Retirement doesn’t usually announce itself with a loud fanfare. More often, it’s like a long road trip — you pass signs along the way that quietly tell you where you are and what’s coming next.
It’s rarely one big event; it’s more like a collection of signals — financial, emotional and personal — that, when taken together, tell you it might be time to take the next exit and start your next chapter.
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Here are eight surprising signposts to watch for — and why paying attention to them matters.
1. Mission accomplished: You’ve met your financial goals
After years of saving, investing and staying disciplined, you’ve reached the number you once thought was far off on the horizon. Maybe it’s $2 million in a diversified portfolio or simply “enough” as you and your financial adviser define it.
You’ve tested your plan, run the scenarios and have the risk capacity that allows you to feel confident that you can handle the bumps in the market.
This is the green light on your financial dashboard. Once you’ve reached it, the question is no longer “Can I?” but “Why not?”
2. Feeling left out
Your spouse or closest friends are retired — and you’re still checking email at 7 a.m. while they’re planning a Tuesday morning round of golf or a weekend trip to a friend’s lake house.
At first, you’re glad for them — but over time, you feel something else: The faint sting of being left behind.
This isn’t about envy; it’s about connection. If the people who matter most to you are living life at a different pace, that gap can grow wider with time. Sometimes the clearest signpost isn’t financial — it’s relational.
3. The kids are launched
For years, you worried: Would they land good jobs? Find stable partners? Get off the family phone plan?
Now they’ve got careers and lives of their own. You’re no longer carrying their financial weight — and your projected expenses have dropped.
With that responsibility lifted, the road ahead looks clearer. It might not be time to downsize yet, but it could be time to reclaim space for your own passions, travel or pursuits long deferred.
4. The technology tipping point
New tools that once sparked curiosity now spark dread. The pace of change — AI, platforms, apps — feels less like opportunity and more like overload.
In a retirement-planning focus group I attended in Chicago years ago, several experienced IBM workers admitted candidly, “We just can’t keep up.” That honesty was liberating.
If your energy is better spent learning new hobbies than learning new log-ins, the signpost is clear: Your talents might be better directed elsewhere.
5. The bad-boss factor
The No. 1 reason people leave a job hasn’t changed in decades: the boss. If you’re still working hard but no longer respected, supported or inspired, the calculus shifts.
Think of it like a stop sign at a quiet intersection. You could roll through and keep going, but maybe that stop is telling you something important: Pause, reassess, and choose a different direction.
6. You’re stuck — but still have energy
Maybe you’ve advanced as far as you can in your organization. You might even be offered a retirement package. While others hesitate, you feel ready to pivot — consulting, freelancing, starting a business or pursuing something entirely new. You’ve “still got game.”
This isn’t about slowing down. It’s about recognizing that the road you’re on has ended, and it’s time to merge onto another.
7. A health event or family priority
A serious medical diagnosis — yours or your spouse’s — changes everything. Suddenly, what seemed urgent at work feels trivial compared with the urgency of time and health.
Maybe you’re called to care for a parent or partner — or even an adult child — and that priority overshadows everything else.
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These events are like flashing hazard lights: impossible to ignore, demanding a change of speed and focus.
8. A deepening sense of mortality
Sometimes the trigger is smaller: Your doctor finds a heart murmur during your annual wellness visit, or you’re reminded of your family’s medical history. You start to feel your own mortality more keenly.
Questions surface:
How do I want to be remembered?
What regrets do I still carry?
What gives me a sense of accomplishment?
These reflections can feel heavy, but they often bring clarity. Retirement becomes less about leaving a job and more about embracing a new stage of meaning and purpose.
A coaching exercise: Reconnecting with age 17
When I coach clients, I often ask them to look back to age 17. Remember when your whole life stretched ahead, and people told you the future was bright? Who were you then? What dreams inspired you? What activities seemed effortless?
Now ask yourself: Which dreams still matter? Which ones deserve a second chance? Retirement can be the time to pick up those threads and weave them into your next chapter.
False signals to avoid
Not every windfall is a true signpost.
If Aunt Sadie leaves you $100,000, it feels like a blessing. But in a 30-year retirement, it won’t carry you far.
A single event doesn’t equal readiness. True signposts are consistent signals that align your finances, relationships, health and priorities.
The bottom line
Retirement readiness is rarely a single destination; it’s a series of signs along the way. You might notice them gradually — like mile markers on a highway — or all at once, like an exit sign that suddenly appears after miles of driving.
The real skill is learning to pay attention. Once the signals are clear, you’re no longer asking, “Am I ready to retire?”
Instead, you’re reinventing yourself in retirement and asking, “Am I ready to live the next part of my journey with purpose?”
That’s the most important signpost of all.
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