Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong


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The inspiring, unlikely, laugh-out-loud story of how one woman learned to lead–and how she ultimately succeeded, not despite her many mistakes, but because of them.

This is the story of how Kristen Hadeed built Student Maid, a cleaning company where people are happy, loyal, productive, and empowered, even while they’re mopping floors and scrubbing toilets. It’s the story of how she went from being an almost comically inept leader to a sought-after CEO who teaches others how to lead.
Hadeed unintentionally launched Student Maid while attending college ten years ago. Since then, Student Maid has employed hundreds of students and is widely recognized for its industry-leading retention rate and its culture of trust and accountability. But Kristen and her company were no overnight sensa­tion. In fact, they were almost nothing at all.

Along the way, Kristen got it wrong almost as often as she got it right. Giving out hugs instead of feed­back, fixing errors instead of enforcing accountability, and hosting parties instead of cultivating meaning­ful relationships were just a few of her many mistakes. But Kristen’s willingness to admit and learn from those mistakes helped her give her people the chance to learn from their own screwups too.

Permission to Screw Up dismisses the idea that leaders and orga­nizations should try to be perfect. It encourages people of all ages to go for it and learn to lead by acting, rather than waiting or thinking. Through a brutally honest and often hilarious account of her own strug­gles, Kristen encourages us to embrace our failures and proves that we’ll be better leaders when we do.

Product Details

ISBN-13: 9781591848295
Publisher: Penguin Publishing Group
Publication date: 10/10/2017
Pages: 272
Sales rank: 184,734
Product dimensions: 5.50(w) x 8.40(h) x 1.10(d)

About the Author

Kristen Hadeed is the founder and CEO of Student Maid, a cleaning company that hires students. She spends much of her time helping organizations across the country improve their own workplace cultures. This is her first book. She lives in Gainesville, Florida.

Read an Excerpt

1 THE 45

It’s a hundred-degree day in the middle of a scorching Florida summer.     

I’m sitting in a comfy armchair, right smack in the middle of a beautifully decorated, air-conditioned apartment clubhouse where the residents congregate to play pool and watch football. I’m checking Facebook and texting my friends to make plans for the evening, and every few seconds, my eyes flick to the big clock on the wall in front of me.     

It’s been three hours, I think to myself. Hope they’re okay out there.     

Outside, sixty fellow college students, all of whom I hired within the last couple weeks, are scrubbing their way through hundreds of empty apartments, attempting to rid them of the filth left behind by the previous tenants—an incredibly tough job, especially when some of those tenants were frat guys (and roaches) who lived there for years without ever so much as lifting a toilet brush. Doubly tough when the AC units are down for maintenance and your novice boss doesn’t even think to offer you a water break.     

I contemplate checking on them but talk myself out of it. They had to have known what they were getting themselves into with a cleaning job. And anyway, they only have to do it for three weeks. Plus, I told them if they needed me, I’d be in the clubhouse.     

I prop up my feet, put in my earbuds, and tell myself I have it all under control.     

As you might have guessed, it doesn’t take long for things to go south.     

Like, way south.

Hours later, I’m still perched in my armchair, congratulating myself on how well the day is going so far. We’re more than halfway through, and no one has run into a single problem yet (well, no one has told me about any problems, at least).     

As I’m about to take the first bite of the Caesar salad I just had delivered, the clubhouse doors swing open, and my employees suddenly start shuffling through single file. It’s not just a few of them: As I watch, fork halfway to my mouth, forty-five out of sixty of them crowd into the room.     

For a split second, I think they’re finished cleaning—which would be surprising, considering the amount of work I assigned them this morning—until I catch sight of their faces.     

As they spot me, freshly showered, with my hair done and makeup meticulously applied, every single one of them scowls.      

Yeesh. Why so serious?     

“Hey, guys! How’s it going?” I ask cheerfully, trying to lighten the mood.     


As they continue to make their way toward me, I can’t help but cringe a little. They’re all dripping in sweat. There are huge black grease marks on their arms and faces from scrubbing ovens and who knows what else, and they smell like a gross combo of body odor and moldy refrigerator.     

