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Meet These 15 Inspiring Chicagoans Who Dropped Everything And Pursued Their Passions

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More and more people are discovering that work doesn’t have to be a task you dread, a stressful deadline or a chain keeping you hostage at a desk you’ve grown to hate. People everywhere are changing things up, trying new adventures, taking risks and leaving previously set-in-stone career paths behind. Many are diving in and embracing life, seeking new opportunities that let them pursue projects and lifestyles that make their lives more fulfilling.

This is especially the case in Chicago where, as architect Daniel Burnham once famously said, "we aren't known for making little plans." In a tribute to our city's indomitable spirit and ingenuity, we talked to 15 inspiring Chicagoans who started over in pursuit of a new definition of success.

  • LaManda Joy, 45, Budlong Woods
    What do you do? I am the founder and leader of a NFP called Peterson Garden Project that teaches people to grow their own food by coordinating community gardens on Chicago's North Side as well as providing classes and educational opportunities.
    What did you do previously? I was a VP of Creative at the galaxy's largest event company: Freeman.
    How do you define success? Success means something quite different to me these days... dollars and titles are empty to me now. Being able to impact peoples' lives by teaching them a skill that they can then impact others' lives with gives me a high I never imagined. I don't see it as a job anymore, I see it as a "calling" and feel fortunate to be surrounded by others who feel the same way.
    What do you wish someone would have told you about making this leap? There's a saying: "Time is what keeps everything from happening all at once." I needed my life experience to this point to make Peterson Garden Project successful. I wish someone would have told me that being frustrated in the corporate world would pay off in the long run.
  • Mike Sosin, 31, Lincoln Square
    What do you do? Co-founder and partner along with Kate Taylor Battle of Sosin Battle, artist management, tour management and publicity for bands and musicians.
    What did you do previously? Sales for several large and small companies.
    What was the moment you knew you had to make a change? When I realized I could no longer sell other people's ideas and products and be fulfilled.
    How do you define success? Certainly not by money, however, continuing to run a sustainable business is of course a baseline goal. Being able to do something I love day in, day out, the rewards of working with extremely talented and interesting people and having others in the industry respect and trust you.
  • Jahmal Cole, 30, Chatham
    What do you do? I'm the founder of Role Model Movement, Inc., an organization that offers a series of initiatives geared toward empowering youth, especially those in underserved communities. In the most basic sense, I'm an author and a public speaker. This year, my focus has been on My Block, My Hood, My City.
    What did you do before? As a member of one of Chicago's leading proprietary trading firms, my focus was directed toward the company's Microsoft Active Directory Infrastructure.
    What has been the biggest challenge for you? I used to be tempted to look for a job—a different job, a better job. I used to conduct job searches to find one that matched my skill set and interests. I'm proud to say that I haven't applied or even been interested in looking for a job since I've taken my initiative full-time. The biggest challenge has been overcoming the internal doubt and excuses and finally stepping out of my comfort and safety zone. Every day is another battle between inclination and obligation, but I've learned that I have been brought to this place in my life for a reason. Rather than worry or second guess my decision, I've chosen to build on it and appreciate the moment and the opportunity.
    What is the best surprise to come of this? It's the internal satisfaction and reward I receive from being able to wake up every day and create my own destiny, while doing what I love to do and am so passionate about. I truly appreciate every flower that's beginning to sprout from the seeds of my dreams.
  • Saya Hillman, 34, Roscoe Village
    What do you do? Owner of Mac & Cheese Productions; I inject summer-camp into adults' lives through unique, fun opportunities to grow community and themselves in environments where they feel comfortable solo and with people they’ve just met.
    What did you do previously? Non-profit sector (program management and associate producer).
    What do you wish someone would have told you about making this leap? There is no "right" way to leap. Don't compare yourself to others. Don't feel you have to do something the "traditional" way. Create your own path. Learn from others. Steal and tweak. There will never be a perfect time. Nike the bejeezus out of life and just do it; whatever "it" is.
    What is the best surprise to come of this? Of course in the moment I didn't feel this, but getting fired was the best thing ever. Who knew?!? And how I'm a magnet for goodness. People, press, freebies, opportunities, Hermann Miller chairs -- they continuously drop in my lap.
  • Kristen Kaza, 28, Andersonville
    What do you do? I promote and produce events with my company, No Small Plans Productions.
    What did you do previously? I was the Director of Marketing for the Chicago Reader. I'm in the very lucky situation that I still work with the Reader, but now as a consultant/contractor with NSP. They haven't kicked me out of the party yet, so to speak.
    What is the best surprise to come of this? An unplanned break helped, rather than hurt business. In July, I wasn't teaching, and I had a few contracts ending in June. I had almost no work lined up but I had two trips planned and I was freaked out. I decided to just give into it, taking the month to relax, travel and be inspired, and made a commitment to get back on the horse August 1st. That first week in August, I secured two new accounts and it's been pretty lively since. I realized I had never taken more than six days off. After the break, I was refreshed, energized, focused and committed.
