Have you ever noticed how something as simple as toothpaste can tell you a lot about your life?
This morning, I walked into the bathroom and, to my surprise, my toothpaste was exactly where it belonged. Right there. In the drawer. Waiting for me. If you have teenagers in your house, you know that’s not always how it works.
In our home, Kim and I joke that some of our things behave a lot like our old outdoor cat, Oliver. He came and went as he pleased. Some days he’d stick around. Other days, he’d disappear without a trace. That’s pretty much how our stuff operates too. Toothpaste, conditioner, chargers, hoodies… here today, gone tomorrow. You get the idea.
Kim said something this morning that stuck with me. “As frustrating as it is, when the kids are gone, we might actually miss this.”
I told her when that day comes, I’ll gladly take her things and hide them around the house just to keep her on her toes. #winning
But there’s something deeper in that.
We don’t always realize what we’ll miss until it’s gone. And that shows up clearly in retirement.
Most people spend decades focused on the numbers. How much have I saved? Will it be enough? When can I stop working? Important questions, and we help answer them every day. But there’s another question that matters just as much.
What will your days actually feel like when the house is quieter, the calendar is clearer, and everything is exactly where you left it?
I’ve seen it often. People are financially ready, but not fully prepared for the shift. They expected freedom. They got it. What they didn’t expect was the loss of rhythm, noise, responsibility, and even the small frustrations that once filled their days.
Retirement isn’t just a financial transition. It’s a life transition.
The people who navigate it best have taken time to picture it ahead of time. Not just the big trips, but the ordinary Tuesdays.
At Rose Street Advisors, that’s a big part of what we do. Yes, we build income strategies and think through taxes and risk. But we also help clients get clear on the life behind the plan.
What does a great day look like? Who are you spending time with? What are you moving toward? Where does purpose come from when work no longer defines your schedule?
Because retirement without a clear picture can feel a lot like that outdoor cat. A little unpredictable. A little disorienting.
But when you define it, something changes.
You stop reacting… and start living with intention.
So here’s a simple place to start. Picture a random Tuesday in retirement. Not a vacation. Just a normal day.
Where are you?
What are you doing?
Who are you with?
Then ask yourself, if nothing changed between now and then, would that day feel fulfilling?
If not, that’s not a problem. It’s an opportunity. An opportunity to start shaping that future now.
Because the goal isn’t just to have enough.
It’s to build a life you’re excited to live.
And if more people approached retirement this way, I think we’d see fewer people drifting and more people fully stepping into what could be one of the most meaningful seasons of their lives.
And maybe, just maybe, keeping a little of that “outdoor cat” energy along the way.