4 Crucial Questions I Wish I’d Asked Myself Before Changing Careers

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After I decided to quit teaching (which was not my first career), I yet again felt like a failure in the career department, and I realized that it was time to take stock of my situation and rethink my job strategy. I’ve had a fair amount of jobs in my day, including: teacher at an environmental after-school program, sales associate at a natural cosmetics company, babysitter, children’s educator at a botanical garden, volunteer coordinator, development associate, canvasser, baker, and men’s skincare maker (and those are just since graduating college!). Some lasted longer than others. And some were part-time. But none ever felt like they held a future, or at least not a future I wanted. I’d built a lot of skills in outreach, partnership development, event planning, and program management, but somehow none of the jobs that pulled these skills together felt right either.

I kept thinking that I just hadn’t found the right organization where I could flourish, or I just had bad luck graduating into the economy at the height of the recession. But I think the real reason for all of my ongoing career dissatisfaction was that I wasn’t approaching my job searches in the right way. Every time I changed careers, I wasn’t asking myself the right questions. And that’s why I kept feeling like I was never furthering my career.

After the panic attack that led to me quitting the Baltimore City Teaching Residency, I did not want to fall back into my old pattern of looking for jobs that I qualified for, whether or not they seemed like a good fit for me. It was time to rethink my approach and reframe the conversation. I did some soul-searching and really thought about what had gone wrong in the past, and how I could change in the future. These are the questions that helped my job search take shape:

1) What brings me satisfaction?

One of the fist things I realized is that external validation is really important to me. I mean, I knew this already (I can ride the high of a compliment for daaaaaays), but I’d never thought about how this affected my relationship with work. As I took stock of my employment history, I started to realize a pattern:

I’ve never really had a job where I knew whether I was any good at it.

At the non-profit, and at my Americorps job, I never had a direct supervisor or received a lot of feedback. I sort of worked alongside staff in various departments and semi-reported to the executive director. But mostly, I just did what I thought I was supposed to be doing and had no real external accountability or understanding of expectations. I’m a pretty self-motivated person, so that wasn’t even the real problem. The major issue was that I had no barometer of whether I was doing well, or if I was improving in the ways I felt like I should be. One time, after a particularly stressful event about eight months into my non-profit gig, a coworker complimented me on how well I’d handled it, considering I hadn’t had much guidance. I immediately burst into tears because I was so surprised to hear that someone thought I was doing well at my job.

2. What makes me feel satisfied/what gives me a sense of accomplishment?

For the majority of my adult life, if you asked me what I wanted to be when I grew up, my answer would be, “I want to work in a non-profit that’s doing some kind of good work.”

To me, this vagueness kept the doors of possibility open: after all, I have a wide variety of interests and I could see myself liking and being good at all kinds of positions. All I knew is I wanted to be a force for good and not leave work hating myself every day.

After my teaching program, I decided that non-profits didn’t have to be my only option. Instead, I needed to start thinking about what I actually like doing. And as soon as I shifted the conversation by asking myself what I enjoy doing, rather than what job I think I qualify for, I had a pretty big revelation: I get satisfaction from a sense of accomplishment.

I like finishing a project. I hate not knowing whether I’m doing something right. I thrive off of the measurable success that comes with a tangible endpoint. And once my brain put it that way, I suddenly realized why I’d had so much trouble in previous jobs. Aside from when I was involved in event planning, my tasks were rarely ever “done.” My work was based on intangibles, like making sure volunteers were satisfied or raising awareness of the organization.

My favorite days are always the ones where I finish something. Suddenly, my years of feeling frustrated in jobs made sense. Of course I felt like I was banging my head against a wall! I was going against one of the core tenants of how I derive job satisfaction. Once I realized this, it became clear that I had no desire to go back into volunteer coordination and that my goal of “doing some kind of good in some kind of non-profit” needed to get tossed out the window for good.

