Finding the Right Career Path: 3 Questions to Ask Yourself

finding the right career path

Finding the right career path has been a much bigger challenge than I ever expected. I graduated college in 2008 with a 4.0 GPA and a Liberal Arts degree. I thought my diploma would be a sure-fire ticket to success: Little did I know that I’d graduated into the worst economic recession in a generation.

I moved to New York City with the hopes of landing a full-time job in the non-profit sector, only to spend 2 years getting beaten down by rejection after rejection. I came back to Baltimore feeling completely hopeless.

In the years since graduating, I’ve had a lot of jobs: I’ve been a teacher at an environmental after-school program, sales associate at a natural cosmetics company, babysitter, children’s educator at a botanical garden, volunteer coordinator at an elementary school and a non-profit, development associate at a non-profit, canvasser at another non-profit, baker, elementary school teacher, and men’s skincare maker. I’ve only recently settled into a career path as a digital marketer and looking back, I realize how many mistakes I made along the way.

Finding the Right Career Path: The Questions I Should’ve Asked All Along

In each of my previous jobs I fell into the same pattern. First, I would apply for any jobs that I was qualified for that related to any of my (many)  interests. When I would get a job offer, I would take the position, whether or not it seemed like a good fit for me (who was I to turn down an opportunity?). Then within 6 months, I would inevitably start to get bored and feel unfulfilled and think that it was time to start doing something new.

After repeating this pattern for the first 5 years of my working life, I realized that I needed to rethink my job hunting approach and re-frame the career path conversation. So I took some time to do some soul-searching and really think about what had gone wrong in the past and how I could change in the future. These are the questions that started to take shape:

1) What work do I enjoy doing?

There have always been pieces of each of my jobs that I enjoyed, so I started by trying to tease out any themes. It was pretty easy to come up with a list of what kind of work I enjoy doing:

  • I love creating things. My favorite days were ones where I got to write a press release or design an outreach flyer or lead a training that I’d organized.
  • 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. I love leading workshops and sharing knowledge however I can.

I initially thought that starting my own business would check off all of these boxes. But I neglected to think about all of the other factors that go into running a business. I hated the lack of structure and I felt totally overwhelmed by having to make every decision myself. I hated not having insurance. And I realized I prefer improving on existing systems rather than creating things completely out of scratch.

2) What do I want out of a job?

I’d spent most of my career path feeling like I should be grateful for any position that would have me (probably a remnant from my desperate and years-long job search in NYC that never came to fruition). Because I’d invested so much time in the non-profit career path, I kept applying to similar jobs even though I never ended up liking the work.

I knew that this time, I had 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. 

I also wanted to find a career path where I could make enough money to be reasonably comfortable. I’ve never wanted my income to define me, but I also don’t want money to be a constant source of stress as it had been with some of my lower-paying gigs. I didn’t want to live on a non-profit salary forever. I also knew I didn’t want to go back to school at the time.

3) What brings me a sense of satisfaction/accomplishment?

As I thought about my job history, I began to realize that external validation is really important to me. I already knew that I could ride the high of a compliment for days, but I’d never thought about how this played out in 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, I never had a direct supervisor.  I sort of worked alongside staff in various departments and I kind of 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 firm understanding of expectations.

I’m a very self-motivated person so that wasn’t the real problem. The major issue was that I had no barometer of whether I was doing well. One time, after a particularly stressful event about 8 months into my tenure, a coworker complimented me on how well I’d handled it considering I’d had so little guidance. I immediately burst into tears because I was so surprised to hear that someone thought I was doing a good job.

This was not good for my mental health or my work self-esteem.

I don’t necessarily need compliments, but I do thrive on measurable outcomes. I strive to constantly become better. I do best with concrete goals to work toward. I do not do well with vague directives. This was my first clue as to why my previous jobs had left me with a constant sense of failure and a lack of career satisfaction.

Be brutally honest with yourself about what you need out of a job

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 being good at all kinds of positions. Isn’t it a good thing to allow room for opportunities as they arise? All I knew is I wanted to be a force for good and not leave work hating myself every day.

finding the right career path
Oh hello it me.

