Getting the Career You Want, Part 2: Deciding you want more

June will mark my third anniversary with Portland. July will mark my third anniversary with my job.

Most jobs I’ve had have had predetermined expiration dates. Not most, all, in fact. Every job I’ve ever had has been a student job. For all of them, with commencement came resignation. Until now. Nothing is stopping me from working the same job indefinitely, except me.

I love my work family—the owners, my co-workers, the regulars. But I can’t stay forever. There’s no real opportunity for growth, no big promotions and raises, no 401k, no health benefits. This job is not a career. And even if it was, it’s not my career.

I want more.

I need to find a job that I am passionate about. Bear calls it your “happy job.” I need to find hedone in work, something I forget about even though I have the word permanently affixed to my body.


I started looking for a new job nonchalantly about a year ago. It wasn’t serious. I wandered through craigslist, indeed, and idealist to see what was out there. Occasionally something would catch my eye, but I don’t remember actually submitting any applications. It was just a flirtation.

Eight months ago, I submitted an application just to test the waters. I didn’t expect to get an answer, and when nothing came of it, I was only mildly disappointed. You see, while I was flirting with the idea of a new job, I felt staunchly loyal to the one I had (and have). These people had given me my first paycheck in Portland, as well as a second home, and friends when I could count the number of people I knew on one hand. I felt guilty for thinking of leaving them at all.

Five months ago, I submitted an application for a job I wanted. I didn’t tell my bosses. I didn’t want to get my hopes up, and I didn’t want to tell them anything prematurely. Why stress them out with the possibility of my resignation. Nothing came from that application either. But, I was no longer flirting. I loved my work, but I was discontented with my job. I was ready to start wholeheartedly applying to things. I sent in another two applications for jobs without tell my bosses. Can we contact your current employer, applications asked? No, I replied, you may not.

Three months ago, I was having dinner with one of my oldest friends in the world who always happens to live in Portland. He was convinced by the end of our meal that I should and could get a job at his work. I waved away his zeal with a humility soaked in self-deprecation, but he was adamant. The idea stuck in my head and I kept my eye on the employment page for his company. When a job opening arose, I sent him a text about it. His response was full of exclamation marks and a promise for a letter of recommendation. This was the first application that seemed not impossible.

I spent a week wrestling with the idea of telling my bosses. I had seen them burned so many times by employees that I was scared they’d be mad or hurt that I wanted to leave. But, as I thought about it, I knew I needed to talk to them. Always a better writer than speaker, I wanted to make sure I said everything I needed to. So I sent them an email:


A job opportunity has presented itself in the last week. A friend from high school works at a company downtown that might have an opening for me.

Nothing has happened yet. I haven’t submitted an application. But I will be because this is a job I think I’d be really good at.

I thought about not telling you guys about it, mainly because it seemed premature. I didn’t want to unnecessarily stress you out about something too soon.  But. Then I remembered that you guys are more than just my bosses. You guys are my family, and you want me to succeed in my life. Why wouldn’t I want to tell you?

Also, whether it’s for this, or another job, I want to give you as much time as I can to process and prepare. I am willing to do whatever you need to ease the eventual transition. I have no intention of leaving you scrambling.

I’d like to be able to tell the HR people at the job that they contact my current employers. I don’t want to do any of this secretly. You’re family and I want your blessing 🙂


I sat down with my bosses the next day and they told me that they loved me, wanted me to be happy, and know that—while they’d keep me on staff indefinitely if they could—they knew I couldn’t work there forever. With their blessing and the promise of a glowing recommendation, I applied for that job.

More than that, my secret was out. I was looking.

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