How to transition into self-employment

By Jonathan Chevreau on July 18, 2014
Estimated reading time: 3 minutes

There are at least three ways to go when you decide to set up your own shop

This is one in a series of posts I intend to write on the mass migration of almost-retired baby boomers moving from large corporations to free agency.

I recently attended a full-day workshop on this topic put on by Mark Venning of ChangeRangers.com. Venning knows well of what he speaks: He has spent more than a decade and a half working with mature (55+) clients who have migrated from corporate employment to self-employment. A big part of his perspective is extended life expectancy and longevity: he prepares clients to continue working at some level well into their 60s, 70s and even 80s. The slogan on his business card and website is Envision the Promise of Longevity.

Claiming your place at the fire

As I’ve said before, 40 years is a long time to go without a paycheque, which is how long someone leaving the paid workforce might have to plan for if they leave paid employment in their early 60s. Add the type of extended longevity that Venning and others envisage (I’m thinking of Lee Anne Davies and her Agenomics blog, or Moses Znaimer of Zoomer Media), and “retired” boomers need to start preparing for this next great stage of their lives. There are of course many books on this topic: we looked at one last week and another I’m currently reading on my Kindle is Claiming Your Place at the Fire: Living the Second Half of Your Life on Purpose.

Leaving the corporate womb

But back to Mark Venning and Change Rangers. I can’t possibly summarize his content in a short blog but suffice it to say that in this economy there are many talented people who are either voluntarily or involuntarily being motivated to consider alternatives to employment in large corporations. One is self-employment, an option that “more and more people 50+ are exploring,” he says.

Compared to 50 years ago, these mature people are in better physical condition, so can expect an extended lifetime. “They’re living longer than they typically used to so they have to plan for a longer period of time,” he told me in an interview, “This is why the word ‘retirement’ doesn’t work for me. It’s about longevity planning. My core message is plan for your longevity, not for retirement.”

A portfolio career

As I see it, there are at least three ways to go when you decide to set up your own shop. One, you may see this as an opportunity to test out clients (and them you) with a view to possible full-time re-employment down the road. Second, you may decide a “portfolio career” is a more attractive route at this stage of life: when you think about it, a single “job” means just a single client, which is less secure than having several clients. And of course, you don’t have a traditional “boss,” although being your own boss has challenges of its own. And third, while many choose to start such enterprises tentatively as a one-person shop working from a home office, there’s always the possibility of growing the enterprise down the road so that one day you are an employer, rather than an employee. And that in turn offers the potential to sell a business.

Free Agent Nation and other books

This doesn’t even begin to scratch the surface but for now, I’ll leave you with a few book suggestions from a list Venning hands out. One I just read on the Kindle is Dan Pink’s Free Agent Nation: The Future of Working for Yourself. Another I’ve just begun is Peter Block’s Flawless Consulting: a Guide to Getting Your Expertise Used. And a third I’ve put on hold at the library is Alan Weiss’s Value-Based Fees: How to Charge and Get What You’re Worth.

About Jonathan Chevreau

As MoneySense’s Investing-Editor-at-Large, he is also author of Findependence Day and co-author of Victory Lap Retirement. Reach him at [email protected], where he is the founder of Financial Independence Hub.