The Right Age to Retire (It’s Not the Number You Think)
When most people ask “When should I retire?” they’re asking the wrong question. After 40 years in this industry, I’ve watched people retire too early, too late, and with the wrong plan entirely. The answer has never been a specific age. It’s a financial and mental state, and until you reach it, no birthday on the calendar is the right one.
The Milestone Trap
The financial industry loves milestones. 59 and a half…. 62… 65… 67…. 70. There’s always a number to chase. But retirement readiness isn’t about reaching a checkpoint. Most advisors will say having enough to live off of is enough. At Freedom Capital Advisors, we take it a step further. True retirement readiness means having enough to live well, absorb the unexpected, and still leave something behind. Legacy isn’t a bonus. It’s part of the plan.
One of the most common mistakes I see is people entering retirement without adjusting their spending. They’ve lived on a salary for 30 years and they keep spending like they still have one. That mental shift from accumulation to distribution is harder than most people expect.
The second mistake is deciding to manage their own portfolios in retirement. Managing your own money sounds empowering until the market drops 30% and your emotions start making the decisions. That’s not a criticism of anyone’s intelligence. It’s human nature. But it’s also why professional fiduciary advice tends to pay for itself many times over, especially in volatile markets.
The Readiness Test: Savings vs. Obligations
Here’s how I define retirement readiness: your savings versus your obligations. Before you stop working, you should be able to answer yes to these questions:
- Are you debt-free, or close to it?
- Have you handled major purchases (cars, home repairs, renovations) while you still have income to absorb them?
- Is your monthly outlay predictable and stable?
Carrying significant debt into retirement is one of the fastest ways to blow up a plan that looked solid on paper. Every dollar going toward a payment is a dollar that isn’t compounding or covering your cost of living. Make the big purchases before you retire. Your future self will thank you.
Two Clients. Two Lessons.
I want to tell you about two clients. One made a mistake I see more often than I’d like. The other made a decision I still admire.
The first had a strong retirement plan, financially. What he didn’t prepare for was becoming the financial safety net for a family member. Before long, he wasn’t funding his retirement. He was funding someone else’s lifestyle. Retirees have to establish financial boundaries before they stop working. Being generous is admirable, but you cannot sustain generosity you cannot afford. If you become the “charity” before your assets are protected, you risk depleting everything.
The second client retired in the late 1990s at the height of the dot-com boom. Everyone around him was chasing tech stocks. He ignored the noise, cashed out near the top, and used the proceeds to fund his children’s education. He wasn’t lucky. He was disciplined. He knew what his money was for and he didn’t let market euphoria change the plan.
The lesson from both: a retirement plan has to survive real life, not just a spreadsheet.
What the Market Can Tell You
Timing matters, and there is data worth understanding. I’ve followed the VIX, the Volatility Index, for decades. It’s the market’s “fear gauge.” When the VIX spikes, markets are under stress. Investors are panicking and selling. That’s historically when the best entry points appear for long-term value investors.
If you have flexibility on timing as you transition into retirement, understanding the VIX is worthwhile. Deploying capital when fear is highest, rather than when confidence is highest, is one of the defining behaviors of a disciplined long-term investor. The best opportunities rarely feel comfortable when they arrive.
What the Industry Isn’t Telling You
A few things worth knowing before you sign anything or make any permanent decisions.
Hidden fees are real. Many complex products, annuities chief among them, bury their costs in layers that are difficult to decode. Before you commit to any insurance-based retirement vehicle, ask for a plain-English breakdown of every fee, at every level, every year. If the answer isn’t simple, that’s your answer.
Social Security is not guaranteed. Long-term projections aren’t favorable and most retirement plans assume full benefits at a specific amount. If yours does, it needs a stress test. Planning around a number that may change is a risk most people aren’t accounting for.
Private health insurance is expensive. If you retire before 65, you’re not eligible for Medicare. The gap between your retirement date and Medicare eligibility can cost significantly more than most people budget for. I’ve seen clients genuinely shocked by the monthly premium. Price it out before you set a retirement date, not after.
If You’re 58 Right Now
This is the window where the decisions you make matter most. Here’s where to focus:
Get a second opinion on your current plan. A fiduciary advisor will model realistic return scenarios, not just the optimistic ones. You need to know what happens to your plan if markets deliver below-average returns in the first five years of retirement. That scenario isn’t rare, and it has a name: sequence of returns risk.
Build a specific defense against inflation. Fixed income sounds safe until inflation quietly erodes its purchasing power over 20 years. Your portfolio needs components designed to grow faster than inflation, not just protect against short-term volatility.
Price out private health insurance now. Get a real number from a broker before you commit to any retirement date. Build that cost into your plan explicitly, not as a footnote.
The Bottom Line
Retirement isn’t a destination you arrive at on a specific birthday. It’s a state you build toward, deliberately, over years. The people I’ve seen retire successfully didn’t retire when they hit an age. They retired when their assets, their obligations, and their mindset were all aligned.
If you’re not sure where you stand, that’s exactly what a second opinion is for.
Is Your Retirement Plan Actually Ready?
Schedule a complimentary Strategy Session with our team. We’ll run a no-pressure Portfolio Stress Test to show you where you stand and what, if anything, needs to change.
Want to go deeper? Read: Ten Things Your Big Bank Brokerage Isn’t Telling You
