In the spring of 2020, I spent weeks on video calls with clients who were convinced they had made a catastrophic mistake.
Markets had dropped 37% in 30 trading days. Some of these clients had retired just months earlier. Others had been retired for years. All of them were watching the same news, seeing the same red-colored tickers, and feeling the same thing: that their financial security was somehow tied to whatever the market did next.
One by one, we pulled up their plans. Updated the numbers. Ran through the things they could control. And one by one, they discovered the same thing — they were fine. Their plans had been designed for this kind of tumultuous scenario.
Not a single one needed to go back to work. Not a single one needed to make a dramatic change. What they needed was a system that could plainly and irrefutably answer the question: Can my retirement plan withstand times of uncertainty?
The Question Behind the Question
I see this same pattern in my office all the time. People who have done everything right. They’ve saved consistently, stayed invested through rough markets, and accumulated wealth. They’re close (maybe they’re already there) and then the media starts fearmongering.
Suddenly they find themselves googling whether now is really a good time to retire.
Markets, inflation, government leadership, trade policy — the specific trigger wears many masks. The doubt behind it is always the same: What if I’ve done everything right, but the timing is still wrong?
This is one of retirement planning’s cruelest ironies. The people best prepared to retire are often the most reluctant to commit. Simply because they’ve spent decades paying careful attention to the world around them, and the world right now doesn’t feel particularly stable.
The problem with letting external conditions drive your retirement decision is that the world has never been particularly stable. At no point in modern history has there been a moment without a credible reason to wait. Markets will always be either too high (making you nervous about a correction) or too low (making you nervous about the damage already done). There will always be an election, a geopolitical concern, a Federal Reserve announcement, or a headline meticulously written to keep you watching — and waiting.
Peace of mind is too valuable to hand over to the news cycle.
How to Gauge Your Retirement Readiness
If “is this a good time?” is the wrong question, what’s the right one?
In our practice, we evaluate retirement readiness against six factors that have nothing to do with what the market did last week. Together, they form what we call the H.E.A.L.T.H. framework — a systematic approach to answering the questions that determine whether a retirement plan holds up through uncertainty.
Healthcare Costs
I’ve seen a health insurance quote stop people with plenty of funds from retiring early. A $1,200 monthly premium can paralyze someone with $5,000,000 in retirement savings because it feels like a new and permanent expense they didn’t account for.
The reality is that healthcare costs are plannable. Bridging coverage from retirement to Medicare eligibility at 65 has a known cost range. ACA marketplace premiums are income-dependent, which means the accounts you draw from and the amounts you take directly affect what you pay. Long-term care insurance is a separate consideration, but one that also has concrete options.
Expenses
Basic retirement income planning mistakenly assumes a flat monthly budget, which doesn’t depict how retirement typically unfolds. Early years tend to run higher due to travel, home projects, and finally doing the things that you didn’t have time for during working years. Middle years moderate as routines settle in. In later years, medical expenses become a growing share of overall spending. A plan that accounts for this arc handles the early surge without panic and builds adequate reserves for later.
Assets
The portfolio that built your retirement isn’t necessarily organized to fund it. Accumulation rewards risk-taking and time. Distribution needs an allocation that generates sustainable income, manages sequence-of-returns risk, and preserves enough growth to keep pace with inflation across a retirement that could span 25 to 30 years.
Account structure is important, too. Retirement accounts, Roth accounts, and taxable brokerage accounts each have different tax treatments and different roles in a retirement income plan. Whether they’re positioned correctly (and drawn from in the right order) has a direct impact on how long your nest egg lasts.
Liquidity
One of the more common mistakes in early retirement is treating an investment portfolio like a checking account. If a large expense hits, the instinct is to liquidate. But if markets are down when that need arises, selling means locking in losses that might otherwise have recovered.
Maintaining accessible cash reserves (typically six to twelve months of living expenses set aside outside the investment portfolio) creates a buffer that lets the rest of your assets stay invested through turbulence. It’s a simple principle with an outsized impact on both financial outcomes and peace of mind.
Taxes
The years between retirement and age 73 (or 75 if you were born in 1960 or later), when required minimum distributions begin, are often the lowest-income years of a retiree’s life. Before RMDs hit, before Social Security turns on if you’re delaying it, drawing modestly from a mix of accounts — you may find yourself in a tax bracket you haven’t seen since the initial part of your career.
This is a window, and it eventually closes. Every year it goes unused is a year of Roth conversion opportunity, capital gains harvesting, and strategic withdrawal sequencing that doesn’t come back. Retirees who plan around this window lower their lifetime tax bill systematically.
Household Income
The foundation of any sustainable retirement income plan is its guaranteed income floor: Social Security benefits, pension income if applicable, and any earned income from part-time work or consulting. Together, these determine how much pressure is placed on your portfolio to cover living expenses month to month.
Social Security timing is one of the most consequential decisions in this category. Claiming at full retirement age, claiming early, or delaying to 70 produce materially different monthly benefit amounts — for life. For married couples, coordinating when each spouse claims, particularly around survivor benefits, adds another important layer.
Does Your Plan Hold When Conditions Don’t?
Running through the H.E.A.L.T.H. framework tells you where your plan stands today. Stress-testing tells you whether it holds under conditions you’d rather not face.
What happens if markets drop 25% in the first two years of retirement?
If inflation runs persistently above 3% for a decade?
If you suddenly need long-term care at 82?
The goal of this exercise isn’t to predict which scenario occurs — none of us can do that. It’s to confirm that your plan remains viable across a range of possibilities, not just the one where everything goes reasonably well.
When Waiting to Retire Is the Right Answer (and When It Isn’t)
There are legitimate reasons to delay retirement that have nothing to do with market conditions: healthcare coverage isn’t planned, guaranteed income sources haven’t been strategically timed, cash reserves aren’t in place, or the early retirement tax window hasn’t been accounted for. These are areas worth addressing before stepping away.
What isn’t a legitimate reason is the news. Markets being down, an election approaching, inflation elevated, a recession being discussed on television — some version of these concerns has been present in virtually every year of the past century. Staying at a job you’re ready to leave because the headlines feel unsettling is a choice with a cost, measured in years, in time, and sometimes in health and wellbeing that you can’t recover later.
Working part-time or consulting is a middle path worth considering if the full transition feels too abrupt. It’s not retirement, but it’s not the status quo either, and for some people it provides both financial and psychological breathing room during the adjustment.
You Could Find Hundreds of Reasons Why Now Isn’t a Good Time to Retire
There is no universally good time to retire — not in the way the question usually means.
If you’re waiting for the general sense of uncertainty to lift before you feel comfortable stepping away from work, you’ll be waiting a long time. Those things don’t resolve. They evolve into new versions of themselves, and the next concern replaces the last before you’ve had a chance to exhale.
The question itself is a trap. “Is this a good time?” puts your retirement decision in the hands of forces you cannot control and could not predict (at least not reliably) even if you tried.
The better question is: Is my plan designed to hold up regardless of what those forces do?
That one is answerable. And for more people than you might expect, the answer is already yes — they just haven’t had a system to measure it yet.
At Pine Grove Financial Group, we help clients run the H.E.A.L.T.H. framework against their specific situation, stress-test the results against realistic scenarios, and come to a conclusion they can actually trust. If you’re wondering if now is the right time, that’s a good enough reason to find out.
Schedule a consultation, and let’s take a look together.
See If You're a Good Fit
Your responses go directly to a senior member of our team, who’ll guide the next steps toward a personal conversation. No automation. No sales pressure.
