Millennials Change Jobs Like I Change Underwear (Both are a good thing)

Every few months one of those “List all the jobs you’ve ever had” requests appears in my Facebook feed and invites me to repost my answers. For the record, here goes:

  • Paper delivery boy
  • Golf caddy
  • Fuller Brush salesman (Google that one)
  • Tennis instructor
  • Newspaper reporter
  • Television reporter
  • Comedian

That’s it. There is no “continued on next page” accompanying my list. Seven means of acquiring a paycheck, encompassing 54 years.

The average millennial would scoff at such complacency.

Whereas multiple jobs on a resume used to be a red flag — signaling the job applicant suffered from poor work habits, lousy team playing skills, awful punctuality, terrible hygiene, or a combination of the four — now it symbolizes entirely different traits. A millennial whose resume reads like the choices on a Chinese menu is seen as aggressive, goal oriented, and willing to take risks.

At least, according to the millennials.

In my never-ending quest to understand this much maligned group of individuals born between 1982 and 2004 — a 2014 Atlantic article about the millennial generation opened with, “We can all agree that Millennials (sic) are the worst” — I decided to go directly to the source.

I had ulterior motives, of course. My 20-year-old daughter is smack in the center of the millennial crowd and, grad school notwithstanding, just two short years from (hopefully) permanent employment. Will she pursue her chosen major of occupational therapy and enter what I would consider a normal daily work routine? Or will she spend her 20s lurching from one job to another, hoping she eventually lands on something that provides economic, cultural and spiritual fulfillment while also allowing her to scoot around the office on a hoverboard? And how will I feel if she chooses the latter path?

I found the answers in 28-year-old Timothy Tyrrell.

Meet Timothy Tyrrell, millennial entrepreneur and Airbnb host

A Denver resident and avid skier, Tyrrell might need a bathroom break if ever faced with the “list all your jobs” challenge. In the last 14 months, his resume includes the following:

  • Uber driver
  • Lyft driver
  • Babysitter
  • Independent Jell-O shot salesman at concert venue
  • Elder caregiver
  • Media salesperson
  • Airbnb host
  • Video production salesperson
  • Cycling and hiking guide
  • Restaurant server


I encountered Tyrrell after agreeing to fork over $67 for the privilege of spending a night in his Airbnb property, a 1985 VW van parked in West Vail, Colo. Despite the lack of heat and plumbing facilities (Read: No toilet on premises), Tyrrell’s van is regularly booked. The Airbnb income, combined with his other ventures, earned him approximately $45,000 in 2016.

“I wanted to control my time outside the norm of a 9 to 5,” he said. “I can travel when I want, and I will still have all of these jobs waiting when I get back.”

Armed with a psychology degree from the University of Colorado Denver, Tyrrell soon realized, like many millennials, that his chosen major would not provide “meaningful” work, a word popular with his generation.

“Your parents may think they have the best intentions, but you have to create work that is meaningful to you,” Tyrrell said. “You have to listen to what’s inside.”

The voice inside Tyrrell’s head told him his forte was sales, which led to the Airbnb enterprise as well as jobs conducting phone sales for two startup firms. In fact, Tyrrell believes the only tools necessary to succeed in today’s work environment are a cellphone, an email account and knowledge of a computer’s innards. He has harnessed the first two in most of his previous ventures. Now he is set to enroll in a seven-month “boot camp” at the Turing School of Software and Design in Denver, hoping to earn a degree in computer programming. He’s confident a starting salary of $70,000 at a more “traditional” company will be the result.

After hearing his story, I no longer fear having the “what are you going to do with your life” talk with my daughter, for her generation will succeed in ways that baby boomers and Gen Xers like me never realized due to our staid vision that success meant steady employment with minimal disruption.

And it certainly never included Jell-O shots.