The enduring allure of working for myself.

Constantly searching for the balance between hustle and leisure.

Apr 09, 2023

a computer generated image of a mountain range

In case I haven’t told you often enough, hi, I’m Emma and I’m 22. Too young for existential questioning but alas, here we are. With every passing day I fall deeper into the trap of a search for meaning, often asking myself ‘Is this the right path?’ when… fuck knows.

I know I’ve done it before, but indulge me because I think it may be valuable to give you my 10-second career recap. I’m doing so with the hope that by the end of this newsletter, you’ll have 800ish words of enough context to give me your best, unqualified advice on ‘where to next’. Yay.

I’m what I like to call a reformed hustler. When I was 18 years old and freshly out of high school I had my eye firmly set on one goal - to work as a writer at Australia’s biggest women’s media company, Mamamia. To do so, I started a Bachelor of Journalism degree and immediately harassed Mamamia’s Head of People and Culture for ‘internship hours’ until they said something along the lines of: “Sure, you can come and see the office… We don’t do internships anymore but I guess you can meet the team if you help us pack bags for half a day.”

Ha. Ha. Ha. Little did they know - I knew the founder of Mamamia, Mia Freedman like the back of my hand. (Mia went on to be my boss and of course, this is an embarrassing thing to admit, but context is important so stay with me here.)

I had a bit of a hyper-focus on Mamamia and so as any normal 18-year-old girl would, I inhaled every piece of content in and around the brand. Sure, that included their podcasts and stories. It also included every interview Mia Freedman had ever appeared on. And it included her memoir.

It was buried a hundred or so pages in that book, that I learned she got her start in the media by harassing Cleo magazine until they pity-let her into an office and she just kept showing up until they hired her.

My plan was in motion. I’d landed my “in” to the office. But what do you know, the showing up uninvited part never had to be. Because on my first day, I found the Mia Freedman right in front of me asking who I was and what on earth I was doing sitting in the back of her office trawling through makeup samples and $5 off Hello Fresh vouchers* to pop in gift bags for their upcoming tour.

*Brands added for vibes only. I simply can’t recall what was in those gift bags, but I’m sure you get the gist.

I railed off my 30-second elevator pitch and I can’t begin to tell you how nervous I was. Do you know that feeling of not knowing how to breathe while talking through a simple sentence? Like you’re running out of breath, but you only notice when it’s too late and now your breath is very audible and fuck me since when was breathing something you have to consider while speaking? Yeah, I never knew that feeling either, until that moment… and the next 15ish times I got to speak to Mia.

Mia was impressed by my tenacity (OF COURSE! JUST AS I PLANNED!) and arranged for me to stay. Bada Bing bada boom. I was hired just 8 weeks into my degree.

Now, I like to fast forward through the next 3-4ish years because that’s where it got less exciting.

Things don’t move that quickly when you don’t have… any experience.

You see, I spent a year or so feeling like a complete impostor. Then I spent another year feeling comfortable and excited about work. Then, I spent a year hustling and asking for something more.

Only I didn’t know what it was.

To everyone I worked with, I was a casual employee who did fairly basic editorial assistant work for about 15/20 hours a week while I completed my university degree.

To me, 2 years into the job, I’d learned all I could in the most entry-level role of the company. Sure, I was yet to work full-time (at all) but I was ready for the next step, now please.

The stagnant growth continued to stagnate and I don’t blame the team for not offering me an editor position despite my overt desperation.

But I’m impatient and pushy and so when a role came up in another team of the company, it was offered to me to give it a try. I’ve written about that one in detail here, so let’s skip to the present.

As you may well know if you read the above, I left Mamamia. It didn't fulfil me like it used to which sucked, because there's something so intoxicating about being obsessed with what you do.

(I’ve also written about how I never want that intoxicating love for a job again here, so I know I’m sounding contradictory but I promise, I’ll get to a point in just a moment).

Because I’m human and I’m complicated, there are parts of me that are deeply conflicted when it comes to balancing career, passion and life.

And right now, the most logical answer to that eternal struggle is the idea of starting my own business.

I love learning. I love growth. I will work hard and passionately if I believe in the people I’m working for and omg could you IMAGINE if that person was myself??

The revelation came to me in a spin class when the instructor’s motivating spiel hit just a little differently and it had me reevaluating my life direction. Isn’t that where all the best epiphanies come from?

Financial security is of course a very large concern and I’m in no rush to quit life to run away to Silicon Valley.

But I’m currently going through a brand new hyper-focus, this time on start-ups and it’s exhilarating.

All I want to do right now is speak to people who started their own businesses and ask them 1568 questions.

Is it really, actually possible?

What do you wish you knew sooner?

What hours do you work?

At what stage were you making enough money to relax about the decision just a little?

Most importantly… should I do it? By do it, I mean start a side hustle with the hope that maybe, potentially one day it could be a full-time thang.

This is not a rhetorical question. I’d love to hear your most comprehensive pros and cons list below.

I could talk about this for hours, so please respond to this email or let me know in the comments if this is something you’re interested in/have tried/would like to try/have succeeded and/or failed at.

I’d love to hear it.

Life Lately

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