How We Win When We Fail Big on Purpose

This piece originally appeared on Shine's blog.

When I first started working with one of my recent clients—I'll call her Suzy—she felt unfulfilled, but she couldn’t articulate why. Her job was fine, she liked her apartment, and she had a great group of friends. But it wasn’t enough—she still felt unhappy. She hired me as a coach to help her overcome her fears of taking risks, hoping it would lead her to more joy.

Suzy was motivated, coming to each session with an idea about a risk she would take that week. She applied to a job that was out of her league. She got an offer—and turned it down. She was terrified of taking care of anything beyond a plant, so she adopted a puppy. Not surprisingly, she grew to adore him. She had been afraid to date, so she set up a Tinder profile. The next time we spoke, she’d gone on three dates.

After a few months, we revisited Suzy’s original goal of sparking joy. Despite the risks she was undertaking, she still felt something was missing. I asked what she had learned from her risk-taking adventures. She thought for a minute and said, “Not that much, to be perfectly honest." So I asked her: “What do you want?”

After some back and forth, she finally replied, “I want to start a nonprofit to support children of incarcerated parents. But I can’t do that.”

Suzy spent the rest of the session explaining, in great detail, why she couldn’t start her own organization. To be fair, she had some good reasons. I left her with an inquiry: What if you just did what you want to do?

Within a month, Suzy had quit her job and started her nonprofit business. But her story doesn't have a traditional fairytale ending—her worst-case scenario didcome true. Six months after starting the business, she ran out of money, time, and energy. She closed her doors.

The next day, she called to thank me. “Starting a business was the best decision I’ve ever made,” she said. And she invited me to her party that weekend. I was surprised, since I thought her birthday was a few months before. “Oh no!” she exclaimed. “This party is to celebrate my failure!”

Failing Big on Purpose

The first part of Suzy’s story is painstakingly familiar. So many of us stay comfortable, taking only the smallest risks for fear of failure. We are terrified of what will happen and what others will think, so we stay inside our tiny box. We flatline, calculating that staying the course is safer than going after our dream. We remain unengaged in our jobs, unhappy in our relationships, and feeling insignificant in our world.

The learning that comes from failing big defines who we are and gives voice to our purpose.

The second part of Suzy’s story is less familiar, and yet, so richly rewarding. I've seen it with other clients, too. An older client, let’s call him George, recently asked, “How will I know if I’ve lived life to the fullest?” I shared Suzy’s story, and, later that day, he called his brother whom he hadn’t spoken with in twenty years. He apologized and requested that they find a path back to one another. His brother hung up on him. Much like Suzy, this client was disappointed in the result but celebrated the journey.

For both Suzy and George, these failures represented some of the most difficult and rewarding moments of their life. While the consequences were vastly different for Suzy and George, the learning was the same: They both took a huge risk that most likely meant failing, but the value of going after something they cared about deeply exceeded the comfort of keeping that vision hidden forever. And the learning that came from failing big gave voice to their purpose.

What Is Failing Big on Purpose?

What Suzy—and so many of us—seek is fulfillment. No one talks about this more articulately than leadership guru, Simon Sinek: Happiness comes from what we do. Fulfillment comes from why we do it.

Suzy’s small risks gave her something to do, and achieving those small goals brought her happiness. But it wasn’t until she uncovered her purpose and went after it that she got a taste of fulfillment. She failed big because she went after something big. Failing big on purpose means going after your why.

Happiness comes from what we do. Fulfillment comes from why we do it.

Suzy’s organization failed, but her "why" is very much alive. Her first pass didn’t succeed, but what she learned along the way will help her refine her vision and create new paths.

How to Fail Big on Purpose

Suzy and George have inspiring stories—but still, taking that kind of leap into failure is scary. If they’ve peaked your interest in failing big on purpose, here are a few tips:

1. Find Your 'Why'

Failing big is not to be taken lightly. Suzy’s learning didn’t come cheap. It was worth it because she was going after her why. This can take time and should not be overlooked.

You can find your own why (I highly recommend Simon Sinek’s new book on this topic) or you can work with a coach or other trained professional.

Once you do find it, reflect. Don’t leap into a half-baked why. When you fail and you’re not on purpose, the learning is usually just that: You weren’t on purpose. Don’t fail big for that kind of information. You’ll have a good sense that you’ve found it when you’re bursting and, like Suzy, can't not do it.

2. Visualize Success

Contrary to the title, you don’t have to fail—that’s not the goal. I call it failing big because the chances of failure are so high because the dream is that big.

You want to be clear about what success looks, feels, and tastes like. Visualization has been proven to lead to better outcomes, and it helps you become even clearer on your purpose.

Try journaling about what happens when you succeed. Write about what success feels like so you can remain grounded in what you’re working toward.

3. Couple Your Vision With Strategies

I don’t believe in throwing caution to the wind. I believe there’s a pragmatic and focused path to chasing your dreams. If your why involves leaving a job, don’t quit the next day; look at how much money you think you’ll need to save to achieve your goals.

As part of your strategy, create a board of advisors to support, challenge, and hold you accountable. Include people you trust, and plan to be vulnerable with them. Your board should throw your failure party (and toast your wins).

4. Bring a Survival Kit

While you will celebrate and learn from your failure, it will also hurt. You’ll need to bring your life vest aboard this journey.

For Suzy, she knew that her friend would hire her to do contract work while she got back on her feet. George expected that his brother might shun his offer so he prepared his wife to support him. Put the emotional and logistical safety kits in place so that the failure is a less painful and you can practice self-care.

As part of the kit, also include your limitations. What will you absolutely not do (ex. dig into savings)? At what point, will you throw in the towel?

5. Take Action

Once you are clear on your purpose and have what you need in place, go after it and don’t look back. Commit to failing big on purpose and don’t second guess yourself. You are making a commitment. Put yourself out there, be fully aware of the chances of failure, keep success front of mind, and start living on purpose.

6. Celebrate

Whether you succeed, and especially if you don’t, please remember to celebrate. This is the ultimate measure of successful failing: Admitting that you’ve failed (maybe you’re still failing) and it hurts.

Suzy knew that she had put it all on the line and had some serious repercussions to deal with (paying the bills, breaking the news to her parents, figuring out what was next), and she also knew how important it was to reflect and learn from her biggest failure accomplishment.

Celebrating failure is critical because fear of failure is what holds us back. As leadership experts, Karen and Henry Kimsey-House, explain:

Most of us learn early in life that failure is bad, even shameful. We learn to hide our failures, make excuses for them, or ignore them. Worse than that, we begin to stop taking risks; we become more cautious in order to avoid even the possibility of failing. We start to limit our choices to only those actions that have a high probability of success. And so our choices become limited, and our field of play becomes smaller.

They explain that failing and being a failure are quite different. Willingness to fail stands in stark contrast to being a failure. Someone who is willing to risk failure is courageous, and we must celebrate that commitment and learning. So often we find what works in what doesn’t work.

Willingness to fail stands in stark contrast to being a failure. Someone who is willing to risk failure is courageous.

As you celebrate, collect (and write down) what you’ve learned, think about what you’ll do differently as a result, and thank those (including yourself) who have helped along the way.

Do this before the dust clears, the emotions have subdued, and learnings start to dim. Being vulnerable and honest while still in the thick of it is a true triumph. Learn and celebrate your failure in the moment, for you have won.