3. What work do I enjoy doing?

At this point, I had a few ideas about what had not worked out in my previous jobs, so I figured I should start taking stock of the aspects that had worked. There have always been pieces of each of my jobs that I enjoyed, so I wanted to tease out any themes. They were pretty easy to come up with:

  • I love creating things. My favorite days were ones where I got to write a press release, design an outreach flyer, or lead a training that I’d organized.
  • I love ongoing learning. I always jump at the chance to attend any professional development opportunities because they helped me understand how I could do my job better.
  • I really enjoy helping people. This is what attracted me to non-profits in the first place and was definitely an ongoing theme in my personal and professional life. I get a lot of satisfaction from supporting people in accomplishing their goals.
  • I love being an educator. My teaching program showed me that I much prefer a somewhat unstructured environment where I can get creative with what I’m teaching. But I also love leading workshops and sharing knowledge in whatever way I can.


4. What do I want out of a job?

I’d spent most of my career path feeling desperate, like I should be grateful for any position that would have me (probably a residual effect from my desperate and years-long job search in NYC that never came to fruition). I felt like my experience was established enough that I had to follow the trajectory I’d started, so I kept plugging away using the same approach.

I needed to figure out what I wanted and needed out of a job, so that I didn’t fall into another position only to get totally burnt out and frustrated after a year. So, I started brainstorming what kinds of jobs I could do that would appeal to my desire to see projects from start to finish.

I also started to realize that I wanted to put myself in a position where I could make a little more money. I’ve never wanted my income to define me, but I also really like feeling comfortable, and my husband and I would like to buy another house in the next few years. Honestly, there are a lot of different career paths that would offer more security and breathing room than if I worked on a non-profit salary forever. I also knew I didn’t want to go back to school because, at this point in my life, I don’t feel like a new degree is worth the investment of time and money.

After a lot of thought, I decided to start down the path of becoming a web developer. My knowledge of coding is pretty rudimentary, but it’s something I enjoy and I’ve always wanted to learn more about it. It’s like a constant brainteaser puzzle, and I love a good puzzle. The idea of actually having a completed, tangible project to show at the end of the day was really enticing. As an extra bonus, there are so many free resources on the web that I could become qualified without going back to school. And the average starting salary is $60k with plenty of demand and upward mobility. So yeah, it sounded good.

The only downside was that I still needed money. ASAP. At this point, I had been living off savings for almost three months after leaving my job. I had to figure something out to tide me over until I’d learned enough about web development to make a go at it. So, I took to Craigslist. I figured I didn’t need a “career job,” just something that would help pay bills (which are thankfully low due to a cheap mortgage and a generally frugal lifestyle).

I was glancing through the writing/editing section when I found a post that piqued my interest. It was for a content creator/social media coordinator position at a local tech company and, as I read through the ad, it felt more and more interesting. I sent along my resumé and cover letter and, within 15 minutes, they’d called me to set up an interview. Within two weeks, I was working there and, suddenly, I was a digital marketer and content creator.

Turns out, I really love the work. I’m learning a ton about marketing and I’m finding that it appeals to a lot of my strengths. Not only do I get to write a ton and practice writing for different types of audiences, but I can also use analytics tools to find out whether or not my strategies are effective. I don’t need anyone to tell me whether or not I’m doing a good job because my success is measurable. I’ve learned that I’m a total #datanerd, and though I still plan on honing my web development skills, I’ve fallen in love with content creation and online marketing.

I can see a future trajectory for my career. My goal is to get to a point where I can freelance full-time, so I can kiss commuting goodbye forever, and it actually feels like that goal is within reach. And I’ve found that this is the kind of industry where the harder you work, the more money you can make. I have so many ideas about how I can transition the skills I’m learning to build the exact career I want, and I’m excited about my work and future in a way that I’ve never felt before. Turns out, it feels really good to have concrete career goals.

Image via Unsplash

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  • buckwheat

    This was so great! From the title, I was expecting a simple listicle but this was really thoughtful and helpful.

  • C K

    wow, this article really spoke to me – i am the exact same way about external validation and feelings of accomplishment from measurable success. i love the way you framed these questions – and i just recently started a new position in a good-but-maybe-not-great job, and i’m pretty sure within a year or two, i’ll be itching for something else. thanks so much for providing this thought experiment – i know i’ll be using it!

  • Ashley Webster

    Helpful and thoughtful! Thanks!

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