The Freedom in Imagining the Death of Your Startup

A founder I've worked with decided to wind down his company.

He dreaded telling his investors, some of whom had come in just months earlier. The amount of time he'd spent rewriting his investor updates was embarrassing, obsessing over every line.

Then he did it.

People were supportive. Several investors asked what he was doing next because they wanted to be part of it. Customers reached out to ask how they could keep working with him.

Then he said something I want every founder to hear:

"No one has judged me nearly as much as I've judged myself."

He went through the actual "failure" to learn that. You don't have to.

There's an exercise I give founders that can get you what he found on the other side of failure, without losing your company. It starts with the one thing you've been avoiding.

Why the Boogeyman Needs the Dark

Most people carry the fear of failure with them every day. The thoughts just pop up: "I'm going to fail. It's going to be terrible." These thoughts get pushed away, and the fear keeps running in the background, shaping decisions and pulling you out of presence. That's rumination, and it drains you.

Facing the fear is different. It's something you choose. You sit down once, with your full attention, and look at it directly. The exercise is exactly what it sounds like: imagining your startup dying.

I think of it a little like taking the boogeyman out of the closet. In the closet, it's terrifying. Then you turn the lights on and realize it's a mop.

The dark is what gives fear its power. As long as your fear of failure stays vague, everything inside it fuses into one undifferentiated dread. The things that would actually happen and the stories your mind tells about them blur together, and the whole thing feels enormous because you never look at it directly.

Turning on the lights means getting specific. Looked at closely, an imagined failure has layers. Some of it is as close to fact as the future gets: the things you'd actually have to do, like emailing your investors and telling your team. On their own, those things wouldn't be difficult. The rest is your mind filling in the gaps with stories about how everyone would respond, what they'd think of you, and what it would all mean. Nearly all of the fear lives in that story layer.

And here's what I've learned about that layer: fear makes bad predictions. From my experience with hundreds of clients, including many who failed completely, 99.999% of those fear-based stories turn out to be untrue. In many cases, the literal opposite occurs. Remember the founder from the beginning: his mind predicted judgment, and his investors asked to back whatever he does next. We live in an ecosystem that rewards risk taking. When founders fail, the response they actually get sounds more like: you went for it, you must have learned a lot, you'll probably be more successful this time.

How to Turn On the Lights

Set aside time when you won't be interrupted. One note before you start: as you go, welcome the raw feelings and sensations that arise. For the fear to fully mature, it must be completely allowed in the body.

1. Imagine your startup completely failing. Total bankruptcy. The email to investors telling them you lost their money, maybe including friends and family. Telling your team you're closing down. The media coverage. Let it be vivid.

2. Notice the stories your mind generates. "I'll never get funded again." "Everyone will think I'm a loser." Just notice them.

3. Pull each fear out of the vague. What specifically am I afraid will happen? And if that happens, what happens next? And then what? As you follow it down, separate what you can be most sure would happen from what your mind is filling in. You'd have to send the emails and have the conversations; that much is close to fact. How everyone responds is your mind's biggest stories. Getting specific is what lets you see the difference, and once you see it, there's surprisingly little substance to the fear.

4. Take your biggest stories and ask: how might the opposite be true? "My investors will think I'm a loser" becomes: my investors say, let us know what you do next, because we want to back you.

Near the end of that conversation, the founder I coached shared one more thing. He hadn't felt this relaxed in years. He was thinking more creatively than he had in a long time. And he wished he could build a company from that place.

You can. Underneath all the stories, the fear was always just a ball of sensation and energy. When you welcome that energy completely, it matures into the recognition of how much you really care. For a lot of people it becomes gratitude: "Right now, this company is alive. I get to do this. I get to build something from nothing."

That energy creates an intense desire to be your best, and it invites the people around you to be their best too. So keep playing to win. For as long as you're playing the game, play to win. It's more fun that way.

But now you can play with the lights on. Because the boogeyman only lives in the dark.

With love,

Dave Kashen