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Meeting at the MAC

Last week, I was able to do something that most nearly-college-graduates searching for a job dream of doing: I spoke with a former CEO of a fortune 500 company. My job search has taken me on some pretty interesting adventures so far, from informational interviews at some of my dream employers in the Portland area to job offers and salary negotiations that left me feeling discouraged about how much my work experience is worth.

It was around the point in any job search that I felt like taking a break after spending hours filling out applications, meeting with potential employers and not getting many calls back about most of the positions I applied for that I first spoke with this family friend. He suggested that I come up to Portland for the day and talk with him about where I was and what I was looking for, so at 7 a.m. on Friday, I caught the MAX train downtown from a station near my parents’ house and was off to what turned out to be one of my most encouraging meetings.

At the MAC Club meeting with "Bob"

After nearly 3 hours of talking and drinking an endless supply of coffee he had reprogrammed the way I was approaching the job hunt and inspired me to follow several steps that would help guide me to achieve two of my biggest goals in my work life – to run a company and to work for myself.

Up until my meeting with this CEO (we’ll call him “Bob” for the purpose of this post), I had formed a great deal of my opinions and expectations of what a job after college would or should look like based on my formal education in public relations and my experiences working as an intern for numerous Eugene and Portland business. In most of these experiences I had learned that being the best at what I did and specializing in my craft was the key to post-graduation success and I approached job searches the same way, seeking out positions that were in-line with my experience with a primary focus in communications.

Five minutes into our meeting, Bob asked me to describe myself and what I was looking for. The first word that came to my mind was “entrepreneurial.” He asked me why, and I was reminded of some of the things that I had been reading in Timothy Ferriss’ book, “The 4-Hour Work Week.” I explained how I had grown up with a father who worked in real estate while working full-time as a checker at a grocery store. I’d tag along when he had open houses on the weekends and helped him collect signs at the end of a long day of showings. I remembered how much he hated waking up early every morning to go work at his 9-5 position and how excited he was when the weekend came around and he could make his own schedule.

It was this fear of being on someone else’s schedule that propelled me to pick up “The 4-Hour Work Week” and was ultimately drove me to describe myself as “entrepreneurial,” or in more direct terms, seeking positions that allow me the freedom to work on my own without conforming to “normal”  9-5 working conditions. I had bought into Ferriss’ explanation of the “NR” or “New Rich,” people who had found a way out of normal working conditions to lead extraordinary, adventurous lives on their own time. I liked his analysis of retirement and how so many people work through their youth so that towards the end of their life they can finally take a break. I appreciated his concept of “lifestyle design,” finding creative ways to reduce stressful work habits and regain the luxury of time. I found the whole thing to be romantic, but more importantly, I didn’t want to end up in my dad’s position, spending the majority of my time doing something I didn’t enjoy on someone else’s clock.

I’m not saying that I expected to be wealthy and self-employed right out of college, but Bob caught on to goals of running a business and working for myself almost immediately, as tactics to avoid working for someone else for the rest of my life and redirected our conversation to how I can accomplish those goals, and what I can do right now that would put me on a path to achieving them. It was at this point in our conversation that he told me something that changed my approach and gave me a new perspective on what I need to do now so that I can live the professional life I want later. He pointed to a table full of older men towards the front of the café and said “over there, at that table, there are 4 former CEO’s, and if you want to accomplish the things that they have accomplished and that I have accomplished, you need to make a list of your weaknesses and find a way to turn them into your strengths.” He pulled out a piece of paper and started drawing a map of a typical organization. He pointed out that all of the positions and experiences that I had had fell under the “Administrative” category and that if I wanted to lead an organization, I would need to understand the other two branches: Production and Sales.

It’s a simple concept, but becoming a “generalist” as he put it and it serves as my new foundation for this job search. Aside from expanding my options to positions outside of communications and public affairs, I think that trying something new might lead to a more enjoyable, less rebellious work experience.

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