How to Deal With Failure: 5 Practices From a Founder Who Crashed

Every big thing in my life came after a failure. The book I had been dreaming about for years? I only had something worth saying once I had crashed enough times to earn it. Big Self School? It would never have occurred to me if I had not burned out first.

So when a founder or a senior leader comes to me after a failure, an exit, or a burnout, standing in a life that still looks right on paper, the question underneath everything else is the one I was asking myself after I walked away from my own startup: how do you deal with failure that took everything, and come out more yourself instead of less?

The answer, as plainly as I can put it: you stop trying to get back up fast. Failure and a life of meaning are two sides of one coin, the way a dark winter turns into spring. But the turn does not happen to you. You have to take an active part in it. What follows is my story, the five practices that carried me through it, and a short section on why your particular way of falling apart is so predictable.

Why did it take burning out to see what I was chasing?

I did not always see it this way. For a long time I was doing everything I could to avoid failure. I was chasing success without once stopping to ask what success meant to me.

In 2014 I started a tech company and soon found myself running at the usual founder pace. The to-do list never got shorter. I was pitching, fundraising, doing market research and a thousand other things, and trying to raise a family in the gaps. I was chasing a dream and living a life that was making me sick.

Three years was enough. One morning I woke up knowing I could not take it any longer, and, harder to admit, that I did not want to.

The next couple of years were rough for our family. Our finances wobbled. My husband and I questioned everything and rethought what we were each here to do. That period is where the seeds of Big Self School were planted, but before anything could grow I had to recover from the burnout itself.

And I could not do it the way I had always done things, which was to pull myself together and push through. That reflex was the thing that had put me on the floor. The people who praise you for bouncing back fast are praising the pattern that broke you. Before I could help anyone else, I had to learn to look after myself. These five practices are how.

How do you deal with failure and actually grow from it?

Recovering from failure means growing from it. The alternative, the one most of us reach for, is to tell ourselves we will be fine and forget it ever happened. Nothing changes that way. Failure is an opening, and these five practices are how I walked through mine.

1. Practice solitude

Failure shows you where you have been listening to other people instead of trusting yourself. People love to give advice, and most of them mean well, but their advice comes out of their life, and it may have nothing to do with yours.

So pull back once in a while. You do not have to become a hermit. Find pockets of time where you can hear your own voice. Drink your morning coffee alone, with no phone. Arrive at a meeting five minutes early and spend those minutes checking in with yourself instead of your inbox. Do it consistently and the voice of your Big Self, the one under the noise, starts to come through.

2. Move your body

For years I could not stand the word "exercise." When my husband suggested a hike or a mountain bike ride, I found reasons to be busy. What changed was the definition. Once I stopped treating movement as a way to reach a goal, like losing weight, and started moving in ways that felt good while I was doing them, I wanted to do it.

Moving because you enjoy it does more than make you healthier. You become more aware of what you actually need: water, food, sleep. Burnout happens to people who stopped hearing those signals a long time ago.

3. Try intermittent fasting (with your doctor)

At 43, my doctor told me I had the heart of a 60-year-old. My body was falling apart. So I decided to give it a break, literally: I started intermittent fasting, which just means longer stretches of the day without food.

The idea is simple. Your cells work like a garbage disposal. As they turn what you eat into energy they also produce waste, and if you never give the body enough time to clear it, the waste builds up. A long enough break from eating gives the body a chance to clear it out. The usual recommendation is at least sixteen hours a day.

Before you decide what is right for you, please talk to your doctor. This is my experience, and it is not medical advice.

4. Find reasons to be grateful

The benefits of gratitude are well documented. In the study that started most of this research, Emmons and McCullough (2003) had people keep a short list of what they were grateful for, weekly or daily, and those people reported more optimism, fewer physical complaints and better sleep than the other groups in the study.

The simplest practice is to write down three things you are thankful for every day. Decide when. First thing in the morning or just before bed tend to work best, because you can attach the habit to a routine you already have. Over time the gratitude muscle strengthens and you start noticing the good without trying to. That change in what you notice is what lets you see the lessons a failure is carrying instead of only the wreckage.

5. Schedule sacred time with the people closest to you

We are social animals. We do well when we feel connected. But real connection takes intention, especially in a crisis, when the temptation is to go inward and handle it alone.

When I left the startup, my family went through a stormy stretch. We had to sell our house and move our kids to a different school. What held us together were our family dinners, which we treated as sacred. Not optional. Not moved for a call.

If you are in the middle of something like that, put non-negotiable time with the people you love on the calendar, in advance, and make it special. Treat it as a ritual, one fixed point in a season when everything else is moving. A good meal together is the simplest version. Most of us attach comfort, safety and joy to that table, and you will need all three, whether the failure was in your business or in your life.

Why do you fall apart in such a predictable way?

The Enneagram adds one thing to all of this that took me years to see. Under stress, nobody improvises. Each of us reaches for our type's default: the One tightens control and raises the standard, the Three performs harder and hopes nobody notices the cost, the Nine goes to sleep and calls it acceptance. Failure does not change the pattern. It turns the volume up. The Self-Preservation One meets a collapse by worrying and fixing; the Social Three meets it by building a better-looking version of the same life. Both feel like recovery from the inside. Neither is. If you know your subtype, you know which reflex will show up first, and you can choose something else while it is still a choice.

What does failure make possible?

"Before the truth sets you free, it tends to make you miserable." Richard Rohr wrote that in Falling Upward, and I have not found a better summary of the years after I left the startup.

I learned a great deal from starting and leaving that business, but the biggest lesson was this: until you fall flat on your face, you cannot find your Big Self. You usually have to trip to find out what matters. To live a life that is true to you, you first have to be disillusioned, and disillusionment hurts, because it is the loss of an illusion you were fond of. It is worth it.

Your Big Self is the version of you that is whole, driven by what you actually want rather than by what other people expect. That is the real success, and I do not think you get there without a failure in the story. When you fail big, it is usually the opening chapter of something larger. The only question is whether you are ready to take the ride.

If you are a founder or a leader standing in the aftermath, whatever the story looks like from the outside, this is the work I do with people. Read about coaching and see whether it fits.