Permission to Screw Up

If you haven’t heard of Kristen Hadeed yet, you’re in for a treat. She’s an unlikely, winsome, fiercely warm-hearted business owner who’s not afraid to share with you all the lumps, bumps and insecurities she faced as she created an unlikely company — and made it thrive. This week, we’re lucky to share an excerpt from her book Permission to Screw Up: How I Learned to Lead by Doing Almost Everything Wrong.

Trust me — Kristen is great company!

Below you’ll find a note from Kristen directly to you — and then the excerpt from her book.

Hope you enjoy, and have a great week,



Kristen’s note:

Today is a hard day.

Today is hard. Today, Maria–one of my longest time employees and an extremely valuable member of my executive team–leaves my company. I’m writing about it because we don’t talk about the hard days in leadership as often as we should. And we should. So, here’s what’s going through my head today. I hope it helps.

Big hugs to any of you who are out there having a hard day as well,



I can remember checking my email many years ago and getting this gut-wrenching feeling every time I found someone’s resignation notice sitting in my inbox.

I’d completely beat myself up. “I must be a terrible leader,” I’d think. “My company will never be able to compete,” I’d say. It didn’t feel fair. Here I was with this dinky cleaning company. I couldn’t offer competitive wages, I couldn’t offer glamorous job descriptions, and I couldn’t even afford to have snacks in our office. Every time someone quit on me it was just another reminder of my fear: That everyone in my company would eventually leave me, and I’d be left to run it all alone.

Now, there are people who need to leave an organization, and I’m not talking about those people. Those who don’t embody the values, those who abuse trust, those who do unethical things, those who hurt others–those people need to go. And fast. I was afraid of losing the wonderful people. The ones who I knew had incredible strengths to offer and valuable contributions to make. Those were the people I wanted to keep forever.

But here’s what I know now, after running this company of mine for more than a decade. People will move on. Even when you treat them like gold. Even when you truly care about them and they truly care about you. Even when your organization has a clearly defined purpose that inspires people, and becomes so much more than a cleaning company. Even when you can finally afford the salaries, the bonuses, and all the sprinkles on top. Not everyone will, but some will. And there’s nothing you can do to stop them. Nor should you. In fact, adding to their compensation packages and promising them more in their roles just to convince them to stay is wrong and selfish. I’m not going to lie–I’ve done that in the past. But now, when someone decides they are ready to move on and grow, I let them. We have to let them. And we must send them off with love, not resentment. Leaders don’t clip wings. They help people get their wings and then stand back when they’re ready to use them.

But here’s the good news: You can make this whole moving-on thing easier.

One day, during an executive team retreat, I had this idea: I gave everyone a blank piece of paper and I asked them to pick a date at least three years down the road and describe what they thought their lives would look like then. What job did they have? What kind of impact were they having on the world? Where did they live? How much money were they making? Were they married? Did they have kids? Then I told them it was perfectly okay if Student Maid wasn’t anywhere on that paper. (A few people looked up in surprise because they had never heard me say that before.)

Some wrote in detail and others wrote only a few sentences, but when everyone was finished, we went around the room and shared. At first it was a little uncomfortable. These were plans that would affect the entire team, and no one wanted to come across as selfish, but after some hesitation, each spoke up. One shared that she wanted to move to Portland to be closer to her family, and she hoped to be able to keep her position and work remotely after she moved. Another planned to move in a year to start a life somewhere else with her boyfriend. A few said confidently that they wanted to be at Student Maid for the long haul.

It was inspiring to see what everyone wanted for their lives and to be able to talk about our individual futures as a team. Now that I knew there were people who wanted to explore other options or work remotely one day, I had time to prepare for that. Talking about what we really wanted for our futures also made us promise to hold one another accountable to the dreams that were important to us, even if that meant moving on from Student Maid.

So today, Maria moves on. But I’ve known for a year, because the conversation we had at that retreat (and the ones we’ve had since then) created an environment where people now feel comfortable openly expressing their wants and desires for their lives. Maria came to our team one year ago and told us she wanted to move on in 2018 so that she could move to a different city and explore other job opportunities. Student Maid is the only place she’s ever worked. She loves us and she loves our company, but she’s ready to learn and grow somewhere else. So, together we decided on her final day, which happens to be today. And our team had an entire year to prepare for her departure, ensuring the smoothest transition humanly possible.

I realize that giving a 365-day-notice isn’t the norm. But, if we can get better at asking our people about their futures and help them feel comfortable sharing their personal goals with us, we can make goodbyes easier to plan for.

So, if you’re like me and goodbyes are hard, here’s what I want you to remember the next time you have to send someone off: A leader’s success isn’t determined by the people who are still sticking around. It’s also determined by the people who feel free to move on and leave even better for having worked with you.

I love you, Maria. We’re really going to miss you. Like…a lot a lot. But we’re also over-the-moon-excited for you. I’m wishing you nothing but the best in this new adventure of yours. The people who get to work with you next are really, really lucky. I will always be your biggest fan and I can’t wait to see what you will achieve in your lifetime.