We’ve all heard of that adventurous couple who plans to retire, buy an RV, and travel around the country. Or that couple who bought a sail boat and plans on living in the Caribbean for the rest of their days. Or the individual who decides to buy a cabin in the woods or a farm and live in the countryside.

…And then they’re miserable.

Sure, some people are cut out for a nomadic lifestyle or a secluded life in the country, but many people simply are not. It is possible that you are the kind of person who is highly adaptable and can readjust from living in a 2,500 square foot home to living in a 400 square foot RV, but you would be the exception, not the rule.

To give a less extreme example, some retirees decide that they would like to permanently move to another part of the country. Then, when they get there, they realize that it’s not quite what they expected. For instance, you might have the idea that you’ll move to Florida…but have you been there year round? Are you tolerant of muggy weather in the summer and buckets of rain during the fall (hurricane season)?

And what about family? Are you willing to live on the other side of the country and only see your children and grandchildren once or twice a year?

Deciding where to land after retirement is an enormous decision and shouldn’t be taken lightly. To help guide you in your decision-making, I’ve outlined four pieces of advice:

1. Reflect on what makes you happy

Do you enjoy hiking in the mountains? Getting together with friends or family? Swimming? All of these interests can factor into your retirement decisions.

2. Ask yourself “big questions” to help guide your retirement decision. For example:

  • Do you prefer rural, suburban, or city life?
  • How important is regular internet access to you?
  • How important is it to have regular access to healthcare?
  • How often would you like to see your friends? Family?
  • Are you more social or solitary?
  • Do you take part in (and enjoy) community activities?

3. From a financial standpoint, assess your ability to “take a gamble”

If you’d like to try living in another part of the country or living in an RV or boat, can you easily return to your “old life” if the experiment flops? Or will you be in financial ruin? Be sure to talk to your financial advisor before making any radical leaps.

4. Try out your new lifestyle

If you are considering moving to a new place, see if there is a way for you to try it out. Stay at a long-term Air BnB or rent an apartment. Try staying for a full year in order to get a feel for all four seasons.


Retirement should be a happy time—a time to live a free life without having to worry about financial stressors. Deciding where to land is a major part of the retirement journey. Don’t take the decision lightly! Weigh your options; discuss potential retirement paths with a financial advisor; and make an effort to try out your potential new lifestyle.

I’d like to help you with your decision. Please get in touch today.

17 thoughts on “Retirement: Deciding where to land

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