Career & Finance

What to Do When You Find out Your Dream Job Isn’t Your Dream


It’s no surprise that nailing the dream job isn’t an overnight process. You go to college, get an internship, put in hard work at the bottom, and sometimes get to the top only to realize the view isn’t as sweet as you thought it would be.

I wanted a life in public relations ever since Samantha Jones made a career out of drinking martinis, wearing fabulous outfits, and managing the career of a waiter-turned-mega movie star (who also just so happened to be her boyfriend. A fate I was certain to achieve had I made it in the PR world, right?). Truthfully, I didn’t quite know exactly what the job entailed, but I was good with people, loved playing mediator, and could promote just about anything. So into my dream career I went.

Post college, I moved to Chicago and ecstatically joined the first agency that would hire me. The joke in the agency world is the best way to get promoted is to find a better position at another agency. So I did just that, which landed me at three different companies in eight years (#killingit). Before long it became apparent that the evolution of my career was going to look a bit different than Samantha’s journey on season six of Sex in the City.

I found myself dreaming about what my job would be ‘if it were up to me.’ A funny way to phrase it, because when is your own career not up to you?

After many late nights at (insert whatever the agency I was), I found myself dreaming about what my job would be if it were up to me. That’s exactly how I thought of it: If it were up to me. A funny way to phrase it, because when is your own career not up to you? Nonetheless, when my mind would escape to my happy place, it went straight to a job in fashion. Maybe it would be working for a brand. Maybe I’d write about the industry. Maybe I’d do my own thing. The 30-second conversation in my head would start something like: “You would rock the fashion world. You know style. This is your thing. Just go for it. You can work your way up. Every Beyonce starts as a Destiny’s Child.”

But then it would quickly turn to: “What qualifications do you have? You didn’t go to school for fashion. And no, people liking your outfit doesn’t count as a qualification. What brand would hire you? You don’t know the right people. Nevermind.” Brushing aside these fleeting thoughts, I continued to move forward on the path I originally started. PR was the right choice. A college major I had chosen at 19 was still totally the right choice for my entire life. People never change in their 20s (insert crying laughing emoji).

In September of 2013, I finally managed to land a job at an agency I had been dying to work for. A success measure I thought would be enough to squash the fashion thoughts all together. Once there, I submitted a request to be moved to the account team of our biggest client. And I got it. Boom. Another success that confirmed this was my place. Little did I know, it was this junction that would change my trajectory for good.

I get asked a lot not only about how I decided it was time to switch careers, but also what I did once I started over…aside from naturally having a freak out moment. Looking back, my journey can be summed up by three phases. And while my story is specific to me, I think what I learned can be applied to anyone going through something similar.

1. The breakup: It’s not me, it’s you.

Landing a spot on our biggest account team was like going from a light jog on a treadmill to a full-on sprint. With your hands tied and maybe blindfolded.It was my sink or swim moment and, dang it, I was determined to swim. But slowly I began to notice work life changes were more like lifestyle changes: 12 hour days became standard. I woke up and checked work email. I ate dinner and checked work email. I got in bed for the night and checked work email. And mind you, this was by no means a heroic effort on my part. This was just what everyone did.

It means you—this place, this time, this career, this space, whatever it is—does not fit with me and where I personally need grow.

I’d like to consider myself an uplifting person, but I reached a point where my positivity began to break. I remember an overwhelmed moment when I asked myself, “How can anyone do this?” Yet as I looked around our bustling office, the answer was not only were people doing it, they were doing it well.

The truth is I had many talented friends who were amazing at their jobs. Things I would find frustrating, they would shrug off. Problems I couldn’t solve, they did with ease. And good for them. This was their thing and they wasted no time being a rockstar at it. But at the end of the day, I had to remember that what was most important to my growth was ME. I was wasting time trying to find my thing, to have my rockstar moment, not realizing my biggest roadblock was chasing a career I thought I wanted.

There are thousands of articles published on the importance of choosing the relationships in your life wisely – your best friends, your significant others, your family. Why isn’t the relationship with our workplace, career, passion, on that same pedestal? Saying “it’s you, not me” in a work scenario is actually the best kind of breakup we can hope for. It doesn’t have to mean negative thoughts or burned bridges. It means you – this place, this time, this career, this space, whatever it is – does not fit with me and where I personally need grow. It’s finally giving yourself permission to move on.

