Brave Living

How I Found My Dream Job at 27 (+ How You Can, Too!)

February 26, 2018

Can I be honest? The “find your dream job” and “chase your passion” Pinterest quotes drive me nuts.

  1. There’s SO MUCH PRESSURE to figure out the ONE thing you want to do with your life, and it’s stressful…let’s get real.
  2. What I’m really passionate about is watching pottery and slime videos on Instagram.
  3. If I didn’t have to have a job I probably wouldn’t, so telling me to find a dream job is like saying “pick out your favorite over-the-counter medication”. Thanks buuuut I’d rather not unless I have to.

I give you those ABC points slightly in jest, but also to say that this “dream job” idea has really gotten out of control, especially for us millennials.

We often have parents and grandparents encouraging us to find a career, stay in it, work our way up, and retire. I’ve found that our generation, however, don’t fit in the box so easily. In the world of social media and never-ending entertainment, we see what’s possible in the world! We want passion, experiences, and fun and aren’t willing to settle or trade our personal aspirations for security, comfort, and monotony. There’s nothing wrong with either mentality, they’re just different!

And while having the options to explore limitless possibilities is pretty great, it’s also caused an unanticipated amount of stress to find that dream career now. It’s almost as if we’ve combined the idealistic and limitless potential of the younger generation with the “find your job now and stick with it” mentality of the older generation…but something has to give.

The other day I was talking to my 57-year old uncle who really does seem to have it all. He was a doctor, sold his practice, has dabbled in entrepreneurship, lived in Paris, tried stand-up comedy, travels the world trying out coffee shops, and generally has the whole life thing figured out. When I was going through my QLC –quarter life crisis –I asked him when he knew what he wanted to do with his life.

“Christiana, I still don’t know what I want to be when I grow up. I just follow my interests.”

Light bulb moment: It’s less about finding your dream job, more about exploring and letting it come to you.

While I’d read tons of self-help and career books up until that point, I decided to take advice from someone whose life I’d actually want to replicate in my own. In the 2 years that followed that conversation, I found my dream job (at 27 years old) and finally put my quarter life crisis to sleep.

Here’s what I learned:


When I first began my journey to finding my “dream job”, I quit my 9-5 career to nanny…and it was a dream. I had a flexible schedule, hung out with the cutest kiddos all day, found myself taking day trips to the pool or the museum, and was financially feeling alright. All of my values were checked off my list! But as I continued to nanny, I felt a pull to do something else –to learn more, use other skills I was learning, and expand into being a full-time entrepreneur. My “dream” changed…and that’s ok! Don’t get too hung up on the “perfect” or “dream” job so much as finding happiness and joy in what you’re doing. If those feelings are gone, time to move on.


Part of the reason I’m convinced so many people, millennials especially, are unhappy these days is because they picked a career path and built their lives around it when really it should be the other way around. I felt miserable and unhappy when I was chasing notoriety, the all-mighty dollar, and prestige because I had to tailor my life (aka the things that make me happy and whole) around meeting deadlines, doing mindless paperwork, and giving myself an edge in an industry I didn’t really care about. I found myself sacrificing things I value in life –like meaningful work, creativity, flexibility, travel, and fun –for necessities dictated by my career path that didn’t light me up inside. When I realized how important the creativity, flexibility, etc. was to my happiness, I could then find a dream career path that met those life qualifications!


While I may live in a school bus, I will say that I’m not one of those people who wants to sell all of their stuff, live off the land, and never put any money away for retirement (not that those people are bad, just not my style). I do want to be successful! I do want to make great money! So when I say “throw money out the window” I mean it figuratively. When you’re thinking of your dream career/life path, don’t let the amount of money you could or could not make dictate your direction. When you chase the dollar, it’s really easy to go down a path you don’t want to be on. If you’re following your heart, doing work you love, and trusting the process, the money will work out as it should. If you don’t believe me, know that there is a professional mermaid out there who makes over 6 figures a year. Google it.


I don’t want you to think you have to quit your job this instant and start teaching kids in Africa to read…we do have to be smart. One of the practices I learned when I used to work for Nike & Disney was the process of shadowing. Look within your organization for someone whose job description peeks your interest and ask to follow them for a day! If the job you’re really interested in is outside of your company, take an afternoon or a weekend to visit their place of work or ask them questions over lunch! I used to think I wanted to be a Brand Sponsorship Manager for Nike until I shadowed someone in the position and realized they work long hours, are on social media constantly, and rarely have an off weekend. Cool job? Absolutely. The cool job for me? Not exactly.


Did you know that the average millionaire has 7 streams of income? Being interested in a bunch of things is actually a good thing, so don’t sweat it if you’re having trouble narrowing down your interests! One of the favorite terms I stumbled across in relation to this idea is called “The Slash Career” by Marci Alboher. You’re allowed to be a Sales Manager/jewelry designer. You can have a fashion blog and also be a CPA. While some people might want to jump right away, I’ve found it’s better to do a bit of exploring before taking major moves.


At the end of the day, the most important thing for you to know is that what you’re going through is normal. We’re all on a path to find our dream career, who we are, and what we’re meant to do with this life we have, so don’t let that voice in your head tell you you’re a failure for not having found your calling yet. When it comes, it comes! I’m convinced we can’t make our journey to finding what we’re meant to do any shorter, but we definitely can make it longer by doubting ourselves. It’s those who embrace the journey that “get there” (wherever “there” is!).

What’s a career you’d like to try out?




Hey, hey! I’m Christiana Hill – just a down-to-earth girl who decided life was too short and dreams are too important to sit in a gray cubicle while wearing a pantsuit. Nowadays, I travel the US in my renovated school bus teaching anyone who will listen about the true Art of Bravery and how it can help you live a life where you refuse to settle. Glad you're here!