Entrepreneurship: The Hard, The Tragic, and Mental Journey of it ALL (Told by an Underrepresented Founder)
By: Cheryl Ingram
Tags: Mental Health Awareness, Diversity And Inclusion, Mental Health, Diversity, Founders

“The culture in startups has perpetuated a presence of overwhelmingness for leaders and we’ve got to change that if we want to see more inclusive cultures and healthier companies and founders.”

Dr. CI

I recently read the article in Forbes that covered the experiences of Tony Hsieh, CEO of Zappos, leading up until the moment he was no longer on this earth with us all. I read about his efforts to “improve the human condition.” An effort familiar to many entrepreneurs and creatives. As I read it, I couldn’t help but erupt into tears. I felt in the very pit of my soul how difficult life must’ve been for him on this journey. I want to be clear that I understand that we are not the same person by any means, but that in the moment I reflected on how I am feeling and many other people are feeling as an entrepreneur in the world right now! It made me think about the inefficient support systems that are built to help founders who struggle with mental health, whether we are doing well or struggling on our journey to create and change systems in the world. I also thought about his journey as an underrepresented Founder/CEO and my mind was racing wondering if there are any similarities and differences in our mental, physical, spiritual, and emotional journeys. I am writing this piece as an informative article to help those who will take the time to read and digest it, understand what it’s like to be an entrepreneur, especially an underrepresented one.

There are a number of influences on the mental health of an entrepreneur, I will list them accordingly:

Understanding that the one place you could once escape to safely, your brain, is in a constant battle with itself and fighting the daily battles that you have about decision making 24-7 Maintaining authenticity Dealing with difficult and verbally abusive investors Loneliness Losing family and friends on this journey (physically to death and based on decisions to self improve where their energy did work in my favor) Maintaining self-worth even when you make a mistake Staying true to your mission and your vision Finding a support circle that truly understands your personal and professional challenges and how the two overlap Trying to define this false idea of ”balance” between life, health, liberty, justice, and all the other shit we shout to the audiences that will listen while we perpetuate a false sense of wellness Being tone policed and forced to conform to white supremacist cultural norms in order to survive (this one is especially for my BIPOC Founders and leaders) Supporting others, including employees, while you are struggling to figure it the fuck out

I am writing this email directly after I decided to turn down a potential million dollar investment in my company. I did it because I read the experiences Tony faced, I did it because during my interaction with investors I experienced 9 out of the 10 factors I listed above while on this journey. There were moments after dealing with these investors that I woke up and said to myself some of the following:

Is this journey really worth it? I know I don’t know everything, but these people are constantly making me feel like I don’t know anything. Is it supposed to be this difficult? I’m good at this…..right? I could just end it all, and start over doing something else. Where’s my possibile in the moments when I’m feeling it is impossible? How will I combat racism, sexism, and all the isms inside of a system that perpetuates it and refuses to listen to me? Where am I going to find the resources to support my people? Did I eat today? Why isn’t this working like they said it would? What am I doing wrong?

These are a few of the 100’s of questions I ask myself on a daily basis. My mind races often with both negative and positive thoughts. I use affirmations daily to help decrease moments of self doubt. I workout, journal, meditate, eat healthy, and all the things but I am also honest with myself when doubt tries to creep into my life. Impostor syndrome on this journey is real and it’s amplified by well intended people, who make you feel incompetent because you’re not like them or what they aspire to be. You handle all of the things while you’re dealing with short runways for raising, difficult people, and all while you’re navigating your own personal shit. Meanwhile, people who need your support are struggling to help you build a company that you have created with the intent to support others in some way shape or form. Do you see the problem yet? If not let me lay it out more clearly.

