Review: Permission to Screw Up

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

Genre: Business Leadership
Maturity Level: 3
View on Goodreads
Rating: ⋆⋆⋆

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.


This book was given to me by my mom, I think because she knows I struggle with feeling like a failure. The title of the book implies that it’s all about giving yourself permission to screw up (which I guess it partly is), and I think she thought that it would still be applicable to my life, like a self-help book. Indeed, at the end of the first chapter Hadeed even tells the reader (likely at the publisher’s request) that it would probably function as a self-help book as her ideas are so universal! But reader, this is a business leadership book through and through.

So here were some of the things I loved about the book. Business leadership books are always so readable, but this one was also very relatable. Hadeed is an open, personal writer, and I felt like her friend while reading. I loved reading from a Millennial’s perspective, especially since she talks a lot about leading Millennials. It was nice to see her blow some of the stereotypes out of the water.

Hadeed is also a very caring individual. I loved her approach to leadership, how concerned she is about the individual and their feelings. She acknowledges that this might come off as hippy-dippy to some, however I found it refreshing to read about such positive environments. Especially since positivity is something I struggle with.

I appreciated that Hadeed was well-read in the genre, that she didn’t just say “Here is what I came up with” but used the wisdom of other great leaders as well. There is even a suggested reading list at the back! That made this feel less like her tooting her own horn, and more like I was getting the collective work of the business world.

Finally, I loved that Hadeed is so open and honest about her mistakes. She doesn’t present this as a how-to manual for success, nor does she present the Instagram version of her life.

Some of the things I didn’t like. Hadeed is both super privileged and super lucky. She presented her results as if they were 100% a result of her hard work. I don’t want to diminish her effort at all, but it would have been nice to see her acknowledge that she couldn’t have succeeded without coming from a certain background, and that lady luck deserves at least some of the credit.

It also really bugged me that she did try to play this off as a book that could be applied anywhere and to anything. As a teacher I am not free to say “My gut tells me you won’t contribute to our positive culture, I’m not going to bring you into my class” or “You have all the tools you need to teach yourself this lesson!” While some aspects of the book can be applied elsewhere (parenting comes to mind) this is DEFINITELY a business leadership book, and I don’t think it made sense to pretend otherwise.

If I had a leadership role at work, was a small business owner, or worked in the business field, I would consider this book a MUST READ. I was picking up what Hadeed was putting down, and I loved her philosophy. However, you aren’t a leader at work, a small business owner, or in business, you can pass on this one. Go find a self-help book instead.

2 thoughts on “Review: Permission to Screw Up

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