One of the questions I get asked most frequently is, ‘How did you start working for yourself?’ The truth is, it wasn’t really planned. There was a certain sequence of events fueled only partially by me that lead me to start my own business. That said, now that I’ve had some time, I find it so fascinating to look back over the jobs and positions I held prior to working for myself to see how everything lead up to where I am today. There are definitely some common threads and indicators, which make it clear why what I’m doing now is such a good fit.

In high school and college… I worked in retail a bit and waitressed in several restaurants. I hated working in retail because it felt like the same thing over and over, but loved working in restaurants because it was very go go go- you were always on your feet making things happen. Working in a restaurant felt like a performance or event- the waiters, food runners, bartenders, and kitchen all had to work in a synchronized manner to produce an exemplary dining experience. I loved the feeling of working behind the scenes, which is very similar to event planning.

Right after college … I was just looking for job. Shortly after I graduated I landed a position as a marketing associate for a healthcare consulting firm in DC. I had absolutely no interest in healthcare, but looking back it’s clear why I both enjoyed and excelled at the position. Number one- there were tons of marketing associates but I happened to be on a team that was marketing products and working with clients that were completely different than anyone else. That made it feel like I was part of a small company within a larger company- very entrepreneurial- which I loved. Two- I had a great boss and co-workers that worked efficiently and just got stuff done. Even though I wasn’t extremely interested in healthcare consulting, I enjoyed it and wanted to succeed because there was no nonsense or drama and people truly cared. It’s become very clear to me that my work environment and the people I work with are just as important (if not more important) than the exact product I’m marketing, content area I’m working in, or type of event I’m planning.

10 months later… I was offered the position of marketer or Associate Director. As an associate I was paired up with a director. Now I would actually be the director- going on sales calls and meeting with healthcare executives every month to sell company products. I was not thrilled about the prospect of being on the road 80% of the month but the higher salary made me think I would like the position enough to stick with it. Boy was I wrong! I was miserable. I was exhausted. I cried to Brandon and my mom all the time. I felt like I was failing. I lasted about 4 months, at which point I told my boss I couldn’t do it anymore. As daunting as it sounds, meeting with people two to three times my age and trying to discuss their area of expertise wasn’t the worst part. The worst part was actually trying to learn the products and content (hospital IT, HR, and philanthropy best practices- what?!?!). Nonetheless, this role gave me boatloads of confidence. Addressing a group, speaking publicly, and working with people who are much older than me (thankfully) come pretty naturally to me now and are all necessary for my current job.

The company was extremely generous and allowed me to stay on while I interviewed internally for other positions. But the ones available were even farther from what I wanted to do, and it became clear that it would be best just to leave on good terms.

So what next? I was unemployed for a month. I sat at home and got really honest with myself. I made myself identify what jobs I actually wanted to apply for, not what jobs I thought I should want. I kept coming back to event planning. I wanted a position in event planning. Even though I was scared to say it out loud because I thought I should want a job that seemed more intellectual, I started applying. A few weeks later I was fortunate enough to land a position as an event planner for a medical association in DC. I was thrilled.

For the next 2+ years…. I worked as an event manager, learning the ins and outs of the business, honing my skills, and gathering knowledge. I had a small team of co-workers, which meant you had to wear a lot of different hats and do a broader variety of work within the event space. So along with logistics and planning I did a lot of event marketing. I learned how to do everything from planning intimate VIP dinners for 15 people to city wide conferences with 8,000+ attendees. It was a really good job for me.

But during the summer of 2011…. we decided to move to New York. I had been itching to get back for a while and was seeking a more creative work environment in event planning. Because of our travel schedule last summer, there was this odd sort of break between the time we left DC and the date we were planning to move to the city- i.e. when I would start a new job. So during that interim period, I ended up doing some remote work for my old boss/employer. That was in July. In August we went away, and when I came back that remote work continued. I hadn’t found a new position in the city so I decided to stick with it until I found something new.

But I never found something new… that remote work grew into outsourcing full fledged events. An event I used to plan and market internally was now being outsourced to me. I was beyond thrilled. And I wasn’t just excited about planning the event, it was the fact that I got to do it on my own- and the prospect of doing this for other companies had me so excited. Once I realized that, the wheels started to turn. What if I could help other companies create, run, and market their events all the time? It became very clear that was my dream. Once I secured that first event, I decided to go for it.

In the next Biz Notes post I’ll talk more about the ‘how’- how I decided to go for it, what first steps I took, how I got my first clients, and so on. But in the mean time, if you’re struggling to figure out what you want to do in your career or which direction you want to take your business, I highly recommend picking apart previous jobs and really isolating what you did and didn’t like, and what you were really good at. And dig deep! Go back to those high school jobs and try and isolate something that could be an indicator for your work today.

And if you’ve already gone through this process, I’d love to hear how that worked for you!

Image via Camille Styles/ Image Credit

  1. It really is funny to look back and see how your past jobs and experiences have led you to today. I wouldn’t even be in graphic design if I had followed my friends and taken the computer class they took instead of the one I chose. I picked up valuable skills in the jobs I held prior to starting my own business, but more importantly, I learned what I DIDN’T want to do for the rest of my life.

    • Clara

      SO true! It definitely is half about figuring out what you don’t want to do.

  2. Love hearing your story and how it brought you to where you are today! It’s so true that our past can help point to our future. Can’t wait to hear more.

  3. Thanks for sharing your story…it is inspiring and great to get the inside perspective on how one starts their own business…always such a daunting idea!

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  6. When you are working, there is a higher risk for you to be unhealthy. You should be prepared and get yourself a health insurance.

    • Clara

      Hi Chris- not to worry, I do have my own health insurance :)

      • Cynthia

        A little bird tells me Chris sells insurance? lol ;^)

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  8. Thanks for sharing this. Very inspiring. I’m going to try that tip with looking back at old jobs.

  9. Cynthia

    I also work for myself and one piece of advice that always proved true is to find a need and find a niche, and become the best person you can to fill that need/niche. There are activities that we might not consider to be ‘chores’ or to be mundane . . . but there are others who will gladly hire someone to do those chores for them. And remember, no educational experience is ever wasted. All knowledge will eventually come in handy and will eventually be put to good use!

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