Jane Genova
Jane Genova

During Fall 2020, marketing genius Don Draper from “Mad Men” and corporate public relations employee Tom Rath from “The Man in the Gray Flannel Suit” would be doing side hustles.

Given so much employment insecurity they would figure out that those gigs were a necessary hedge to prevent homelessness. Also, with all the longer hours and escalating pressure, they might decide to stock a war chest for a FIRE (Financial Independence, Retire Early). In addition, the revenue and confidence from those gigs would, in themselves, reduce worry.

Typical side hustles range from leasing out a room or several residential properties through Airbnb to launching an ecommerce enterprise. In sophisticated circles they are being called “multiple sources of income.”

Strictly speaking, that term—multiple sources of income—denotes all the ways in which human beings build, hold and scale wealth. The most common are day jobs/owner’s business, spouse’s earnings and investments. But, recently, that term has been poached by debt-burdened millennials to apply to how they are going about earning a living. That brings some status to a career path which involves the continual search for work. Deloitte studied the phenomenon of millennials and gig work.

Marketers and public relations representatives are in a position to gain from the pioneer efforts of the younger generation. The stigma associated with side jobs is lessening. There also is a cool about not being so traditionally bound to The Man for one’s livelihood. Employers and clients are less apt, if they find out about the side work, to assume a lack of commitment. They are aware of how dicey the economy is. There was a time when even owning a Kaplan franchise had been held against a corporate communications manager. Freelancing? That too presented a risk.

A sign of a changing work ethos, MarketWatch featured millennial Kevin Ha. He works as a lawyer full time in a large law firm. His wife also works. Simultaneously, he had 13 side hustles, bringing in an extra $2,000 to $3,000 monthly. They include food delivery, dog walking and returning scooters. The version of The Man at Ha’s day job is a system of Up-or-Out. Ha could be one performance review away from being out.

In the multiple sources of income model there are myriad options. No, marketers and public relations representatives do not have to be out there, like Ha, so open about doing menial tasks. They might assess that they have to protect their personal brand. It could be career suicide to wind up delivering the pizza to someone who is a client of the public relations firm.

Technology has opened opportunities to earn multiple sources of income anonymously.

One example is the Louisiana based digital marketer whose business depends on two major clients. They could be lured away by a competitor. To him, they trigger all the same angst employees have about their own version of The Man.

The serial hurricanes, along with increasing competition in his niche, got him thinking. That resulted in him setting up an anonymous ecommerce venture selling survival kits. The production, fulfillment and payment processing are outsourced.

The wrench in the works on that one and so many other side gigs which have a number of moving parts is this: What if his boutique demands longer hours or if a health problem develops? What is needed is a back-up. For him, that is his wife. He has trained her to parachute in. For others it is a good idea to place a help-wanted listing on Craigslist to assess how to custom-make types of back-up systems.

Other proven-out anonymous ecommerce side hustles include selling used merchandise; creating matches for dating and professional referrals; consulting about, selling and shipping e-bikes/scooters; and providing hard-to-find specialty products such as ethnic spices.

For those who do not require absolute confidentiality, there are infinite possibilities. Before experimenting, marketers and public relations representatives must assess risk. What if The Man, clients or prospects discovered evidence of extra-curricular hustles?

Here are options:

  • Tutoring in-person or online. At the high end is the standardized-test niche. Here is a help-wanted in New York City which pays up to $140 p/h.
  • Creating a paid newsletter on Substack or Ghost. In Vanity Fair, Joe Pompeo reports that some authors are generating six-figure revenue. The challenge is to attract, hold and scale an audience.
  • Doing freelance assignments in marketing or public relations. Online, those are available through Upwork, Mediabistro, JournalismJobs, ProBlogger, BloggingPro, Craigslist and LinkedIn Groups. Business can also come through offering finder’s fees for referrals.
  • Set up a blog on Google’s Blogger. Then apply to Google’s AdSense program. Ads are placed on the blog. Depending on how many take the call to action, there can be significant revenue.
  • Sell unneeded personal items on Craigslist and NextDoor. Both platforms are free. Offer to handle this for others, collecting a facilitation fee. The entrepreneurial can cruise city streets scouting for discarded merchandise, haul it home, get it ready for sale, then post it.
  • Do voice-over assignments from home.
  • Research what are underserved niches, create podcasts for them, then monetize one or more. In business, as in life, not everything pans out.
  • Apply online and then do part-time customer service work remotely on weekends.
  • Grade standardized tests such as high school essays remotely.

It is arrogant to predict the future of work. However, the embrace of multiple sources of income by all generations, ranging from Z to Silent, seems to indicate that relying on one job or one core business is reckless.


Jane Genova (https://yourcareercoachingwithjanegenova.blogspot.com/) is a career coach and ghostwriter for work issues. Complimentary consultations ([email protected]). Fees customized to fit clients’ unique budget.