Should you ‘Do What You Love’ for a career?

How a generation of millennials are working and dreaming in the new gig economy

When Britany Robison’s $1,200 a month lease on her Manhattan apartment came up for renewal, she did what her mother had hoped she wouldn’t do: she walked. Instead of renewing the lease, she struck out across the country searching for a better place to call home. And she catalogued her trip in true millennial style: with a hashtag, #RTHUSA.

That stands for “Road Trip Home USA” and is part of her larger social media project on her blog. Embodying the most essential values of her generation, Robinson wanted to travel across the United States — and get paid while doing it. It was part of her realization that life, career, and family just were not going to happen in the same way as her parents’ generation. And as a budding travel writer who had already seen a fair amount of God’s green earth, Road Trip Home USA was the perfect way to express the uncertainty, restlessness, and dreams of her generation.

She’s in Portland. For now. She says even though she has stopped travelling — life on the road burnt her out a bit — she has a sense that Portland isn’t “it.” As a writer, she says she’s looking for a city where the cost of living was lower than New York, but where she can pursue the work she loved.

Part of Robinson’s philosophy has been DWYL (“Do What You Love”), but she’s discovering  what so many others have in the new freelance economy: it’s much easier said than done.

DWYL has emerged as the millennial generation’s mantra. In part, because creative opportunities are now widely available thanks to innovations in technology. But this philosophy has also been adopted as a result of the unique challenges faced by millennials — DWYL is as good approach to a career as any in a sluggish economy. Because when jobs are scarce, you might as well do something you love.

Millennials grew up in an economic slump, then were hit by another one right as they walked across the graduation platform. They have received more honours awards than job prospects. Now, many like Robinson are accepting this reality and jumping into what is being called “the gig economy”: a massive, often remote, on-demand workforce able to perform any job imaginable, at a moment’s notice. As early as 2012, Fortune magazine was calling our times the “Age of the Freelancer,” a nod to the increasing millions of people who work on contract, and who are making more money doing it than ever before.

In some ways, DWYL is as good approach to a career as any in a sluggish economy. Because when jobs are scarce, you might as well do something you love.

Roxanne Stone, vice president of publishing for research mogul Barna Group, says the freedom of the new gig economy isn’t all rosy. “You could do anything, which becomes overwhelming,” she says. “And it takes a lot more personal drive [or] initiative to create that life. And there aren’t as many of those jobs that are just stable.”

With lack of stability comes lack of funds. Robinson identifies one of the key components of DWYL culture is thrift and frugality. Millennials who are trying to make their way are willing to forego some creature comforts. “There’s a huge movement of writers and artists who are finding cheap housing and doing what you love, without going out to eat and not shopping,” she says. “The new lifestyle that we’re creating for ourselves … values fulfillment over paycheques.”

Robinson funded her 5,000 km trip across the U.S. by freelancing. For the first six cities she visited, her first stop was always to the local tourism board to pitch travel blogging content. And largely, it worked. She stayed in hotels for free, and had her excursions around the city comped.

But she soon ran into a challenge: to make it work (at least initially) a freelancer has to do a high volume of work that’s not always appealing. Robinson says, “The more I pulled in other people and was writing for them, I realized I was distanced from the work that I love.” Landing in Portland, at least for a little while, has enabled her to pivot away from blogging to doing more of the work she really wants to do. “You spend two days on a blog post and then nobody reads it because you’re not good at marketing it,” she says. “Now that I’m pitching publications that already have audiences, I’m finding much more success.” is one among many burgeoning freelance hubs that is emerging on the Internet. The website’s description reads, “We currently list over 3 million Gigs (trademarked) in 120 categories across more than 192 countries. As the leader of the Gig economy, we are proving that everyone has a chance for financial independence by doing what they love.” Sounds pretty darn good. But is it?