As an entrepreneur you experience a number of different things. The first is a heightened awareness of yourself and others. As your awareness heightens, so does the potential for heartbreak, loneliness, and a sense of security. The sense of security requires sacrifice, accountability, and acceptance of all things positive or negative. Second, is the need for changes in your life in order to meet your goal. These changes include losing friends, creating new circles, having to build new relationships, and this takes hard work, intentionality, and time. Third, is dealing with the disappointments brought on by the people you trusted to help you on this journey. I have taken pride in the fact that I hire marginalized identities and I have had to fire underrepresented populations for a number of different reasons. Some of these have been due to a number of different mistakes. Many of these mistakes have unintentionally and intentionally harmed my business. It’s like I was watching people fail to support our mission in a society that wasn’t built to support them. I didn’t have the resources to help them because the same systems we are fighting did not provide them. These are some of the lessons I have learned and here are a few others:

Startup culture is not built for the purpose of sustainable mental health for its employees. If you are an underrepresented founder (BIPOC, Parents, Women, People with Disabilities etc.) this is amplified if you don’t come from wealthy backgrounds or have access to others that do. Populations that are often underfunded and attempt to create startups more often than not, fail on the journey. Here are some reasons why: The presence of White Supremacist Cultural Norms that have created expectations based on the exclusionary experiences of the people who have created them. The isms/phobias- Racism, Sexism, Homophobia,Transphobia, Lingualism, Xenophobia, Ableism, Educational Discrimination, Classism, Ageism, Familial Discrimination, and all the other isms/phobias that make our startup cultures difficult to exists in for non heteronormative and majoritarian identities. Relying on people who share in the identities that you have, that also fail to support you because they’re trying to figure out, is not sustainable. We are forced to figure out how to stay above water temporarily in a system where many, if not all of us drowning due to feeling underappreciated and being underpaid!

I am an entrepreneur who works to change these cultures, and as I am working to change them, I am finding my way into my own authenticity. In finding my way to my own authenticity there is this unwavering permanence of increased hypersensitivity that is making harder and harder to exist in the world. As my awareness increases here’s what I am recommending that some of us can do to help support ourselves and our employees during these challenging times:

Community-level efforts, including health communication strategies, should prioritize young adults, racial/ethnic minorities, essential workers, and unpaid adult caregivers. Redistributing workplace resources to cover mental health resources for part-time employees and having grief counselors on retainer for staff who are struggling. Normalize this as a part of your budgets moving forward. Also, work with different mental health agencies owned by underrepresented founders to support their businesses and amplify their mission This is a little unconventional but we need it. Have health coaches and addiction recovery services available for your employees. People are relying on other means of support and outlets in order to just get through these difficult days. Have systems in place without judgement to help those who are struggling and need it. Shorten work days, weeks, and virtual meetings. Not every meeting needs to be an hour and some can be handled via email. Identify meetings based on priorities and needs and then align it with efficient means of communication (email, slack, meeting etc.). Start focusing on milestones, encourage your leaders and employees to take time off, pay them for it, and don’t discipline them for it. Stop with this minimal managing of spelling, grammar, and punctuation in emails and on documents. People are working through the integration of work-life responsibilities, trying to stay alive, and find a piece of mind during this time, grant them some grace. If you want to be the “grammar police” go teach a class! Investors: You have the money, and the network that we need to thrive, but humanize founders in a way that doesn’t always have to remind us of your power and the right to mistreat us because you have money. Our company is your investment, we’re not your gotdamn property. We work better and more intensely when we feel respected, appreciated, seen, and heard. Provide a resource list for your employees of different outlets, podcasts, meditations etc. that they can view while at home. Create a space for employees to complain or vent about managers/colleagues/ or anyone affiliated with your company who is perpetuating the mistreatment of them in the workplace. Be prepared to create coaching plans for people managers who are trying to stay above water but are harming others unintentionally because they are under extreme stress. Fire the people who do it intentionally if they’re not willing to change.

Entrepreneurship is hard. It shouldn’t perpetuate an untimely and imminent death either. If we want these systems to change we have to be willing to change them without sacrificing our livelihood to do so.