But after working in a number of non-profits, I realized I didn’t actually like the work I was doing. Instead of focusing on some lofty ideal of what I wanted my job description to be, I needed to start thinking about what tasks get me in flow. And as soon as I shifted the conversation, 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. 

At work, my favorite days were the ones when I facilitated a workshop I’d been working on or completed a report. When I see a project through from start to finish, I gain satisfaction from the fact that the finish line is physical and visible and concrete.

However, these days were generally few and far between. Most of my work was based on intangibles, like making sure volunteers were satisfied or raising awareness of the organization.  Aside from events and reports, my tasks were rarely ever “done.” 

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. 

So I started brainstorming what kinds of jobs I could do that would appeal to my desire to see projects from start to finish. Jobs that would give me a concrete sense of completion. Jobs where I could feel a sense of success without the need for compliments from bosses.

Putting Together a Career Path

After a lot of thought, I decided to explore digital marketing. I’ve always enjoyed writing and I knew I wanted to get into a tech-related field.

I didn’t have any formal experience in digital marketing, so I thought about how I could get my foot in the door and that’s what led me to SEO copywriting.

I started keeping an eye on the writing/editing jobs section of Craigslist when I found a post that piqued my interest. It was for a content creator/social media coordinator position at a local marketing agency and as I read through the ad, it felt more and more interesting. Write engaging weekly content for clients across a wide range of industries? Hone my social media marketing skills? Learn more about SEO and marketing best practices? Yes please! I was sold. My plan was to hone my higher-level marketing skills in my off-time and then move up in the ranks.

I sent along my resume and cover letter and within 15 minutes they’d called me to set up an interview. Within 2 weeks I was working there and suddenly I was an SEO copywriter, a possibility that had never even crossed my mind.

While the agency turned out to be a nightmare, I found that I really loved the field of digital marketing and content creation. It allowed me to practice writing for different types of audiences and 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. Turns out I’m a total #datanerd.

After freelancing for a while and honing my skills, I landed my dream job doing digital marketing at my alma mater. For the first time in my life, I’m on a career path that I truly love. It feels good.

Finding the right career path all started with asking  myself the right questions.

4 thoughts on “Finding the Right Career Path: 3 Questions to Ask Yourself”

  1. “But guess what?
    Turns out I really (like?) the work”
    Go for it, Michelle. Everything satisfying takes much effort and some luck……

    1. Thanks for catching my typo, dad! I’ve been thinking a lot about that impostor syndrome article you sent me a few weeks ago and it’s definitely been motivation for me to have more faith in myself and my abilities. Now it’s about putting in the work!

  2. I couldn’t wait to get to the conclusion of this article, since the beginning sounded so much like me! I have very similar work preferences, and while I sometimes enjoy my work as a librarian and teaching, the never-ending uphill struggle to improve something that can never be perfected has been very trying for me. The days when I have a discrete project to complete, rather than a nebulous goal like “improve instructional services” or “increase student engagement” fly by and leave me energized rather than exhausted.

    I have actually also seriously considered switching directions to web development and have been learning for the past year or so. I do most of our graphic design work and actually led a project to redesign our library website, which has improved the situation some, but I’m still looking to move on. I’ve dabbled in social media marketing, but not seriously, so I’m definitely looking forward to future posts on the topic.

    This is great advice, and something I wish I’d considered sooner. Still trying to figure out where I’d like to go and how to get there, but it’s helpful to see somebody else’s path.

    1. Thank you for commenting, Chelsea! It’s always nice to hear that I’m not the only who fell into a path that maybe just wasn’t right for me.

      That’s so awesome that you’re learning web development! I’ve sort of let it fall by the wayside because I’ve gotten so busy with writing and marketing. I really would love to add development to my skillset, but right now I’m trying to hone in a little more clearly on analytics, SEO writing, and social media. Are you taking classes or learning it on your own?

      If you have any specific questions about social media marketing, I’d be more than happy to answer in a future post. I’ve been trying to write about it, but it’s a little hard to start from scratch and figure out what would be helpful for folks who are just starting out. So if you have any topics that you’d love to see addressed, let me know!

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