How’d I Ever Wind Up in the Gig Economy?

Welcome to the gig economy

I’m definitely not the brightest Baby Boomer I’ve ever met—for example, I never secured myself enough money to retire—but I have learned two things:

  • Things never turn out the way you expect.
  • Change is the only constant

I never imagined I’d be a father of young girls in my 60s, or that I’d have to be building a new career as others my age are winding theirs down.

Surprise! Unretirement

Like a lot of Baby Boomers, I expected money would just work itself out. Were we too optimistic? Too entitled? I didn’t have a normal salary until I was 40, and when I was laid off in 2013? Well, let’s just say I’m not retiring in this lifetime. Sound familiar?

I found that companies responded to my job applications with silence, even though I was a qualified and experienced technical writer. I’ve concluded my age was the issue. Through countless job applications, I’ve only gotten three callbacks! Again, familiar, Boomer buddies?

Eventually, at Doc’s urging, I applied for a full-time writing position at Upworthy, at the time a hot internet company. When they decided to bring me on as a freelancer, I was disappointed, but I was desperate enough to give it a go. During the year I worked for them, I put in much too much work for too little money, but felt that at least I had some, and I enjoyed being “internet famous,” as Doc puts it. I watched jealously as full-timers got health care, free computers and internet service, vacations, first crack at important work tools I had to wait in line for, company retreats and on and on. Eventually I left for another company—again as a freelancer—and then another and another and so on. Do companies even offer the security of full-time jobs to people our age? That was a trick question. The answer is generally no.

I’m still not even making half of what I made at the job I got laid off from. But I do seem to be growing my client base—putting far more energy into work now than I ever did when I was young.

Welcome to the Gig Economy

I felt like there was something wrong with me until about a year ago when I discover I’d simply landed in the “gig economy,” or the “on-demand economy” if you like. It’s apparently how Baby Boomers who can’t afford to retire work once full-time jobs are no longer open to us.

The gig economy is often hyped for the flexibility it offers its workers, but that’s just a nice way to say it affords them no security. It’s really all for the benefit of companies who gain access to experienced, reliable, highly motivated people without having to give them anything other than a per-piece fee. No healthcare, no unemployment insurance, no vacation, and no promise of continued work, even. Workers are stuck paying Schedule C taxes as if we’re running businesses when in fact we’re just workers without the benefit of a full-time job. We’re not entrepreneurs. We’re drones.

Forget Who You Thought You Were

And what I mentioned about accepting change? To survive, you basically have to tear down who you thought you were professionally, take an inventory of your raw skill set, and try to find a use for it. It’s also important to keep adding new skills all the time. If you enjoy learning new things and technology—as I do—the learning can be an invigorating, if exhausting, process.

I’d love to hear other Boomers’ thoughts about finding themselves marooned in the gig economy. It’s a weird way to survive, and going forward I plan to offer help in this blog for others out here on the bleeding edge with me.



9 thoughts on “How’d I Ever Wind Up in the Gig Economy?”

  1. I worked i various industries throughout my life.
    I have always been an avid reader and learned everything I could and took advantage of every course I could.
    In 1980 I started out working on aircraft in the Marines and can read all types of blueprints, hydrolic diagrams, pneumatic s, mechanics and have two years of Electronics Engineering.
    I was a Real Estate appraiser for ten years and a licensed builder as well as a property manager and re-modeler for 16 of my own properties.
    In 2010 I sent out over 3,000 resumes in three years and today still don’t have a job.
    I was told by a human resources manager that my age, my self employment, my time out of work, my physical problems, my ‘over qualification’, and other factors would guarantee my unemployment.
    I feel like if anything, I have proven I can do anything.
    Now companies want a 4 year college degree to work in an office filing papers !!!!

