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A Love Letter to Boomers: Crushing It In the Gig Economy


Since I keynoted an AARP event this week (shout out to Houston!), I’ve been thinking a lot about the Baby Boomer generation lately.  How much underutilized skill and personality lays wasted because new technology may be overwhelming, or the (mistaken) opinion that “only Millennials that use that stuff.”  So, here is my love letter to folks over 52, because I want more Boomers crushing it in the gig economy…and loving it, too.

By now, you’re probably pretty hip to the gig economy.  Perhaps you use Uber, order food from Grubhub, get deliveries through Postmates, have someone from Rover walk your dog, and rely on a Task Rabbit to organize your garage.  If not you, then someone you love uses these services. Really, it’s tough to avoid the gig economy these days.

Grubhub and other Gig Delivery Platforms
Apparently Using the Grubhub App to Not Talk to Anyone is a huge "Feature" for Millenial Users! Don’t worry; you can still talk and gig.

Many Boomers’ interest in gigging has grown in recent years, as the savings gap has widened and earlier retirements have left room for other pursuits.  The question anymore isn’t why get involved, the question is more often how.

Changing Your Perspective On Gigging

The biggest shift that needs to happen for Boomers to enter the gig economy isn’t a change in the way they do business–it’s a change in perspective.  No longer is there shame in a side hustle. It’s the new norm to bounce from one thing to the next, making money along the way. Most companies employ temp and contract workers in one way or another.

It’s no longer a “downgrade” if decide you want to drive Lyft for four hours a day–even though you used to be an IT administrator or school principal.  I’ve even heard stories of Silicon Valley CEOs picking up gigs in order to be more in touch with the on-demand environment.

Gigging By The Numbers

Research has shown that 66% of Gen X and Boomers “prefer to work from home.”  In addition, labor economists have noted that the number of Americans moving for work has been cut in half as of late.  I recently heard about a Boomer woman in Florida, working as a VP and earning $300K, who was offered a promotion and a raise, but chose not to relocate because she shared custody of her kids.

It’s not just about “flexibility.”  People want to be there for their families, provide as much stability as possible, and be actively involved in their communities.  The work-life balance we’ve been hoping for for years has finally arrived. Good mental health, a happy home life, and excellence in your professional life are no longer mutually exclusive.

Of course, it’s not just about personal stability; it’s about financial security too.  According to USA Today, only 24% of Boomers are “confident that they will have enough savings to last throughout retirement (down from 36% in 2012).”  Some Boomers would happily work longer, but have gotten laid off before retirement age. Some have lost their jobs to robots and AI.  Some have gotten sick and needed to leave work for medical reasons. Unanticipated problems can cause people to drain their 401Ks. In these circumstances, working a side gig can be an imperative, not a choice.  Of course, there are others that choose to gig proactively…just in case of any of the above.

For 30 years, you were told that if you just worked harder in your job, you would be rewarded.  Has that been true? Probably not. You’re not alone if you feel like you got a raw deal. The rules have changed.  Fortunately, gigs don’t just offer increased financial security, but personal and professional development, as well.

Getting Started With Gigging

So, if you are ready to go, let’s figure out where to begin.

First thing’s first: download a handful of gig economy apps and start using them.  Browse the App Store and see what appeals to you. Start by taking Lyft rides, using Takl to get someone to assemble your new dresser, getting lunch delivered via Eat24, staying at an Airbnb.  The options are just about endless.

Next, pay attention to those people you met through the apps.  Was anyone special? Did somebody go above and beyond? Maybe you have other kinds of work for those “stars.”  Hiring someone for a one-time project might turn into a longer working relationship. Of course, there will be times when you’ve “wasted time” and it didn’t work out.  Those are valuable lessons too. The more you learn about how the gig economy works, the better prepared you’ll be to become a part of it.

Now, it’s time to take those lessons and apply them to yourself. Are you ready to get hired, again and again?  Go from app user to app worker. If one of the apps or platforms appealed to you and you felt like “I could do that!” then start there.

In addition to the in-app details to fill out, also make sure that your LinkedIn profile is full of details and completely filled out.  (People will look you up!)  Get a friend or family member to help you create a video about the kinds of services you can offer.  The better you can represent yourself and your skills, the more opportunities you’ll have.

Boomers Have The Upper Hand…If They’ll Just Take It

As a Boomer, you have a lot going for you that younger workers may not.  You’ve been around the block before. You show up early, you look professional, and you’re willing to go above and beyond.  You communicate seamlessly and put people at ease. You know how to build relationships and garner respect. You anticipate people’s needs and wants and understand the importance of repeat business.  You get that freedom and flexibility means you have to adapt to change–all the time. You know your strengths and weaknesses very well. You’re able to answer the question “Why choose you?”

The fact is, if you knew what Millennials do about technology (and were willing to experiment), you’d be wiping up the floor with them.  Why? Because you have more experience. Even being a great homemaker could make you an excellent AirBnB host…if you understand the tech.

But I can’t make you love technology.  So, take an afternoon, and sit down with your kids and grandkids and have them teach you how to do new things.

Gigging isn’t the final destination.  Use one app and a $15 an hour gig as a learning experience–a place to start.  Once you’ve gotten some practice and wins under your belt, you can make money teaching other Boomers how to be successful on those platforms.  Walk into your local SCORE office or Chamber of Commerce, or create a paid Meetup and show your contemporaries how you succeeded.

The technology of the gig economy is not hard, it just takes practice.  And there’s no time like the present to get in. Remember when texting scared you?  Now everyone texts. (The only thing different is the size of the font!) The same will be true of your newfound apps…as soon as you Boomers start crushing it in the gig economy.

Order The Gig Is Up on Amazon

1 thought on “A Love Letter to Boomers: Crushing It In the Gig Economy

  1. Hey, Olga!
    What a great letter. It gives hope to folks of a certain age. We are not done, and we have so much to offer. I call it wisdom, which lies beyond knowledge. We can obtain knowledge, as you said: Technology is something we can learn. Wisdom comes with age.
    I hope your letter inspires everyone to keep contributing, not just for money, but also to give back their wisdom and their gifts to make a better world.

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