When Investments Cover 50% of Expenses, You Can Work Every Other Year

Jon Middaugh
3 min readJun 6, 2023
Photo by Nastya Kvokka on Unsplash

Here’s a cool thing: If your investments are generating 50% of your living expenses, you only need to cover 6 months of living expenses from savings.

When that runs out and you work for another year, your investments will automatically generate another 6 months of savings.

That’s it; that’s the story.

But there is one problem: how do we make this sustainable? Many employers won’t be fond of an employee having several ‘gap’ years on their resume.

Grow A Business During Your “Off” Year

I have a constant goal of creating a business that adds value to others while doing work I deeply enjoy.

I have had a partial success, or maybe a partial failure, that I thought would replace my job income.

I wasn’t reducing work in order to travel or indulge myself. I was seriously pursuing a business that used my dev skills to aid thousands of other developers every day.

I believe this improves my resume and enhances my opportunities now that I am back to near full time hours at my job.

I also have vastly more respect for those who have “made it” with their business, and more appreciation for the benefits of a job.

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Jon Middaugh

I have been: individual contributor | tech lead | manager | JS boot camp teacher | community college instructor.