Karen O'Connor enjoying life.

Karen O’Connor lives light. Fourteen years ago, when she retired at 52 from her career at IBM, she sold everything she owned and went off sailing with her second husband. “We wanted to really see the world,” she says, “so we’d sail maybe 30 miles, then stop at the next town; we traced the coasts of Mexico, Central America, the Eastern Seaboard, the Caribbean, and the Mediterranean.”

After eight years on their 50-foot ketch, they sold the boat in Spain “Then,” Karen says, chuckling, “I got divorced.” And she stayed possession-free: “I rent completely furnished apartments—including dishes and linens.” That’s so she can get in and out of town fast. She’s been pursuing her keep-on-moving-to-another-city dream ever since her sailing days. Wherever she settles (briefly), she expects to make friends fast. Here’s how she does it. —Ed. 

My post-retirement life-change was a rather dramatic transition from a 30-year career at one company to the sailing life. When I chose that life, I knew nothing about sailing, and I still don’t. I was the galley slave and did watches; my husband was an accomplished sailor and could sail the boat himself. I knew enough that if he fell overboard and died, I could get the boat to shore. I knew how to turn the engine on.

When that phase ended, I wanted to continue traveling. Since all I owned was my clothes and a few other personal possessions, I had a lot of flexibility. So I made up my mind to move to anyplace in the United States that interested me and that I had never lived in before. I would be there for at least a year, no more than two. That would force me to be a resident, not a tourist; it would mean I’d need to get involved in the community and make local friends; that I would have ample time to really explore and understand the community, rather than just hitting the tourist highlights.

So I tried it. I rented a completely furnished house in a community near Austin, Texas—and found I liked living there so much that I couldn’t leave in a year, or even two; I stayed nearly three. Then I followed my plan and moved to New York, renting a furnished apartment in Manhattan. I’ve stayed here nearly two years, so now it’s time to move on—in May—to my next destination, San Diego.

I am certainly not proposing my lifestyle for others. My life—during my career (which required many moves) and since retirement—has given me a lot of experience in making transitions and meeting people in a variety of circumstances. Here are my suggestions for figuring out what you are going to do with yourself, and how to make new friends, after a major life transition . . . whether you’re moving to a new place, retiring, losing your spouse/partner, or whatever else has dramatic impact of you.

What pleases you?
Do you like to sing, samba, sail, do Zumba, hike? Are you looking to meet other thoughtful, articulate book mavens? Do you own a small business? like rock-climbing? do artful digital photography? play poker? Are you an environmentalist? Meetup.com, a free Internet site, lists shared-interest-group meetings all over the country. (There are 3,362 of them in and around New York City alone.) You can search for these gatherings by city or Zip Code.

This group of friends, who met in The Transition Network's San Francisco chapter, go hiking in the hills near Berkeley.

Meetup has been an invaluable help in getting me connected in a new city. I’m reluctant to go to the gatherings that are held in a stranger’s home, but many groups meet in public places. I’ve joined hiking groups and explore-the-city groups that met in public spots. Fitness groups meet in parks, book clubs meet in libraries; movie groups meet at the movies and then go to a restaurant afterward for a meal and discussion, When you have a spare moment, why not check Meetup out? The “Drinking Skeptically” or “Pomeranian” or “Witches” Meetup Groups may not be for you (or they may!), but—as I did—you might actually find something you want to do.

The Web has guided me to lively groups full of savvy, likeminded people—potential friends. I suggest using phrases like “professional women’s groups in . . .” or “weekend hiking groups in . . .” That kind of search turned up, for me, The Transition Network. (I can’t remember what search term got me there.) This nonprofit organization was founded expressly to kindle professional women “50 and forward” into continuing their lives of learning, engagement, and leadership in the world—that is, to finding new passions and new friendships in the second half of life.

If you live in a city that has a TTN chapter (11 cities do, with more in formation), I most definitely recommend that you check the organization out—I sincerely believe that TTN has something to offer you, no matter what you may be looking for. I joined the flagship New York City chapter, whose 500-plus members are organized into more than 60 peer groups that hold intimate monthly gatherings.  If there isn’t a chapter in your city, you might want to contact the national organization at the link above to see if there are other women in your city who are interested, and then you can work with these women to start a chapter.

