Millennials: What Does it Mean to Find “Meaningful Work”?


Too busy to read the whole article? [1500 words, a 6-minute read] Here are the takeaways:

  • Many millennials struggle with the balance between finding meaningful work, being happy, and protecting financial security.
  • Smiley Poswolsky struggled with a nontraditional career path and wrote The Quarter-Life Breakthrough to help others like him. He also happens to be one of my personal mentors and friends.
  • Check out a free excerpt from the book here.
  • To win a free copy of the book (5 available), leave a comment by Tuesday, April 15. For a second entry, shoot me an email too.

Time to pull back the curtain a bit.

The reason I first created this website was because something in my work life didn’t feel quite right. At the ripe old age of 26, I wasn’t feeling as fulfilled at work as I once had and knew it was time for something new.

Whenever I told my friends and family about my plans (quit my job and start a publishing company for young people) they invariably thought I was nuts. I wondered: am I the only one who feels this way?

Then, I discovered StartingBloc, an incredible 5-day business seminar/meditation retreat/all-night rager that introduced me to over 100 young people (and some not-so-young people) desperate to make a change in their lives and find meaningful work.

During StartingBloc, I met Smiley Poswolsky. Smiley has found himself working everywhere from a film festival in Buenos Aires to the headquarters of the Peace Corps in Washington, DC. Yet, throughout a varied and often rewarding career, he kept finding himself struggling to find a balance between purpose, happiness, and financial security.

he kept finding himself struggling to find a balance between purpose, happiness, and financial security.

And Smiley’s not alone. American millennials increasingly find themselves defined not by their jobs, but by their personal narratives.

The difference is, Smiley’s actually doing something about the problem. In his new book, The Quarter-Life Breakthrough, Smiley profiles changemakers who have found meaning in their lives and provides effective exercises and step-by-step to-do lists for young people looking to do the same.

In my opinion, the list of helpful books, internships, grants, and supportive communities alone is worth the price of the book.

Now, without further ado, a short excerpt from The Quarterlife Breakthrough that illustrates two actionable ideas that can help you get a job that means something.

Enter Smiley

(Excerpted from The Quarter-Life Breakthrough, page 105)

Try on jobs to see if they fit

Finding meaningful work is all about experimentation, and being open to new opportunities. Remember Kristen, who left her sales job at Google and by pursuing her esthetics certificate, found that she has a gift for doing make-up and making others feel comfortable in their own skin? Or Zack, who taught himself how to code, got a full-time job at a tech start-up and is now developing his second app? Both Kristen and Zack were okay with being beginners. They admitted what they didn’t know and experimented with a new opportunity to see if it was the right fit.

The job search process is time-consuming, and the last thing you want to do is start a new job and realize a month later that it’s not at all what you thought it would be. A great tactic when you’re considering a career transition is to try on a job in person to see if it fits before you even apply.

When I was considering other opportunities for after the Peace Corps, one thing I considered was teaching. I researched teaching credential programs, master’s programs in education, Teach for America, and New York City Teaching Fellows. I spent countless hours preparing for my Teaching Fellows interview, reading books, and watching documentaries about education. I talked to my teacher-friend Gayle about my job search, and she said, “Smiley, you should just come visit my class next week.”

When I visited Gayle’s class, not only did I realize what an amazing teacher she was, but I also realized that teaching (at least in an elementary school classroom) was not for me. I found the smell of the building nauseating and twenty-five kids running around like maniacs made me freak out. By 2:15pm, I was exhausted. I kept looking at the clock to see when class was over, and I realized I had no interest in classroom management, which is a huge element of good teaching. I still care deeply about education. But spending one day in a 4th grade classroom made me realize that being an elementary school teacher is not for me, at least not right now.

Reach out to people that work in environments you’re interested in working in. Ask if you can shadow them for the day, or even a morning. Can you picture yourself in their job? Why? Why not? If you’re interested in two or more opportunities, test both. If you can’t shadow someone, consider interviewing her about the work she does, her environment, and what her day-to-day is like to get a sense of the job.

Seek short-term entry-level experiences

Six months after graduating from college, when I moved to New York City to do freelance work in the film industry, I took any job on a film set I could get. For a few months I worked as a production assistant (or PA, as they’re commonly referred to) on several different films. For one gig, my job was to sit on the back of the grip and electric truck, and make sure no one that wasn’t part of the crew took anything (like lights or cables) from the truck.

For twelve hours a day, six days straight, in 20 degree weather, I sat on the back of a truck near Bryant Park and froze my ass off for $100 a day. Since the truck was a few blocks away from set, I didn’t learn anything about film production. I barely interacted with anyone, except for a few grips who chain-smoked all day and a few tourists who wandered by, asking if anyone famous was in the movie.

On my next gig, I worked for $50 a day as a PA on a small independent film, but told the line producer I didn’t want to watch a truck, I wanted to be on-set. Because the film was a low-budget project, they were highly understaffed, and I ended becoming the assistant location manager, helping the location manager and the line producer scout new locations and manage on-set logistics for the film. I saw first-hand how involved making a movie really is.

While I got paid half as much, the experience of being an apprentice on-set taught me infinitely more than making $100 a day guarding a truck. Two months later, my location manager brought me onto another gig as her assistant location manger and paid me $200 a day. After that, I worked for nearly two years doing freelance location work. I learned so much that after two years of freelancing, I produced a short film about a day in the life of two Iraq War veterans struggling with post-traumatic stress disorder.

Taking the skills I learned on various film sets, I managed a cast and crew of over 40 people, something I never would have been able to do had I not turned the  experience of getting frostbite on my toes into an opportunity for an apprenticeship.

If you’re new to a field, look for short-term, entry level experiences in the form of internships, apprenticeships, consulting opportunities, or freelance gigs that offer on-the-ground learning and mentorship from people with expertise. While these experiences may pay less, they can often be much more valuable than entry-level jobs where you do something you already know how to do (like watch a truck, answer a phone, or schedule meetings). The best thing about short-term experiences is that if they aren’t the right fit, you can easily move on to something else.

Often the best entry-level experiences are not advertised on websites or job boards. You may have to create one for yourself, like Zack did when he convinced the Vice President of TaskRabbit to give him an internship, or when I told my line producer I wanted to work on-set.

If you’re having trouble coming up with an idea for an apprenticeship, check out the Leap Year Project, created by Victor Saad. Interested in going to business school but worried about the cost, Victor created a self-directed, multicity master’s degree in design, business development, and social innovation. He developed 12 different experiences in 12 months for himself, apprenticing with places like a leading architecture firm in Seattle, an art and apparel community in Chicago, and a digital agency in San Diego.

Inspired by his leap year, he decided to create an actual school for others to learn by doing, called Experience Institute. Victor’s story teaches us that it’s possible to create any kind of short term apprenticeship that makes sense for you.

Your next action: join the Quarter-Life Breakthrough Community

  • Liked what you read? Simply leave a comment below about what “meaningful work” means to you for a chance to win Smiley’s new book (5 free physical copies available). For a second entry into the random drawing, shoot me an email about life, work, or just to say hi. I’ll announce the winners on our email list next week. Deadline to enter is Tuesday, April 15th.
  • Smiley would love to hear from you about your own stories or questions—to get in touch, simply email him.
  • Don’t forget to buy the book. Even if you win a free copy, I bet you can think of at least one friend who could benefit from their own copy, no?