Quitting Time

Want to Quit? Overcome Your Fear of Failure

LinkedIn – March 13th, 2015
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My parents have always given me special gifts. But the one that has most transformed my life in recent years was the gift of a simple paperweight for my 30th birthday. It was engraved with the question: “What would you do if you could not fail?”

At the time, I was living the life as an executive in international real estate, climbing the corporate ladder, traveling the world and closing deals at every turn. With every deal I closed, I felt one step farther away from happiness. I saw success but didn’t feel successful.

I asked myself a ton of questions and felt paralyzed by indecision. My life’s purpose up to that point was exact and pointed. Then it became muddled between a desire to create change and a need for stability. Yet, reading the paperweight’s question helped me see what I most needed to overcome – my fear of failure.

This realization changed my life. It’s hard to believe that such a simple gift and, more important, such a simple question could set the wheels in motion for S’well.

During my real-estate days, I often wondered what my next move would be, yet I took no action. That’s when I knew it was time to quit my job, take control of my future and create a new, meaningful purpose for my life. But I had to overcome my fear of failure to do it.

Fear of failure is not uncommon. It holds people back starting something new. Many times we don’t know how to overcome fear in a way that enables us to chase our innermost dreams. Here are the steps I took to overcome my fears of failure and plunge into the unknown world of entrepreneurship:

  • Do your homework: I wanted to make a positive impact on the environment, so I did homework on where I could add the most value. The link between a global water crisis and plastic bottles surfaced to the top. With research, I found there was a gap in the marketplace not only for a reusable water bottle – but a better reusable bottle that was functional and fashionable. With proper research to identify opportunity, you’ll be able to determine an idea’s potential for success and what steps to take to feel confident enough about quitting your day job.
  • Assess your network: Whom do you know who can provide emotional and/or financial support? Because of my time at Harvard Business School, I had a network of friends who had started companies. It was really helpful to talk to people who had gone down this path before. I was able to learn from their successes and failures. Look for like-minded people who have been successful in doing what you’re about to embark on.
  • Play to your strengths:As a former CPA, working with numbers comes easily to me and gave me a level of confidence when deciding to make the jump. That said, I didn’t have design experience or the understanding of what was needed to physically manufacture a product. Don’t think you have to do it all. Seek out people who can supplement your areas of weakness. Determine what assets you bring to the table and what support you need.
  • Create a roadmap: Anything worth doing is seldom easy. I invested almost all of my life savings and spent 100% of my time and energy on designing a water bottle with a purpose. While passion is a great starting point, it isn’t always going to keep your business and your entrepreneurial journey alive. A roadmap that focuses on both qualitative and quantitative goals can keep you on track for when certain milestones should be met. Consider using Excel spreadsheets for basic logistical monitoring and a journal to document how you’re feeling and how people are responding to your ideas. This monitoring will enable you to see the bigger picture and have a gut check for if you’re on the right track.

Having these items in place allowed me to not only be aware that it was time to quit, but also allowed me to take action and do it. I rode the “swell” and haven’t looked back since. You can too.