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Cheryl Bennett is the owner of Just Swim Consulting, a leadership training, and personal development company. She has nearly 30 years of management and leadership experience; and has been a certified PMP since 2009. Cheryl works full-time as the PMO Director for NewWave Technologies in Baltimore, MD. She holds a BS in Computer Science, and M.Ed. in Cognitive Science, with a minor in Adult Education, and is currently working on her Doctorate in Leadership.
Cheryl is passionate about mentoring, coaching, and sharing her experiences as a project manager to help the next generation of managers develop their leadership skills. She believes that all managers can become exceptional leaders.
In her free time, Cheryl serves on the Board of Directors for the Baltimore Community ToolBank; is an active member of Toastmasters International; enjoys traveling; and, most importantly, spends time with her children and grandchildren.
1. Tell us about your side hustle.
My business is called Just Swim Consulting. It is a leadership and professional development training consulting company. I provide leadership and project management training, speaking, and mentoring to aspiring leaders.
2. What inspired you to start your business?
I have been in project management for more than 30 years and get the greatest joy from mentoring and helping new managers develop their skills. I love sharing my experiences and the best practices I’ve learned as a leader.
When I first moved from a technical person (computer programmer) to leadership, I was left to figure out how to lead on my own. So I took as many classes and workshops as possible and modeled the behaviors of leaders I respected.
I want to make it easier for managers in similar situations not to feel overwhelmed and drowning in the new world of management. My company name reflects this. I want to be their lifeline and help them to “swim.”
A second meaning for Just Swim comes from my desire to encourage others, especially women, to try new things, not be afraid of trying before everything is perfectly aligned, and being ok with ‘good enough.’ In other words, after you’ve done some prep work, it’s time to jump in and ‘just swim.’
3. How did you make your first dollar?
Initially, I had hoped to include a networking component in my business to help bring adults in my area together. That was in early 2020, and circumstances (aka Covid) were not kind to that idea. I offered a couple of virtual cake-decorating workshops that year and earned about $300.
Otherwise, I volunteer to speak for professional networks, including local chapters or the Project Management Institute (PMI), which got me visibility with my target audience: project managers. I also went back to school because I love learning new things and because the idea of ‘Dr.’ sounds pretty cool.
2021-2022 was spent refocusing, learning, and planning for my ‘exit strategy’ from corporate America. I made $0 but continued volunteer speaking for PMI-Baltimore and PMI-New Hampshire. 2023 is my year to earn enough to supplement my retirement income (future planning).
I have earned a whopping $86 through a productivity workshop I published on Eventbrite. But, I also just won (yesterday) a contract to lead a 6-week Project Management Training with a local community college (you’re the first to know!) I also have an interview with a software company next week to discuss their leadership development needs. My goal for 2023 is $40K.
4. When can you work on your side hustle? How do you make time for it?
I reduced my hours at my corporate job to 4 days per week, which allows me all day Friday, evenings, and weekends to work on school and my business. IT IS TOUGH, though. I have to spend at least 3 hours per night on schoolwork, with Friday (my day off) being my catch-up day.
Friday and the weekend are also my time to focus on Just Swim. If things go well, I hope to reduce my corporate hours further, but I need them for health benefits, at least until I earn enough through Just Swim to cover the high costs.
5. How has your side hustle impacted your personal and professional life?
Professionally, I am meeting new people.
Personally, the biggest impact is that I’m tired. My house is a wreck, and we eat out way too much. I also have to find a quiet spot on weekends (like today) when my grandchildren are with us (every other weekend), so I can focus on school and work.
Today I am at the public library. My youngest grandchild doesn’t understand “grandma can’t have you climbing on her lap right now” or “grandma needs a few hours to do homework.” The library works well, and I’ll have the rest of the day today and tomorrow to spend with them.
6. What challenges have you faced while working on your side hustle, and how have you overcome them?
My biggest challenge is a fear of marketing myself. The fear is that if I win work, will I be able to fit it in with my corporate job? And, more importantly, will I do a good job (aka Imposter Syndrome)?
My strategy for time is to reduce my hours and/or retire depending on how much work I get. I also have a mentor encouraging me to market myself (holding me accountable), which helps. Knowing someone else is counting on me makes me more likely to move.
7. Do you have any resources to recommend to someone looking to start a side hustle?
“The One Page Business Plan” helped me get my thoughts on paper and create, revise, and finalize my business plan. I entered a business plan PITCH contest in 2020 and won $7K (4th place) on the strength of my business plan.
I have stacks of books I plan to read one day, but finding that time is difficult. The only book I read entirely in 2022 was “The Trusted Black Girl,” which discusses various stereotypes of Black women. Highly recommend it for any Black woman who wonders, for example, “did that really happen?”, “am I overreacting?” or “why am I so exhausted just living?”
8. What advice would you give to someone considering a side hustle?
Do your homework, and then jump in. Don’t wait for everything to be perfect….perfection is impossible anyway….so jump in at “good enough” and learn as you go.
Mistakes are learning opportunities, so don’t beat yourself up over them. Instead, learn from them and keep swimming.
9. Is there anything else you’d like to share about your experience with your side hustle?
Never stop learning. There is always something new to learn and experiences that could help you with your side hustle or simply help you with your sanity. Be curious and keep learning.
Although this is year three since I officially registered my company, it is still in its infancy. Part of the reason for the slow development is fear and hesitation.
My advice, therefore, is not to let fear get in the way of trying new things. And if you so desire, try many things.