2. The investment: Doubling down on yourself.

Real talk: Wouldn’t the world be a simpler place if we could all get through the breakup phase and head straight to the part where our dreams flourish? It’s a lovely thought but I wouldn’t be doling out the right advice if I skipped the part where the rubber meets the road.

You may be like me, a girl who wants to start something on her own but doesn’t have the faintest idea of where to begin. Or you may be someone who already has mastered their thing – a killer graphic designer, an eloquent writer, a sales savant – all amazing talents. Either way, my guess would be there is something holding you back from exploring the unknown.

What else is more important than taking the time to invest in a passion? If you have a 9-5 job, what else are you doing from 5-10?

I decided to quit my job all together—and I had no real plan. My only plan was to sit and do and experience and invest. If you ever want to see an extremely confused reaction from a co-worker, tell them you’re leaving the company and you have no idea what you’re going to do next. Heads will spin, I promise. I had the outer shell of what I thought would be the next chapter, but I needed to actually believe in myself long enough to see its evolution. The idea was to solidify a career in fashion. So I booked day trips to tradeshows where I could learn about buying inventory. I watched YouTube’s on how to filter photos like a pro. I asked friends of friends to grab coffee so I could gain new perspective.

I googled A LOT.

I admit, I did have what’s deemed as a luxury: No job and nothing but time to invest. But I know that’s not everyone’s story. Even so, when you think about pursuing a passion, what else is more important than taking the time to invest in it? If you have a nine-to-five job, what else are you doing from 5-10 p.m.? Would it be the worst thing to skip one girls’ weekend to pay for a class you’re dying to take? Would it be the craziest idea to wake up 30 minutes earlier every day to read up on the trends in your want-to-be industry? Does that Netflix series have to be binged or can you write three new cover letters instead?

I read a book by Elizabeth Gilbert recently called Big Magic: Creative Living Beyond Fear, where Gilbert believes that a creative idea actually chooses you—it’s up to you to decide what you want to do with it. The same can be said for boldly pursuing a passion, even in the midst of self-doubt. Gilbert says, “You can measure your worth by your dedication to your path, not by your successes or failures.” No one knows where this newfound drive will lead you. Maybe it surpasses your wildest dreams. Maybe it takes you to a place that’s harder than you imagined. What I do know is that your road will be long if you don’t invest in yourself enough to really try.

3. The leap: Creating your own job description.

Preparing to finally take a leap into a new career can be a mix of emotions. I recall feeling like I had left the job, I had spent the time investing, and I was just waiting for the next stage to get easier. It didn’t. I made a bold move in my life to fight for something that made me happy. So now landing just a so-so gig would simply not do. After tirelessly searching for an open position that matched everything I’d wanted in my head – great work environment, standard work hours, a prestigious job title (one I would earn with no prior experience), maybe some dental and health benefits for good measure – it became clear that I was going to have to create this job for myself.

If we’re not writing our own material, plotting our own path, defining our own job descriptions, why did we make the bold move in the first place?

Having worked just about anywhere prior to changing careers, you’ve already spent time building valuable core skills. You probably get how to manage a project or properly allocate a budget or solve a problem in a pinch. These are the skills that take you from “I’m totally starting over” to “I have experience to build off of.” Sure, I didn’t know how to run my own company nor had I ever been a merchandise buyer. But I had managed a team, run a high-profile social media account, developed financial forecasts and yeah, I think I put together an outfit like a boss.

On a recent podcast, actor Jason Siegel talked about why he writes many of his own parts. He says, “I was educated…on the Albert Brookes approach which is: You’re an unconventional leading man; the only way you’ll make it is if you write your own material.” I’d like to think that if you’re bold enough to make a life change in order to pursue a passion, then you also fit into an “unconventional” category. And if we’re not writing our own material, plotting our own path, defining our own job descriptions, why did we make the bold move in the first place?

The beauty in this phase is that no two stories will look alike. I’m only a year into my business and I’m still not only defining my job but also measuring my success. Maybe my script will have to be rewritten down the road. Your job could lead you off on your own, could connect you with a whole new work force or simply lead you to another department in your same company. Whatever your journey is, define it for yourself because no one else could dare to give it justice. Start over 25 times. It may never get easier, but it also never loses the thrill.

Have you ever left a “dream job” to pursue your passion? Share your story in the comments below!