Give Yourself Permission to Screw Up!
Every business owner has a moment they’d rather not talk about: the bad hire, the money spent on the wrong thing, the decision that blew up in front of everyone. This book is entirely made of those moments, on purpose.
Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong by Kristen Hadeed. She started a college cleaning business to pay for a pair of jeans and grew it to 60 student employees, then watched 45 of them quit on the same brutal summer day. What she did next is most of the book.
Hadeed’s early leadership style was hugs instead of feedback and parties instead of real relationships. It didn’t work. What makes the book worth a business owner’s time isn’t that she eventually got it right; it’s how honestly she walks through every version of getting it wrong first.
Leaders don’t clip wings. They help people get their wings, and then stand back when they’re ready to use them.
Six mistakes worth learning from secondhand
Cheaper to read about than to live through.
She skipped the trademark, and paid for it
Her father told her to trademark the business name. She didn’t, and got sued by a company that had already claimed it. He let her handle it herself. The lesson wasn’t about trademarks specifically; it was about which unglamorous paperwork tasks are actually load-bearing.
Accommodating isn’t the same as helping
One employee’s chronic lateness turned out to be a substance abuse problem Hadeed had been quietly working around instead of addressing. Letting her go was what finally pushed her toward treatment. Kindness that avoids the hard conversation isn’t always kindness.
A $10,000 loan met a sushi dinner
Expecting a big contract, she took out a loan and spent a chunk of it on team dinners and branded coffee mugs before the contract materialized. None of it could cover payroll when the timing didn’t work out the way she’d planned.
Fun isn’t the same as culture
Keg stands with employees felt like team building at the time. It wasn’t building the kind of respect a company actually needs. Real culture came later, from a mastermind group and a stack of leadership books instead of a party budget.
The code word that changed how she led
Her team used “shepherd’s pie” as the signal for a real emergency. When one hit while she was boarding a flight, she didn’t turn around. By the time she landed, the team had solved it without her. That’s the whole test of whether the systems you’ve built actually work.
Retreats did what meetings couldn’t
Multi-day retreats gave her managers room to plan, fix what wasn’t working, and actually get to know each other as people. The business decisions that came out of those trips didn’t happen by accident; they happened because the space for them existed.
None of these moments look like success while they’re happening. What comes through in the book, and what’s worth borrowing for your own business, is that Hadeed treated every one of them as information instead of proof she wasn’t cut out for this. That’s a hard habit to build, and it doesn’t happen by accident either.
Running a business is hard. Your books shouldn’t add to it.
We work with business owners through the messy parts, not just the clean year-end numbers. If you’d rather have a partner who’s seen the sushi-dinner version of a cash flow problem than judgment, we’re a good fit to talk to.
Enjoyed this one? Our take on Mike Michalowicz’s Clockwork: Design Your Business to Run Itself is another business book worth your time, and pairs well with the delegation lesson above. If leadership mistakes have you thinking about how you pay yourself through the mess, see our note on owner pay too.
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