“Bet you can’t wait to shower!” I joke awkwardly, desperate for just one of them to crack a smile.     

More silence.     

What is going on?     

Suddenly they start whispering to one another, and they begin nudging one person forward. I hear someone say something that sounds like “Do it.”      Little do I know that I am about to experience the most humiliating thirty seconds of my life.      Slowly, one steps in front of the group. And then, carefully avoiding eye contact with me, she says, “We quit.”     

I almost drop my fork.     

Wait . . . wh . . .     

Before I can even think of a response, all forty-five of them turn around at exactly the same moment and begin to make their way out the big double glass doors, dragging their vacuums, buckets, and sponges with them.     

Forty-five people quit.     

At the same time.  

Seventy-five percent of my team.     

That’s the moment that inspired my obsession with learning how to be a better leader.

I had no idea what I was in for when I started a cleaning company that hires only students while I was still in college. I—a millennial with hardly any leadership experience—decided I would hire other millennials—a notoriously tough group to work with and retain—to do backbreaking, dirty, physical labor that would include cleaning filthy toilets and scouring mildewy bathtubs. Somehow, I thought it would be easy. Ha.     

It was anything but easy. I didn’t know the first thing about building a business, let alone one that’s part of an industry as unenticing as housecleaning. The day forty-five people walked out on me foreshadowed the many trials I’d face as a leader, which would only get more and more difficult. But with time, patience, and a lot of screwing up, I eventually learned how to overcome the challenges I had unwittingly taken on.     

This is the true, imperfect story of how I went from that humiliating summer day to where I am now. It’s about how I built a company where people want to be, and where millennials are loyal, productive, and empowered. Even as they do someone else’s dirty work.     

But before we get to all that, let’s back up a bit. To the beginning.     

I need to explain how I ended up in that clubhouse in the first place. You see, it was never even my intention to start a company.

In my sophomore year of college, I was studying finance at the University of Florida. Why finance? Well, I scoured for the highest-paying jobs, and investment banking was at the top of the list. My dream was to move to Manhattan after graduation and get a job on Wall Street that paid a starting salary of no less than $100K per year.     

At the moment, however, I was—as most college students are—broke. I had a scholarship, but it barely covered my expenses. This became a problem for me when I walked into the mall and fell in love with a pair of $99 jeans. (Designer jeans and living beyond my means: my nineteen-year-old self in a nutshell.)     

I called my dad to see if he might be willing to help with my fashion emergency, even though I knew he’d say no. (If you saw what my dad wears every day, you’d understand that fashion is not exactly an emergency in his eyes.) He told me the one thing I didn’t want to hear: Get a job.     

Getting a job just to buy one pair of jeans sounded a bit extreme, and besides, college was my chance to live it up before I made it to the real world and had to work for the rest of my life. Scholarships had my basic needs covered. I didn’t want a job with demanding, inflexible hours getting in the way of studying for midterms (or tailgating at football games), so I decided to figure out a way I could make the money quickly on my own.     

This entrepreneurial way of thinking wasn’t new to me: I’ve been a self-starter since I was six, when I started a babysitting service (even though I still needed a babysitter myself) and sold fake nails made of Elmer’s glue to my first-grade classmates. After that came the Girls Club, a “friendship” club that members had to pay $5 to join. They also had to follow my thirteen rules (the seventh of which was simply “Obedience”). I signed the list, “Thanks, Your Leader, Kristen.” Yeah. Definitely the same thing as friendship.     

So when I found myself needing $99 in college, I wasn’t in completely uncharted territory. Because Elmer’s glue nails were no longer the hot commodity they were in elementary school, I went with the first viable enterprise that came to mind: cleaning. I figured it would be the best way to make enough money to buy my coveted denim in one go. I was willing to do whatever it took to get those jeans, even if it meant scrubbing a stranger’s bathtub.     

I put an ad on Craigslist to clean just one house. It went live on a Monday:

UF student will clean your entire house for $99 (plus tax). I’ve never been arrested, convicted of a crime, or anything else like that. I’m an extremely good student and have made the Dean’s list each semester. I have a 3.8 GPA. Available immediately.     

