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The Article I Wish I’d Read Before I Quit My Job to Go Freelance

hree months ago, I left a marketing job that should, in theory, have been perfect for me. It’s a story you’ve heard before: I was burnt out, having an existential crisis and completely lost on what to do next.

Scared and confused, I decided to embark on what I branded a ‘summer of experimentation’. Three months to break my own boundaries, work on a series of projects, and see how much I could learn and earn along the way.

I didn’t want a sabbatical, or to go backpacking in Bali. I wanted to spend some time — real time — understanding my professional self better.

As a risk-averse person, I knew it’d be hard. What I didn’t know is that it’d change my working life in new and unprecedented ways. I definitely didn’t know how much it’d change me.

This story is for anyone who feels like big career leaps are beyond them. For anyone who understands the excitement of leaving the 9–5 grind, but still feels crippling fear. For anyone who’s ever wondered how it works in practicality.

In sharing this, I hope you gain clarity, feel bravery, and make a profitable, positive change. Because — spoiler alert — positivity and prosperity don’t have to be mutually exclusive.

Start by gathering real data on yourself and those around you

It’s June 2019 and I haven’t slept through the night in months.

On paper, my rational self knows I have to leave my job: it’s not a good fit for me, I’m physically dreading going there every day, and it’s draining to the point of disbelief. My emotional self, however, is wide awake every morning at 4am, wondering how I did everything “right” but still ended up here.

It’s an older, wiser friend who tells me to start analysing my life like I would a marketing campaign.

“Gather the data,” she says. “Look at where your energy flourishes and where it fades. Make notes on the kinds of work that made you feel alive. Make notes on the work that drains you. Observe your thoughts. Analyse them. Draw conclusive patterns from them.”

For me, this life-changing piece of advice took the form of a very simple journal, and I advise anyone making a big life decision to do the same. Every day, make a note of:

  • Your feelings ahead of the day — what does the day entail? How do you feel going into it?
  • Your feelings during the day — who are you surrounded by? How is your energy fluctuating?
  • Your feelings at the end of the day — what did you spend most of your time on? How are you feeling now the day is done?

After two weeks, you’ll start noticing patterns. For me, I saw that I actually liked learning from others more than I realised. I also saw that I valued the opinions of much more experienced people, and was drained by having to be an ‘elder’ all the time. Interesting and unexpected. Try it. I guarantee you’ll surprise yourself.

Invest time in understanding your chosen industry better

My next step was to fully understand the landscape I was entering. How? By inviting as many people as I could for coffee (on me!), to understand the things that articles alone would never tell me.

I chose people who I knew, and people who I didn’t. The purpose was two-fold: I wanted data on the marketing consultancy landscape, and I wanted — I needed — inspirational examples of people who were doing similar things and not starving to death.

As people are busy, I ensured no meeting was longer than an hour and went into each with three focus areas:

  • How and where do you find clients? (Disclaimer: this was my OBSESSION. I couldn’t, for the life of me, understand how people actually got work as freelance consultants. I later learned it’s a combination of contacts and cold-pitching. Boom.)
  • How do you work? Aka do you invest in a co-working space or work from home? Do you work a conventional Monday-Friday? What’s amazing and what’s difficult? Basically, tell me your (professional) life story.
  • …and the most awkward question of all: How much do you charge per project?

Talk openly about money or earn less money

Ok, this is a short point, but arguably the most important of all:

Unashamedly ask other people what their rates are. We all profit from having these open conversations. Talk openly about money, or earn less money. It’s that simple.

Oh, and the best piece of advice I heard: Clients aren’t just paying you for the hours, they’re paying you for your years of experience. Calculate how you put a price on that.

Launch your freelance career as you would a product

Hands up if marketing yourself feels like effort? Or super uncomfortable? Or both? Believe me, I get it.

Over the years, I’ve launched many things: festivals, co-working spaces, apps, products… you name it. As a marketer, that’s part of the territory. Launching myself, however? I was hesitant to say the least, but the truth is: A closed mouth doesn’t get fed.

To combat the feelings of discomfort, I decided to write my story just as I would to a friend on WhatsApp (albeit with fewer emojis). I posted it on Instagram and LinkedIn and stepped away.

After a few hours, my LinkedIn post started gaining some traction. My theory is simple: because my post was more ‘human’, many of my LinkedIn contacts took the time to post comments. The LinkedIn algorithm picked up those comments, spreading my post to my extended network’s timelines too, and within a few days I had five leads (five! leads!).

All from one post. All from LinkedIn.

If you tried your best in every job you’ve had, been kind, and kept in touch with people, there will be freelance work for you. And when people see your announcement post, they’ll want to help however they can. Fact.

Your first projects will be experiments — and that’s ok

So, thanks to LinkedIn, I’ve landed my very first clients and, bitch, I’m flying.

Everyone around me is telling me I need a clear pipeline! A content strategy! An assistant! I ignore them. After ten years of meticulously linear plans, I decide to simply say yes to the work and observe myself. In the name of experimentation, I end up selling a huge variety of projects including:

  • A thorough website and content audit
  • A user research project and messaging recommendations
  • A full marketing strategy document
  • Full social media management
  • 1:1 marketing coaching
  • In-person branding workshops

Sounds like a hot mess, right?! I know. And yet it was exactly what I needed to do to fully understand myself and the work I enjoyed most. It was what I needed to do to prove to myself I could.

I wasn’t working in a formulaic way, I was going on feeling. I said ‘yes’ to everything and watched what happened. I worked less and made more than I did in my job.

I survived.

The only limits you create are your own

Month one comes and goes. It’s late July and, between projects, I’m enjoying reading in the park on a weekday for the first time. I feel calmer.

Throughout, I’m documenting my learnings on Instagram, and it’s there that one day, out of the blue, an old friend slides into my DMs.

She’s working with a major client who needs a logo. A logo. She’s seen my posts and knows that I’m doing something in the realm of branding. I’m not a designer, but I’m intrigued enough to take the conversation. I’m saying yes to everything, after all. The beauty of experimentation.

What happened next is a combination of serendipity and intuition.

Career challenges happen for us, not to us

Summer is ending. The leaves are glistening with a little more orange. The air’s a little fresher. I’m alive.

Everything I thought would kill me — the uncertainty, the lack of a secure monthly salary, the depths of the great unknown — has, instead, made me bolder.

I trust myself more now. I respect myself more. Hell, I like myself more. To spend the summer experimenting professionally is indeed a privilege, but, for me, it was a necessity. I didn’t want to spend money on another vacation. I wanted to finally, FINALLY figure this out and, to do so, I needed to go through the problem, not around it.

Career challenges happen for us, not to us. It’s our personal responsibility to analyse them, understand the cause of them, and experiment because of them to understand what to do next.

You deserve to know that — whatever happens — you’ll make it work. You’ll figure it out. We are far more resilient and resourceful than we believe. There is far more waiting for us on the other side of fear than we realise.

I wish I’d known that sooner, but I also wouldn’t change what it took for me to get here. From this point onwards, I’m being driven by curiosity, not fear. Feeling, backed by my own personal data.

That client that needed a logo? I’ve decided to focus on them. With them, I’ve found a place I can learn from much more experienced people, and successfully share my own marketing experiences, too. It feels right because I now, officially, know what doesn’t.

I sleep through the night now.


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