The Messy Underbelly of Success

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3 min readJul 16, 2019

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

Permission to Screw Up

Oh man, I loved this book. Kristen Hadeed tells her own story, from feckless student who on a whim advertises herself as a cleaner so she can earn the money to buy a must-have pair of jeans to millennial business icon as the head of Student Maid, and all the screw-ups along the way.

Like Shoe Dog, it’s a glorious antidote to the airbrushed perfection of most business biographies, but what’s particularly wonderful about this is that Hadeed admits that when she sat down to write her book she started by writing the airbrushed version. It took real guts to bin that and write a new version, one that owns every misstep and shows the messy underbelly of success, but I’m so glad she did.

There’s no 7-step formula here (though there are some useful tactical gems, like the FBI feedback method — Feeling, Behaviour, Impact — and the WOW wall Student Maid uses to celebrate great customer feedback). Instead, Hadeed tells us stories of key ‘Oh crap’ moments in the growth of her company — the time 45 students quit simultaneously, her failure to confront one toxic employee and her overly rigid adherence to hiring guidelines that made her miss out on a potential star, for example. The personal stories are gripping, and trace the evolution of her management style — from hands-off to best buddy to cheerleader to visionary leader — experience by experience.

This is perhaps the central message of the book — it’s trite to say we learn from our mistakes, but that doesn’t make it any less true, or any less important for an entrepreneur to grab hold of. In a world in which most people are terrified of failure, to the point of failing to act, there’s enormous power in Hadeed’s enthusiastic embracing of it as the route to success. Her energy and resilience are infectious.

It’s often laugh-out-loud funny, sometimes moving, and kept me absolutely gripped throughout.
Plus, how can I NOT love a woman leader who aims to read at least one business book a week?

‘When it comes to my business philosophies and my mindset as a leader, I owe it all to the books I’ve read. They’ve inspired me, taught me, challenged me, and shaped me into the person I am today.’

If this is millennial leadership, we’re in safe hands.

Permission to Screw Up is available from Blackwell’s here.

Alison Jones (@bookstothesky) is a publishing partner for businesses and organizations with something to say. Formerly Director of Innovation Strategy with Palgrave Macmillan, she hosts The Extraordinary Business Book Clubpodcast, regularly speaks and blogs on publishing, business and writing, sits on the board of the IPG, and is the author of This Book Means Business (2018).

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