Overcoming the Dark Side of Being an Entrepreneur

Cynthia Wylie
2 min readFeb 20, 2024
Photo by Steve Knutson on Unsplash

I have experienced it from time-to-time when cash flow was tight for various good reasons.

I’m talking about the dreaded “bag lady syndrome.”

That’s when you catastrophize a rough patch and imagine you are going to lose everything including your home and end up living out of your car.

It’s the equivalent of having a sore throat and thinking you have throat cancer.

During one particularly tough period, I even came up with a plan.

I’d park at my gym where I had a parking pass and was grandfathered in at a ridiculously low rate of $38 a month from yes, decades of membership.

In addition to parking, I could continue working out every day (important!) and I’d have access to a bathroom and shower. As an added bonus, it’s only two blocks from the beach.

None of that ever happened.

It brings to mind that well worn Mark Twain quote, “I’ve had a lot of worries in my life, most of which never happened.”

Learning how to handle the stresses of running a business and making sure you have enough cash flow to do so, is hard.

And it’s always there.

It really never goes away.



Cynthia Wylie

Founder of Bloomers Island. Published children’s book author at PRH. Writes about big kid’s stuff like economics & business, too. TheProjectConsultant.com.