Why I Stopped Dreaming About My Bucket List — And Started Crossing Things Off

Welcome to the new retirement. It’s about having the freedom to decide when and how you want to take a break from work — to rest, recharge or start a new adventure — no matter your age. In our Redefining Retirement series, you’ll learn how real people are living their lives to the fullest, and the steps they took to get there. 

Like so many people of my generation, I started working as a teen, worked my way through college, and worked during most of my sons’ formative years. I firmly believe in hard work, but sometimes that means sacrificing personal time. 

That work ethic helped me become the executive vice president of a construction trade association of over 300 contractors, where I helped the membership with things like collective bargaining and workforce development. I enjoyed the work and my colleagues, but as I approached my 50s, I realized I wanted more flexibility.  

In the past, I’d spent a lot of my life talking and dreaming about the day I would retire. I had a bucket list of exciting things I wanted to do, like a family trip to Costa Rica, but I also wanted more time for the everyday things — like taking my 81-year-old mom to the grocery store, spending time with my nieces and nephews, and doing fun and memorable things with my teenage and college-age sons. I saw myself spending my retirement volunteering in the community and perfecting my culinary skills, and I couldn’t wait for the day to arrive when I could finally start living that life.  

MAKING THE MOST OF TODAY 

Retirement, however, always seemed so far off. So a year ago, at age 50, I decided that instead of waiting for some magic age, I would quit my demanding job and work part-time. I wanted to begin tackling my bucket list while I was still strong and healthy. 

To facilitate that, I started my own consulting business, Gregory Executive Resources. I help a local school district connect with local businesses, help young entrepreneurs with their finances and even do cybersecurity work. My work life is both satisfying and varied, and I love what I do. But because I can do all these things in my own time, it doesn’t really feel like work — and it’s much less time-consuming. Sometimes I work 15 hours a week and other times I work 50, but I have more freedom and control over my time.  

With the help of my new freer schedule, I didn’t just go on that family vacation to Costa Rica. My husband, Hal, and I also took a road trip from our hometown of Elmore, Ohio, through the lakeside towns of southwestern Michigan. We visited friends and family in Chicago and Pittsburgh, and I spent a lot more time on our boat. I also got to spend quality time with my uncle who died this year. If I hadn’t been semi-retired, I wouldn’t have shared so much of the last year of my uncle’s life with him, nor seen him and my mom talk and argue and tease each other, as siblings do. 

I haven’t regretted my decision for a minute.

If I had still been working full-time, I also wouldn’t have taken up yoga, and I would have missed out on the fun girls’ nights out that I would normally have been too busy for.  

Still on my to-do list: Traveling to Nordic countries, learning simple carpentry, taking dance lessons, hiking, going on bike tours and rowing crew again — all demanding activities that I might not be physically able to do in 15 years, when I was “supposed” to retire.   

Hal and I are healthy, strong and curious now, so we want to get some adventure travel in while we can and while our sons are able and willing to go with us. With a year of this new lifestyle under my belt, I haven’t regretted my decision for a minute. 

THE NOT-SO-SECRET SECRET TO SAVING 

What made this possible for my family was that during my last 10 years of work, we lived below our means and socked away as much money as possible. We didn’t do this because we planned for me to step back from my career, but because we’re just good savers. Having stuff and status is not as important to us as hanging out with friends and family. But when we looked at our finances and realized this was a possibility, we decided the time was right.  

Hal still works full-time, and I’ll continue to work and put more money aside for retirement. The difference now is I’m working in between fun and family time and not living just for a two-day weekend. 

I’ll keep working this way for as long as I physically can, as I love to work. When I truly retire, maybe I’ll become a drummer in an ‘80s tribute band. After all, learning to play the drums is on my bucket list.