    How do you definite success? I define success by the evolution of growth - taking risks, facing challenges head on, creating and seizing opportunities, solving a problem. Personally, I don't measure success by a bank account or staff size, but by the effort and impact the work has made, and if I feel good about it. If I can't get behind it, who will? At the end of the day, you gotta do you.
  • Searah Deysach, 40, Rogers Park
    What do you do? Own a feminist sex shop.
    What did you do previously? I worked in the Continuing Studies Department at the School of the Art Institute.
    What was the moment you knew you had to make a change? When I realized that with my art degree and lack of artistic drive that I was looking at working in offices the rest of my life. Also, I spent pretty much all day talking about sex at work anyway and thought I should make THAT my job.
    How do you definite success? Still being in business after this long of a time and still loving my job every freaking day. I may not make a lot of money but I look forward to going to work and that is awesome.
  • Malik Turley, 42, Evanston
    What do you do? Own Hip Circle Studio, a dance and fitness studio for women and families, which grew out of my work as both a doula and a bellydance/fitness instructor.
    What did you do previously? I spent a decade in technology, as an end-user trainer and a techy (tech support, network administration). I took an intermediate step away and worked in the social service arena for two years before going out on my own.
    What was the moment you knew you had to make a change and leave your previous job? When I went from attending a birth to a day full of teaching adults how to double (as opposed to single) click.
    What is the best surprise to come of this? Seeing the benefit of the time I spent in the corporate world in helping me make this venture work. It seems so far from what I was doing that it was surprising to discover some overlap.
  • Brian Hofmeister, 38, Andersonville
    What do you do? I am an artist and I also own a for-profit artist's collective which specializes in live art as entertainment for private events called Atomic Arts Studio.
    What did you do previously? Small business owner with partners.
    What was the moment you knew you had to make a change? The business I was in was the result of someone else's passion and instigation; I was just along for the ride. I knew it wasn't something that I wanted to do for the rest of my life, but I didn't know what I wanted to do instead that would allow me to live and make a decent wage. When I came up with an idea that I thought could incorporate stuff that I love (art and working with other artists) with the possibility of making money, it was really all that it took.
    How do you definite success? Success is being able to find something you love in what you do while being able to live the life you want to live, while seeing in the horizon that there is the possibility for more of both of those things.
  • Kiam Marcelo Junio, 29, Pilsen
    What do you do? Yoga teacher, visual and performance artist, videographer, photographer, graphic and fashion designer.
    What did you do previously? Hospital Corpsman in the U.S. Navy for seven years.
    What do you wish someone would have told you about making this leap? That no one is going to be an advocate for you if you don't do it for yourself. That it takes faith in one's self to see it reflected from others. That life constantly showers us with opportunities to change, even change just the way we think, and it is up to each person to decide what to do with that creative power. I wish someone had told me that free will and collectivity are not mutually exclusive.
    How do you definite success? There was a strange comfort in the security that military service provides. You are told where and what to be and how. Things are defined, your job is clear. I was successful in those terms within the military because I knew what I had to do to advance myself. But I see success differently now. Navigating the world with free will and having the space to explore my own boundaries is true success. Having the capability, love and support to nourish you is success. For me, it has nothing to do with monetary wealth or comforts, or status or rank. To be able to live happily is the greatest success.
  • Jeremy Leven, 28, Logan Square
    What do you do? I am the chef and founder of Tuesday Night Dinner, an underground supper club hosting pop-up dinner events in Chicago.
    What did you do before? I was a paralegal working for a law firm in the loop. I had gone to school for Poli Sci at Champaign/Urbana.
    What was the moment you knew you had to make a change? One of the younger attorneys invited me out for beers after work with some of his attorney friends. Sitting around listening to them talk about their bullshit, I knew that I couldn't do it. It wasn't me. That wasn't the life I wanted. Shortly after I took a trip to Chile to visit family and had one of those "pacific-ocean-a- ha!' moments. Returning to the law firm, I knew I was done. That was October 2008. In January 2009 I left the job and began culinary school full time at the Illinois Institute of Art.
    What do you wish someone would have told you about making this leap? It's going to take a long time, and you have to constantly fine new ways to reinvigorate yourself with these challenges. But don't despair because what you are doing will have a tremendous impact on people, and it's f*cking worth it!
  • Christy Tyler, 32, Albany Park
    What do you do? My husband and I are wedding and lifestyle photographers.
    What did you do previously? I worked at a real estate tax law firm downtown. (James managed a camera store when we met and was laid off during the recession in late 2009 shortly after we got married. He had trouble finding work again so he decided to go back to school and is still in school part-time now.)
    How do you define success? Success for us is about living a life we're proud to tell our future children about. Success is doing something that we are passionate about that hopefully we can manage to pay our bills with, and not just working a job we dislike because it pays the bills. It's about spending more time with our family and each other than we used to spend with our co-workers every week. It's about working with clients who love us for us and for our work, and creating work we're proud of that they can pass on for generations. It's about helping people realize that they are beautiful and making them feel good about themselves. It's about never getting so busy making a living that we forget to make a life together. I guess basically it is just doing what we love and hopefully inspiring others to chase their dreams too.
