Confessions of a Workaholic: Turning Work Experience Into Expertise

I’ve never only held one single job. Ever since college, I’ve always balanced freelance and side work while being fully employed in either a full-time job or school.

I have Craigslist to thank– I am a Craigslist addict. To me, Craigslist is not just a site, but a gateway to a world of opportunities, and I’ve probably applied to and been hired to over 30 jobs and gigs on Craigslist. Even though I did go to college, I would say that I learned more lessons and real life skills from Craigslist than I did at UC Berkeley.

In college, I worked for the school paper and tutored at the same time (a job I found on Craiglist), and at one point also juggled a part-time legal assistant position (Craigslist) and some freelance design work (from Craigslist). It paid the rent, and it provided me with the kind of stimulation I love– new and diverse challenges that weren’t just in the classroom.

After graduation, I was gainfully employed in corporate marketing for a company in San Jose not, I feel, because I was a UC Berkeley student, but because I had so much job experience. Yes, the degree did help, but I felt it was just the bare minimum, and what helped me stand out was my long list of extracurricular ventures.

But even when I got my first full-time job out of college and didn’t really need any extra income, I still did graphic design on the side and eventually applied for not one but two tutoring centers in the area (Craigslist). I loved teaching and didn’t quite want to let that go, and built a network of students and parents through one-on-one and group English enrichment classes. My routine was to work my 9-5, then drive to Cupertino 3+ times during the work week and once on Saturdays to tutor.

My definition of “free time” was always time I could be working on one or more projects, whether it be designing an SAT curriculum, creating a new layout for a flyer, or noodling a problem with the corporate budget. I found that the problem with this isn’t that I was driving myself insane. I thrive on this kind of activity and still do. The problem with being a chronic gig worker is a lack of focus.

While my resume may boast a long list of diverse employment, I feel that only recently have I really begun to focus on a singular career. I learned a lot in corporate marketing, as a project manager at a startup, as a customer service representative, as a legal assistant, as a graphic designer and a tutor and a writer, but all these lessons don’t add up to expertise.

While at that corporate marketing position in San Jose, my title was Corporate Marketing Specialist. When I knew I wanted to leave, I began looking at job postings (on Craigslist) of positions I could transition to, and I saw that “Project Manager” was a way I could do that while leveraging what my current job responsibilities were. I convinced my manager to change my title to “Marcom Project Manager,” which I felt was more accurate anyway, without asking for a raise. Eventually, I was able to secure a position as Web Development Project Manager at another company.

I also ended up dropping the tutoring and moving to San Francisco, where I was hired to be a graphic designer on the side by a few bars and clubs. My role at the new company also changed to Editor, and I was dealing with more content and copy. It is here where I truly felt like I could gain not just just experience, but expertise– my main job and side jobs were for the first time coming together under a common set of skills: copywriting, design, and web development.

And here is where I stand now. My fulltime job is now at a marketing agency where I do web development and design fulltime, and I also have a few clients of my own for which I do copywriting, SEO, and design. I don’t tutor or coordinate or project manage– though all those past professions have provided invaluable experience. Now, I’m a writer/designer/developer, and while I might still hold multiple jobs, at least now I’m focusing more on an area of expertise.

To anyone finding themselves working many different side jobs like I did, or having trouble finding what it is they want to do, I would advise that you try to find your focus of expertise early, and start working towards it even if it’s not your primary profession. Think of your career like a ball of clay– you can mold and remold it as you go along, working on different parts of it and strategically cutting and adding to it until it begins to resemble the shape you want.

Don’t make the mistake of equating your current job with your career, or equating your current job with your identity– you are not defined by a single company or by an explicit or implicit org chart. What you do with your hands and your time is completely up to you. Have a vision of what your career could look like, and use every opportunity that comes your way to get there, even if it might be a little unconventional.


2 Responses to “Confessions of a Workaholic: Turning Work Experience Into Expertise”

  1. Bernadette B says:

    Hi there,
    Your word are wise beyond your years. My path has been winding but much more single minded. I wish i had had more determination to work on the hobbies that interested me. I was too busy partying and travelling! :) but i shall heed your advice now…its never too late.

  2. Katalin says:

    Hello Jessica,

    I love your point of view in things. I went to Uni couple of years ago overseas, although up to now I’m not sure If I did the degree that I liked.

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Jessica Chan
Jessica Chan is a graphic designer ( and Creative Director at Demand by Design, and enjoys running, dining at new places, traveling for fun, reading books on her iPhone, and staying fashionable. A devourer of fashion sites and beauty blogs on the one hand, and an avid listener of public radio and NPR on the other, Jessica is constantly filling her short-term knowledge to capacity with both the latest trends and the latest public issues. She was born in Canada, raised in LA, went to school at UC Berkeley, and has been living in the Bay Area for 8 years.