Leaning into the hard stuff

© Pete Longworth

© Pete Longworth

I received an email last week that inspired me. It read:

How does your team respond to sharing your internal company experiences with others? I would like to do the same, but I'm a bit concerned about how my team would respond. How do you approach the pushback a team would have from having our shortcomings discussed with audiences? Any advice would help!

It inspired me because it shows that there are people out there who understand how important it is to give the world an unfiltered look at their lives. They understand that success stories might motivate people to reach for more, but stories of struggle and setbacks are what help people feel less alone if they fall short. This email shows me that there are others who want to change the conversation, and that’s exciting. 

But the answer to these questions isn’t simple. I haven’t always publicly shared hard things, tough times, and the weaknesses of both myself and my company. It’s been an evolution for us, and it started when I began writing my book, Permission to Screw Up.

The early drafts of my book painted a butterflies-and-rainbows version of building Student Maid. When I did mention a hard moment, I glossed over it with a joke and moved on. Months into the process, I realized that what I’d written felt empty. It wasn’t about the real stuff. The hard stuff. The times I hurt people. The times I had to walk away from failed business ventures. The times my poor choices got us in so much debt, I didn’t know how we’d ever move forward. As I was going through all these tough moments, I wanted to know that I wasn’t the only one who had ever felt this way. I wanted to know it was normal to feel like I wanted to give up sometimes. But rarely did anyone validate those feelings. I’d ask entrepreneur friends of mine how they were doing in their businesses, and the answers were always the same: “Everything’s great!” I felt like I was the problem. That I was a failure.

The direction of my book changed when I asked a friend of mine—who is a bestselling author—how I’d know if I was writing the right book. I’ll never forget what he said:  “The right book is the one that is the hardest to write.”

That’s when I started leaning into the hard stuff. I began writing about all the times I screwed up. It felt vulnerable. It felt scary. I had to relive moments I didn’t want to relive and ones that didn’t paint me in the best light. When I submitted the final manuscript, I had a panicked moment of, “Oh no, what have I done?!” But it was the right thing to do. The response to the book was beyond anything I could have ever imagined.

Putting my failures out there gave people permission to talk about their own. People would write to me after reading the book and share their own tough moments and what they learned from them. In my speeches, I began incorporating a part where audience members could share screwups in front of the room. People cried. It was freeing. And most importantly, on my own team, we began talking about our shortcomings more openly and honestly. We began looking at our screw ups as gifts: Each one came with a lesson that made us better and stronger, both individually and as an organization. We realized how much we could help people by sharing our collective failures and what they’ve taught us.

As a team, we’ve chosen to be transparent about our journey with the world. We’re all in. But only because we are so open and transparent with each other. We trust each other. We’ve worked really hard to create a culture where leaning into the hard stuff is the norm. If it wasn’t this way behind our doors, sharing our failures would feel like airing our dirty laundry. Everything I write and speak about are things we’ve talked about as a team. My team is proud to share these stories. They want me to share these stories. They aren’t ashamed. We want to change the conversation in leadership from filtered to real. This is our way of doing that—together.

Now, I will say this: When you share your experiences and viewpoints with the world, sometimes, you’ll be met with disagreement. Some people will disagree kindly, and that’s great. But some will disagree not-so-kindly. They will make you feel stupid and less-than and make you wish you’d never shared anything at all. It’s easy to get hung up on this stuff, but there’s a phrase we use in my company that helps when this happens: Hurt people hurt people. It means when someone is hurting inside, they will unintentionally hurt those around them. My team and I recognize that when a person is unkind, or angry, or harsh, it probably isn't about us at all. It's about them. They are hurting. They are reliving or remembering something that happened to them in the past. And instead of approaching the person with the same anger or with equally unkind words, we choose to enter the conversation with empathy and compassion. We choose kindness. And we never ever let it prevent us from sharing again.

It takes a lot of courage to lay it all out on the table. It isn’t easy to write about the stuff you’re screwing up. But we need more people with the willingness to do so. We need more leaders and organizations with the courage to be transparent about their shortcomings because when we don’t hear about others’ struggles and challenges, we feel alone. We compare ourselves to filtered stories of success and feel like we’re the only ones who can’t get it right. Our world is becoming an empty, lonely place. The more real we can be, the more connected we’ll feel. That’s the kind of world I want to live in. Don’t you?

Hope this idea inspires you as much as it inspires me.

Big hugs,