City: San Francisco, California 

Passion: Writing, Community


The common thread amongst those who are looking to live a creative, meaningful life in San Francisco is one person. Adam is known as Smiley because he is always smiling to you, and to life in a big way. And in his own words:

"Why do I smile a lot? Well, there is so much beauty and joy in the world. I've always been someone who looks at the world, and feels good. It doesn't mean I'm always happy, but there's an inclination to look around, and I can't help but notice beauty. And when you smile a lot, it makes other people smile, too." 

With an inspiring tale of a writer, and so much he wants to give back, Smiley helped me personally honor my dreams of being a writer, when I had known him for just two hours.

We met up with Smiley at his favorite morning spot in NOPA, Matching Half Café, ( the library where he writes was closed), to talk about his first book, out in two weeks, The Quarter Life Breakthrough, on how to find your voice and purpose when you hit your mid 20s. 




I have always really enjoyed telling stories. Growing up, I loved movies, I loved reading books, and I loved the transformation that happens when you read a story. I was huge into The Hobbit as a kid, The Lord of the Rings, A Wrinkle in Time; books that kind of take you to another world. In school, I was really interested in sports, but realized since I wasn’t really good at sports- I was really short and skinny- that I should write about them instead. So I started with sports writing.

In 2008, I worked for the Obama Campaign, and then got a job working for Peace Corps headquarters in DC. I was doing a lot of writing at my job, because I was good at writing and I liked it, but it was a little more bureaucratic. It was writing in a government context; a lot of memos and talking points and policy papers, so it wasn’t very creative. I wasn’t fired up by what I was writing about. A writer needs to find their voice, and be able to write about things that they’re truly passionate about. I realized what I wanted to write about was personal transformation and people taking risks in their lives. So basically it was my own journey that inspired my writing.


First and foremost, the key is accepting that everything is a work-in-progress. I always think, I am a beginner. When you have the perspective that this is a learning opportunity, that you are a work-in-progress, it opens you up to realizing that you are always practicing and honing your craft. The process of writing my book has made me become a better writer. Every blog post I write, I get better and better, and closer to my voice.

Mastery is about learning. It’s about learning how you do your best work. I’ve learned that I am an extrovert, a people person, so I need to set intentional habits when it comes to writing. This means saying no to people, blocking a day to write with no email, no Facebook, no lunch dates. The last thing that a writer wants to do is actually write, so you have to put yourself in a place where you can actually do your work.


I had a great job on paper, but it was not the right fit for me. I was really nervous to leave a job that provided salary, benefits, and job security, because it was the recession and the job market wasn’t great. But something inside me knew I needed to listen to my heart, and make a change. It was only when I met other 20- and 30-somethings facing the same kind of situation, the same question of how do you figure out what you love and then get paid for it, that inspired me to make the leap. So my passion came out of finding a community of supportive people.

I did a program called StartingBloc, which is a social innovation fellowship. There, I met many young people who were starting their own businesses, and working for organizations that aligned with their values and the change they wanted to see in the world. That made me realize that anything is possible.

I finally found the courage to overcome my fear, quit my job, listen to my heart, and move to San Francisco, a place I’d wanted to live for 10 years. I moved with the intention of being a freelance writer, and writing about people who were following their dreams.


Failure is writing. Inevitably when you write, some people aren’t going to like what you say, and some people are going to resonate with it. So if you’re going to write, you have to accept failure. I have sent parts of the book to people and they really didn’t like it, they had a really adverse reaction based on their own experience. But that’s part of the process, you have to accept that as a reality.

Once, I wrote a piece for a social impact publication and they didn’t pay me for it. I called to ask for the money and the editor told me that the piece was the worst thing she had ever read. I’ve also written blog posts that people said had changed their lives. I’ve never met anyone who created something magical in this world that hasn’t failed.

My book, The Quarter-Life Breakthrough, can’t be a New York Times bestseller because it’s not yet in bookstores, but does that mean the book failed? No! For me, success is the growth I went through, and from people hearing my story or reading about the book. Even if the book simply helps others think more about what they are going to do with their life, I’ve already won. I have already failed and already succeeded, and my book hasn’t even launched yet!


I have a lot of fear about money. That issue of knowing how deeply I care about what I’m doing, but also knowing how much stress it causes me to worry about money, and balancing that.

I have overcome the fear of failure and what others think. Often people project their fears on you. “What happens if you get a bad review?” That is other people’s fears about themselves. Then you have to realize which fears are your own, and which are the fears of others. I learned this when I was leaving my job, that I was internalizing others’ fears about leaving a job. People can only really give advice based on their own experiences.

The big thing is accepting fear. I am scared about the money, but that makes me work harder, that makes me figure out alternative ways to make income. In a way, you can use fear as a source of energy and inspiration. So if you are scared of something, it probably means you should do it.


The biggest challenge for any artist is the balance between doing your work, and making a living. I’ve recently found that it’s this struggle, this balance, that makes you an artist, and figuring out how to navigate that. That’s how you end up doing your best work. The people that discover that balance are the ones that succeed as artists, and don’t give up.

I’ve found a variety of different projects to balance writing my book and doing the work I love. I do writing and storytelling for companies that I think are doing good work, which allows me both to write and get paid. This allowed me to work on my book, which took me 10 months and didn’t pay me a salary, but was a project I deeply believed in. I think the key is finding side projects that pay money, but also where you are not compromising who you are, what you believe in, or what you’re good at.


A lot of the times we think success and finding a job is about hustling and networking. But I think it’s about spending time with people you love and finding rituals that make you joyous. For me, that means spending time with my sister, going on Sunday walks. I’ve also started meditating and eating better.

Self-love is the essence of any good work. Surrounding yourself with people that love you makes you better.


People that inspire me are people that build communities to help others find their dreams: the Passion Company, StartingBloc, Hive, The Bold Academy. Those who are building accountability and support systems inspire me, because you just can’t do this stuff alone. My book is not just a book, it’s about building a community of young people who want to find meaningful work. I am inspired by people who are looking beyond themselves to create a network for people to do this work together.

I get inspiration from people who are younger than me; they’re not yet influenced by the late 20s pressures of “I have to get married and have a high-paying job.” Young people are still audacious and naïve, which allows them to do great things.


I have a lot of mentors. I try to surround myself with a lot creators. One of them is Ryan Goldberg, who is a freelance writer for the New York Times. He has an ability to play with words like no one else. He reminds me to keep going, no matter what. I have been mentored a lot by my friend, Evan Walden, who co-founded ReWork, which helps people find meaningful work. My sister is the one who deals with the most of my freaking out, she is my biggest source of inspiration and support.


Listen to the voice within. If something inside is telling you to do something, do it. If you have to start Sunday afternoons or Tuesday evenings, do it. But no matter what, start, and have someone hold you accountable for it. Ask yourself: what is the one thing that you know you need to do, but haven’t done yet? For me it was starting a blog while I was at my old job. It took me 20 minutes and $20 to start my blog. And just that simple beginning (writing that one blog post), helped me connect to other writers and pitch stories to publications, which eventually led me to start writing my book. There is beauty in putting yourself out there. There is beauty in beginning.