Photo courtesy of Chris Michel

Whole-Hearted Risk: Don’t Take Yourself Too Seriously

Career risk is real and can be daunting — whether it’s risk-taking at your present job or starting a startup. A few months ago, I was invited to share thoughts on the topic “whole-hearted risk” at a Women Tech Council summit held in Salt Lake City, Utah. In the process, I realized that though it is difficult to isolate the risk I’ve taken, let alone give it so grand a descriptor as “whole hearted,” I am able to more clearly call out the risk taken by those with whom I’ve operated. I cited three stories from different points in my last startup and have broken each story into three bite-sized blog posts. Here’s the third…

Part 3 — Life’s Too Short for Taking Yourself Too Seriously

Final story, final chapter of our business. Our company was acquired in 2011, which is a credit to Anne (see Part 2) and a stellar team, life-changing for us as founders, and a win for our other stakeholders. I continued to build with the acquiring company for several years before our eventual IPO. Part of that journey included plans for international expansion, which, at one point, meant that I needed to pitch the plan to my CEO.

In the final slide of that pitch, I had a series of requests. My last request was for “our CEO’s blessing” on my plan. As I presented the plan remotely and over the phone, our CEO, Dan Rosensweig, responded, “Sid, how do Mormons give a blessing?”

I was taken aback. “What?” I mumbled.

He continued, “I know you’re a religious guy. I’m a Jewish kid from New York. You’re a Mormon from Utah. Please tell me, how do you give a blessing?”

So, I went on, still a bit stunned, to briefly describe how one would give a blessing in my faith. “Well, the person giving the blessing typically places their hands on the head of the person receiving the blessing… then offers a prayer and petitions a higher power…” At this point I was confused and now not sure what to expect from the conversation.

After my explanation he said, “Sid, look at your phone.” I proceed to pull out my phone to see a picture Dan had just taken of himself in his office holding out his hands as if blessing my imaginary head. “I just blessed your plan,” he exclaimed. “Go for it!”

My confusion turned to laughter. This simple, thoughtful gesture by Dan quickly lightened the mood. Not only had he taken the time to get to know me, but he’d keyed in on something important to me personally that isn’t often talked about in a work setting. And he perfectly pulled what might be otherwise taboo, a reference to my faith, into the work setting. At a time when our startup was supposedly as “corporate” as ever, Dan struck a chord both personal yet light-hearted. During my time at Chegg, I had never felt more appreciated for who I am, comfortable with my colleagues, and charged-up to move forward building toward our company vision. Dan became a mentor and friend and has continued as a great support to me in my life and career.

You will put yourself out there as you take career risk. That brings with it long days, late nights, and stressful moments. But look. Life is short — so enjoy the journey, the people, and don’t take yourself too seriously!


Part 1 of this series: Whole-Hearted Risk: Problems to Solve & The People Involved

Part 2 of this series: Whole-Hearted Risk: Those Who Take Risk on You

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