‘Tis the Season for Thinking About Your Next Act

The holidays are a great time for stock taking and reflection.

For many of us, this holiday season provides a rare extended time away from work. It also ushers in a fresh start, a shift in perspective, and the promise of a new year. It’s a good time for stocktaking and reflection.

If you have the time and space in the next few weeks, consider setting time aside to consider your post-work life. With physical and mental distance from work, it’s a great time to think about your next act. Moreover, it’s a great time to step into the role of being retired—just for a day—and try it on.

So, dear readers, in this first holiday issue of Notes from the Road, my gift to you is a plan for a Holiday Break Retirement Trial Run.

Take a day and cosplay being a retiree. It’s up to you to decide if you want to dress up. Download our plan (also available in Word), plan your perfect post-work day, live it, reflect on your experience, and identify your next steps.

Also, notice how you’re feeling along the way. Content? Unsettled? Excited? Bored? Confused? The objective is not to fix it but rather to notice it. Know that you’ll need to pay attention to it now or in the future.

To support you, this entire newsletter is devoted to the transition to post-work life. To get you started, here’s a deep dive into structuring your day.

Last point: there are different stages to retirement. It’s a transition. It’s a process. You’re not going to solve it all in this one day.

The key to this little game is to understand what might come up for you so you’re not surprised, alarmed, or overwhelmed if it happens again. And to give you time to figure out what you need to thrive.

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Helping you thrive in your 50s and beyond. Advice, tools, and inspiration for navigating midlife and post-work life (with just a tiny bit of travel thrown in).