When Is the Right Time to Retire?
The Most Important Retirement Question Isn't "Can I Afford It?"
For decades, retirement planning has revolved around a number. "How much do I need?" "What's my retirement income target?" "Will my portfolio last?" These are important questions. But they may not be the most important ones.
At Advice First Wealth, we've learned that many people spend years preparing financially for retirement but very little time preparing personally for retirement. In fact, some retirees discover that walking away from their career creates challenges they never anticipated. They have enough money to stop working, but they haven't figured out what they're retiring to.
As lifestyle financial planning pioneer Paul Armson often reminds us, life is not a rehearsal. The goal isn't simply to accumulate enough money. The goal is to use your money to live your best life while you still have the health, energy, and opportunity to enjoy it.
So perhaps the better question is: When is the right time to retire?
Retirement Is Not an Age. It's a Transition.
Many people still think of retirement as a date on a calendar. Age 60. Age 65. Age 70.
Mitch Anthony, author of The New Retirementality, challenges this thinking. He argues that retirement should not be defined by a specific age. Instead, it should be defined by readiness, purpose, and the desire to move into a new chapter of life.
The old retirement model was simple: Work hard. Stop working. Relax indefinitely. But that model no longer fits how most people live.
Today, many retirees continue consulting, volunteering, mentoring, caring for grandchildren, serving their communities, or even launching new businesses. They may stop working for a paycheck, but they don't stop contributing.
At Advice First, we often say, Retirement is not about stopping. It is about choosing.
Choosing how you spend your time. Choosing who you spend it with. Choosing work because you want to, not because you have to.
Five Signs You May Be Ready to Retire
1. You Know You Have "Enough"
Paul Armson's famous question is simple: "Enough for what?"
Many people continue working because they don't know whether they're financially secure. Others continue because they're afraid of the unknown.
Through proper financial planning and cash flow modelling, you can answer questions such as:
Can I retire now?
Will my money last?
Can I spend more?
Can I help my children?
Can I travel?
Can I survive market downturns?
Confidence comes from clarity and contentment. When you know what "enough" looks like for your lifestyle, retirement becomes a choice rather than a gamble.
2. You're More Excited About the Next Chapter Than the Current One
Retirement works best when people are moving toward something rather than running away from something. Think about people you know who have retired well. What do they have in common?
In our Retirement Coaching process, clients often identify characteristics such as:
Strong social connections
Meaningful hobbies
Volunteer involvement
Physical activity
Purpose-driven pursuits
Ongoing learning
Family relationships
Community engagement
Conversely, people who struggle in retirement often experience boredom, loss of identity, isolation, or a lack of structure. The question isn't just, "What will I stop doing?". It's also, "What will I start doing?"
3. Your Work No Longer Gives You the Energy It Once Did
Mitch Anthony asks a powerful question: "What is the expiration date on your intellectual, relational, and experiential capital?" Some people love their work right up until their final day. Others notice that enthusiasm has been replaced by fatigue. Perhaps you're:
Less curious
Less energized
Less challenged
Less patient
More interested in other pursuits
That doesn't mean you need to retire tomorrow. But it may mean it's time to start imagining what's next.
4. You Have a Vision for Your Time
One of the exercises we regularly do with clients is asking them to describe a perfect week in retirement. Not a vacation. A regular Tuesday. What would you do? Who would you spend time with? What would give your day meaning?
Mitch Anthony's work shows that the happiest retirees tend to maintain balance across four areas:
Leisure
Connection
Renewal
Engagement (purpose and contribution)
If your retirement plan consists only of golf, travel, and sleeping in, you may be surprised how quickly those activities lose their novelty. Retirees have regularly shared that there is a diminishing return on leisure. A fulfilling retirement needs structure, relationships, and purpose.
5. You Have the Health to Enjoy It
This may be the most overlooked factor. Many people delay retirement for "just one more year."
Then another year. And another. Sometimes that works out beautifully. Sometimes life has other plans. Paul Armson often speaks about how personal loss shaped his understanding of financial planning and led him to realize that life is precious and finite. His message is simple:
Life is not a rehearsal.
At Advice First, we've witnessed clients who retired early enough to travel, hike, play sports, volunteer, and enjoy grandchildren. We've also seen people delay so long that health challenges dramatically limited their options. The goal is not to retire as early as possible. The goal is to retire while you can still fully enjoy the life you've worked so hard to build.
A Better Question
Perhaps the real retirement question isn’t, “When should I retire?". Perhaps it's, "When will I have enough money to sleep well at night and enough purpose to get up in the morning?". Mitch Anthony captures it beautifully:
We need enough money to sleep at night, but enough purpose to get up in the morning. When both sides of that equation are in place, the timing often becomes much clearer.
The Advice First Conversation
At Advice First Wealth, we believe retirement planning should focus on more than investments and income projections. Yes, we want to ensure your financial plan supports your lifestyle.
But we also want to help you answer questions such as:
What are you retiring to?
How will you spend your time?
What gives your life meaning?
Who matters most?
What experiences still need to be lived?
What does "enough" look like for you?
Because retirement is not simply about reaching a number. It's about creating a life worth retiring into. And after all, life is not a rehearsal.
If you're within five years of retirement, let's have a conversation about both sides of the equation: having enough money to sleep at night and enough purpose to get up in the morning.
