The Cycle of Meaningful Work

Meaning is the journey, not the destination.

Smiley Poswolsky
Personal Growth
6 min readDec 10, 2015

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Photo: David Marcu / Unsplash

Have you ever been told by everyone around you that you’re “killing it,” but known that you needed to make a change? Have you ever gotten to a point with your work where, on paper, everything is going great; you’re making money, you’re getting recognition for your work, you’re making an impact — and yet, something is missing? Have you ever wondered why — after the long journey towards completing a creative project, building a profitable business, or landing your dream job — the end result seems less fulfilling than the months and years it took to get there?

Sound familiar? Well, you’re not alone.

Lately, I’ve been feeling unfulfilled. I’ve been stuck in a creative rut. On paper, I shouldn’t feel stuck. I should feel like a king, sitting on his throne. On paper, I’m pretty damn successful. On paper, I’m “killing it.”

I recently got a book deal based on my first book, The Quarter-Life Breakthrough, a guide for millennials to find meaningful work, which I self-published last year after running a crowdfunding campaign on Indiegogo. I’m getting paid to speak about a topic I am very passionate about: empowering millennials to overcome their quarter-life crises and find meaningful work. After years of hard work, I’m finally starting to make money from writing — which is the exact dream I set out to achieve when I quit my comfortable, well-paying government job, four years ago. So why am I feeling lost and empty?

Because I accomplished something worth accomplishing, and now I’m ready for a new challenge and I’m not sure what I’m going to do next. I feel overwhelmed by all the possibilities. It’s hard for anyone to be having a quarter-life crisis, but can you imagine how hard it is for the guy who wrote a book about the quarter-life crisis to be having one?!

Whenever you finish writing a book, the requisite question everyone asks you is, “So, now that the book is done, what’s next?” I’ve been responding, half-jokingly, but totally honestly, “Well, I’m not sure exactly — I need to read my own damn book!”

My breakthrough four years ago was that I had no interest in working an administrative role in a large government bureaucracy, and that I wanted to be a writer, and support young people going after their dreams. The breakthrough I’m beginning to going through right now, four years later, is that I’m ready for a new challenge as a writer, speaker, and creative.

Maybe I’ll write my next book about how companies can do more to empower millennials and build meaning into the workplace. Maybe I’ll write a book about my grandmother who passed away a few years ago. Maybe I’ll write a book about dating. Maybe I’ll write a book about the creative process. Maybe I’ll write a book about why real life is better than Instagram. Maybe I’ll write a fictional tale of a young man (okay, okay, a 30 year-old man) moving to San Francisco, trying to figure out the meaning of life. Maybe I’ll host a talk show on television and interview millennial entrepreneurs.

The truth is, I don’t know what’s next. Yes, I wrote a book that teaches people how to figure out what’s next, and I myself don’t know what’s next.

When I told a friend about my existential crisis, he said, “I wouldn’t tell people you don’t know what’s next. As a career advisor, that’s bad for business.”

He’s probably right. But what’s right for my business might not be right for my heart. My book teaches twenty- and thirty-somethings to re-invent their careers and pursue what’s meaningful to them. Instead of the failed metaphor of a career ladder moving in a straight line, my book treats careers as a pond of lily pads moving in all directions — you can hop in whatever direction makes sense for you, given your unique gifts and the impact you want to have on the world.

It’s time for me to hop to a new lily pad. If I can’t practice what I preach and give myself permission to have my own breakthrough, then why the hell did I write the book in the first place?

Most career advice is about finding your one passion, purpose, or calling. This is an exercise in futility, and wasting a shit ton of money on self-help books, expensive coaching programs, and traveling to Bali to find yourself. Instead of teaching people how to find their calling, maybe we should actually be teaching people how to be okay with not knowing the answers. Instead of talking so much about passion and purpose, maybe we should talk more about permission. The permission to not have it all figured out. The permission to discover something new.

Careers do not move in straight lines. There comes a point when any artist, creative, entrepreneur, intrapreneur, or leader, has to grow in order to reach their full potential.

And when I say “grow,” I don’t mean you have to quit your job tomorrow. I don’t mean you have to abandon your previous work and lock it in a dungeon. I don’t mean you have to start from scratch. Your previous work doesn’t die, it shines even brighter as you open doors you thought would remain locked forever. Your previous work, the experiences you gain, and the skills you master, become leverage for future opportunities.

A lightbulb recently went off in my head when I realized that I had completed a full cycle of meaningful work. This cycle goes from DISCOVERING LEARNINGBUILDINGTHRIVING.

It took me four years to discover my purpose, build an audience, learn my values, find the persistence to commit to my writing, hustle to reach my potential, make a living running my own business, and I’ve gotten to a point where I’m thriving — where I feel like I’ve achieved an important part of my mission. Now I’m ready for a new challenge. I’m ready to give myself permission to do it all over again.

Just as you start to reach a peak level of THRIVING, you realize there is no finish line. There is no beach to relax on, no piña colada to sip. You have keep learning, growing, and creating. Society has trained us to believe that success is “killing it,” that success is getting there. As Gertrude Stein wrote, “there is no there there.” This is why so many people are unhappy. They are trying to spend their whole lives “killing it,” but “killing it” isn’t the point. Surrendering is the point. Not knowing the answers is the point. Going from THRIVING right back to DISCOVERING is the point. Repeating the cycle is the point.

Meaning is the journey, not the destination. Meaningful work is not really about quitting one job, starting one business, or writing one book. It’s the ongoing process of putting yourself out there, exploring your interests, becoming really good at something, creating something that matters, and leaving a legacy of impact over time. Truly brilliant people never stop creating.

If I can give myself permission to not know what’s next, then you can too. If I can surrender to what my heart is actually saying — even as everyone around me is saying, “Smiley, you’re killing it!” — then you can too. As I embark upon my second quarter-life breakthrough, I can’t wait to share with you what I learn along the way.

Smiley Poswolsky is the author of The Quarter-Life Breakthrough, a guide for millennials to find meaningful work. His follow-up book will be published by Tarcher Perigee/Penguin Random House in 2016. Follow @whatsupsmiley and get free quarter-life resources like the Career Resources Guide at smileyposwolsky.com.

Cycle design by Max Brody.

Special thanks to Makespace Community Coworking in San Francisco for providing the creative space where this post was born. If you are looking for a Quiet Tribe where you can get your creative work done, come join us!

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Smiley Poswolsky
Personal Growth

Keynote Speaker. Workplace belonging expert. Author of The Quarter-Life Breakthrough and Friendship in the Age of Loneliness. http://smileyposwolsky.com/