The Chicago Wellness Challenge

The Chicago Wellness Challenge is designed to demonstrate the importance of taking a comprehensive approach to success through self-care.


Entrepreneurs are always under pressure to perform. Stress builds and it takes a toll both mentally and physically, which impacts their ability to lead and grow a startup. I’ve been in those shoes, so I can totally relate.

Earlier in my startup career, things were cranking. The more I worked the better the business got. Even though it was hectic and full of stress, I never complained. Every entrepreneur I knew had that attitude, “work until you drop”—or so it seemed.

As you might imagine, the never-stop-working lifestyle came with a price. Upon reflection, I realized that I wasn’t taking time for myself. I would tell myself that I’d go to the gym after I completed one more task. But it didn’t happen. So I would push it off to the weekend when I would have more time. But it rarely happened. As the days, weeks, and months went on, I went from 170 pounds to 180 to 190 to 200 to just under 210 pounds, which was not a healthy look on my frame. The weight gain was very symbolic of how I was treating myself: shitty. My blood pressure was high, my fitness was poor, and my energy dwindled.

Like most people, I finally hit a tipping point and knew I had to make a change or end up dead before I was 50. What happened as a result improved my life in multiple ways. As I started to take more time for myself, I began to feel better physically, emotionally, and mentally, my life grew more satisfying, and I became a better, more productive entrepreneur.

I have since switched roles from entrepreneur to investor, but I still interact with countless entrepreneurs daily. Unsurprisingly, I see more and more entrepreneurs hit the wall just like I did. The constant grind impacts their overall performance, both professionally and personally; it’s a real problem.

I believe that, in order for an entrepreneur to do their best work, they need to ensure that they’re ready and able to perform. This means taking care of mind and body to maximize performance. To prove it, I created The Chicago Wellness Challenge to challenge folks to make their wellness a priority.

JOIN THE CHALLENGEand make wellness a priority in your life!

  1. Set a wellness goal that you want to accomplish over the next 6-weeks.
  2. Share via social media using #ChiWellnessChallenge.

The following individuals were The Chicago Wellness Challenge Founding Participants. They were the first to sign up to demonstrate the importance of taking a comprehensive approach to success through self-care. They agreed to kicked off the six-week-long initiative on April 22, 2019 and share their progress to reach their personal wellness goals while they encouraging other Chicagoans to join them. They include:

The following Founding Partners helped us build the foundation of the challenge before it was launched. Their services and products include goal setting, strength training, meal planning, healthy nutrition options, performance optimization, meditation instruction, and much more.

Throughout the challenge, participants and partners will share their experiences, tips, trials, and successes on Instagram, Twitter, and LinkedIn, in hopes to call others to engage, learn, and start moving towards their own wellness goals.

I can’t wait to see how the challenge progresses! Stay tuned for updates via social media and

* Calm subscription support provided by Listen Ventures, a Chicago-based venture capital firm that was one of Calm’s first investors.


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