Ambitious Women Thriving with Chronic Conditions: Cally Cripps

Written by Cally Cripps, Founder of Systemagically & Vice President, Information Technology and Analytics

At the age of 18, I was fortunate to receive my diagnosis of endometriosis—remarkably, without the typical 6-8-year wait that many women face. At the time, I didn’t understand the journey that lay ahead of me. It’s been decades of fatigue, pain, bloating, and five major surgeries. The physical toll was significant, and I struggled without the right tools to cope. 

Despite these challenges, my resilience shone through. Over time, I’ve learned various skills to help manage my symptoms, and the surgeries have been the biggest help to me physically. 

Turning Passion into Purpose

My journey with endometriosis fuels my passion for corporate wellness. I strive to understand how people can take care of themselves in the workplace. I’ve established a company, Systemagically, dedicated to helping individuals design systems that work for their unique needs. We are all different, and I believe that workplaces should reflect this individuality, providing support for personal well-being.

My career has unfolded in the health IT sector. I began in behavioral health and have stayed in the field ever since. With the health advocacy work I do, I quickly recognized the disproportionate impact of chronic illnesses on substance use and mental health. This realization drove my commitment to health advocacy, as I saw the difference we could make in this space through health technology.

Now, as an IT executive, I’m dedicated to corporate wellness and ensuring that individuals with chronic conditions can thrive in their professional lives.

The Impact of Endometriosis on Work Life

My experience with endometriosis has undeniably affected my work life. There were periods when all I could manage was work and sleep. The fight to get to work often felt overwhelming, but I needed health insurance to cover my medical expenses. 

I’ve taken several weeks off to recover from surgeries, but this experience has also impacted my work for the better and enriched my leadership style. I recognize that people have to take care of themselves first, and this is better for both the individual and the business.

To other women navigating their careers, I urge you not to let anyone convince you that your health should limit your potential. While there may be times when you can’t do something, that doesn’t mean you won’t ever be able to. Seek out environments that value you as a whole person. Non-profit organizations, in particular, can be great spaces for growth and understanding.

Another piece of advice: you must fight for yourself. In my experience, not all medical systems nor workplaces are set up for individuals to succeed.

We shouldn’t have to be resilient, but the world we live in requires it, and it often becomes our superpower as Chronic Bosses. Take the time to discover what works for you, and build on those strategies over time. Finding an environment where you can thrive is crucial.

Embracing the Title of “Chronic Boss”

My illness has made me the leader I am today, and it’s my responsibility to take others with me. I am a leader who understands the complexities of chronic illness, and I will always advocate for my team’s well-being. Being a “Chronic Boss” as a leader is to create a workplace where everyone feels supported and valued.

If you’re navigating a chronic condition while prioritizing your career, I urge you to advocate for yourself and your needs. If you’re in a position of leadership in your workplace, be your team’s advocate, because when they are taken care of is when they will thrive the most at work.

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