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Boomerang Retirements

woman walking on beach with computer in foreground

Some agents just can’t quit the real estate business—and it’s not that uncommon

By Luanne Mandeville, CRS

I began retiring over 20 years ago. Actually, I retired and unretired four times.

Looking back at my real estate career that began in 1981, I see a consistent theme: I love real estate. Becoming a Certified Residential Specialist (CRS) in 1991 was one of the best things in my career. That opened a new world of professional education, networking and referral connections.

My first retirement in 2002 was a reorganization of parts of the business I enjoyed and parts I was eager to dismiss. My goal was to work about half as much and make about half as much income while still being able to resume business as usual if I chose.

What do I love to do? Prospecting, marketing, listing appointments, negotiating offers and placing referrals. What would I like to eliminate? Most buyers. Solutions were to co-list properties for sale, refer buyers to other agents or employ an assistant to handle escrow coordination, communication, inspections and follow-up. This was a critical time for me because I had moved out of state and needed to handle business in two locations. If there was an overwhelming “why,” it was to have more leisure time—more time with my family and friends in the present, without waiting for retirement.

My next retirement was in 2014 when it became more difficult to do business in California, so I decided to focus on real estate in Sun Valley, Idaho. I sent a letter to my clients: “As I celebrate my 35th year in real estate, I want to thank all of you who have chosen me to be your real estate agent. Your trust and confidence in me have been professionally rewarding and personally meaningful. The real estate relationships I have had over the years have been such a big part of my life, and I will always be grateful. After much deliberation, I have decided the time has come for me to retire from full-time real estate in Truckee and Lake Tahoe.”

Unretirement isn’t uncommon

Seven-time Super Bowl champion Tom Brady announced that he was planning to return to the game, but a 2023 retirement party his friends threw changed that. He said there were many factors to consider for a player to retire or stay retired. “You’re only allowed one unretirement, and I’ve used it up,” he joked. Skeptics are still not sure he is really retired. Clint Eastwood, now 90 years old, has retired several times. Frank Sinatra retired in 1971, only to return two years later and continue making music until the mid-1990s. Boxer Sugar Ray Leonard retired and unretired four times. Writer Stephen King retired in 2002, only to reemerge and write over a dozen books after that. English musician Ozzy Osbourne retired and came back to singing three years later. “Retirement sucked,” Osbourne said. “It wasn’t too long before I started getting antsy and writing songs again.”

retirement callout

But back to real estate, there are many reasons to go back to work: money, new financial goals, a sense of purpose, social interaction, boredom, not enough to do, fulfillment and more. Catherine Collinson, CEO of the nonprofit Transamerica Center for Retirement Studies, said: “Twenty years ago, the vision of retirement was that we would all stop working at age 65, have cake and punch, get a gold watch and never set our alarm clocks again. We’d play shuffleboard and wear aloha shirts.”

That is more myth than reality. Over 75% of Americans plan to work past a traditional retirement age. Massachusetts financial planner Catherine Valega pointed out, “Are you sure you have enough activities to keep your body, mind and spirituality occupied for the many years you have ahead of you?”

In a 2017 REALTOR® Magazine article, “Life After Real Estate,” Cindy Marchant said: “Learn to let go. It is very hard to be fully engaged in real estate, helping hundreds of people with one of the biggest purchases of their lives, and then just stop. For anyone who’s successful, simply paring back will probably never happen. We are a competitive breed, which makes it tough to slow down. There is life after real estate, and you can continue to receive the fruits of all of those years well into retirement if you have a plan.”

Is retirement right for you?

My Retirement Timeline

First retirement — 2002
Second retirement — 2014
Third retirement — 2020
Fourth retirement — 2022
Fifth retirement — ???

There are questions to ask to see if unretiring is right: Do I want to work? Do I need to work? Am I able to work? Returning to work may mean working part-time, working remotely or taking on a partner.

Skipping ahead to 2020, I retired again, utilizing the principles of Nick Krautter’s “The Golden Handoff: How to Buy and Sell a Real Estate Agent’s Business.” He has guidelines for agents to maximize their database and brand as legitimate assets that will keep paying them into the future. He says to watch for signs such as decreased interest in day-to-day real estate activities and longing for more free time. If income streams can cover expenses, it may be the time to retire, go part time or become a consultant. His method involves transferring your database to an agent who has the same values and will continue to care for your former clients on a schedule of decreasing referral fees over three years. Both the retiring agent and the adopting agent have specific duties to ensure the success of the transition.

My attachment to the business led me to prospecting for buyers and sellers again and opening up new referral channels. But on the eve of my 75th birthday, I asked myself why I was doing this. I had enough money. I didn’t need to lie awake at night worrying about a transaction and always having my phone with me. So, I transferred my new prospects to trustworthy agents and retired again for the third time.

My company, Mountain Realty Destinations LLC, specializes in linking buyers and sellers with top professional agents in all locations. I realized that my years of experience in resort and second home markets provided me with extensive contacts. My day-to-day involvement in real estate is now limited, but I have created the mechanism to “keep my foot in the door” and satisfy the real estate commission’s requirement of being actively licensed. Will I retire a fifth time? Stay tuned …

Plan your future with the RRC recording, Retiring? What’s My Business Worth, hosted by CRS Certified Instructor Dale Carlton at CRS.com/education/education-catalog.

Photo: Getty Images/SimonSkafar