How to Land Your Dream Job at Any Age

March 19, 2018

How To Find Your Dream Career | The Elgin Avenue Blog

Recently I was listening to Goal Digger, by Jenna Kutcher – one of my all-time favourite podcasts. The episode I was listening to featured podcaster Cathy Heller and was all about pursuing a career which TRULY fulfils you.

Jenna and Cathy delve deep into what it’s like to ‘give up your day job’ to pursue the full-time job you love.

I felt so grateful listening to the show, knowing that I’ve built a career around activities I genuinely enjoy. Creative elements like styling, photography and copy. As well as business aspects like negotiating and building my brand. 

Whilst I love the career I’m currently pursuing I’ve definitely gone down forks in the road. I’ve pursued work and life options (like University courses) I didn’t like one bit.

In a bid to help you to navigate your own career route, towards your dream job, I’m handing over the reigns to Chelsea for her deep dive into the subject.

If you’re currently struggling with your career path, or feel totally stuck in your job, this post is for you.

Over to Chelsea!

Love, Monica x

How To Find Your Dream Career | The Elgin Avenue Blog

How to Land Your Dream Job at Any Age

Like most people, one of my biggest struggles as a twenty something surrounded my career.

We grow up in a world of people telling you “you can be whatever you want”. The phrase “dream job” is thrown around like confetti.

In college, you start to get an idea that finding that dream job isn’t as simple as it sounds, and even though you CAN be whatever you want, that doesn’t mean we know what *that* is!

At least for me.

I switched majors four times before settling on a teaching credential, something I haven’t used once since graduating.

And again, like a lot of people, I sorta fell into a job after college – one I wasn’t incredibly passionate about. And a lot of my friends were the same!

We were working to pay the bills and to live in a big city – the details of a career didn’t seem to matter much.

If you take the time to learn about and get to know yourself, it’ll start to become clear what direction you should go in.”

But then my mid-twenties rolled around and the idea that I’d be in that same job or field forever hit me – and it didn’t hit well.

I didn’t want to wake up for life in a job that had fallen in my lap. I didn’t want to feel uninspired and bored everyday.

So I did some major soul – or passion – searching and was lucky enough to figure out what I wanted to do – kinda.

I quit my nannying job to take a content job, which eventually turned into freelance writing full-time (read more about that journey here).

And I’m not the only career-switch success story out there! I have several friends and even family friends who at some point during their adult life jumped ship and took on their passions. WHICH I LOVE!

One of those being my editorial assistant, Chloe.

Just two months ago, Chloe (well into her twenties) left her full-time job as a social media coordinator to freelance full time (focusing mainly on writing and other editorial gigs). We work closely together every day, and I’m beyond inspired by her drive to find a new career.

In today’s article, instead of only sharing my thoughts or tips for changing careers and finding a dream job at any age, I decided it would be fun to turn the table on Chloe as well. And what better way to get straight answers than a classic Q&A?!

Chloe and I  might not have pivoted careers at age 45, but that doesn’t meant it wasn’t scary, risky, and foreign. I think and hope that these answers can be applied to you at any age, in any industry!

Let’s get to it.

How To Find Your Dream Career | The Elgin Avenue Blog

Real Life Q&A – How To Pivot Your Career

Q: How did you figure out what your dream role was?

Chloe: I had a few jobs I didn’t like and really put a lot of time into thinking critically about why I didn’t like them.

It’s all about self discovery. If you take the time to learn about and get to know yourself, it’ll start to become clear what direction you should go in.

Chelsea: A friend sat me on the couch one night after hearing about me complain – once again – about my job, and simply said “Carry your hobby into your passion. You talk about blogs all day long, you love sports, and you love to write.”

So boom! Follow what it is that you do in your spare time, and then figure out how that can translate into making money.

How did you find your dream role after figuring out what it was?

Chloe: Once I discovered what it is I really liked doing, I started reaching out to people via email that I wanted to work with. It’s how I found Chelsea!

If you surround yourself (digitally or physically) with people who are on the same path as you or are involved in the kind of work you’d like to be doing, you’ll undoubtedly find yourself heading in the right direction.

Chelsea: After realizing I wanted to combine blogs, writing, and sports, I started my very own sports blog – since I didn’t have any experience or a degree to match. From there, I took an internship (yep, at age 24!) at a sports website. After working in sports and the health field for a few years, I decided that my passions grew into fashion and lifestyle content, which is where I eventually took it.

It’s all about figuring out your hobbies, then thinking outside the box with a role to match. Try things out, experiment, search job boards to learn about the millions of jobs out there. Also, when I started freelancing, I no-joke got my first client by reaching out to them on Snapchat – the opportunities are endless, people!

the reality of it all has forced me to stay very focused.”

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How did you feel after you found your dream role and pivoted?

Chloe: It’s honestly been very nerve-wracking. Knowing that I was in a position to make a change was incredibly exciting, but the reality of it all has forced me to stay very focused.

I’m constantly thinking about keeping myself busy and not enjoying my new found freedom (self employment) too much. Of course, though, it’s been amazing to have more say and control over my own life — something you don’t really have as much of in corporate America.

Chelsea: Grateful, anxious, happy. Grateful that I made the switch, anxious about things working out – I was making a lot less than my friends since I had technically started my career/internship about four years late – and so happy to be doing what I wanted every day.

3 biggest pieces of advice for landing your dream role?


#1. Let go of fear – Fear of failure, fear of judgment, fear of not making enough money — letting go of any and all of these things is what absolutely gave me the extra confidence I needed to start to make the needle move.

#2. Don’t let judgement stop you – Ultimately this boils down to letting go of fear like I mentioned in #1, but there are going to be A LOT of people that don’t understand you or your goals and they might judge you for doing something “non-traditional” — don’t let that stop you!

#3. Keep learning and be open – If you know what you enjoy doing most, that’s fantastic, but don’t pigeonhole yourself. Always be open to learning new skills and taking on different projects. This is especially important if you’re venturing out on your own.


#1. Don’t worry about what others think. Including your parents. You might seem crazy to pivot roles later in life, but happiness goes a lot further than extra money in your paycheck. Do you!

#2. Make it work. Yes, interning “late in life” sucks. Yes, eating macaroni and cheese 5 days a week sucks (believe me, it sounds great, but not when it’s the only thing you can afford), and yes, you likely need to work a couple jobs at first, but it’s so worth it.

#3. Network – If you think you have zero percent chance of getting into an industry, you’re wrong. Make friends with anyone and everyone – you never know how they’ll be able to help or who they know. Attend networking events in the industry, go to a conference, comment on a website . . . Whatever you do – just get your name out there.

OK I need a #4!

#4. Save! As an adult, it can be scary to give up a bigger paycheck, especially when bills and mortgages are involved. Something that gave me major peace of mind was feeling confident about my savings before making the jump. It wasn’t like I’d saved $500K, but there was enough. I felt OK making a lot less for the first year or so.

That’s all from us!

What’s Your Take?

Have you thought about pivoting your career? Have you done it as well? What’s  holding you back? Let’s chat!

Love, Chelsea x


 – Chelsea Becker is a regular contributor to The Elgin Avenue. Chelsea is a California native with a penchant for beach days, Napa wine tours and pilates. –

Photography by Charlotte Bryer-Ash


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