10 Lessons From A Year Self-Employed

It’s been a year since I decided to work for myself. I quit my previous job in an erratic act of self defiance, romanticising the millionaire sob story to live my own dreams against a backdrop of improbable success.

With $1000 to my name, not a single client, $4000 of debt and my only mode of transport (a 2001 SR250 motorbike) without brakes, I was well and truly in the deep end of the pool.

I was determined to swim.

My parents offered me 3 generous months rent-free in their garage, where I hauled a second hand kitchen table to the centre of the room, pushed a bed under the dusty, exposed roof and set up shop. If I couldn’t afford rent by the end of 3 months, I was going to go job hunting. That was the deal.

I moved out within the first month thanks to some quick but significant wins. During the year I flew interstate 6 times, went to Sri Lanka for two weeks and spent 3 months driving around Europe. I turned 24, paid off my debt, saved a bunch for travel and managed to spend 4 months working ~8 hours a week. AND NOW YOU TOO CAN BUY MY E-COURSE AND DISCOVER HOW YOU CAN MAKE MILLIONS FROM THE COMFORTS OF YOUR HOME. Jokes. I’m not rich.

But the important thing is, I survived, and I’ve got enough to keep on surviving.


Here’s a bunch of stuff I’ve learnt thanks to patient and understanding clients. This list looks pretty much identical to any other you’ll find on the internet, but I find that recommendations from people I actually know seem more legitimate. So friends, here’s what I’ve got.

For the record, I’ve been working as a writer/digital marketer/community engagement consultant predominantly in the social impact/education/environment space.

1. The “hustle”

Eugh, I’m so cynical about the word “hustle”, but it’s probably the best word we’ve got to describe exactly what it is. If you don’t enjoy sniffing out opportunities and the constant “I’ve got to find a client this week otherwise I can’t pay rent lol”, then freelancing is not for you. You need the hunger, because it’s the hunger that motivates you to crawl out of bed, open up your laptop, stare at an empty inbox and press “Compose” for the 800th time that week.

It’s also important to use the hustle to upskill so that you can offer your clients more, especially if they’re startups. My lack of graphic design skills have been a real hinderance.

2. The importance of networking

Every time I collect a business card, I write where I meet the person and something interesting about them on the back and file it. Sometimes I run off to the bathroom directly after a conversation at a conference, sitting down on the loo and hurriedly jotting down their favourite sporting team and the fact they have a son.

On the first day of my Brand New Life™, I pulled out all the business cards I had saved over the years, wrote a long list of friends and mentors and proceeded to send everyone a personalised email. I sent about 20 per day at the beginning. Sometimes they were simply “let’s grab a coffee”, while others were more explicit in relation to my service offering. All of them referenced that tiny personal detail from when we first met.

Keep in mind, if you collect business cards from people during events paid for, hosted or attended on behalf of a previous employer, you cannot initiate conversation. I made sure only to reach out to those I had met independent to previous employment. Most employment contracts are pretty explicit about this, so be sure to read the fine print. My previous short-lived job said I couldn’t work for another innovation consultancy company for three years after leaving.

Don’t look at networking as something you have to change yourself for. Just look to befriend interesting people in interesting industries. Share your contacts in a way that you’d hope someone would share theirs with you. This is less about what you can gain and more about what you can offer.

Finally, if you’re a freelance writer, don’t just go to writer-related networking events. If you’re passionate about makeup, go to conferences and trade shows about makeup. Talk to the vendors. Become an expert in the area. If a vendor holder asks you what you do for a living, say that you’re a writer in the cosmetics industry. Ask for their card.

3. Schedule follow up emails

Just because you don’t hear back, it doesn’t mean it’s a no. As soon as I send an email, I write myself a reminder to follow up 7-10 days later. If you’re a service provider, personalised touch-points are incredibly valuable.

4. Pitch ideas you want to execute

If you’ve got a good idea that another company could execute well, pitch it to them. Pitch it in enough detail to land a meeting, win them over with your personality and what you can offer, then send over a proposal to deliver it. I did this with a Federal Politician who wanted someone to run her social media. I came to the meeting with case studies and a half baked idea to do more than just “run social media”. I pitched a concept and ended up writing a strategy, executing a campaign and writing a speech for the House of Representatives.

I’m not worried about people stealing ideas and running with them without me. I just monitor the heck out of them if they do, learn from their failings, and pitch something better to someone else.

5. Ask questions first

If you manage to score a meeting with an individual or company you want to work with, try and spend the first 5 minutes asking them questions and figuring out their pain points. Then you can tailor your response and your service offerings to their pain points, as opposed to shooting in the dark and hoping the way you word your offering lands. 

6. Invest in great project management tools

Set up these structures from day 1. You’ll thank me later.

  • Toggl is amazing for time tracking and it’s free (!!). Make sure you label your tasks so that when a client asks exactly why a particular week or month is higher than others, you can download a report and send it their way. If you’re charging for project-based work, it’s important to track your hours anyway. This way, you can figure out how much you worked per hour based on what you charged, and whether that was fair for you.

  • Asana is incredible for project management and I don’t think I could do life without it now. You can add people to projects, create deadlines, add to do lists and tasks within projects. Amazing. Oh, and it’s also free.

7. Values-driven opportunities

I find it incredibly difficult to concentrate if I’m working on something I hate. I have turned down opportunities purely for this reason, which kept my space free to say yes to opportunities that aligned with my values.

It sucks writing content about things you’re not passionate about. You spend so much time researching and if you’re paid per word, you end up in the red. In contrast, writing content about something you know a lot about means you’re more valuable to the people that hire you, and you have a much higher profit margin because you can pump those words out without having to think too much about it.

8. A mentor is the most valuable thing to have

Meet with them regularly. Stress that you’ll buy their coffee even though they always refuse and beat you to the counter. Listen to them, especially when they scrawl in pen “CHARGE MORE MONEY” (hi Phil). Do the worksheets they send you. Value the people they introduce you to. Remember that their reputation is on the line as well.

It’s easy enough to find a mentor. Find someone in your life that you know, or know of, or are connected with on LinkedIn and simply ask them. Slide into those DMs. Ask them for coffee because you have some questions about their industry. Keep meeting them for coffee. Most of the time, the relationship will form organically.

Make sure to give back and mentor others when you’re ready. Be the person you wish you had when you were starting out.

9. Know why you charge what you do

People will question you on it. Be prepared to break it down, especially if you’re working for SMEs. Deduct tax, deduct super, deduct HECS payments, reinstate your years of experience, reinstate how much they’re saving by hiring you as opposed to hiring someone on the books. Stress your flexibility and (if true) your out of office hours access. 

10. Subtly allude to your other skills in emails

“Sorry I can’t make it Tuesday! You mentioned you were struggling getting bums on seats - I work in digital marketing if you haven’t explored that avenue yet. Happy to help :)”. A little line like this has been surprisingly helpful and quite an organic way to provide a service to a client. Choose when to use this wisely.


There’s a false illusion that being a freelancer is smooth sailing. In truth, I built up to becoming a freelancer for years, albeit unintentionally. Your networks are your strongest asset.

I wanted to live a particular lifestyle and I didn’t know of an employer who would afford me that. So I carved my own. The current employment landscape is giving us unprecedented freedom to do so, so I grabbed the opportunity and ran as fast as I could. What a ride!

If you have any questions, or want an e-intro to someone, I’ll do what I can to help. Slide into my DMs.

Yours in love and procrastination,