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How Entrepreneurs Can Keep Their Heads Without Losing Their Hearts


Entrepreneurship is difficult and can feel like a lonely journey. Sheryl O’Loughlin learned the hard way, as many entrepreneurs do. “The extreme challenges and isolation we face are our dirty little secret,” she said. But it doesn’t have to be that way. The more entrepreneurs share the ups and — especially — the downs, the more likely we are to not just survive but thrive.

If you think this couldn’t happen to you, think again. “Anorexia is just one of any number of demons that entrepreneurs are vulnerable to,” said O’Loughlin. “Others include alcoholism, drug abuse, depression, attention deficit disorder, divorce and even suicide.”O’Loughlin has an MBA from a prestigious university, worked in large multinational corporations, ran a fast growing business  — Clif Bar —  launched and sold Plum Organics and was Executive Director of the Center for Entrepreneurial Studies at Stanford. She also nearly went bankrupt and became anorexic.

She tells her tale of success, failure and recovery in her book Killing It! An Entrepreneur’s Guide to Keeping Your Head Without Losing Your Heart. “I rode the highs — like sales wins and investors agreeing to fund the business — all the way up,” said O’Loughlin. “I also crashed with every rejection, product problem, or employee set back.”  The book is a great read. She shared with me four hard-learned lessons

  1. Connect to your tribe and share what’s real.

Entrepreneurs are a community. Don’t hide things from each other. It’s a natural instinct not to share your weaknesses and your failures. “Let go of your need to self protect,” said O’Loughlin. However, she warns that you should share enough but not too much.

Others — such as family, friends, employees, investors, customers, advisors and mentors— want and can help. However, at times you may need to shield them from some of the terrors you feel, such as how scared and worried you are, how you’re not sleeping or how you feel like you’re falling apart.

“Your fellow entrepreneurs are your best resources, referrals and sounding boards,” said O’Loughlin. They can ask hard questions, provide feedback and help you through the weeds. Groups like Entrepreneurs’ Organization (EO), OwnersUp, SheWorx, Vistage, Women Presidents’ Organization (WPO) and YPO are designed to provide a safe space for entrepreneurs to talk about their problems and discuss solutions. Or form one of your own as Diana Lovett of Cissé Trading Co. did.

  1. Protect your self-worth.

“Your self-worth can get tangled up in your profit and loss statements, such that you feel like a failure when the numbers fail,” said O’Loughlin. You are not your business. You have to separate yourself. “Your self-worth does not equal your business worth,” she continued.

You are a daughter, sister, wife, mother and friend. You have value to those aspects of yourself, too, whether your business succeeds or not. The people in your life who make you a daughter, sister, wife and mother are your greatest assets. Nourish these relationships. You also should have interests and hobbies outside of your business, which can help you re-charge.

  1. Bring love into everything you do.

Without love for what you are doing, you won’t have the natural curiosity and motivation to solve the big challenges you face. Remember why you became entrepreneur.

“Marketing a brand doesn’t have to be a dispassionate exercise in analyzing data,” said O’Loughlin. People with your values and sensibilities want you to be a success. These people have the potential to be your employees, customers and vendors. They want to come along for the ride because they believe in what you believe in. Bring them along by sharing your passion.

  1. Have bold humility.

Entrepreneurship is about going for the brass ring but it is also about minimizing risk. Being bold is not the same as going out a limb.

When you love your business, you can be blind and deaf to signs of trouble even when they’re glaring. Naysayers point to every minor obstacle as a reason not to continue. Don’t let these people guide you. You want people who see possibilities, know it’s never a straight shot to success and have experience navigating rough seas. These people can help you see your blind spots and get past them.

The journey never ends and it hasn’t for O’Loughlin. She is passionate about natural, healthy and delicious food, and fell in love with another company that she is now running — REBBL. It uses super-herbs in its drinks. These adaptogens are natural healing substances that help calm the adrenals and decrease the flood of stress hormones into the body, which may be aging you and making you ill. Importantly, it’s yummy. If that’s not enough, REBBL gives a percentage of net revenue to Not for Sale so growers of these roots, extracts, berries, barks and leaves are not vulnerable to human trafficking.