Lessons Learned: Leaving Entrepreneurship for a 9 to 5

Jessica Gaddy always aspired to be an entrepreneur. As a new therapist, she hoped to run a private practice while becoming a wellness expert in media. She paid her dues after graduation; working in case management, school-based mental health, policy, and program management. With the high caseloads, workplace politics, and red tape, she looked to entrepreneurship as her saving grace. 

When the COVID-19 pandemic began, Jessica saw an opportunity to transition to full-time entrepreneurship. With lockdown orders in place, people were seeking mental health support. Having worked in a group practice, Jessica felt comfortable with EHR systems, the ins and outs of billing, and teletherapy. With a continually growing waitlist, Jessica felt it was the perfect time to launch Nia Noire Therapy + Wellness. With teletherapy, Jessica wouldn’t have to worry about office rent or daily commutes.

What could possibly go wrong?

Gaddy soon learned that even with all her prep, full-time entrepreneurship was more challenging than she envisioned. Jessica Gaddy spoke with More Than A Therapist and shared vulnerable moments of her career, along with considerations for therapists contemplating full-time entrepreneurship.

How was your first year of entrepreneurship?

“Do we have time? The first year was a rollercoaster. There was so much I had to learn independently (and so many mistakes were made, like taxes!), that I found were a necessary part of the journey. Within my first year, I was seeing clients at full capacity, often having upwards of 30-35 sessions per week to meet the growing demand. This was a signal to expand my team with additional clinicians and a billing specialist. But of course, that meant increased overhead and expenses that I didn’t properly prepare in advance (think—EHR fee increases for additional clinicians/clients; billing dues when insurance hadn’t reimbursed; email server fee increases; more clients to manage; etc.).”

In between sessions, Jessica was cementing her status as a thought leader in the wellness field with media appearances in Forbes, HuffPost, BuzzFeed, and Fox5. As she navigated new territory, Jessica attempted to process her own experience in the pandemic. Unfortunately, Gaddy found herself feeling burnt out as she balanced high caseloads, media appearances, ongoing pandemic stress, and the weight of being a full-time entrepreneur.

Looking back, what shifts would you make?

“Transparently, I’m not sure I would do anything differently. I encouraged myself to ‘fail fast.’ When I finally allowed myself to release the ridiculous expectation that I’m magically supposed to know how to perfectly do this brand new thing… I was truly able to zoom out and see how to improve the journey at a pace that made sense to me.

With that being said, self-care was a vital lesson I needed. I did a lot of internal work to release the guilt that came with rescheduling appointments, taking extended time off, or referring out clients that weren’t aligned with my expertise. “

What advice would you give to other clinicians who are considering full-time entrepreneurship?

“Take. Your. Time.

There’s a weird push on social media that everyone should be an entrepreneur, but it’s no small feat and doesn't adequately show all the ins and outs of entrepreneurship.

Before taking the dive, ensure you have a steady cash flow that supports your lifestyle. Have adequate savings to account for unexpected expenses and taxes.

Remember, it's COMPLETELY okay to try entrepreneurship, decide you don’t enjoy it, and return to something that is more stable or fulfilling to you. Eliminate the idea that you 'failed' or were 'inadequate,' if you go full-time and return to a corporate role. It just means you found something more suitable for YOUR lifestyle.

Everyone is different, embrace your own journey in whatever form that takes on.”


Jessica Gaddy, LICSW

Licensed clinical social worker, psychotherapist, and wellness media correspondent specializing in helping women of color through life transitions via self-care and self-restoration, what she calls "self-ish." Jessica is the Founder and Clinical Director of Nia Noire Therapy + Wellness.

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