Millennials and the Real Job

Originally published in Mazing Magazine, Issue 5.

Is it just my Instagram feed, or do the majority of millennials really pay their bills from travelling around pushing products and writing semi-intuitive motivational captions? Alright, that’s a bit of artistic exaggeration, but the rise of the social influencer as a career choice says something about the millennial life strategy. According to Google Trends, the number of United States Google searches for “How to become an influencer” more than tripled in popularity in November 2018 as compared to the same time in 2017.

Likewise, the search terms “How to work for yourself” and “How to travel for work” have risen steadily in relative interest since the start of Google’s trend data in 2004—a 161% and 387% increase respectively over those fourteen years. This could mean one of two things: one, that more people believe Google searches are a viable first step in making drastic career decisions (sounds about right). Or two, that as a culture, our priorities are actually changing.

The appearance on social media and otherwise is that more and more millennials are pushing the envelope on not only unorthodox living situations (#vanlife), but also taking some serious liberties with bringing home the bacon. As someone who rocks the 9-5 desk job at an established company, I have definitely stood in a small circle of young adults and bonded over the special fact that we all have “real jobs,” i.e., no, we can’t make it to mid-afternoon coffee and jogging tomorrow, but feel free to chat us on our work email around that time.

The question is—Google search data and Instagram observations aside—are millennials actually ditching the “real job” for more glamorous alternatives, or does it just feel that way?


According to a study conducted by the U.S. Small Business Administration, “In 2014, less than 2 percent of Millennials reported self-employment, compared with 7.6 percent for Generation X (born 1963 to 1981) and 8.3 percent for Baby Boomers (born 1944 to 1962).” So turns out, the hoards of self-employed millennials out being the captains of their fates are actually an illusion; there are significantly fewer millennials who’ve made the big bucks being self-employed than have our parents, despite the perception that Baby Boomers are wound up in their long-time careers and pensions. 

Don’t take it too hard though—research from the Kauffman Foundation shows that a lot of factors are working against millennial entrepreneurs, like precipitous effects of the Great Recession, and the fact that we just have less life and work experience to bring to the table. We sure are a spunky bunch though.

Multiple Employment

If less than two percent of millennials would actually identify as self-employed, where are all these freelance travel bloggers coming from? That got me thinking about the people in my life that I actually know (myself included)—people with side hustles. According to a recent study conducted by CareerBuilder, 39% of workers aged 18-24 have a second job, as well as 44% of workers aged 25-34. 

Financial reasons aside (I know, I know, the Great Recession), millennials are more inclined to seek work for personal fulfillment than our predecessors, according to the Kauffman Foundation. That CareerBuilder survey also noted that 30% of millennials making over $75K per year still work a second job, just for kicks. The New York Daily News has gone so far as to dub this job strategy the “portfolio career,” in which one experiments with their skill sets across a series of part-time jobs, either to figure out what they’re best at, or just for the joy of variety. Does the IG bio, “lifestyle blogger – health coach – actress” ring any bells?

Working Remote

While fulfillment is a big factor for millennial careers, I would be remiss not to include our generational affinity for freedom and flexibility. Turns out, you can make it to mid-afternoon coffee and jogging, or travel on weekdays, with a little thing called remote employment. A survey from FlexJobs in 2015 showed that 85% of millennials want telecommuting opportunities, and boy are we pushing for them. Big companies like Dell and Deloitte have been tracking the influence of remote working opportunities on their bottom line, and the number of the U.S. workforce that works remotely more than half the time has more than doubled since 2005, according to FlexJobs. So what that means for our Instagram people: yes, you can still grab that overhead shot of a morning croissant in Paris, but you might have to wake up at 3 am to tune in for a conference call. As they say, do it for the ‘gram.

Despite all the glamorous poolside posting, maybe millennials aren’t actually living our best lives all that unconventionally. What we are doing is toying with the systems in place—moving our offices online, trying to turn dream jobs into real jobs while still working a couple of real jobs, and yes, posting about our adventures incessantly. Our priorities are shaping and expanding the priorities of our companies, from less stuffy workplace culture to more vacation hours. And we definitely are fueling our dreams with Google searches, because you never know if searching “How to make money online” won’t work if you don’t try it.