Volunteer work really makes you a part of the community. I happen to be addicted to reading, and libraries have played an important part in my life, so I tend to look for opportunities in libraries everywhere I go.  But I also pursue other opportunities—and there are plenty: museums, schools, hospitals, senior centers, zoos, parks. You can even find short-term volunteer jobs.  For example, I have volunteered at the New York City Marathon for the last two years.  Volunteering not only serves to give you something to do that you enjoy and to help you meet people with similar interests, it also is a nice way of giving to others.

Groups like New York Cares, New York City’s largest volunteer organization, can be an easy portal to volunteer work. Click on the link and find what the new “hot projects” are. There are all sorts of jobs—spontaneous, “I can do that tomorrow” work as well as short and long-term commitments. You may choose to spend an afternoon next week (say, spending a few hours helping Afghan women study for their naturalization exam, or helping kids play at a shelter); or short-term projects like helping sophomores study for their PSATs; or much longer projects. New York Cares works with 1,200 city organizations, schools, and libraries; 53,000 volunteers a year “give back” with New York Cares. There may be a similar organization where you live: Chicago has one (Chicago Cares), and so does Washington, D.C. (Hands On D.C. Cares).

In this, your fresh phase of life, try something new. I had never really ridden horses before I moved to Austin, so when I as there I took horseback riding lessons. Not only did I meet people at the ranch, but now I have another interest that I can pursue wherever I am.  If you’re a New Yorker, think about becoming a Big Apple Greeter. This is a wonderful way to meet other locals and tourists (who, in my experience, often become good friends who live in interesting places to visit!), and it lets you show off your knowledge of Manhattan. The Greeter website actually makes tourists this touching offer: “How can I spend time with a New Yorker?” Can you imagine that?

And two final bits of advice. First, while you’re working to identify activities and people you’d like to spend time with, get out there and do things you enjoy even if you have to do them by yourself. I can’t tell you how many movies I have gone to alone, how many hikes and walks I have done alone, exploring an area new to me, how many restaurants I have tried for lunch alone (although I do seem to have a problem trying restaurants alone for dinner), how many museums I have explored alone. In fact, I discovered that I really like exploring museums on my own; now I always make visits alone, in addition to trips with friends. To me these are two completely different experiences. These experiences have led me to appreciate that I enjoy doing things on my own in addition to doing things with friends.  So I make time in my life for both.

The second tip: See beneath the shell. In my first temporary hometown, Austin, people are extremely outgoing and know no strangers. If you stand in a line to checkout in the supermarket, you will be best friends with everyone in the line within 10 minutes. People in Manhattan are quite a bit more reserved . . . in fact, they rarely even make eye contact. I found this alarming at first.  However, I discovered that although they generally won’t make the first move, New Yorkers are extremely friendly once you have approached them. Now I end up talking at length with people on the bus just by saying “Good morning” to them, or admiring their outfit, or commenting on the weather. In most cases, they are astounded, but they’ll talk to you till they get off the bus.

Good luck!

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  • Hollis Wagenstein-Hurturk February 1, 2014 at 11:17 am

    Inspiring article, Karen! Great suggestions, too. I host three meetup groups and they have opened up my world tremendously. It seems like I have spent the last couple of decades pre-paring for the next phase of life (de-cumulating all the possessions that seemed so important when first acquired) to make it easier to travel and explore. I truly admire how you were able to leave all the “stuff” behind to focus on the joy of travel and experiences. As a New Yorker, I hope I’ll get to meet you before you move on!

  • Laura Crisafulli March 2, 2012 at 8:53 am

    I am just becoming acquainted with TTN.
    Your story is certainly inspirational for anyone who is *in transition*.
    Thank you.

  • Mary Hope Boynton February 28, 2012 at 12:08 am

    Hi Karen,

    Not everyone can do what you are doing. I find it very appealing, though it;s too late for me. I admire your fortitude in comitting to a plan for life and living it to the fullest. Enjoyed the times we were on hikes together in Texas. Mary Hope Boynton

  • RozWarren February 27, 2012 at 12:07 pm

    You’ve turned me on to some great resources, Karen. Thanks!