Retirement Dating 2.0: Before You Jump, Test the Waters

An older man relaxes on the beach with a tablet. — (Image credit: Getty Images)

One of my favorite concepts for those approaching retirement or newly retired is retirement dating. I wrote about in my article For a Happy Retirement, Try ‘Retirement Dating’ First and thought it could use a refresh, hence the 2.0 in the headline. As I’ve described this little concept to clients, it has seemingly grown in how many areas of your life it touches and even to whom it is applicable.

Original concept of retirement dating

The original concept of retirement dating is as follows. Many people are so caught up in the here and now, they haven’t given real thought to what the retirement lifestyle looks like. I often see this when it comes to where people want to live in retirement. They wake up one day and say, “Time to retire. Let’s move somewhere warm.”

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Then they head to Florida and buy a place. Next thing you know, they wake up and realize they don’t want to spend their entire retirement in Florida, or sometimes they find they bought in the wrong place, as that area is not “them.”

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This is where my advice is to retirement-date. Start a few years away from retirement and visit different warm climates you think you’ll like. Test the waters and make this your purposeful vacation leading up to retirement. Try the East Coast or West Coast. Try cities and mountains. Try beaches and lakes.

Also, as you start to narrow your ideal location down, maybe try renting a house for a few weeks and get a sense of what it would be like to live there and do so in different seasons.

Basically, retirement-date often and everywhere is my advice. Then you can really start to narrow things down and not waste time when your retirement comes making wrong decisions. Plus, you have the added benefit of making this a fun way to travel as your retirement date approaches.

2.0 refresh

Now, I’ve been giving this advice for years, and people seem to really like it. I find people make it a little hobby of theirs, and often they come back, telling me their likes and dislikes of different areas. Essentially, I’ve found this concept has been so successful that I have two more great practical ways to retirement-date.

Refresh one: The first way to expand this concept is outside of simply where you want to live. I have plenty of clients who are so busy with their lives, work and families they haven’t had a chance to explore retirement lifestyles or hobbies. All they know is someday they’ll stop working, and that is it. They don’t know what they are going to do with their days, they just know it won’t be working. This is a great instance to use retirement dating.

My advice: Start trying hobbies. Coach a sport, take up photography, learn how to paint, play an instrument, start going on hikes, join a club, volunteer or do whatever you think you might enjoy. Remember, you are soon going to have a lot more free time to pursue your passions. The issue I often see is people don’t know their passions. This, to me, is a great use of low-stakes dating. If you take a photography course and halfway through, you realize it isn’t for you, quit and try something else.

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To me, this form of retirement dating has two great, practical benefits. First, you get to figure out the things you’ll enjoy in retirement to make it as fruitful as possible. Second, and likely more important, you’ll start to really get excited about this next chapter and have the wonderful benefit of retiring to something, not from something.

Refresh two: The second way to expand this concept is to start much younger. For instance, I look at myself and my wife. We are in our 40s and still have three kids who are 11 or under at home, so retirement is far away. That said, I am slowly introducing this concept to my wife.

The other day, we were having a nice discussion about how happy the change in weather has made us. We realized the warmer weather makes us more active, healthy and happier.

Next, we started discussing how when we retire, we really have no need to experience cold anymore, which was great that we are aligned on this.

Then we went on to have a nice discussion about how we will likely be snowbirds in retirement. Ideally, keep a place up here and a place down South, possibly Florida. I then told her when we go visit my mom each year, who currently snowbirds in Florida, we should check out other areas nearby to get a flavor of what speaks to “us.”

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We both loved this idea and are going to start to embed it into our lifestyle. It will be a fun project over the next bunch of years, and most important, when we do eventually retire, we won’t waste any time making the wrong decision, as we’ll have spent all this time dating our retirement.

Happy anniversary

It feels fitting that I am writing a dating article on my 13th wedding anniversary with my beautiful wife. I hope you and your loved one can take some of this advice and help optimize your golden years.

As always, stay wealthy, healthy and happy.

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In March 2010, Andrew Rosen joined Diversified, bringing with him nine years of financial industry experience. As a financial planner, Andrew forges lifelong relationships with clients, coaching them through all stages of life. He has obtained his Series 6, 7 and 63, along with property/casualty and health/life insurance licenses. Andrew consistently delivers high-level, concierge service to all clients.