Two years ago, Smiley Poswolsky was wrestling with a brutal quarter-life crisis. When he went home and told his roommate that he hated his job and wanted to move across the country, write, and support social entrepreneurs who were going after their dreams, his roommate would say something like, “Dude, everyone hates their job. That’s part of life, man. Suck it up.”

He wasn’t ready to give up so easily.

“I was like, man, I’m 28,” Poswolsky told writers at a session of the 2014 American Society of Journalists and Authors conference. The panel on how to find meaningful work was organized by Project Otter. Poswolsky is author of The Quarter-Life Breakthrough. “I’ve got a long ways to go. This is gonna suck.”

That was before he made his quarter-life breakthrough which grew out of a quarter-life crisis, which he defines as a period of time when you suddenly have no idea what you want to do with your life. Some people face such a crisis in college. Others after. Poswolsky’s Baby Boomer mom thinks she’s having one now.

During his talk, Poswolsky offered some tips on finding meaningful work. Heavy social media use can be a downer, he noted. Facebook, Twitter, and Instagram are constantly bombarding you with others’ accomplishments at a time you may feel vulnerable and uncertain of your next move. Poswolsky’s first lesson when finding meaningful work is to stop comparing yourself to others. Focus on who you are and what you want, he says. Move beyond FOMO, or fear of missing out, he says.

Early on, he went to the StartingBloc Institute for Social Innovation, where he met 20-somethings and 30-somethings who were starting organizations and going after their dreams. They included Debbie, who was starting a toy company to inspire the next generation of female engineers; Ted, who was starting an organization to teach financial literacy to urban teenagers; and Tom, who was starting a company that would employ people with autism.

When they learned Poswolsky wanted to write, move west, and support social entrepreneurs, they told him he definitely had to go after his dreams. “I was like, oh my God, dreamers,” he recalled. “This was like an awakening for me.”

Making a career transition or quitting a job or doing something new can feel really scary, Poswolsky said. But it’s a good practice to find communities of people who will support your breakthrough. Perhaps it’s people with similar interests or similar values that are aligned with what you’re trying to do. Find those communities and build those relationships, he advised. “You cannot do this alone.”

Having someone hold you accountable for taking the actions you say you’ll take can make a big difference. At StartingBloc, Poswolsky said he was going to quit his job. His buddy Evan’s first reaction was: When? He texted Poswolsky every week after the program. Then his friend started calling him, sometimes interrupting him at work, asking, “Have you had your talk with your boss yet?”

“The only reason this book exists. . . The only reason I’m standing in this room right now is because Evan held me accountable to my dreams,” said Poswolsky.

Tips for making your own career transition or quarter-life breakthrough at any time of life

    • Stop comparing yourself to others
    • Find dreamers
    • Find people to hold you accountable to your dreams
    • Find a like-minded community that will support your breakthrough
    • Create a personal advisory board


If you’re going through a career transition, Poswolsky suggests you build a breakthrough advisory team. It’s like a personal board of directors. Pick five people who can offer guidance every time you come to a crossroads or decision points. Bringing in people who are both older and younger to your team helps. They may be more experienced or less jaded go-getters. Include people who live in your geographical area.

For work to be meaningful, gifts (your skills and interests) should align with the kind of impact you want to make and the work should be financially viable given your desired lifestyle, Poswolsky says. What’s meaningful for one person might not mean much to someone else.

Somehow, the Peace Corps in Washington, DC didn’t feel right to Poswolsky. He’s a social person. He didn’t fit into a bureaucracy approving memos and talking points for bureaucrats. “It wasn’t the right fit for me,” he said. “It doesn’t make me a bad person. It just means it wasn’t aligned with who I am.”

Thinking back, he said he would have been better suited to working as a Peace Corps volunteer in a rural village in Botswana. “I did not belong in a 500-person office building in a cubicle.”

To learn more, read The Quarter-Life Breakthrough.