    What is the best surprise to come of this? That we've been able to make this work! I was afraid of failure for a long time (and still occasionally am from time to time). Also how much time I get to spend with James working together day in and day out, and how much we enjoy being together all the time, working towards this goal together. And I've loved how much we've gotten to travel together because of this job recently and that we get to do that together!
  • Masha Alexander, 41, Printers Row
    What do you do? Consultant and owner at Social Good, Inc. working on dream projects with nonprofits in the arts.
    What did you do before? I was a digital strategist and project manager at a large marketing communications firm also working with nonprofits.
    What is the best surprise to come of this? When you do what you love it really is possible to jump out of bed on Monday excited to get to work. And event the challenges, and there are many that I've encountered in learning to run my own business, can be invigorating. I've never worked harder in my life, at anything, or enjoyed it more. That's a surprise.
    What do you wish someone would have told you about making this leap? What I wish someone had told me is that people buy big projects when you've earned their trust and that in the meantime it's important to have services at various price points. That and that you're going to be failing for a really long time, but that it's normal.
  • Gregory Berlowitz, 42, Rogers Park
    What do you do? I am the founder of Chicago Cooperative, a start-up large-scale and full-service grocery cooperative.
    What did you do before? After college, I started a theatre company with a group of friends; I eventually abandoned the theatre to pursue writing fiction. To support myself, I waited tables at some great restaurants in Chicago: Harvest on Huron, Everest, Blackbird. I went to law school when I was 32 with a desire to work with organic farmers and food safety advocacy, and I ended up working as an environmental lawyer for two big Chicago law firms for about seven years.
    What is the best surprise to come of this? That so many people in Chicago are excited for the co-op to succeed, and motivated to help make it happen. And that I’ve met so many amazing people who have made the same leap/life-change I’ve made.
    What has been the biggest challenge for you? Aside from transitioning from a pretty good income to making exactly nothing, it’s hard to move as quickly as I want to when everyone I’m working with is a volunteer with busy lives and full time jobs. And sometimes thinking about the cost of something I previously took for granted: like beer.
  • Sharonmelissa Roberson a.k.a. Chef Fresh, 30, South Shore/Rogers Park
    What do you do? I'm a community-based activist especially around food justice issues, a chef and social entrepreneur. I'm currently working on a community cafe project, Fresh 82 Cafe. And I'm the @MuppetLyft driver.
    What did you do before? I was the program director and chef for a senior center in the Near North/Old Town neighborhood that had been open for over 40 years.
    What was the moment you knew you had to make a change? I loved the work I did, but I knew I needed to start my own thing for a while. Sometimes there are so many obstacles to actually serve the community in non-profit work. I kept getting resistance when I wanted to create and develop programming in ways to really serve the community in areas they wanted and needed, not just do things that were "easy" and the same.
    What do you wish someone would have told you about making this leap? There's a line in a Dead Prez song I like that says simply: "Just cause you work for yourself doesn't mean it's gonna be easy." This is a 7-days-a-week, 24-hour-a-day job really. You're always thinking about your business. And you dream about it when you get to sleep. I'm waiting for the magic formula to figure out how to find that balance between all the work that needs to be done and the time I need to set aside to take care of myself.
  • Rex Brink, 26, Lincoln Square/Logan Square/West Loop
    What do you do? I take pictures, mostly of graffiti, protests, and textures. I tag from time to time. I'm spending a lot of time writing and revising.
    What did you do before? I worked for Whole Foods for 3.5 years, and I spent the huge majority of that time working as a cake decorator.
    What do you wish someone would have told you about making this leap? DO IT SOONER. YOLO. (No for real, I've got that tattooed on my left hand.) I don't want to sound like a hipster/millenial/complete cliché, but at some point you have to realize that the things we're "supposed" to do with our lives are abstractions and constructs. We're "supposed" to chase money, and I think this generation has seen really clearly how that can go wrong, and we've come up with some really great alternatives to that particular way of life. When you figure out a way to not just live and survive but be able to really provide for yourself without spending a whole lot of money, you end up being able to do what you love for very little compensation while building a portfolio or a resume or a set of life experiences that'll be the foundation for a real career doing something you'll be happy doing.
    How do I define success? I consider myself a success whenever I manage to accomplish the things I have to do and the things I want to do in any given day or week, no matter how big or small they are. I feel like a lot of definitions of "success" assume some very large, ideal goal to accomplish; that they envision some way of being that is ultimate and final and sort of utopian. I cannot see my life or my journey that way. I know well enough that things are going to change all the time, so it's not about working toward some goal, it's not about achieving that goal and calling it "success," it's not about trying to shove your life path into your "success" goals and guidelines and make some idea of yours happen no matter what obstacles pop up in your life. It's about accepting what you want and what you need TODAY and doing whatever it takes to make it happen. You'll figure out what success was for you at the end of your life, so long as you just keep doing what's right for you day by day.

For more inspiring stories of people redefining success beyond money and power, visit the Third Metric.