You’ve worked hard. You’ve saved diligently. But now you’re staring down a question that carries more emotional weight than most spreadsheets can handle:
“Should I wait until I’m 60 (or even 65) to retire?”
The surprising truth is that many people are waiting longer than necessary, not because their finances dictate it, but because they fall prey to outdated beliefs, industry dogma, and fear-based retirement planning. After years of working with professionals preparing for their next chapter, we’ve seen it again and again: retirement was much closer than many originally thought.
Let’s break this down.
The 4 Myths That Keep People Working Too Long
It’s not always about the math, but is often about the mindset. If you’ve ever felt unsure about retiring before 60 or 65, you might be operating under one or more of these common (but flawed!) beliefs:
1. “I need a magic number in my account to retire successfully.”
We’ve all seen the commercials: a person walking around with a dollar amount floating above their head like it’s the key to happiness. But retirement readiness isn’t about achieving something mystical. It’s about sustainable spending, timing, and flexibility.
2. “65 is the safe retirement age.”
Whether you blame Medicare, Social Security, or just tradition, there’s a little societal script that says 65 is the “correct” time to retire. This makes it feel risky (or even irresponsible) to retire sooner. But let’s be clear: the right retirement age is the one where your plan works successfully.
3. “I need to wait for the market to hit a high.”
We hear this one a lot. But if you’re three years into retirement and the market dips, are you going to un-retire? Of course not. A strong retirement strategy doesn’t rely on market timing. Instead, it prepares for volatility.
4. “Everyone else is still working — maybe I’m making a mistake.”
This one's more emotional than financial, but it’s real. The idea that leaving work early is a badge of irresponsibility — or that you’ll regret the change while others are still grinding — is more about pride and peer comparison than planning.
The Real Risk Is Missing Your Best Years
There’s a silent cost to waiting too long to retire. You trade your irreplaceable healthy years for money you may never need or spend. For many, that’s a raw deal.
One of our clients (let’s call him James) was stuck in this trap.
He had solid savings, was a responsible spender, and even ran his own retirement projections using online tools. But he wasn’t sure what (or who) to believe, so he kept working, just in case.
Until we challenged his assumptions.
How James Retired Sooner And More Confidently
Once we unpacked James’s concerns — market drops, medical expenses before Medicare, what-if scenarios — we could focus on facts. Here’s what made the difference in his plan. It might just make a difference in yours too.
1. Customized Spending Projections
Instead of establishing a flat $120,000/year lifestyle forever, we planned for higher spending early in retirement (when he’d be most active) and lower spending later (as travel slows and health needs grow). This adjustment alone changed the game.
2. Smarter Risk Modeling with Regime-Based Monte Carlo
Most retirement tools use long-term average market returns. We used regime-based Monte Carlo, which considers current and near-term economic conditions. This offers a more realistic lens on your retirement, especially for those retiring in uncertain markets.
3. Guardrails, Not Just Probability Scores
James had been trying to push his retirement plan to 100% probability of success. This might sound smart, but often leads to over-saving and over-working.
So we implemented risk-based guardrails instead. This is a system that monitors his portfolio monthly and provides a signal that indicates he’s either okay to keep spending according to his plan, or that it’s time to modestly adjust that spending to stay on track.
This gave James real clarity and flexibility, and it made early retirement not only possible, but sustainable.
The Real Strategy Behind Early Retirement
James wasn’t a startup executive with a $100 million exit under his belt. He didn’t win the lottery either. He was a smart, steady saver who simply made a strategic shift: he stopped chasing a "perfect number," he stopped waiting for the market to cooperate, and he stopped comparing himself to others on different paths.
Instead, he got personalized advice and built a retirement strategy perfectly tailored to his lifestyle, spending needs, and portfolio.
What About You?
If you’re still stuck in “wait until 65” mode, ask yourself:
-Are you holding back because of facts or fear?
-Are you optimizing your strategy or relying on generic advice?
-Could you be trading time for money you’ll never use?
Let’s Find Out How Close You Really Are
Brindle & Bay Wealth Management helps professionals like you create a personalized retirement strategy using real data, holistic planning, and guardrails as opposed to guesswork.
Want to know if you're closer to retirement than you think? Click here to schedule a free retirement analysis! We’ll help you ditch the fear and focus on the facts.
Because the goal isn’t to die with the most money. It’s to retire with the most life left to enjoy.
The client stories shared in this blog post are intended for illustrative purposes only. While inspired by real-life experiences, these examples are composites drawn from a range of client situations and do not represent any one individual. They may be considered indirect testimonials. Actual client experiences will vary. No clients were compensated for sharing their stories.
