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If You Could Rewind 5 Years Before Retirement… What Would You Change?

If you could go back to 5 years before you retired, what’s the one decision you’d change that would have made the biggest difference in your first 1–3 years of retirement and what do you wish you’d done sooner? Examples:

When to claim Social Security?

How you structured withdrawals/taxes

Whether you carried a mortgage?

Where you lived?

How you planned for healthcare/long-term care?

thanks,

Jeff

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23 Comments
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eludom
9 months ago

I would have started reading HumbleDollar sooner.

achnk53
9 months ago
If we have understood what was coming for us after we turned 65 with IRMAA and the 2 years look back, we would had done much more smaller Roth conversions, as like a Roth conversion ladder, but instead we did 3 mega large conversions & was hit with the highest tier for 3 years into our unplanned retirement. That was something we should have researched and planned differently for a redo 5 years look back.

achnk53
9 months ago
Reply to  achnk53

Sorry about my mistake about the post above. My laptop was dying and doing some crazy things.

If we have understood what was coming for us after we turned 65 with IRMAA & 2 years look back, we would not have done 3 mega Roth conversions, and were hit with 3 highest tier IRMAA years. We would had done much smaller Roth conversion ladder instead. That 3 years hit were almost as bad as the sequence risk for our early unplanned retirement years.

Rob Jennings
9 months ago

I would have hired our financial advisor at that time-5 years out-rather than 1 year before retirement.

mytimetotravel
9 months ago

I agree with Dan. I have been very happy with my retirement. I also hear Richard on Roth conversions, but Roth IRAs, never mind 401ks, didn’t exist until two years before I retired. Also, I’m not sure my income once I retired was often low enough for conversions to make sense.