Fast-track your podcast launch

Get Instant Access To A Free Podcast Training

How To Quit Your Job And Start A Creative Career

by | Emily, Podcast

Let me just start by saying that to this day, I still have no idea what I’m doing or how I’m going to do it. The thing about building a creative career, or any career, is that most of the time, it’s just guessing until you figure something out. Once you’ve figured the same things out a few times, it becomes much easier to grow your career, but there will never not be a time when a curve-ball is going to come at you hard and fast, when you least expect it. Look I don’t know much about sports, is it possible to have a hard and fast curve-ball?

I started with a very clear and deliberate vision for my future.

For the majority of my childhood I just wanted to be a filmmaker. I loved anything to do with visual media and narrative film. Specifically comedy. I would make silly shorts with my neighbourhood friends most nights of the week. If there was an opportunity to do a video for an assignment, I’d fabricate some insane narrative to execute on the project. In the summer between grades 11 and 12, I produced, directed and edited a 46 minute long adaptation of Macbeth that a friend wrote for English class.

Things were very clear cut for me until I was rejected by all five of the film schools I applied to. At the tender age of 17 I had convinced myself that my true calling was totally wrong and I should just stop pursuing it entirely.

This led me to live a “double life”.

Half the time I’d be pursuing traditional business careers (because an English degree is going to help me do that?) and the other half I’d be curled up on my very uncomfortable futon, depressed, watching hundreds of movies over and over again.

In all these movies I’d watch I’d think to myself “man, I haven’t made a short in years.” and then I’d do this crazy thing where I’d start pursuing the careers of various cool female characters in the movies I was watching.

From pastry chef to starup marketer to filmmaker… and so on

First, I became a baker after watching Stranger Than Fiction. I did two years of Baking and Pastry Arts Management at George Brown College, and started my own designer cake company. I quickly realized that no one wanted to actually pay money for designer cakes.

Then, I decided that I’d work in hospitality. Specifically that I’d work the front desk of a hotel in Hawaii, just like Mila Kunis in Forgetting Sarah Marshall. It is not lost on me that the message of that film is to pursue your creative interests. I didn’t make it to Hawaii, but I did make it to Vancouver where I worked midnights on weekends as a phone operator in a tiny office with a 1’x1′ window. Needless to say, depression came back HOT AND FAST and I started watching hundreds of movies again.

Finally I became an event planner after watching Krysten Ritter in “She’s Outta My League” (what the fuck is up with my movie choices?). She had her own event company! And I was like, I CAN DO THAT! So I moved to Ottawa and got a post-grad certificate at Algonquin College for event management.

I cannot emphasize enough how much it would have helped me to know that it was possible to do more than one thing at a time.

I really just thought that I was totally hopeless and would NEVER figure out what I wanted to do with my life! It was a daily battle for me, doing online quizzes, taking so many classes, thinking “oh, if only I didn’t have to work at this communications agency doing data entry I’d know what I want to do!” But that’s just not how it works! Because I did quit that job and came out the other end with a kid’s album called Gross Kid Songs, which is truly not appropriate for children. I do not know anything about entertaining children.

Like I said before, no one knows what the hell they’re doing!

I met my partner Justin Decloux at the end of the event management program and moved to Toronto. As luck would have it, he had already begun his filmmaking career with a film called Teddy Bomb. I swear to god I was like HOW CAN THIS BE? FATE IS REAL! So I helped him finish it by voicing the role his ex-girlfriend played (she was very far out of the picture by this point) and writing the score. I had no clue how to write a score, but Justin insisted that I could do it. So I did. And here it is:

Then, we began putting together Impossible Horror.

I want to note something here before I get into Impossible Horror. I was working full-time at an incubator for tech startups. It was an incredibly stressful job. But it gave me some marketing skills that would truly change the trajectory of my career. More on that later.

Impossible Horror was the first time I was able to put ALL of my skills together to create an immensely complicated project. Ah the joys of indie filmmaking with $0!

To summarize, I was responsible for producing (event planning), craft services (baking), props and special effects, marketing, crowdfunding, managing various emotions on set (hospitality), accounting, sound design and editing, the musical score, PR, editing the behind-the-scenes doc… and probably some other stuff. Here are Justin and me talking about the film:

The crazy thing is, I didn’t even realize that I had created a multi-hyphen career for myself. The only way I figured it out was when I was invited to speak on a panel at the Scary Movies Film Festival in New York with two other multi-hyphenate women, also presenting horror movies they had produced and acted in and composed the score for.

But that’s not all, folks!

During this time I also did these things!

By the end of it all, we were in debt. So I started building websites to pay off the debt while I was still working my full-time marketing job. (Here’s where the later part comes in!) This period of my life was incredibly important for my career. Not only did I learn that I have ADHD, I also proved to myself that I could do everything I wanted to be doing while working this full-time job.

So it wasn’t as cut and dry as people had always said!

I got REALLY good at building websites, and a few months into it was making enough money to leave the full-time job and venture out on my own. Thus began the first iteration of The Ultimate Creative, a company that acted as an out-of-house marketing department for small businesses that needed a high level of expertise with enough budget to hire an intern. Somehow, I managed to create a job for myself! HOW COOL IS THAT?

But it honestly wasn’t everything I had ever wanted.

We were in New York for the screening of Impossible Horror at the Scary Movies film fest and I decided to go walk up and down 5th Avenue on Sunday morning. I found myself suddenly at 30 Rockerfeller Plaza by chance. I only realized that I was there because I was trying to get the last drop of coffee out of my cup, and I tilted my head back and saw THE BUILDING. You know, the one where great TV is made? The one in the opening credits of 30 Rock? THE ONE THAT TINA FEY BECAME AN ICON IN?

So I immediately got on the phone with the Second City training centre in Toronto and booked myself in for the next available sketch writing class. That class gave me such bad anxiety I forced myself to sign up for improv in the next term. That class made me feel like a million bucks and suddenly I was making two different web series! One called Venture Shark and the other one called Date Kate. A bunch of us formed a comedy troupe called Weird Town and produced a few shows together, but it didn’t last long. I’m PLEASED AS PUNCH to say that I’m now in a troupe called Big Chick Energy with some of the same people and I’ve never felt more creatively satisfied in my life!

My business continued and I officially joined forces with a friend to evolve into The Concept Agency which is now one of my creative strategic partners. Although the partnership didn’t work out it still provided me with a great opportunity to learn and grow, to understand my limitations and my preferences, and a great body of work.

So now what?

Well now I’m writing this blog explaining myself! And I like telling this story because if I had read it 10 years ago, I would have been a lot less hard on myself to be majorly successful immediately at everything I set out to do. The fact is, I’m doing well for myself now, both financially and mentally, and I’ve created a career that lets me be me all the time.

And guess what, you can do it too!

[convertkit form=1519090]

Podcast Rocket with Emily Milling

Free Training!

Want to fast-track your podcast launch? So many amazing podcasts are never heard because getting started can be so overwhelming! That’s why I created a free masterclass, “5 simple steps to start your podcast” to help you create an easy podcast launch plan!

Subscribe To The Podcast



Buzzsprout Ad