Retirement income is not one decision. It is roughly forty of them, taken over several years, most of which cannot be revisited once made.
In this full-length session, Gary Korolev works through the sequence: when to file for Social Security and why the month matters, how federal benefits coordinate with it, what Medicare actually covers, and where long-term care costs land when nobody has planned for them.
Three Pillars
3:46 — 4:52 The framework the session is built on. Each pillar answers a different failure mode, and a plan missing one of them is exposed regardless of how well the other two are constructed.
Страхование
Protection against the events that would otherwise consume the portfolio — health costs, long-term care, and the loss of a spouse's income.
Guaranteed Income
The floor beneath everything else: Social Security, pensions, and annuitised income that arrives whatever the market is doing that year.
Growth & Inflation
The invested portion, whose job is to outpace the rising cost of living across a retirement that may run thirty years or more.
What the Session Covers
Social Security Strategies
5:10 — 47:20The largest portion of the session, and rightly so — this is where the irreversible decisions live. Filing anywhere between 62 and 70 changes the benefit permanently, and the arithmetic differs sharply for a single claimant, a couple with an earnings gap, and a surviving spouse.
Also covered: spousal and survivor benefits and how they interact; the Windfall Elimination Provision and Government Pension Offset, which reduce benefits for those with non-covered pensions; and the lesser-known buy-back and suspend options, which exist to correct a claim made too early.
Federal Employee Benefits
47:20 — 50:24For FERS employees the calculation has moving parts that private-sector retirees never encounter — the pension formula itself, the treatment of accumulated sick leave, the handling of annual leave at separation, and how the whole coordinates with Social Security.
Given how many households in this region hold federal service, these few minutes are worth more than their length suggests.
Medicare & Healthcare
50:24 — 57:09Parts A, B, C, and D explained in the order they actually matter, followed by Medigap — with particular attention to Plans G and N, the two most commonly compared.
For federal retirees there is an additional question that has no universal answer: how Medicare interacts with Federal Employee Health Benefits, and whether carrying both is worth the combined premium in a given household's circumstances.
Accounts, Taxes & Markets
58:09 — 1:21:29Roth conversions and when the arithmetic favours them. Managing qualified accounts — 401(k)s and, for federal employees, the Thrift Savings Plan — with attention to withdrawal sequencing and the tax consequences of getting the order wrong.
And the concept most retirees have never heard named: sequence of returns. Two portfolios with identical average returns produce entirely different outcomes depending on when the bad years arrive. For someone drawing income, an early drawdown does damage that a later recovery cannot undo.
Long-Term Care
1:21:29 — 1:27:29The part of retirement planning most often deferred and least often reversible. Costs have risen faster than general inflation, and a single extended stay can consume a plan built carefully over decades.
The session covers traditional long-term care insurance alongside hybrid structures — life insurance and annuity products with care riders — which address the objection most people raise to the traditional version: paying premiums for years for a benefit that may never be claimed.
The Acronyms, Briefly
Why the Sequence Matters
Each of these subjects is manageable alone. The difficulty is that they interact — a Roth conversion changes the taxation of Social Security, which changes the Medicare premium, which changes what a long-term care policy needs to cover. Decisions taken in isolation tend to work against one another.
That is the argument for treating income planning as a single exercise rather than a series of separate errands, and it is the through-line of the full session.
This webinar is educational and does not constitute financial, tax, or legal advice, nor a recommendation of any strategy or product. Rules governing Social Security, Medicare, and federal benefits change, and their application depends on individual circumstances. Confirm current provisions and consult a qualified professional before acting.
Run the Numbers on Your Own Situation
A webinar covers the general case. Filing age, conversion timing, and coverage decisions all turn on figures specific to one household — and those are worth working through properly, before the irreversible ones arrive.
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