Day 4: The question people usually keep to themselves.

You’re now on Day 4 working towards your perfect retirement summit. We've covered the day-to-day, money, and yesterday we talked about identity.

Today's section of the retirement mountain is one people don't usually say out loud, and they definitely don't tell their advisor. Maybe not even their spouse.

Recently we worked with Tom, who was 10/10 financially secure on paper, but he kept delaying his retirement date for reasons he couldn't quite figure out. We asked him,

"What's holding you back?"

Asking the direct question is what finally got us to the root of what was keeping him stuck. He was worried about maintaining a real connection once he stopped working.

Saying it out loud made it click. After identifying his true worry, we walked him through an exercise to help him map out what meaningful friendships and community could look like outside of work, and with that clarity, he was finally able to retire earlier this year.

Tom’s still adjusting to the full feeling of retirement some days, but one thing is already clear: He doesn't miss the stress and fatigue of work one bit.

Over 18 years of working with people preparing to retire, I've found that almost everyone has their own version of Tom’s question.

Brian Portnoy says it usually shows up as a version of two main questions:

“Do I have enough?"
or
“Am I going to be okay?”

So, what about you?

What's the retirement question you're most afraid to ask? The one you keep circling around but haven't actually said to anyone.

Today, I want to give you permission to ask that question, even just to yourself. It's a helpful first step in preparing to eventually ask it out loud, whenever you feel ready to.

There's no wrong answer here. What matters is saying it. An unspoken question will just sit there quietly weighing on you. One might call it a worry. I love the quote “when has worry ever added time to your life?” Recently, my daughter reminded me that 90% of the things we worry about never actually happen.

Now, it's perfectly normal to worry. One thing I've noticed about worry is that it only takes, it never gives. So speak your question out loud. Write it down. The moment you put it into words, it becomes something you can actually work through instead of something you carry.

I encourage you to skip the softened, polite version and write the question you'd actually say if no one were listening. This is the one, if you're ready, to try saying out loud to your spouse or a close friend, even if it feels uncomfortable.

Fred Rogers said it best, "Anything that's human is mentionable, and anything that is mentionable can be more manageable."

Stay tuned for the final question tomorrow. It's the one we’ve been building towards.

Talk soon,

Tim Meisenheimer, CFP®, CFA
CEO, Streamline Financial