Upticks: Reasons to Retire in Your 50s (Before It’s Too Late)
By Luke Sullivan on August 14, 2025
Thinking about retiring in your 50s? Jake and Cory break down ways it could be the best decision for you. From burnout and health risks to purpose-driven living, they share real stories, practical strategies, and a five-question framework to help you make your early retirement decision.
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Read an overview of the conversation below
Reasons Many Work Beyond Their Passion
Many professionals in their 50s continue working not out of passion, but out of habit. As Cory notes, “Not everybody is super passionate about what it is that they do and their work… a lot of people do work out of habit.” This sentiment is echoed by Jake, who adds, “Between the two of us, Cory, we’ve got what, coming up on around 900 clients… I don’t have a lot of conversations where clients feel passionate about their work, sadly.” The reality is that while some may enjoy aspects of their job, few feel it aligns with their deeper purpose.
This habitual continuation of work often stems from fear—fear of the unknown, fear of losing identity, and fear of financial instability. Jake explains, “Many people in their fifties… are rich in money… but they’re bankrupt when it comes to time, energy and freedom.” The fear of stepping away from a familiar routine can be paralyzing, especially when one’s identity is closely tied to their professional role. Cory emphasizes, “We are creatures of habit and routine… and it’s very practical… to say, ‘Well, I’m not sure exactly what I would do if I stopped working.’”
Waiting Could Cost Health, Time, and Regret
Delaying retirement can come at a steep cost. While few retirees express regret for leaving the workforce early, many who wait too long could find themselves facing missed opportunities. Jake illustrates this with a vivid example: “You wanted to hike Mount Everest when you retired, but you worked until you’re 70 and your hips won’t let you hike.” The point is clear—health and energy are finite resources, and waiting too long can mean sacrificing the experiences that make retirement fulfilling to you.
Cory adds a sobering reminder: “Not everybody lives until they’re 90… I’ve worked with too many clients… that have passed away in their 60s and 70s.” The unpredictability of life underscores the importance of timing. Retiring in your 50s doesn’t mean stopping—it means starting a new chapter with purpose. As Jake puts it, “Retiring in your 50s… means you start really living.” The early years of retirement, often called the “go-go years,” are typically when individuals are healthiest and most financially secure. Extending these years can lead to a more fulfilling retirement.
Retiring to Something—Purpose and Personal Fulfillment
A successful early retirement hinges on having a clear vision of what comes next. Jake stresses, “You’re not leaving work and just doing nothing.” Whether it’s travel, hobbies, volunteering, or consulting, retirees need a purpose. Cory shares a story of a client who retired in his 50s and now enjoys traveling and family time, adding, “He’s happy and content… doing the things that he wants to do.”
Jake also recounts his mother’s retirement decision: “She was scared… she opened up a small shop… and she was so wrapped up in her work.” Her story highlights the importance of aligning retirement with personal interests. Couples, too, must navigate differing visions. “Everyone thinks… just because you’re married… you’re going to have the exact same vision for retirement, and you’re not,” Jake explains. Open communication and planning are important to help ensure both partners find fulfillment.
Another example is “Greg,” a client who retired young, moved to Florida, and began consulting. “He’s making way more money than he ever could have thought of… and he’s loving it,” Jake shares. These stories reinforce the idea that retirement should be intentional and aligned with personal goals.
Busting the Myth: You Don’t Have to Wait Until 65
The notion that retirement must wait until age 65 is outdated. Cory challenges this directly: “Why do you have to work until you reach some magic number?” These default ages—65 for Medicare, 62 for Social Security—are legacy constructs from the 20th century. Jake adds, “You’re not retiring early. You’re just not retiring late.”
Retirement should be based on individual circumstances, not societal norms. Comparing oneself to others—parents, coworkers, or friends—can be misleading. Cory emphasizes, “It does not matter what they all did… what really matters is your own situation.” The FIRE (Financial Independence, Retire Early) movement exemplifies this mindset. While extreme cases aim for retirement in their 30s or 40s, the underlying principle is planning and flexibility. Cory cautions, “Someone’s ability to live on two grand a month today might not be the same 10 years from now… think that through and plan for it.”
The Five Retirement Readiness Checkpoints
- Can you generate sustainable income from your assets?
“I don’t care if you have 1 million or 10 million,” Jake says. “What is that income stream going to look like for you?” - What’s your healthcare plan until Medicare kicks in at 65?
Cory explains, “Getting coverage for healthcare is not the barrier… planning for the expense is where people really need to be thoughtful.” - Do you have a tax strategy for early retirement?
Jake highlights tools like the Rule of 55 and 72T, noting, “You might not be able to access your retirement funds as easily as you think.” - What are you retiring to?
“You want to be social in retirement,” Jake says. “You might have to get new friends… and that’s hard for a lot of people.” - Do you have enough liquidity outside of retirement accounts?
“Build the brokerage,” Jake says. “This can be the ultimate flexibility, liquidity.”
Retiring in your 50s isn’t just possible—it might work for your plan. If you’re ready to explore your options, start with the five checkpoints and connect with us whenever you’re ready.
Thank you for tuning in, we hope you have a great week!