Career Counseling, or the Story of my Winding, Rocky, Bumpy, Not Very Traversed or Well Cleared Career Path

Insert Inspirational Quote Here
18 months ago I quit my job at a large investment firm in Boston. I spent nine years at this company, where I started on a three- month temporary receptionist assignment, and ended up in a mid-level position managing event technology and supervising day to day conference support. At some point, over those nine years, without my realizing it, my job had become a career of sorts.

One night, I was working late—something I did often—supporting a talk that one of our U.S.-based investors was giving to our Asian offices via videoconference. The talk was part of a series called "Lessons Learned", during which senior executives shared personal and professional anecdotes and offered advice. This particular investor happened to be a career changer, and prior to becoming an investor was a doctor. Aside from marveling at how relieved his parents must have been with the sentence that followed, "I don't want to be a doctor anymore", the part of his talk that resonated with me was the moment he realized he no longer wanted to be a doctor.

I'm paraphrasing here, but he was at a work event, looking around the room, and he realized there wasn't a single person there that he aspired to be like professionally. In the weeks that followed the talk, I found myself thinking about this sentiment at every high profile event I supported, and in every meeting I attended. During this time, many of my peers were enrolling in MBA programs, or studying for the CFA—an exam for investment professionals that, when passed, makes people think you are an even more professional investment professional. They were also receiving promotions and officerships from the company, and initially I was a little jealous and confused as to why none of these things seemed to be gelling for me.

Around the same time, my manager accepted a role at a different company, and another colleague—my work spouse—departed under less than awesome circumstances. Day to day conference support was being transferred to a different team, and suddenly I was responsible for overseeing two separate teams of consultants, and working with managers on multiple teams to document and assist with the knowledge transfer. I wasn't sleeping Sunday nights, because I was so anxious about the next five days. I tried talking to my new manager—my former manager's manager—about it, and admittedly was more emotional than I expected or wanted to be. I later found out he'd made fun of the incident during a one-on-one with one of my teammates. I wasn't learning on the job, or enjoying my time at work nearly as much as I had in the past, and I was no longer proud of who I was as a professional.

Perhaps if there had been any forewarning about any of this, I would have felt better prepared to handle things emotionally and professionally. But there wasn't, and I wasn't, and eventually, my decreasing passion and increasing stress levels converged. So, I gave four months' notice, and decided to close the gap on a long distance relationship by moving to Austin.

Last Day on the Job
This is the entry I put in my calendar for the sake of accountability.

As it turns out, when you decide to change careers, it can be incredibly helpful to have an idea of what you'd like to do before quitting your job and moving halfway across the country. I also most definitely took for granted the significance of the social capital I'd taken thirteen years to build in Boston. I conducted a very passive job search prior to moving, and attempted to network once I got down there, but without being able to qualify at least an idea of what I was interested in doing, I sounded wishy washy and didn't do a good job of selling myself. I spent five months trying to figure out my dream job, then trying to find any job, eventually landing a contract support position through a former colleague of Casey's.

At first, the cube farm felt like familiar territory. Conversations over coffee in the break room and corporate buzzwords were well within my wheelhouse. I liked the people, and they liked me. They even asked me to interview for a full time position that had become available. For a split second, it seemed like a great idea, but as I thought about every email I received that was a "Reply All" or a reminder to wish a person I didn't know a Happy Birthday, I was reminded that familiarity isn't always a good thing. I declined the interview and eventually left that job.

During the last couple of months in my contract position, I'd started working in the taproom at one of my favorite breweries in Austin. Despite doubling production every year over the four years they'd been open, the brewery was still relatively small, and I saw an opportunity to put myself on the path to achieve a career goal I'd written off almost a decade ago. I loved going to work. I was able to learn and talk about beer on the job, I met so many members of the incredible Austin beer community, and I found the motivation to educate myself outside of normal working hours. I felt like I'd finally found an industry that gave me the drive I was lacking in my previous career. Being away from a big corporate job without the salary or the benefits had allowed me to find my passion. Unfortunately, as time went on, growth opportunities didn't seem as readily available as I had hoped, and my chances of moving beyond the taproom any time in the near future were slim to none. I also realized that I hated living in Austin. So I left that job, and I left Austin.

Arriving in Asheville, I was able to use my experiences in Austin to formulate a more effective job search strategy. I also developed a strong appreciation for how difficult it is to break into the beer industry as someone new to the area. The one day I spent cleaning kegs at a small brewery downtown, two people came in to drop off resumes, one suggesting he'd be willing to work for free, and it seems like any time I'm somewhere that makes or sells beer, at least one person walks through the door looking for work. I'm not completely abandoning the idea of a career in the beer industry, I'm just taking some steps to turn it back into a hobby so I can go out and enjoy a few beers without putting pressure on myself to hustle for a job.

I recently accepted a position managing a small dance studio about ten minutes from our house. As someone who has always had a special place in my heart for the arts—dance, in particular—I'm excited to bring my organizational and customer service experience to the studio. There's also a ton of potential, once the administrative dust has settled, to flex my marketing and social media muscles, and I love that there seems to be a huge opportunity to grow the role. Will this make me rich financially? Probably not, but I do think there's a good chance it will make me rich in experience.

I don't really know what my point was in writing this. It's something I think about a lot, and I figured since a lot of people change jobs at the beginning of the year, maybe it's something on other people's minds at the moment too. I have read a ton of career articles about people who make a big change and find their dream job, but, from what I can tell, that's not really how it works. When I first quit my job, I was ecstatic. Then, as time went on, I started getting bored, money was going out but not coming in, and then I started getting worried. I found jobs that didn't challenge or compensate me, and then I started getting frustrated. Then worried again. But the one thing I've noticed is that I have never missed my corporate job.

An interesting thing happens once you remove yourself from a routine you've had for almost a decade. You suddenly start thinking again, and I've thought a lot over the last eighteen months. Do I feel entitled, or that I am owed something? Not really, but sometimes I do get discouraged that after four years of school and nine years in the professional world, I rarely hear back from jobs I've applied for, or at most, receive some sort of form rejection email. When I have money-related concerns, it's easy for me to think back to my corporate life, and how money wasn't something I had to worry about. I wonder if I shouldn't have stayed for another year, or at least stuck around to receive another year-end bonus to pad my savings account.

It's so easy to forget how miserable and bored I was there, because shit gets kind of scary when you go from a situation that was seemingly reliable and stable to something that is much less certain. It's so easy to feel like a loser when you're in your thirties and essentially starting over, despite not being entirely sure what you're actually starting. But—and I don't know how to say this without sounding like a complete douche—it's also incredibly freeing to hear that former colleagues and friends who've talked about hating their jobs for years, still hate their jobs—confirmation that some sea change or paradigm shift hasn't occurred and magically made things suck less.

Even though it's a little terrifying at times, I'm reminded that the decision I made was the decision that was right for me. And now, whenever I fly into panic mode over my employment situation, I've got some reading material to help talk me off the ledge.