Risk, Sacrifice, Reward: Swapping Your Day Job For Your Passion, by a 22-Year Self-Employed Writer

I lost almost everything and more than once… until the scales finally balanced.

Joel Eisenberg
7 min readJun 4, 2024


Wilhelm Gunkel; Unsplash


The adage goes something like this: “If you do what you love, you will never work a day in your life.”

There are variations of the wording of this philosophy, but you get the picture.

As for me, for as long as I remember I wanted to be a writer. I simply would never be happy doing anything else for a living.

And so, some 22 years ago when I was 38, I leapt off the proverbial cliff and never looked back.

I had just quit my 100th day job.

I will not tell you during my journey to self-employment I earned half a million dollars monthly from my genius blog, in-demand consultancy or course offerings.

No. The truth more resembled jumping off the cliff and leaving a bloody splatter on the ground underneath.

That truth, depending on the day of the week, consisted of selling cherished possessions to pawnshops, nearly losing my house (three separate occasions), having utilities cut-off, being bombarded with collection calls and very…



Joel Eisenberg

Joel Eisenberg is an award-winning author, screenwriter, and producer. The Oscar in the profile pic isn’t his but he’s scheming. WGA and Pen America member.