In January last year, a writer for scoffs at the mantra, claiming it both devalued work and dehumanized labourers. Citing DWYL progenitors like Steve Jobs and Oprah Winfrey, the author’s main complaint is that the philosophy serves an elite class of people who could afford to come to work in jeans and Birkenstocks, while some sweatshop full of people half-a-world away slaved to buoy them up. Events like the 2011 Foxconn iPad tragedy in Beijing that claimed three lives stand in grim contrast to the DWYL possibilities afforded to tablet owners in the West.

While it’s true that it requires a degree of privilege, comparing sweatshop workers to those who live by the DWYL mantra is a bit misleading. Bloomberg reports that five years into the economic recovery, college grads are still more likely to find jobs than those without (the unemployment rate for people with a bachelor’s degree is only a third of the rate for those with only a high school diploma). But they’re settling for jobs in a buyer’s market that are unrelated to their fields of study. As a result, DWYL can mean a meandering career path with many concessions or even dead-ends. Case in point —Robinson moonlights as a bartender while she builds her writing portfolio. “There was a shame that vouching for the DWYL lifestyle was insensitive,” she says, “but I was able to overcome that [by] acknowledging that I did [work I don’t love] before and still do. But focusing on what I love will eventually allow me to do that full time.”

Earning a college degree used to be a secure path to success, but it seems it no longer is. It’s a statistic that has become a joke, albeit a particularly unfunny one: college degrees do everything, it would seem, but help graduates get jobs. Is college a waste of time? According to the Barna Group, 47 per cent of millennials think so, and they’re adjusting accordingly. The U.S. census reports a drop in college enrolment of nearly half a million students for the second year in a row.

Kio Stark is a Yale graduate-school drop-out who wondered if anyone else was having success pursuing their dreams sans diploma. She launched a Kickstarter campaign and then published Don’t Go Back to School, a book exploring how people learn, as well as alternative ways to shoehorn a career into any industry.

“[There’s] a common perception that if you don’t have a degree, your resume won’t make it through the slush pile. The good news is that this is starting to change,” she writes.

Stark says that while degrees are still essential for acquiring credentials in a few key fields — doctors and lawyers will still need them — the job landscape is changing almost everywhere else. But for engineers and scientists and business leaders, the rules for cobbling together a career from scratch are the same for anyone pursuing DWYL in any other profession: deliver insanely good work, germinate your dream job from humble beginnings, and leverage those connections like mad.

The Work God Loves

The Barna Group published a series of books last year called Barna Frames, each one covering a particular challenge facing young adults today. One entitled Multi-Careering is written by Bob Goff, a popular Christian author and conference speaker known for his refreshing approach to life and vocation.

“Everything you love doesn’t need to be a career,” he says. “In fact, if you make a career out of some of the things you love, you won’t love them anymore. What you can do, though, is have several careers at the same time and do lots of things.” Sage advice coming from a man who has been a career lawyer, launched his own airline, and done everything in between.

If you make a career out of some of the things you love, you won’t love them anymore.

“A lot of people choose their careers based on what they are able to do,” says Goff. “I think the better question is this: What are you made to do?”

Another way to put it might be “Do what God Loves”.  It’s a slogan with the potential to free all of us, especially the selfie-generation, from the self-centredness that becomes the idol that replaces God.

It’s true, God loves work. It’s something that’s baked-in to His plan for humankind from the start. To be human is not only to be relational and rational, but industrious —any effort to flee work is counter to who we are. God’s can infuse all the types of work we do—work we don’t feel passionate about— with a profound dignity and worth.

In the DWYL approach, there is a danger that we lose sight of how work shapes us as people—that God might have an agenda for our hearts and lives when we do work we don’t necessarily find stimulating.

In the new freelance economy, millennials will have to learn when to stay at a job that’s not fulfilling, in order to build towards something better.  Or it may look more like Robinson—striking out across the country into the great unknown, armed with only a dream and a blog.

Photo (CC) by S Zolkin.

Originally published in Issue 21 of Converge Magazine.