Dance me to your beauty with a burning violin. Dance me through the panic ’til I’m gathered safely in. Lift me like an olive branch and be my homeward dove. Dance me to the end of love.  –  Leonard Cohen

Our “Free at 55” Meetup has attracted a group of more than 100 lively, adventuresome and interesting people.   We’ve talked and learned about travel, collaborative housing, financing travel, life transitions, and – did I mention it? – travel.  Last month, a dozen of us braved sudden snowstorm to discuss one of our most popular topics:  “After I retire, what will I do for work?”

Like many of us near retirement age, we would have thought this question ludicrous a few years ago.  “What kind of retirement is that if I’m still working?”  But the financial sea change of the last decade led us to new realizations.  We started by coming to terms with the fact that our investments were not going to deliver the kind of sustainable income we’d built our plan around.  Working after “retirement” began to look like a requirement.  For some of us in the Meetup, a supplementary income might not be needed to keep us off cat food – but to finance the international travel experiences we had on our bucket lists, it was essential.

However, once we begin to accept the necessity of continuing to work well beyond 55 or even 65, we began to see it had many non-financial upsides.  Most of us can expect to live 20, 30, or even 40 years beyond that traditional retirement age.  For a good many of us, a career of some sort will be an essential part of our mental and social life, not to mention a sense of purpose that gets us up in the morning.  For those without financial constraints, volunteering, sports, and hobbies may fill the bill, but for the rest of us, why not do something that also tops up the pension.

So we brought together our dreams, plans, and experiences, as well as our favourite ideas from some of the preparation reading we’d done before the Meetup.  In this post and the next, I’ll offer a sampling of what we shared.

For most of us contemplating second-act careers, the most important advice was to envision your lifestyle, and let that vision drive your career planning.  How are you going to travel for several months out of every year, if you’re chained to a desk with three weeks off?  What many of us are looking for are “lifestyle careers” – determine a desired post-retirement lifestyle, and then find or create the career, business or job that is compatible with that life.

This takes work.  You need to toss out your assumptions about how life “is”, and take a fresh look at how you’d like it to be.  Where do you want to live?  Who do you want to hang out with?  How close do you want your kids, ageing parents, or other family?  How, when, where and how much do you want to travel?  How much are you willing to work?  What kind of daily rhythm suits you?  And how much is all this going to cost, … really?

Determining your post-retirement costs can be challenging, especially if you anticipate a lot of lifestyle changes:  downsizing, empty-nesting, collaborative householding, going rural or even overseas, changing priorities.  Many financial consultants have their own perspectives and agendas, and their well-meaning advice can only take you so far.  At some point, you’ll have to do some research and crunch some numbers:  basic budgeting, rent-buy calculations, cost-of-living differences in your planned new location, expected rates of return from investments or annuities.  Our Meetup participants reported success with two key approaches:  talk to retirees who are similar to you and ask them what they are spending – get a reality check!  And practice living on your post-retirement income – now.

Another key piece of the puzzle is what do you really like to do, that you are good at, and that people would pay you for?  For some of us, this has the feel of a second adolescence:  an identity crisis of growing into the “third age.”  We can fall prey to a belief that this “new me” has to be a complete break from the past.  However, the experience of some in our group and of others we read about suggests a different approach:  a repositioning of our lifetime of training and experience in the service of new dreams and goals.  Most likely that “second act” butterfly of a new career is hiding in the desiccating shell forming around the “first act” worm of the old one.

We discussed some ways to leverage our current work experience in the service of a new lifestyle and new goals.  Members shared their research and experience regarding consulting.  Aim for a narrow and well-defined niche;  don’t try to do it all.  Test it out with small companies or non-profits with better work-life balance.  Build off your existing networks.

Some of our group were investigating teaching options: at home, overseas, or online.  These days entire university curricula are being offered online.  Why not your expertise?  People are consulting and teaching skills online that only recently required personal instruction:  learning a language, a musical instrument, or even natural childbirth (as one of our Meetup members is already doing, while living part-time in Spain).  Personal and career coaching is now routinely delivered to international clients via skype and similar technologies.

Becoming a teacher may have other benefits as well.  Keeping your skills up might require some overseas study.  Many foreign universities offer inexpensive room and board to visiting students.  Why not go to Florence for a month – or a year – and study art?  Teaching also offers other potential opportunities to travel.  Besides teaching English as a second language, you might be able to teach a non-work related skill, such as swimming, fundraising, or even cooking.

In the second half of this post, we’ll share some other ideas that our members had about starting a new Internet or other business.  And talk a little about where this journey has taken us so far.  We’ll also explain what any of this has to do with Leonard Cohen’s dancing to the end of love, and include some more resources.

Meanwhile, here are a few to get you started.

• Second Act Careers, by Nancy Collamer (Blog: MyLifestyleCareer)
• 100 Great Second-Act Career Resources (also by Nancy Collamer)
• Your Money or Your Life, by Vicki Robin   (book summary)
• Making a Living without a Job, by Barbara J. Winter (Blog: Buon Viaggio)
• Do What you Love for the Rest of your Life, by Bob Griffiths (used, or library eBook)
• The 4-Hour Workweek, by Tim Ferriss
• Wishcraft, by Barbara Sher   Barbara Sher also created the Idea Party concept – look for an idea party in your area.

Here are a few that came up during our evening:

• CoolWorks.com – a job board for jobs in cool places
• ContrarianConsulting.com –  from the author of Alan Weiss on Consulting – A guided journey with “the rock star of consulting” and over 40 other books
• Two places to look for jobs in higher education:  The Chronicle of Higher Education, and HigherEdJobs.com

And, if you’re already dancing your second-act career, we’d love to see your comments on how you did it.

Till next week… dance me to …