Ep 71: What Issues Should I Consider Before I Retire?

Let’s go through the retirement checklist to cover all the key issues you should think about before retirement. How prepared are you?

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The View From The Pinnacle

Let’s go through the retirement checklist to cover all the key issues you should think about before retirement. How prepared are you?

Click the timestamps below to fast forward to certain points of the episode.

Thing’s You’ll Learn Along Today’s Journey

Ever feel like you accomplish more with a list? On today’s episode of the podcast, we go through the retirement checklist to make sure you are ready for retirement.

Will your cash flow needs change in retirement? After you retire from getting a paycheck, you might have a moment of panic without the regular paycheck. What do you do to cover expenses? If you’re receiving a pension, what pay-out option do you take?

Are you considering retiring early? Make sure to take the time to plan for the optimum time to take Social Security. There’s a certain period of time that’s ideal for Roth conversions. Are you spending your IRA strategically? You want to coordinate your cash flows to give you the most beneficial and most strategic withdrawal strategy for your plan, both for the short-term and the long-term financial benefits. 

If you are divorced or widowed, did you know you may still be eligible for your ex-spouse’s Social Security benefits? This spousal benefit is there for spouses who are not in the workforce. If you are permanently disabled, you may qualify for Social Security benefits earlier.

If you retire early, what are you planning to do about health insurance? You have a few different options, but it’s important to find the right fit for you and your budget. What additional insurance do you need to keep in mind to protect you? Dental and vision insurance aren’t covered, so you may choose to pay for it separately. If you have an HSA now, you don’t have to spend it down every year. Some families choose to save this every year to help cover the gap in retirement. 

Finally, are you worried about coving long-term care expenses? Instead of making it an emotional decision, view it as a math problem. Do you have enough to self-pay? Or will long-term care insurance help you? Talk with your financial advisor to make sure you are making the right decisions based on your situation.

Listen to the entire episode or skip ahead using the timestamps below.

0:50 – What should we consider before we retire?

2:52 – Are you retiring early?

4:24 – What is the Social Security elimination windfall? 

5:38 – What do you need to know if you’re divorced or widowed?

8:13 – What health insurance issues do you need to cover? 

9:48 – What about dental or vision insurance?

11:03 – What happens to your HSA?

11:32 – What about Medicare?

12:41 – If you’re disabled, what do you need to know?

13:16 – Are you concerned about funding long-term care?  


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Looking Back From The Mountaintop

“When you start to look at retiring early, a big portion of that is how do you coordinate your cash flows to give you the most beneficial and most strategic withdrawal strategy for your plan.”

-Sean Lee


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For over a decade, Sean Lee has helped families reach and maintain their financial goals. As a trusted advisor, he coaches and assists his clients with their financial goals by focusing on the fundamentals and takes a practical and personal approach when working with them.

As a trusted professional in Utah, Sean has been featured in The Wall Street Journal’s Market Watch, The Deseret News, The Salt Lake Tribune and USA Today. He has also been featured as a local financial advisor on Utah’s NBC station, KSL 5.

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