DYLW Featured / Tips for Designing Your Life / Women / workshop

Choosing Odyssey Plan 3: Why the Risk has Been Worth the Reward

By Jessica Klepper

In 2018, I attended the Designing Your Life for Women workshop in Pacific Grove, California. At the time, I was in my tenth year in sales for a Fortune 500 company. I loved my job, the people I worked with and my clients, but I didn’t feel as though I was living out my purpose. It felt like I was unable to shine in that environment.

During the DYL Workshop, I was able to focus on me, my skills, strengths and joys without distraction.

I created three Odyssey plans during the workshop:

  1. Plan/Life 1 (Status Quo): Stay at my current company in my current role.
  2. Plan/Life 2 (If Plan 1 were gone): Stay at my current company, but pivot into another role.
  3. Plan Life 3 (If money/image were no object): “Life Creation Consultant.” I didn’t really know what this meant yet, but I knew that I enjoyed connecting people to resources, tools, and each other to achieve their highest potential.

It was a beautiful, inspiring weekend. And then I went home… and did nothing. I had defaulted to Plan 1. But something inside was still gnawing at me, so I dusted off my DYL workbook and decided to attempt Plan 2. I applied for a training role and made it to the final interview but was not selected. My fiancé could see my disappointment. He said to me, “Why don’t you try doing something on your own? If you’re passionate about this, I will support you.”


Enter Plan 3. I wasn’t sure how to go about this. Then in the Spring of 2019, I was invited to attend a Women in Sales event. I was blown away by the experience and wanted to learn more. The organizer said it was a one-time event. I asked if I could take this concept and run with it. She said yes. We easily found another woman leader and the Society of Saleswomen was born.

I left my job in November 2019, and SoS had our first, albeit tiny, event that December. Six women who already knew each other attended. It served as the first prototype in what would become an organization that now has over 250 members and hundreds of followers on social media.

Choosing Odyssey Plan 3 was frightening, but once I believed in a concept and prototyped it, it all worked out. My two pieces of advice? Don’t let fear stop you. And finally, just do the thing. There is a point you will look back and say, “What was I so afraid of?” It’s okay to make mistakes if it leads you to live with purpose and believe me, it was all worth it.