Just a warning, you’ll have to practice saying this to others a few times before you can get it to come out of your mouth. Be sure you’ve made it through all the stages of mourning first.

New Beginnings

On the way out of my last trough I learned something pretty cool: among the people in the know, the ones who are infected by the startup bug and have been round the merry-go-round more than once, being able to confess that you’ve failed in a startup already is a badge of membership. It shows that you know something most other people don’t. And that you’re a real entrepreneur, not a wantapreneur.

For every 10 people that arrogantly dismiss my “startups” as a pseudonym for “unemployed” or freelancing, there is one who looks at me with more respect. Who nods knowingly and tips their glass my way. Who, the next time they’re looking for a cofounder, will think of me. Because I’ve been through the fire and I’m tempered. I’ve been down in the trough and I climbed out the other side and kept going.

That’s what real entrepreneurs do. And if you can do that too, I’ll tip my glass to you.

Need more inspiration? Check out this great book.
Like what you just read? Get my Saturday Digest (yes, just Saturday).


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