Dream Job: 3 Awesome Locals And How They Got Their Gigs

If you're over talking about the recession, the job market, and how to write a better resume, well, it's time to get a little more hands-on with your professional pursuits. Meet three successful Chicagoans who have the jobs they always wanted. We're getting all the goods on how they got here, why they love what they do, and how up-and-comers can score a dream job of their own. Take notes, take aim, and then take over Chicago. We'll be watching!

What exactly do you do? "I own Outfit Chicago, a contemporary women’s apparel showroom, along with my partner, Jules Branaghan. We represent fashion brands for the Midwest and manage all sales to boutiques in our 11-state territory. We cover a broad range of women’s apparel categories including denim, cashmere, pants, leather, printed tees, and several collection lines. Our job is to show these brands to buyers at boutiques and department stores and help create an assortment of merchandise that will appeal to their specific clientele."

What tips do you have for a young person trying to follow in your footsteps? "Be persistent. This is a niche business and sometimes it can be difficult to get your foot in the door. We bring in interns—most often students studying fashion in the city—to help us at fashion trade shows. This is a great opportunity to get an inside perspective into the wholesale side of the industry, and particularly to gain access to an event that is not open to the public. Most showrooms in the city also take interns throughout the year and this is a great way to network, gain experience and potentially land a full-time position. Our first employee started with us as an intern and proved to be indispensable to us, so we had to hire her!"

What was your previous job? "I worked as a 'road rep' for two different showrooms in Chicago, before opening my own. I basically managed all direct sales. It was a natural progression to eventually open up my own showroom. Through my positions, I got to know all of the stores and buyers in the Midwest, and met professionals in the biz that would later become influential in many aspects of our success."

Did you ever have a "big break?" If so, what was it? "My 'big break' was getting the call to come in and interview for my first position with a multi-line showroom. I had submitted my resume months before, which they had luckily kept on file. When an opportunity opened up, I was working at a boutique in Chicago, maintaining all of the displays and visual merchandising. The owner of the showroom took note of the new look in the store and offered me the interview."

What is the biggest challenge in your job? "The biggest challenge is maintaining the ability to multi-task. You have to wear many different hats throughout the day. It is a constant juggling act to try to maintain a balance between all of the responsibilities of running a successful business. I am unbelievably thankful to have an amazing partner who helps to maintain this balance."

What is the best part about your job?

"I absolutely love working with my buyers and helping them put together their orders. To be responsible for helping other small-business owners achieve success is an incredibly rewarding experience. Some buyers I have worked with for over five years and they have become true friends. It's all about the relationship and connection to others who share this passion for fashion."

What exactly do you do? "I live life and do whatever sounds like a fun time. I started off as a 'designer' and floated into photography, which is one my bigger passions, and all that ended up leading me to different creative endeavors that allowed me to get out the ideas that I am always coming up with. I have done many things over the years; been a recording artist, opened my store, RSVP Gallery, and launching an events company @superfun. My role in each of the projects is different. Overall I think if I had to be pinned down as doing something exactly it would be lending my taste level to creative projects and bringing my personal touch and knack for creative problem solving to the project."

What tips do you have for a young person trying to follow in your footsteps? "I have always believed you are only limited by your mind and, with that, your imagination, too. Start exploring today. Don't be limited by what others tell you or what is ordinarily accepted. I would never make it my goal to be ordinary. I believe in being in the practice of executing creative ideas rather than spending too much time 'planning' and never executing anything. My belief is with every execution, you learn from the mistakes and get in the habit of making each execution better. Also, backup plans don't exist, maybe in the back of your head, but ignore that and devote yourself to your passion. With RSVP Gallery I had sooo many obstacles that kept popping up and signs saying it would never work, but I believed in my dream and I had to create my own reality."

What was your previous job? "I worked as a maître d' at restaurant downtown and I was training to be a restaurant manager. The funny thing is one of my mentors, Daniel Faylor, kept telling me I wasn't going to enjoy it and that I should be doing something 'bigger' and I didn't want to hear it. He probably believed in me before I believed in myself, which is always helpful. Thanks to him! However, the restaurant business is something I could still see myself getting into one day, and my days working in the restaurant business prepared me a lot for leading a creative team."

Did you ever have a "big break"? If so, what was it? "I would say I have had two "big breaks." Getting fired from the restaurant was a blessing in disguise, it gave me the opportunity to take the plunge and start working for myself. The other was getting my first freelance job doing Leaders 1354's website. I had never done a website, but I had heard the story of Bill Gates' first big break of promising IBM he could make MS-DOS before he knew it was a reality. So, I just took the plunge and that opportunity allowed me to meet lots of friends and associates I still work with today."

What is the biggest challenge in your job? "For me, the biggest challenge is organization. I have so many people contacting me every day and to remember who I have to call back, and meet with, etc. I have a really good memory and relied on it for too long, but writing things down is now essential for me. I am also not the biggest people person. Many would find it hard to believe I am shy, and I often times find myself not wanting to talk to people. However, my life thrives on good communication, so that is one of my biggest hurdles."

What is the best part about your job? "The best part of my job is that it never really gets too boring—I don't do the same thing for too long. RSVP Gallery and @superfun are the longest endeavors of my life and they are never the same, so it always stays interesting. I love being able to creatively problem-solve any issues and always keep both @superfun and RSVP Gallery evolving. Also, one of the best perks is meeting like-minded creative individuals from all over the world. In all different industries, from fashion, to music, to film, to design, I have had the opportunity to see some amazing things behind the scenes and meet a lot of people I have always looked up to and admired."

What tips do you have for a young person trying to follow in your footsteps? "Network and let people know who you are. I get the majority of my business and opportunities through referrals and friends talking to friends. You need to be in front of people, let people know what you are looking for, and make an impression. It is fun and exciting, and will pay off. Also, have a presence on social media. I usually try to blog, Tweet, or Facebook what I am doing daily. People do notice what you are doing and it is an easy way to build your credibility."

What was your job before this one? "I have worked at Fig since I graduated college, seven years ago. Yikes! I started as a video editor, moved into managing our video production, and then, always having a passion for music, sort of fell into DJing. My boss James held an awesome vision of me being this great, hot female DJ, and I really took off from there."

Did you ever have a "big break"? If so, what was it? "I think one of my big breaks was when Jam Productions asked me to open for Samantha Ronson, and be her backup at one of the opening parties at the Art Institute's Modern Wing. This was when Sam was hot, and I got to do an opening set, up high on a scaffolding platform before the Modern Wing was open."

What is the biggest challenge in your job? "I think being a female DJ is a challenge and also a great asset. It is a very male-dominated field, and I would say at every other event someone will tell me they have never seen a female DJ. I feel I am constantly trying to figure out how to play into being a female DJ while be authentic to myself, and letting my skills and music define me."

What is the best part about your job? "The best part of my job is how versatile it is. For example, this week I DJ'd a book launch at the W Hotel, tomorrow is a huge 3,000-person fashion show, and then Saturday I am DJing a meet-and-greet with Rachel Roy—that is just one week! I get to attend so many cool events, work with amazing people across the city and in many fields, and it is never repetitive. I also just have a huge passion for music, and usually at every event, I am feeling the party, the vibe, and the music just makes sense. I love that moment."