(I may have rounded up a bit on the GPA.)     
By the end of the day, I had a potential customer: a busy mom with a traveling husband, two dogs, two kids, and one messy four-thousand-square-foot house. She emailed me asking for a list of references and wanted to know if I supplied my own products.     

References? Hmm.     

I gave her the name and phone number of my aunt and my boyfriend at the time. I didn’t tell her who they were—just that they were “previous clients” of mine. Luckily, she didn’t call them.     

Supply my own products? I think I can do that. . . .     

I looked under my kitchen sink and found a bottle of glass cleaner and a sponge. I figured I could use my own toilet scrubber. (Gross.)     

Yep, got everything I need.     

She asked me the soonest date I had available, and we agreed on the following Wednesday afternoon. She gave me her address, and that was that.     

The night before the big day, I went out to celebrate my friend’s twenty-first birthday—which, predictably, meant I wasn’t exactly feeling that great when I woke up. I slept through several alarms and desperately wished I could reschedule, but then I remembered the jeans. That’s all it took to get me out of bed.     

I pulled into the driveway just in time.     

Wow, this place is huge!     

I got out of my car, grabbed my small bag of cleaning supplies, and rang the doorbell.    

“Hello!” she said as she cracked open the door, holding the collars of two horse-sized dogs as they tried to jump all over me. They were clearly dying to eat me alive. “Don’t worry!” she said. “They’re harmless! Come on in.”     

I stepped into her house. It felt like a sauna.     

“Sorry it’s so hot,” she said. “Our AC unit is broken.”     


Head pounding and already breaking a sweat, I followed her to the kitchen as she locked the dogs behind a doggie gate that looked like it couldn’t prevent a Chihuahua from escaping.     

“You can put your cleaning supplies here,” she instructed, pointing to the dining room. “I’m sure you have more to get out of your car, but I don’t have a lot of time, so perhaps you can get them after I give you a tour?”     

“Sure!” I said.     

More supplies to get out of my car? Nope, this is it. Hope that isn’t a problem.     

“So here’s the kitchen, and the big thing here, as you know, is using the right products on the glass stove top.”     

I didn’t know.     

As I followed her from room to room, I quickly learned there was a lot I didn’t know about housecleaning.     

Make all beds with hospital corners? Remove mildew in the master shower? What does mildew even look like?     

She continued giving instructions as she gave me the tour, but I couldn’t keep up. I knew this probably wouldn’t end well.     

“Okay, I think that’s it!” she concluded. “Any questions?”     

“I think I’m good!” I said in my fake-confident voice.      “Great. Well, I need to get back to the office. By the way, how long do you think it will take? Just want to time it right with bringing the kids home.”     

Let’s see. Four thousand square feet. Umm . . .     

“Two hours?” Sounded reasonable to me.     

“Wow! You’re quick!” she exclaimed as she walked out the door. “Call me if you have any trouble!”     

I decided to clean her daughter’s bedroom first. By the time I’d removed the five million Barbies covering the floor and meticulously dusted three shelves of porcelain dolls, an hour had gone by.     

I needed to pick up the pace. I went through the house, gathered all the laundry, and stuffed as much as I could into the washer. Then I moved on to the kitchen.     

Special products for the glass stove top . . . like glass cleaner? Perfect. That’s the one product I have with me. What are the odds?     

Thirty minutes later, I realized my off-brand Windex was not cutting it; there were still grease spots everywhere. My two-hour time limit was up, and I had successfully straightened up one wing of the house and semicleaned the kitchen.     

How was this taking so long? Even the dogs were judging me.     

I decided to call her. I told her it would take another hour, and she was okay with that but warned me she would be coming home soon with the kids.     

One hour later, she pulled into the driveway. I was still cleaning.     

In the end, my two-hour estimate turned into more like seven hours. I was still cleaning while she made her kids dinner, gave them baths, and put them to bed. But somehow, with a throbbing head, no AC, and only glass cleaner, a sponge, and a used toilet scrubber, I got through that entire house.     

