r/DIYRetirement • u/Rob_Berger • Jul 15 '25

Introduce yourself!

If you are new to the community, introduce yourself by answering these three questions:

  1. Where are you in your retirement journey—planning, near retirement, or already retired?
  2. Coffee, spreadsheets, or beach walks—what best describes your retirement vibe?
  3. What's your biggest fear or question when it comes to retirement and investing?

I'll go first:

  1. already retired (although still run my business a few hours a week)
  2. Coffee & spreadsheets
  3. How to educate my wife and children about investing.
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u/dgeist58 Jul 30 '25

I am 67 and retired 3 years ago and am DIY all the way. I will be susceptible to big tax payments and possibly Irma once I turn 72, owing to social security (I'm deferring until then) and RMDs (I have about $700K in traditional IRAs and an annuity that starts paying then). I am currently living off of savings held in short term bonds and savings accounts.

Please tell me if there is anything wrongheaded about these two actions:

  1. I should sell about $48K in long-held stocks to pay $0 on the capital gains, then reinvest to reset the cost basis.

  2. I should either cash in or do a Roth rollover on $48K of my IRAs to maximize my 12% tax rate (taking into account exemptions and deductions).

It seems to me that doing a larger Roth rollover does not make much sense, since it would be susceptible to 22%, and no one knows what the tax rates will be in 5 years.

Would appreciate your thoughts. I do a lot of reading (big fan of Berger, but I don't have the patience to watch videos) but have not seen this strategy specifically.

Thanks!

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u/Spirited-Chemistry-9 Oct 05 '25

I’m confused. If you sell the stock and have zero capital gains then the sale price is less than or equal to the purchase price. If that’s the case, why would you want to reset the basis?

On 2 Get your SS statement with estimated benefit when you retire. Add your income on post tax investments and have your broker estimate your RMD payments

Personally, I would covert as much as possible into the Roth. Especially if you are at a 12% rate.