Quit your day job smartly & safely (review of How I Built This by Guy Raz)

Dreaming of being your own boss?

Don’t quit your day job. At least not yet. Keep putting in your 40-hour work week and spend your free time being entrepreneurial.

That steady paycheque will buy you a longer runway for getting your business off the ground.

“Most of the successful entrepreneurs I’ve met left the comfort of their previous lives as safely and smartly as possible,” says Guy Raz, who’s interviewed hundreds of entrepreneurs as an award-winning journalist and author of How I Built This.  Very few entrepreneurs made blind leaps without safety nets.

Daymond John continued to wait tables at Red Lobster for six years after launching his hip hop apparel company FUBU. John used a month’s worth of wages and tips to buy a classified ad in the New York Times. That ad secured funding at a pivotal moment for his fledgling company. Nike co-founder Phil Knight kept working for five years as a certified public accountant while Southwest Airlines co-founder Herb Kelleher ran his law practice for 14 years. 

“Having a fallback plan does not mean you are building an escape hatch from your dream,” says Raz.“It’s not an excuse not to try hard, nor is it a ready-made reason to quit. It just means you’re given yourself a cushion at the bottom of your entrepreneurial leap of faith so that if you do crash, you can bounce back to fight another day.”

Raz shares key insights, lessons learned and inspirational origin stories from entrepreneurs who’ve launched companies that include Five Guys, Away luggage, the Headspace meditation app, Slack, Method, AirBNB, the Boston Beer Company, 5-hour Energy Shots, Shopify, Dropbox, TRX, Clif Bar, Dippin’ Dots, Rent the Runway and Netflix.

“It’s never been easier to make this journey,” says Raz. “So many entrepreneurs have done what you are about to do. You have a chance to prepare for what’s coming your way – if you are willing to learn from these unwitting helpers. They’ve made every mistake. They’ve fallen into every trap. They’ve taken every wrong turn. And the good ones – the successful ones – only made those mistakes, fell into those traps, took those wrong turns…once. Because they borrowed from the entrepreneurs who came before them as well. They heard the stories and learned the lessons. Now it’s your turn.”

Raz made the entrepreneurial journey himself as a radio host and podcaster. And like all entrepreneurs, he’s wrestled with crippling despair, doubt and anxiety. There will come a point when you’re ready to quit. You’ll feel completely alone and believe your world is collapsing.

This is when you put down Raz’s guidebook and crack open a notebook. “Starting a business is difficult. It is a twisting road with hours, days, weeks and months filled with struggle and failure and self-doubt and even tears,” says Raz.

“When that happens, I want you to pull out a notebook and write those worries down. I want you to trap them on the page, so that you can look at them the next day, the next week, the next month, the next year and realize that while every challenge and crisis you face in the pursuit of your idea feels like it could be the end of it all, it’s not, I promise.”

Launching a business during a pandemic is scary. But putting your entrepreneurial dream on indefinite hold and staying in a soul-crushing job that makes you miserable and fills you with regret is far more dangerous. Start your journey by reading Raz’s book, putting a notebook on your nightstand and sticking with your day job for a little while longer.

This review first ran in the Oct. 30 edition of The Hamilton Spectator.

Jay Robb serves as communications manager with McMaster University’s Faculty of Science, lives in Hamilton and has reviewed more than 500 business books for the Hamilton Spectator since 1999.

Published by

Jay Robb

I've reviewed more than 500 business books for the Hamilton Spectator since 1999 and worked in public relations since 1993.

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