Upticks: 5 Things to Sell Before You Retire
By Luke Sullivan on August 7, 2025
What should you sell before you retire—and why does it matter? From employer stock and rental properties to unused vehicles and old 401(k)s, Jake and Cory break down five key assets that could be dragging down your retirement plan. With practical examples, emotional insights, and a clear framework, they help you rethink what you’re holding onto and how selling strategically could simplify your retirement life.
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Read an overview of the conversation below
(1) Employer Stock: Diversify Before You Decumulate
One of the most important financial moves before retirement is selling concentrated employer stock. Many retirees hold large portions of their net worth in company shares, often due to emotional attachment or long tenure. But this can be risky.
Jake explains, “When you have a concentrated position and you’re entering retirement, that is a very risky way to go about living.” He emphasizes that holding 30–60% of your net worth in one stock can disrupt your entire financial plan. Cory Bittner adds, “If they were working with a fiduciary wealth advisor for retirement planning and that advisor recommended that they put 50% of their money in one stock, they’d probably think it was crazy.”
The emotional connection to employer stock often clouds judgment. Falcon recounts a client with over half his portfolio in one stock: “I was like, look, you need to trim this back. It’s done extremely well… If you want to leave a legacy to your kids and grandkids, this is a reason to trim it.” Diversifying before retirement helps reduce volatility and can better align your portfolio with income needs rather than growth speculation.
(2) Rental Properties: From Passive Income to Active Headaches
Rental properties are often seen as a reliable income stream in retirement, but they can quickly become burdensome. Maintenance costs, tenant issues, and unexpected repairs can turn a passive investment into a full-time job.
Cory shares a story: “Husband and wife owned three properties… They made the decision to sell their lake house… completely changed the trajectory of their financial plan.” The emotional attachment to properties can make selling difficult, but the financial relief and simplicity gained can be worth it.
Jake paints a vivid picture: “Envision you’re 68… everything is great… then boom, 12 o’clock at night, you get a call from your tenant. The toilet is overflowing with crap.” He warns that renters don’t cover taxes, insurance, or major repairs. “If your mortgage is $2,000 a month and you’re charging $2,000 a month for your rent, you’re still losing money.” Unless property management is your passion, selling potential headache-inducing rentals before retirement could free up time, reduce stress, and improve financial clarity.
(3) Unused Vehicles and Lifestyle Drains: Sell the Stuff, Keep the Memories
Retirement is a time to simplify, and that can include letting go of unused vehicles, toys, and lifestyle assets that no longer serve you. Boats, RVs, jet skis, and extra cars often sit idle, and can drain resources.
Jake says, “Don’t confuse selling the item with selling the memory.” He encourages retirees to document memories through photos and stories, rather than clinging to depreciating assets. Cory agrees, “That’s really good… selling something isn’t just losing it, you’re repositioning yourself for the future.”
RVs, in particular, are a common retirement purchase. Falcon notes, “They’re very expensive… I’ve got clients that have used the heck out of them and loved it… but others didn’t use them as much and lost money.” His take: rent before you buy, and be honest about your lifestyle. Selling unused lifestyle assets could declutter your finances and your home, allowing you to focus more on experiences rather than possessions.
(4) Old 401(k)s: Consolidate for Clarity
Many retirees enter their golden years with multiple old 401(k)s and scattered investment accounts. These can be inefficient, costly, and confusing to manage.
Cory explains, “Selling an old 401(k)… maybe people have limited investment options, expensive costs… keeping it there for the sake of comfort can complicate financial planning.” Jake adds, “It’s extremely inefficient to have four 401(k)s out there floating around… and nobody’s watching it.”
Consolidation can simplify estate planning and make it easier to manage required minimum distributions. Jake emphasizes, “Most retirees… don’t want to track down old 401(k)s when they’re retired. They want to talk about their grandkids, their travel, their golf game.” Whether you roll them into a single account or cash out smaller ones, cleaning up your investment landscape before retirement can help align your assets with your goals and reduces future headaches.
(5) Small Business Stakes and Timeshares: Exit Complexity, Enter Simplicity
Owning a small business, partnership stake, or timeshare can add complexity and liability to your retirement. While these assets may have served you well during your working years, they can become distractions later on.
Jake cautions, “Do you want to be tied to this small business instead of being able to travel?” He recommends having an exit plan and considering tax implications. Cory adds, “We want to sell complexity and buy clarity and simplicity in retirement.”
Timeshares, in particular, rarely work out as planned. Jake notes, “Very rarely have I seen them work out for clients… maybe a handful are getting the max benefit.” Selling these assets can help you focus on what truly matters—your time and freedom.
Whether it’s a commercial building, private equity, or a vacation property, simplifying your holdings before retirement can help you enjoy the next chapter without unnecessary burdens.
Thank you for tuning in, we hope you have a great week!
