How to Find Meaningful Work: Start With Asking the Right Questions

Finding meaningful work is about asking complex questions rather than coming up with easy answers.

“How we spend our days is, of course, how we spend our lives.

-Annie Dillard

The traditional “American Dream” retirement mindset you learn from a young age tells you to go to college, climb the ladder, find a well-paying job that allows you to support a family, retire at 65, and you’ll be fulfilled.

There’s one slight problem with this retirement mindset: it doesn’t actually lead to fulfillment. Gallup’s 2013 State of the American Workplace report showed that as many as 70% of American workers are disengaged at their jobs. Nearly one-fifth of those people were so disengaged at the office that they were actively undermining their co-workers’ work.

I think part of this lack of fulfillment stems from our failure as a society to encourage people to ask themselves simple questions which often don’t yield simple answers: Who am I? What do I want? Why am I here? What do I want for the world? What is my purpose? Why?

I’ve asked many of my peers why? over the last two years and not once has someone answered, “make lots of money so I can buy nice stuff,” “run a corporation so I can have lots of power,” or “pass the time as quickly as possible, doing as little as possible, so I can retire with a pension in 40 years and go on a cruise with my partner.”

Rather, they’ve said things like: “I want to teach urban teenagers how to avoid debt and become successful entrepreneurs,” “I want to inspire young girls to think they can become engineers, and not Barbie dolls,” “I want to teach kids living in a food desert how to grow their own food,” and “I want to ensure that large corporations reduce their carbon footprint.”

Rather than waiting for retirement, millennials are asking what their purpose is now, and they’re determined to find the opportunities, organizations, and companies that share their dreams.

A lot of books about finding meaningful work ask you to determine your calling in life. Those books scare the shit out of me. Instead, in The Quarter-Life Breakthrough, I propose that finding meaningful work is about asking complex questions rather than coming up with easy answers. Let’s accept the idea that very few people have only one purpose, one truth, or one calling. Our purpose actually changes throughout our lives as we try different jobs, travel to new places, meet new people, and grow older. Over the last 30 years, I’ve had numerous different “callings,” from being Big Bird on Sesame Street to being a sports writer to making movies—and I’m currently doing none of those things.

We each have to define meaning for ourselves and accept that our definition might change over time. Viktor Frankl’s bestselling and still-relevant book, Man’s Search for Meaning is about his experience in a Nazi concentration camp, during which he lost his pregnant wife and most of his family. Frankl wrote: “Being human always points, and is directed, to something or someone, other than oneself—be it a meaning to fulfill or another human being to encounter. The more one forgets himself—by giving himself to a cause to serve or another person to love—the more human he is.”

Building from this ideal, my book discusses five essential components of meaningful work: meaningful work reflects who you are and what your interests are, allows you to share your gifts to help others, and is financially viable given your desired lifestyle.

Any kind of work can be meaningful: the challenge is discovering what in particular makes you come alive. Here are a few questions that can help you find work that is both personally fulfilling and makes a positive difference in the world.

1. Meaningful work reflects who you are. So, who are you? What do you love about yourself? What makes you weird? (Being weird is good.) Who do you want to show up as every day? When was the last time you were really happy? When was the last time you were really sad?

2. Meaningful work reflects your interests. What do you care about? What injustice infuriates you? What social issues are you most passionate about? What happened that made you change the way you see the world? What personal life experiences have shaped your beliefs?

3. Meaningful work allows you share your gifts. What are you really good at? What are your unique skills and strengths, your gifts to the world? Which of your gifts do you actually like doing? What areas do you need to deepen your knowledge in? What types of classes do you need to take? What experts or mentors do you need to talk to? What research do you need to do?

4. Meaningful work allows you to help others. What type of impact do you want to make? What type of impact have you had in previous jobs? Do you need the results of your work every single day? Do you need to have a face-to-face relationship with the people you’re serving?

5. Meaningful work is financially viable given your desired lifestyle. What are your estimated weekly and monthly expenses? What is your ideal quality of life? How much money do you need to live a quality of life that suits you? Will a particular job or opportunity allow you to be fulfilled outside of work? Will you have healthy work-life balance? Will your work environment and co-workers energize or drain you?

As you begin your meaningful job search, look for positions where you can share your unique gifts at organizations that match your values and provide the opportunity to make an impact, and the quality of life you desire. In other words, find the sweet spot where as many of these pieces as possible overlap.

Fitting these pieces together often takes time and patience. I dislike delayed gratification as much as the next millennial, but there’s no easy button, especially in today’s job market. While certainly challenging, finding meaningful work is not impossible. Unlike 70 percent of Americans, the millennials profiled in my book are excited about how they spend their days and all of them started their journey with asking the right questions.

Adapted from The Quarter-Life Breakthrough, available on Amazon. Resources, including job boards and suggested reading, are available at



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