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Published: September 29, 2025

7 key questions to ask before you retire

"Retirement is wonderful if you have two essentials — much to live on and much to live for." — Unknown

What happens when you retire and life doesn't go according to plan?

It's a question worth asking before you commit to a fixed income and assume your bases are covered.

That's because even the best-laid plans can come up short. If that happens to you, you could have far less to fund the lifestyle you expected in retirement.

To avoid that, it helps to step back and ask yourself some questions:

1. What expenses do I have that could spike without warning? Am I prepared for that?

2. Have I budgeted for things that don't happen monthly, like gifts, travel, and repairs?

3. What happens if I live longer than I expected? Or if I spend more each year than I planned?

4. If prices keep rising, how would that impact my income and lifestyle over time?

5. Do I have room in my plan for one-time shocks, like medical bills or a family emergency?

6. Could I adjust quickly, if needed? Do I know what I'd cut first?

7. Am I depending too much on one income stream? What's my backup?

Honestly reflecting on your answers can be the first step to building a more resilient, realistic retirement plan.

As a financial professional, I've seen well-prepared retirees get caught off guard with surprise expenses that slowly chip away at their savings.

I've also had the privilege of helping many people rethink their assumptions, strengthen their plans, and build in more flexibility for real life.

I'd be honored to do the same for you.

Haven't read this month's Visual Insights Newsletter? Click here to check it out!

P.S. I'm also here to help your family and friends. If they could use advice about retirement or finance in general, forward this email to them. I keep spots in my schedule open, and I'd be honored to help them as well.

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