Freelancing Through Our Golden Years

05/18/2016 02:19 pm ET Updated Dec 06, 2017

When my father turned 65, he traded in his wing-tips for golf shoes and didn't look back. His law firm gave him an "office for life," and from time-to-time he would have lunch in the City (what we in the SF Bay Area call San Francisco) with his cronies, then retire to his office for a nap before heading back over the Golden Gate to home. I don't believe he ever set foot in a courtroom again.

For many of us, particularly those of us who've more or less made our living from some business-related manifestation of our creative output, such a retirement simply isn't in the cards. For those of us that can retire in relative financial comfort, it might be an opportunity to finally create what we want to create, whether it's writing, music, theater or some form of the visual arts. Even if we don't become the creative rock stars we think we might've become had we not "sold out," we'll get the satisfaction of "art for art's sake."

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For those of us that need to continue to generate some form of income until we're physically and/or mentally incapable of doing so, retiring from the eight-to-six office life (by choice or otherwise) may be akin to getting thrown in the ocean without a life preserver. Even for folks like myself, who made a go of freelancing early in their careers. Suffice to say things have changed.

Last summer I wrote a post about how Boomer's exiting the workforce can leverage their knowledge in written form, and perhaps make a little coin in the process. Since I've spent the better part of my post-corporate years (and several years early on) doing exactly that, I thought I might share what I've learned.

A Boomer's Freelancing Journey - Lessons Learned

First, if in the course of your career you've enjoyed the camaraderie and shared sense of purpose working on a team, you may find transitioning to lone wolf difficult. I know I did, and I honestly thought that I preferred to work alone. That's not to say that a team player can't become a lone wolf and love it, but it's still a big change. Even as a remote team member with colleagues spread around the world, I had the banter and support of others. When I was 100% freelance, I really missed those connections.

Another important consideration for would-be freelance creatives, writers and consultants: can you be a happy mercenary? A "free lance" originally referred to one whose weapon - the lance - would be employed by the highest bidder. If you've spent the bulk of your career in an environment where beating the competition is paramount, writing a blog for IBM and a blog for HP on the same day can be rather jarring. Of course some clients will ask for a non-compete agreement, which are generally not worth the paper they're written on for one-off, work-for-hire gigs. If you're lucky enough to get a long-term contract - a declaration of allegiance, of sorts - signing a non-compete for the duration of the contract is a small price to pay in return for the steady work.

When I retired from my corporate gig and returned to freelancing, I thought, "now I'll get to spend all my time doing what I love to do - writing." I had forgotten that freelancing, at least in the beginning, is far more marketing than writing. Aside from the cold hard cash required to build and host my online portfolio, I learned that I should have been prepared for a much longer, drier spell than I anticipated. Of course there's a plethora of online advice, from DIY marketing to paid services, which promise to bring the gigs in faster. Just keep in mind that there's an entire online industry devoted to "servicing" freelancers. Proceed with caution.

I guess the biggest shock of all was the stark realization that globalization has effectively gutted the economics of the freelance writing business. Imagine my surprise when I came across want ads for native English speakers that paid as little as $.01 a word. Of course there are clients out there that understand the value of quality work and originality and will pay a fair price for it, but it may take a while to ferret them out.

We all know that, in this day and age, holding onto that full-time gig until you're 66 and walking out the door with a gold watch is a rarity, especially in the private sector. We've all heard stories about "vitality initiatives" that effectively cull the workforce and send those over 60 packing. We've also heard stories about our contemporaries hanging out a shingle. Still, regardless of your talent, your expertise, the depth of your portfolio and your pedigree, it can take a year or more to get a freelance writing business going. Then there's managing the ebb and flow of freelance work. If a steady income, regardless of the amount, is your goal, freelancing, at least at the one-off, work-for-hire level, may not be practical.

A Happy Medium

Fortunately there is a middle ground between the total freelance mercenary lifestyle and the full time office gig. I've found that a combination of long-term (six months or longer) contracts, coupled with a handful of freelance clients that are willing to be flexible with deadlines, is a good mix for the time being. (Like many Boomers, I have adult kids that aren't quite financially self-sufficient yet. Call it personal weakness, but I'm happy to keep working to help them get established in their careers.)

The contract provides the camaraderie, personal contact and team spirit that I've missed, while also keeping my verbal and interpersonal communications skills up to snuff. It also keeps me up-to-date with the latest technology, from video editing tools like Videolicious to collaborative management tools like Box and Trello. And though I can't say that any of my younger colleagues have directly solicited the advice of the old silver sage, there have been instances where my both my management and creative experience have been valued.

There are numerous consulting firms out there that specialize in providing contract creative resources to both private and public sector businesses. I'm working with Clarity Consultants, but have also been contacted by Mondo, The Creative Group, Creative Circle, The Alliance of Professionals and Consultants (APC) and others.

Meanwhile, while the freelance blogging gigs allow me to wax poetic on a veritable cornucopia of topics, it's not as fun as fiction writing. Nor does it exactly leverage my investment in my MFA, but it's a good placeholder until all those bestsellers on my hard drive barnstorm the fiction market. Every blogging project is also a learning experience, which helps keep those synapses firing. And, as a contractor and a freelancer, I'm responsible for keeping track of my hours, invoicing, managing my 1099s, and all that. Fortunately there is no shortage of online tools to help manage the numbers.

Though I don't see myself retiring to the golf course and card room like my father did, I do hope there will come a time when the pressure to earn begins to ease up. That said, while I can't admit that I would love to keep doing this gig forever (and I doubt my clients would want me to), it's as good a port in the Boomer job storm as any, or at least until the next economic conflagration comes along.