Upticks: 6 Retirement Surprises After 6 Months
By Luke Sullivan on May 21, 2025
Retirement might be the goal—but what happens after you get there? Jake and Cory unpack six surprising truths that often surface in the first six months of retirement. From emotional curveballs to unexpected spending and shifting routines, they cover what most don’t tell you about life after the paycheck. Whether you’re nearing retirement or already there, this episode can help you prepare for what’s next—and make the most of it.
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Read an overview of the conversation below:
More Time Doesn’t Always Mean More Peace
One of the most surprising realizations for new retirees is that having more time doesn’t automatically lead to more peace or happiness. As Cory puts it, “The freedom that comes with having that much time can actually create emotional chaos without structure or purpose.” Many people assume retirement will be a blissful escape from the demands of work, but the sudden loss of routine can be unsettling.
Jake adds, “To have peace, you need to create peace. And I would argue you can create peace while you’re working. You don’t need retirement necessarily to create peace.” Retirees should consider identifying their core values and building a new sense of purpose around them. Jake shares his own process: “I wrote down a list of all of the words that aligned with my personal values… then I boiled it down to a phrase that’s easy for me to remember: to inspire others to live a happy and healthy life.”
Spending Often Exceeds Expectations
Another common surprise is how much more money retirees spend in the first six months than they had anticipated. Jake notes, “Some people actually find that they spend more than they had budgeted or more than they thought.” This is often due to increased free time, which leads to more opportunities to travel, shop, or take on home projects.
Cory agrees, adding, “I can look at my monthly credit card statement and see it’s literally on the weekends I’m spending more money because I’m not here talking with you and talking with clients.” Jake recommends building a cushion into the financial plan: “If a client tells me they need $10,000 a month, I might tell them let’s do $12,000.” He also encourages aligning spending with personal values and embracing “guilt-free spending” once essentials and savings goals are met.
The Calendar Gets Weird
Without the structure of a workweek, many retirees find their sense of time becomes disoriented. Cory describes it as “every day feels like Saturday at first,” but warns that this can quickly become disorienting. The lack of routine can lead to a loss of direction or even a sense of being overwhelmed.
Jake emphasizes the importance of time-blocking: “Go ahead and time block and put things on your calendar.” He also warns against becoming the default helper for family members simply because you’re retired: “You don’t want to be the default where people are like, well, Jake’s retired. He can go do all the stuff I don’t want to do.” Setting boundaries and proactively filling your calendar with meaningful activities can help maintain a sense of purpose and autonomy.
Relationships Are Missed More Than Expected
Even if you think you won’t miss your coworkers, chances are you’ll miss the relationships more than you anticipate. Jake explains, “You might like them more than you think… you’ve built a relationship with these people. And good or bad, I think a lot of our clients miss that when they leave.” The loss of daily social interaction can lead to feelings of isolation.
Cory encourages retirees to be proactive: “Be the person that builds that community if it doesn’t already exist.” Whether it’s a monthly lunch, a weekly golf game, or a regular walk with a friend, maintaining social connections is crucial. Jake adds, “Don’t just connect on social media… go and spend time with these people in person.” These relationships can be a vital source of emotional support and well-being in retirement.
Emotions Can Come in Waves
Retirement is a major life transition, and with it comes a wide range of emotions—some expected, others not. Cory notes, “People who choose retirement can find themselves asking, did I do the right thing? Did I make a mistake?” Jake emphasizes that these feelings are normal and temporary: “Recognize that whatever emotion you’re experiencing is temporary.”
He shares a helpful acronym for managing emotional waves: Separate, Embrace, and Evaluate (SEE). “Fully embrace whatever you’re feeling and don’t try to resist it,” he says. “Then evaluate what is my most productive next step.” Whether it’s joy, guilt, grief, or aimlessness, acknowledging and processing these emotions is important for a healthy transition into retirement.
The Spouse Dynamic Shifts
One of the most overlooked surprises is how retirement can affect the relationship with a spouse or partner. Jake explains, “You are not only impacting yourself by retiring, you are now impacting arguably the person you love most on this planet.” If one spouse is already retired or works from home, the sudden presence of the other can disrupt established routines.
Cory shares a real-life example of a couple navigating this shift: “He retired at the beginning of this year… she works 100% from home… it’s clearly an adjustment.” Jake acknowledges his 10 AM on a Tuesday test. “Ask, what do you normally do at 10:00 AM on Tuesdays?” He also stresses the importance of not judging your partner’s routine and being willing to seek help if needed. “If you and your loved one are quarreling… it’s okay, go seek help. There’s no shame in that.”
Retirement is full of surprises—some uplifting, others unexpectedly challenging. By anticipating these shifts and planning with intention, you can better navigate the transition. If you’re approaching retirement or already in it, now is a great time to reflect, realign, and help make sure your plan supports the life you truly want to live. And if you’re not sure where to start, don’t hesitate to reach out for guidance.
Thank you for tuning in, we hope you have a great week!
