
Tom Stivers
Paraplanner at Jim Saulnier & Associates, a retirement planning firm, and guest on The Retirement and IRA Show podcast.
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Oct 17, 2026
COBRA, Social Security, Pension Deferral, Annuities: Q&A #2642
21:55
22:06
22:21
22:26

Tom StiversGUEST
I'm not just saying that as, you know, the classic financial planning podcast comment of the day, but it, it's contingent on the plan itself and what that plan requires of en- of enrollees at Medicare age.

Tom StiversGUEST
So when you look at the IRS's revenue ruling that ruled on something remarkably similar to this, they basically established a three-pronged test where all of the following things need to be true in order for the 36-month period to be extended.

Tom StiversGUEST
So the spouse or dependent child must be a qualified beneficiary in connection with the employment.

Tom StiversGUEST
The spouse or dependent child must still be a qualified beneficiary at the time it occurs, and it must be a qualifying event.
7 MINS LATER
Single Life Pension Tradeoffs: EDU #2640
6:20
6:28
6:37
6:42
6:50

Tom StiversGUEST
But, uh, you know, jokes aside, I think I'll start first by framing sort of the, the career transition.

Tom StiversGUEST
So as Chris alluded to, I'm not really a traditional financial planner in the sense that I was schoolhouse trained in financial planning and then, uh, came aboard here.

Tom StiversGUEST
Actually, before this, so in the, the pre-2026 era, I was actually an infantry officer.

Tom StiversGUEST
So in about, let's see, I commissioned in May of 2018 out of the University of New Mexico, and I joined the active duty Army as an infantry officer.

Tom StiversGUEST
From there, I went to Fort Benning, Georgia, for my initial entry training, Ranger School, Airborne School, before I get my first assignment in 2019 at Fort Campbell.