As retirement approaches, most conversations tend to center around numbers—How much is enough? When can I retire? Will my money last?
In our recent By Your Side Chat, I sat down with our managing partner Tony Slezak to explore a different side of retirement: the human side. As Tony prepares to retire at the end of this year—on his own terms—he offered a candid look at the emotional, behavioral, and practical realities of making the transition.
The “Magic Number” Isn’t What You Think
One of the most common questions people ask is: What’s my number?
Tony’s answer may surprise you. “Your ability to retire has less to do with the amount of money you have, and more to do with the lifestyle you created prior.”
He shared a powerful example from his own experience. On the same day, he met with two retirees:
One couple lived comfortably on Social Security alone, choosing not to touch their savings.
Another individual, with significantly higher income sources, wasn’t sure he could retire at all—because he didn’t understand his expenses.
The takeaway? Retirement readiness isn’t defined by a single dollar figure. It’s defined by clarity—specifically, understanding your lifestyle and spending.
Start with Your Timeline, Not Your Balance
Rather than chasing a specific savings goal, the planning process should begin with a more personal question:
When do you want to retire?
From there, financial planning becomes a process of working backward—aligning income sources, savings strategies, and investment plans to support that vision.
For Tony, that meant adjusting his own timeline. Originally planning to retire at 65, he ultimately chose age 63.
“You’ll know when you know.” What once sounded like a vague answer he would regularly hear from clients over the years became very real. It's hard to understand until you get there.
The Retirement Readiness Checklist
To help bring structure to the process, our team has developed a Retirement Readiness Checklist—designed to guide clients years before retirement, not just months.
Key areas include:
Income planning (including Social Security timing)
Expense awareness and budgeting
Tax strategies and withdrawal sequencing
Investment alignment
Healthcare and insurance considerations
One critical planning component is bridging the gap to Social Security or Medicare—especially for those retiring early. These are the types of details that, if addressed proactively, can help avoid costly surprises.
Needs vs. Wants: A Simple but Powerful Framework
As Tony evaluated his own readiness, he leaned on a foundational concept:
Needs: Essential expenses required to maintain your lifestyle
Wants: Discretionary spending that enhances your retirement experience
By simplifying his finances this way, Tony realized something important: “Social Security could cover our needs. What I was working for beyond that was the wants.
This clarity made the decision to retire feel more tangible—and more achievable.
The Reality of Healthcare Costs
While many aspects of retirement planning can feel theoretical, healthcare is anything but.
For Tony, it represents the single largest expense before age 65 with over $2,000 per month in premiums, significant deductibles and out-of-pocket costs and limited flexibility due to income-based pricing structures.
It’s a reminder that healthcare planning isn’t optional—it’s central to any retirement decision, particularly for early retirees.
The Emotional Side of Retirement
Beyond the numbers, one of the most profound challenges Tony identified was psychological:
“The biggest question for me is—where do I belong?”
After decades of structure, purpose, and routine, retirement introduces a new kind of freedom—but also uncertainty.
What replaces your daily routine?
How do you redefine purpose?
Where do you find fulfillment?
For Tony, the answer lies in intentional planning—building a new rhythm that includes hobbies, family time, and personal interests.
Retirement Is a Shared Decision
Another key theme: retirement doesn’t happen in isolation.
Tony and his wife began having deeper conversations about what this next phase of life would look like together—how they would spend their time, balance independence, and align expectations.
Those discussions, while sometimes lighthearted, were essential in creating a shared vision for retirement.
The One-Year Transition Period
One of the most insightful takeaways from Tony’s experience is what he calls the “one-year process.”
In the year leading up to—and following—retirement, it’s completely normal to feel:
Uncertainty
Anxiety
A need for reassurance
Even for someone with decades of financial expertise, the shift from earning a paycheck to relying on savings introduces a psychological hurdle.
“You still have to take that leap of faith."
And that leap feels different—no matter how well-prepared you are.
Final Thoughts
Tony’s journey reinforces an important truth: retirement is as much an emotional transition as it is a financial one.
Yes, planning matters. Numbers matter. Strategy matters.
But so do mindset, lifestyle, relationships, and purpose.
If you’re approaching retirement, the goal isn’t just to reach a number—it’s to build a plan that supports the life you actually want to live.
Start the Conversation
If you’re beginning to think about retirement—or even just starting to wonder what your timeline might look like—this is the time to start the conversation.
Our team works closely with clients to bring clarity to the decisions that matter most, from income planning and tax strategy to healthcare considerations and lifestyle alignment. Whether you’re five years out or simply exploring what’s possible, having a plan in place can make all the difference.
We invite you to contact our office to schedule a conversation and begin building your personalized retirement plan. You can also request a copy of our Retirement Planning Checklist and Guided Timeline, designed to help you organize your thoughts, identify key decisions, and take the next step with confidence.