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Ready For Retirement

Your Tax Planning Window Won’t Last Forever | Top 3 Strategies to Prioritize

Ready For Retirement

James Conole, CFP®

Investment Planning, Bonds, Education, Stocks, Cash, Business, Dividend Investing, Retirement Planning, Retirement, Investing, Tax Planning

5706 Ratings

🗓️ 25 October 2025

⏱️ 21 minutes

🧾️ Download transcript

Summary

Retiring early isn’t just about having enough money, it’s about using the right tax moves in the right years. This conversation between James and Ari maps the three biggest levers for early retirees: Roth conversions, ACA health insurance subsidies, and 0% long-term capital gains. A real-world case study shows how account mix and spending levels can flip what’s “best,” and how small income shifts can change the math in a big way. The episode breaks down when Roth conversions pay off versus wh...

Transcript

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0:00.0

Almost every person who wants to retire early is facing the same three things if they want to truly optimize for their early retirement.

0:08.1

Number one, they're wondering, should I try to massage my income to get like a health care subsidy?

0:13.3

Number two, should I try to do those Roth conversions where I move money from a 401k to Roth because most of my money is in that pre-tax account.

0:22.7

And number three, should I do that tax gain harvesting, that paying zero percent in taxes

0:28.8

potentially if you massage your income well?

0:31.6

And you have what's called a tax window to be able to do this.

0:35.3

And this is what I imagine most of your retirements are looking

0:40.4

like. So here's a visual to see that more clearly. Here's someone who's 55 making a very

0:46.0

healthy income. They want to retire at 60. That's when their income is going to drop. And then

0:50.5

what's going to happen here at 75, those RMDs.

0:54.4

Hey, everyone.

0:55.0

I'm James Cannell, CEO of Rout financial.

0:56.9

I'm with R.A. Talibb, Chief Growth Officer of Rout Financial.

0:59.5

And we are here today to do a collaboration to help you understand what's the right

1:03.4

tax strategy to implement as you're moving into retirement.

1:06.5

And R.A., as you mentioned, there's three big ones that we think about, that most people

1:10.0

think about.

1:11.0

That's the easy part.

1:12.2

The harder part is understanding what do you prioritize, and it's very much based on your situation,

1:17.2

and we're going to walk through a case study to help show people why.

1:20.0

Let's learn about the couple.

1:21.4

James, so here is a couple John and Jane.

...

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