  2. I’ve been a part of the gig economy for a while, both as adjunct higher ed teacher (we constitute the majority of community college and university faculty now) and a remodeling contractor. I’m glad I do both so I don’t get tired of either. However, we are getting screwed. I am almost 60 with no retirement in sight. Everything you say about watching full timers get healthcare and all the other benefits rings so true. When enrollment was up, I taught five classes every semester. Some “full-timers” taught less. Now the enrollment is down, so I’m scrambling to get more remodeling contracts. I thank god I have two incomes; I see a lot of bleak looking adjuncts at my college.
    I also see the gig economy spawning a lot of lower quality work, just from the fly-by the-seat-of-the-pants mentality that comes with it.
    I’m glad some politicians are starting to talk about protections. We need them.

    1. Yep. Freelancing or contract work is nothing new, but the extent to which businesses are taking advantage now is stunning.
      I actually think companies often squeeze really good work out of gig-economy people since we feel like we always have to impress in order to get the next project. Personally, I go above and beyond all the time for this reason, as a result working for much less, really, than my hourly wage.

  3. Hey Boomer;
    Sure times are hard and the fat cats have screwed us. But in the face of any odds, planning and good choices make a difference. You say you ‘re not the smartest. For the sake of economy,that information did not need to be isolated or included. Let’s see: You didn’t plan financially for your future, but that didn’t stop you from finding a nice fertile female half your age and producing another mouth to feed. Way to go studmuffin.

    1. lol. First of all, you’re right about my not planning properly for my financial future. But Doc is 50, not half my age, and when we adopted our two girls we both had good jobs. Still, thank you for calling me “stud muffin.” That’s a first. 🙂

  4. Yes, for me the *gig economy* started in 2007. I had been working at one of the Big 10 Universities in IT, but when the economy caught a cold, the State got double pneumonia, and bronchitis (ie: without General Fund, there is no job)
    So, I had to keep food on the table and a Family to raise, so I began contracting, that is truly a scary prospect to someone who had never done it before. You learn about the *bench* very quickly, and that it really does not exist, once that client is done with your services, your contract house is done with you. Now started the brave new world of not even a W2 contract, but having to rely on 1099s (incorporation and getting a LLC is VERY expensive, not to mention all the paperwork and accounting involved)
    Self-employment tax, in addition to all the other regular taxes and benefits (if you can afford them) take what you thought was a great hourly, down to less than what you were making FTE. It’s not like you can simply raise your rate to take care of your expenses, you immediately price yourself out of competition, a huge catch-22.
    So nothing goes to savings, there are no dinners out to celebrate the great job, it’s all just work work work just to get by, you can forget retirement. Anytime spent waiting for the next gig to come in, absorbed and savings there may have been
    Still waiting for the pendulum to swing the other way, or is that just an axe?

    1. Dan,
      Wow, this sounds familiar. If I’m feeling (a little) more positive than you, it’s only because I’m trying very hard to. My life is racing by regardless of these difficulties, and after feeling like a loser for so long, I’m just doing everything I can to have a life anyway (by which I mean setraline). I’m also really thankful I have young kids who provide comic relief that’s otherwise hard to come by, and healthcare from my wife’s job.
      The tax thing especially is nuts. We’re just workers, not really companies. I’m hopeful the IRS makes a more sensible category for us, and soon. It’s hard out here.

  5. This is demoralizing to think you have come to a point in your life where your experience should be of value, but the overriding aspects in the view of employers is all about the youth, who can be paid less, have a lesser chance of becoming a burden to their group insurance and the possibility of the retirement age employee might have the mobility to actually retire. So one, like myself fins he is forced to retire with no hope of finding the employment that they need to continue in the lifestyle they are accustomed to, as frugal as it may be. Now rather than being able to sustain one’s life they worked for they are also forced to humble themselves to live with less by selling those comforts they worked for and restructure to an economic style one can hopefully sustain.

    1. All that’s true, sadly, though I’ve found that after a period of being angry and depressed about it, I’m just down to dealing with it. One hopeful sign is that some politicians are starting to talk about protections and more sensible tax rules for those of us working this way.

Leave a Reply

Your email address will not be published.