40-year-old who retired early as a millionaire: It was ‘boring’ and I only lasted 5 months—here’s why

My entire life used to be about maximizing my time for work. I spent over a decade building a career in New York’s tech scene.

I worked at Foursquare and Google, and in 2014, I started my business, Tech Ladies. My goal was to help women in the industry find jobs, negotiate and network. I hired a team and bootstrapped the company from $0 to millions in revenue.

I was proud of the mission, but I never exercised or took a vacation, and I rarely saw friends. I didn’t realize how burned out I was. I finally sold my company in 2021, but stayed on for a year to help with the transition.

Since I had seven figures saved, I realized that I could consider leaving the working life behind. So in 2023, I turned 40 and decided to retire early. The funny things is, I only lasted five months.

When I retired, we moved from New York City to New Jersey for my husband’s job. For the first time in years, I had a blank calendar.

I planted a flower garden. I started weightlifting and took long walks with new friends. I volunteered a few hours a week at the local soup kitchen and animal shelter. I fostered dogs and adopted a rescue named Addie.

Five months in, my quality of life had vastly improved. But I had mixed feelings, and at times it felt boring. I knew I couldn’t go back to 80-hour workweeks, but through volunteering at the shelter and spending time with my dog, I had come up with a business idea: an online community for Gen Z and Millennial pet owners.

I missed the creative outlet of entrepreneurship. I’d been in extreme work mode for so long that I thought cutting myself off entirely was the cure to my burnout. While I enjoyed my new hobbies, I was a little bored and didn’t feel challenged like I did when I was running a startup.

The truth is, I never had balance in my worklife before, but I owed it to myself now to try.

When I ran Tech Ladies, stealing even a 15-minute break felt impossible. I was obsessed with how much time I didn’t have, when I should have been paying more attention to where I put my energy and how it made me feel.

The most valuable lesson I learned is that you shouldn’t wait to do the things you dream about doing in retirement. So I asked myself five questions as I began my next chapter:

1. If you didn’t have to work, what is on your list of things you’d do that brings you joy?
2. How many hours a week would it take to actually do it? 
3. What can you take off your plate to give yourself more time and energy to do it?

Your ability to free up time and energy will vary, especially if you are taking care of kids or older parents. Push yourself to be honest and audit your time relentlessly. Just don’t give it all to a job.

I started working in earnest on Juniper, my business idea, this past August and it launched in November. I’m bootstrapping the business again, and in the last few months started to bring in revenue. I’ve gotten a lot of joy from growing this new community.

Most importantly, I’m working a more manageable 40-hour workweek. I also have some non-negotiables: I carve out time to walk my dog, work out and cook every day — and I take weekends off. My husband and I also don’t skip vacations anymore.

I want to build another successful company, but my definition of success now is accomplishing my goals without sacrificing my health, or the things that bring me joy and purpose.

Allison Esposito Medina is the founder and CEO of Juniper, an online community and pet product discovery platform. She also founded Tech Ladies, an online network for women in technology. Before that, she spent a decade working at various startups like Foursquare and Google.

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