You've been working for decades. You've saved something. Maybe even a lot. But when retirement starts feeling less like a distant idea and more like an actual date on the calendar, a nagging question tends to surface: Do I actually have enough?
We put that question to two experts. Tom Buckingham is Chief Growth Officer and an actuary at Nassau Financial Group in Hartford, Connecticut, specializing in retirement planning. Scott Siff is founder and CEO of Pivoters, a job-matching platform built for workers 55 and older. Their answers might make you rethink a few things.
1️⃣ Know your "must-cover" number — not just your account balance
"Total savings matter," says Buckingham, "but what really determines your retirement security is knowing which monthly expenses are non-negotiable. Once you know that number, you can match it to reliable income sources. Housing, healthcare, groceries, and utilities are examples of expenses that don't retire when you do."
Once you have that baseline, he says, you can decide how much of it needs to be backed by guaranteed lifetime income rather than market performance.
2️⃣ Plan for a retirement that lasts longer than you think
The retirement age of 65 was written into law in 1935. "At the time," Siff points out, "life expectancy was 61. In other words, most people never reached retirement age." Today, life expectancy for men who reach 55 is around 82 — and for women, closer to 85.
Buckingham puts the financial risk plainly: "The biggest financial risk isn't the market, it's running out of money while you're still healthy and active."
3️⃣ Don't count on Social Security the way your parents did
"Social Security is now predicted to run out of money and face serious cutbacks in just a few years," says Siff. "Given that the government is already facing record high debt and deficits, the fix may well be significantly reduced or delayed benefits. If you're counting on Social Security for your retirement, don't count on it."
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4️⃣ Factor inflation into every number
A million dollars is the rough expert consensus for a reasonably secure retirement — but Siff flags a catch: "That's in today's money. It is important to consider inflation and understand that $1,000,000 in today's money might not be worth the same amount in 20 to 30 years. Even modest inflation can erode purchasing power significantly and should be taken into account."
Try out our Retirement Reality calculator to see an estimate of what you'll need:
Educational purposes only. Not financial advice.
The $1M target is a commonly cited benchmark. Not financial advice.
Historical U.S. inflation has averaged ~3% annually. Not financial advice.
Simplified model. Actual results vary. Not financial advice.
Does not account for Social Security delayed credits or taxes. Not financial advice.
5️⃣ Understand the real — and often hidden — cost of healthcare
"The incidence of depression is around double for people who retire," Siff notes, "so retiring can come with significant extra mental health costs as well. Those are often silent costs that not enough people plan for, and they can really wipe you out financially."
He also cites research showing that people who continue working live as much as 7.5 years longer than those who retire — and with lower healthcare costs along the way.
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6️⃣ Consider making part of your income predictable
"Retirement gets a lot easier," says Buckingham, "when part of your income shows up every month automatically, the same way a paycheck once did. It removes stress, simplifies budgeting, and helps you stay focused on living, not worrying."
He's an advocate for insurance products — fixed and fixed indexed annuities specifically — that guarantee lifetime income. A note on context: this is Buckingham's professional specialty, so weigh his product-specific recommendations accordingly and consult an independent advisor before committing. That said, LIMRA reports annuity sales hit a record $460 billion in 2025, suggesting a lot of retirees are reaching the same conclusion on their own.
7️⃣ The concept of a retirement age needs to be retired
"People and businesses should update their concept of retirement to catch up to today's reality," says Siff. "People 55+ are actually in great health, with lots to contribute. Consigning them to retirement leaves them bored and probably broke, and cheats businesses and the economy of a huge workforce of experienced people ready to work.
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8️⃣ Working longer may be the best financial — and physical — medicine
"Studies show that people who work live as long as 7.5 years longer than people who retire," Siff says. Beyond longevity, he cites research linking continued work to reduced rates of cancer and heart disease, improved mental health, and stronger overall well-being.
This is one perspective worth weighing, not a universal prescription — plenty of people retire happily and healthily. But for those on the financial edge, it's a data point worth knowing.
9️⃣ Structure your income, don't just accumulate savings
LIMRA research cited by Buckingham shows 95% of pre-retirees say protection and predictability are essential to feeling secure. His framing: "Once you understand your baseline, you can decide how much of it should be backed by guaranteed lifetime income rather than relying on how the market performs."
The question, in other words, isn't only how much have I saved — it's how reliably will it reach me every month, for the rest of my life.
🔟 The gap between where most Americans are and where they need to be is larger than most people realize
"The median age that people have saved for retirement in the US is $50,000," says Siff, "but experts say you need a million dollars to have just a reasonable amount of money for the decades that you may well spend in retirement. That should be the main metric for preparing for retirement — and then when, and if, you retire."
That gap isn't a footnote. For tens of millions of people, it's the whole story.
Tom Buckingham is Chief Growth Officer at Nassau Financial Group in Hartford, Connecticut. More at nfg.com.
Scott Siff is Founder and CEO of Pivoters, a job-matching platform for workers 55+ (currently in beta). More at pivoters.com.
