A couple of years ago, after we sold our house, moved our family, and I unexpectedly lost my job, I remember feeling completely untethered. I wasn’t sitting there staring at spreadsheets or retirement projections. The question felt much simpler and more immediate: Am I going to be okay?

Death Readiness Dispatch

May 27, 2026

Hi there,

 

A couple of years ago, after we sold our house, moved our family, and I unexpectedly lost my job, I remember feeling completely untethered. I wasn’t sitting there staring at spreadsheets or retirement projections. The question felt much simpler and more immediate: Am I going to be okay?

 

I think a lot of us are asking versions of that question, and the question is about more than retirement. It’s about helping our kids, helping our aging parents, worrying about long-term care, wondering whether we’re saving enough or spending too much. We're wondering whether we’re the only adult secretly thinking, “Wait...am I doing this right?”

 

This week, I sat down with my longtime friend and financial advisor, Blair Martin. It was refreshing to hear her voice the things that worry us, problems that we think we're the only ones facing:

#1: Most of us don't know how much we spend.

#2: Most of us are feeling overwhelmed.

#3: Most of us think we're already supposed to know all of this.

 

Many of us assume everyone else has color-coded spreadsheets and a perfectly organized financial life. Apparently they don’t.

The rest of us are winging it, too

Here's one practical takeaway from our conversation: If you have no idea where to start, don’t start with perfection. Pull up your checking account or credit card statement and get a rough baseline for spending, just a starting point. Are you spending $40,000 a year or $400,000?

In this episode, Blair and I talk about:

🤔 How to know whether retirement is even possible,

👨‍👩‍👧 Helping adult children without undermining your own future,

📋 Required minimum distributions and why they can become a headache,

🩺Long-term care planning,

❤️ And why financial planning is often much more emotional than financial.

How to Prepare for Retirement Without Panic

If you’ve been putting off talking to a financial advisor because you feel overwhelmed or like you’re somehow supposed to already know all of this, Blair Martin is exactly the kind of person who helps take that pressure off.

 

Retirement readiness isn’t really a finish line. And neither is death readiness. Both are about movement in the right direction. Looking back at this photo, it feels fitting. Blair and I have been helping each other move forward for a very long time.

Thanks for being here.

PS: Fun news: I recently joined Robert Brokamp on The Motley Fool podcast to talk about estate planning, incapacity planning, and why having documents isn’t the same thing as having an estate plan. If you’d like a little extra Death Readiness this week, take a listen.