Can I Retire Now?

The Retirement Readiness Checklist You Shouldn’t Ignore (Ep. 48)

Nick J. Russell, CRPC® & Becky Wagoner

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0:00 | 34:24

Retirement gets a lot more real when the calendar starts counting down. Questions around healthcare, taxes, income, routines, and timing can suddenly feel overwhelming.

What happens if you miss Medicare deadlines? How do you avoid tax surprises? And what does life actually look like once the work routine disappears?

In this episode, Nick Russell and Becky Wagoner walk through a retirement readiness checklist covering the final 12 months before retirement. They discuss Social Security timing, Medicare enrollment deadlines, tax planning opportunities, Roth conversions, investment income strategies, beneficiary reviews, and how to prepare emotionally for life after work. They also explain why retirement is more of a strategy game than a finish line and why planning early can help reduce stress during the transition.

Key takeaways:

  • Medicare enrollment deadlines can affect premium costs for the rest of your retirement years
  • Retirement tax planning may create opportunities for Roth conversions and lower taxable income
  • Building cash reserves before retirement can help stabilize income during market downturns
  • Weekly routines and lifestyle planning matter just as much as investment preparation before retiring
  • PTO payouts, pensions, and retirement timing can all impact taxes during your first retirement year
  • And more!

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