This post is adapted from a recent episode of the Scholar Financial Advising podcast. Listen here for the full discussion.
A listener asked:
“I think I’m in good shape for retirement, but I don’t know what I’ll do when I don’t have to show up for work every day. The honey-do list is going to wrap up quickly. What’s the best way to handle the unknown of how to fill the empty calendar?”
This is one of our favorite questions—because it highlights something that often gets overlooked in retirement planning. Most people spend their working years focused on reaching retirement, but when that day starts to approach, the abstract idea of “freedom” can start to feel a little overwhelming.
The Empty Calendar Problem
For many people, the fear isn’t financial—it’s personal. They wonder what they’ll do when Monday rolls around and there’s no job to go to. Most people have a list of home projects or travel plans, but those can run out quickly. What comes after the to-do list? What comes after the trips?
The good news is that retirement schedules tend to fill up fast. In fact, many retirees find themselves busier than they were while working. The difference is that they now have full control over how they spend their time.
Still, it can be difficult to plan for a life stage you’ve never experienced. That’s why we often recommend “test driving” your retirement before making the leap.
What Is Test Driving Retirement?
Instead of going from full-time work to full-time freedom overnight, try easing into retirement by experimenting with what your new routine might look like. This can involve two main approaches:
1. Start Adding Retirement Activities Now
Begin building a retirement-like schedule before you stop working completely. That could mean:
- Cutting back your work hours
- Saying no to extra contracts or overtime
- Making time for activities you expect to enjoy later
Try volunteering, travel, or hobbies in smaller doses and see what sticks. Try a different volunteer organization every month. Sign up for a few one-off events or sports leagues. See how you feel with more flexible time—and notice what you naturally gravitate toward.
2. Start Subtracting Work
If you’re one or two years away from retirement, reducing hours or scaling back responsibilities can be more valuable than adding another year of full-time savings. At that point, contributing another $50,000 to a retirement account is unlikely to change your retirement outcome. It might be more rewarding to spend some of that money now on meaningful travel or time with family while you’re still working and healthy enough to fully enjoy it.
Volunteering: A Retirement Win-Win
Volunteering is a perfect fit for retirees because it offers structure, purpose, and flexibility. Many people nearing retirement have developed skills that are in high demand at nonprofit organizations—leadership, operations, project management, finance. And since those organizations don’t have to pay you, it’s a win for them too.
The best way to find your fit is to rotate through a few groups and causes. You’ll quickly figure out what feels energizing and what doesn’t.
Explore Hobbies and New Experiences
We once worked with someone who took a sabbatical to “test drive” retirement. Every week, they tried a different hobby: sailing, surfing, bowling, softball, and more. Most of it had nothing to do with what they did professionally. That was the point. They were actively figuring out what they liked doing when the calendar was blank—and that exploration helped narrow the overwhelming list of possibilities into a lifestyle that felt exciting and real.
Try Travel—Before Retirement
A lot of people plan to travel once they retire, but that can leave a gap in the years leading up to it. If you’re only a few years out, consider using some of your time and money now to take those trips. You’ll get a better feel for the pace, locations, and style of travel you enjoy most. Plus, it helps you avoid the common “travel all at once, then what?” problem that can follow retirement.
You can also test out vacation destinations you’ve considered living in or buying property in. Take weekend trips. Spend time in different seasons. See what daily life actually feels like there.
Final Thoughts
Retirement is not just a financial event—it’s a lifestyle transition. The more clarity you have around how you want to spend your time, the more confident you’ll feel when the day finally comes.
You don’t have to figure it all out now. But the sooner you start experimenting, the more likely you are to land in a retirement that feels fulfilling—not just financially, but personally.
For more insight into how to prepare for retirement beyond the numbers, listen to the full podcast episode here.