When I was done, it looked okay. Not great, but better than it did before. She paid me, and I left.     

I thought that was the end of the story.     

But really, it was just the beginning.

The next day, two hours after I left the mall triumphantly holding my new jeans, a funny thing happened. The woman who had hired me called again.     

I was afraid she’d found the mildew I’d covered up with a shampoo bottle, so I let it go to voice mail. (How millennial of me.) But she wasn’t calling to complain. Her message sounded something like this: “Hi, Kristen! Hope you’re having a great day. Just wanted to touch base and see if we could set up a weekly schedule? I could really use the help.”     

It had never occurred to me that this could be more than a one-time thing. I decided I would love to have an extra $99 a week, so I started cleaning her house every Wednesday.     

She was kind enough to let me use her products and teach me how she preferred things to be cleaned. I befriended the dogs and finally figured out the mystery of the glass stove top. (Use the clearly marked bottle of “glass stove top cleaner” under the kitchen sink.) Life was good.     

Then she started telling her friends about me, and then they told their friends, who told their friends. As if that weren’t crazy enough, I also forgot to take down the Craigslist ad. I woke up each morning to a few emails from people who wanted to hire me.

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Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong 4.5 out of 5 based on 0 ratings. 4 reviews.
Anonymous More than 1 year ago
Kristen Hadeed discusses how she overcame considerable problems on her way to creating a very successful cleaning business. She is frank about her screw-ups, and explains how she learned from her mistakes. The lessons will be useful to anyone in a leadership position, not just entrepreneurs. It's written in a very entertaining, easy to read style, and I have been recommending this book to my friends.
Anonymous 5 months ago
To often it seems like those that lead us at work have all the answers and all together. This book shows that everyone is human, even our leadership. Great book!
Anonymous More than 1 year ago
Very inspiring to open up and be vulnerable. I appreciate its real world application and humor! I LOVED it!
SherryF More than 1 year ago
First off, I want to say I enjoyed Permission To Screw Up by Kristen Hadeed and had my share of laughs and chuckles while reading it and shaking my head. BUT, I would not classify this as a guide to success. It reads more like a biography than a How To Succeed story. I feel Kristen Hadeed had a great idea and stumbled her way into success, but many others would fail if they followed her path. It all started with a pair of $100 jeans, that her parents wouldn’t buy for her, and an ad on Craig’s list to clean houses. Just goes to show, where there’s a will, there’s a way. I tossed most of the notes I took as I sat here trying to write this review. Like any nonfiction book, you take the information that works for you and you leave the stuff that doesn’t. Millennials – 1982 to 2004. I like that Kristen was upfront about her mistakes and her feelings about millennials. It’s just like any generalization, it doesn’t apply to everyone. When she blew off checking into her trademark before using it, I thought that about summed up my opinion of some of the pitfalls of millennials. They can be lazy. They are handicapped, only have one hand available, because they have their phone in the other one. They think Google has all the answers and their parents will take care of everything for them. But, again, this is only a generalization and doesn’t apply to all millennials. I like that she wasn’t too proud to ask for help, and find the place to get the answers she needed, though it’s not like she didn’t try to have someone do it for her…at times. I like that she talks about the Participation Generation, where you get rewards just for showing up. Helicopter parents – parents who hover, overprotective, over involved, and over indulging their children. How can a person like that accept criticism. Kristen learned that there is “a time for pep talks and a time for reality checks.” I like that at the end of each chapter is a quick summary that hits the highlights. I do look at this as her story, not so much a business book. She does share some helpful hints and reminds us that even the most experienced leader can learn something new and improve their leadership style. She does share her thoughts about the value of employees being happy, even while mopping floors or cleaning toilets. Would I recommend Permission To Screw Up? Yes, especially for the younger generation and the beginning entrepreneur, to show that mistakes are not failures, just learning experiences. Also, for anyone who likes to read biographies, Kristen Hadeed does have a fun and interesting story to tell. I borrowed a copy of Permission To Screw Up by Kristen Hadeed from a friend.