20 Lessons from 2 Years Self-Employed

It’s been 2 years since I quit my 9-6 corporate job 3 days in to build my ideal work-life balance. At the time, I had no financial stability and no cashed up (or business-savvy) parents to fall back on. Due to the lack of safety net, I worked a lot harder than I think I would have otherwise.

Last year, I put together a 10 Lessons blog post, which saw mild success. I thought I’d put together the top 20 lessons I’ve learnt in the last 2 years to help those who may want to make the plunge, or those who are, like me, already knee deep.

Here are a couple of things for context:

  • I had $800 to my name when I quit my job and a broken motorbike as my only form of transport.

  • My folks generously offered 3 months in their garage rent-free. Then I had to start paying board. I moved out in the first month and have paid rent in various share-houses ever since.

  • I was on Centrelink for 6 weeks during the 2-year period (I was studying full time). I don’t own a credit card. I have only had to borrow $900 from my parents during that time.

  • In 2 years I’ve spent 3 months in Europe, 2 weeks in Sri Lanka and a week in Fiji. I spent 2 weeks in Alice Springs, 3 weeks in Western Australia, have been to Tasmania 3 times and have spent about 3 months in Melbourne. A lot of this travel has been due to work. I usually don’t work more than 10 hours per week.

  • I make most of my income through writing, digital marketing strategies and community engagement consultancy.

photo cred: chasteffenphotography.tumblr.com

photo cred: chasteffenphotography.tumblr.com

Please note that I am a single 25-year-old with no mortgage, no kids and no real responsibilities beyond taking the bins out on a Monday night. My advice certainly isn’t relevant for everyone!

Heeeere we go:

1. Figure out your Survival number and your Thriving number

I was being coached through my finances by a friend of mine a few months ago. He told me to figure out what my Survival number and my Thriving number was. I looked over my bank statements and went a little spreadsheet crazy. I tallied up rent, averaged out bills, food, superannuation, tax and petrol, and arrived at a neat $350p/w. That’s my Survival Number. That’s what I need in order to (just) make ends meet. I wrote it on a post-it and stuck it on the wall. 

Then I thought about my ideal lifestyle. What luxuries would I like to afford myself in order to feel like I’m thriving? I’m not talking million dollar cars and thousand dollar dinners, I’m talking the small luxuries. Dinner at a nice restaurant once a week, 10% to charity, the ability to buy a few cocktails when I’m out with friends, a flight here or there, some more petrol money for road trips, some money to save. I arrived at a modest $1000p/w. This is a 52K salary (before tax), something most freelancers (with no kids, mortgage or other major responsibilities) would be quite content with if they’ve managed the work/life balance to their liking. I have no need for more money, because my fulfilment comes from very affordable activities like hiking, swimming and napping in the sun. I imagine it would be a lot higher if you had expensive hobbies and didn’t rely on op shops to clothe you each season.

I stuck my Thriving number on the wall as well.

Having these numbers in front of me makes my finances tangible. I’m very erratic with my money, and in the past have certainly found myself scraping the barrel. This drastically helped me consider the hours that I work and how they translate into my lifestyle. 

2. Make your money on Mondays

As my Survival number is quite small (compared to those living in the heart of Sydney, or those who have 4 mouths to feed), I am able to make all the money I need on a Monday. If I can earn $350 on my Monday, I am free to relax and take the pressure off for the rest of the week. 

I am studying a Masters and a Diploma, and I also run a small community support group and digital content platform. I have a veggie garden and I go for swims in the ocean and I have a one hour bath at least 4 times a week. By making my money on Monday, I have ample time to study, do the activities I love, work on my passion projects and, if I work on other days, get the joy of feeling like the money I’m earning is for all the things listed beneath my Thriving number. 

3. You need the “hustle”

While I’m supperrr cynical about the over-used word “hustle”, 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.

4. 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.

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. 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.

7. Try to secure project-based work or contracts with a retainer

Project-based work means that there’s an end in sight. For those of us who love week-long or month-long adventures, project-based work allows for intensive work, a sweet cash reward, and no commitment thereafter. Project-based works allows you to charge a higher rate too, because you include buffer hours into your proposal. It keeps you motivated to get the work done well and quickly, because it won’t affect that final number. 

Retainers mean financial consistency and security. From a budgetary perspective, it’s nice knowing how many clients will be paying you what each month. Some months I’ll work over the amount that I’ve projected, and some months way less. The key is setting explicit standards with the client, so you have the ability to communicate if they’re pushing the boundaries. 

8. Invoice 50% of big projects up front

I had a project that kept growing in size, and silly me didn’t think to pause and shoot over an invoice for 50% of the cost. I spent a long time chasing up my money. I sent a Letter of Demand. I threatened court.

I was finally paid, but I had to reschedule some activities that I assumed I’d have the money for.

Freelancers never get paid to chase up invoice. It fucking sucks when we spend an hour chasing and re-sending invoices and writing Letters of Demand. If you’re reading this and you employ contractors, please pay us on time.

9. 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.

10. People are watching you on social media

I get most of my clients through connections on Facebook. On Facebook, I am never explicit about the work that I do and the services that I provide, I just share things I’ve written, and projects I’ve worked on. It’s important to note that I never use a call to action. Mostly because that is not why I share my work on Facebook. I share the stories I think will resonate with my community and I share the projects I think may be useful to them. It does mean you have to put yourself out there. You never know who in your network needs someone with the skills you have.

11. If you’re looking for more work, ask current clients

If you’re producing work that your client is happy with, and your schedule is looking a little bare, instead of cold-emailing random companies and living your life in their Spam folder, email those happy clients and let them know you have finished up some projects and are looking to take on some new clients. I have been e-introduced to a number of clients/contacts that I otherwise wouldn’t have thanks to the kindness of the teams I work with who are happy with my work.

12. 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.

13. Know how to sell yourself

Know how to position yourself in front of a potential client as a money making machine, rather than another machine in their team that costs money. You need to know what value you add to their business, and you need to know how to communicate that in monetary terms. This is where case studies of your previous successes are helpful. You need to get comfortable with articulating your value in their terms.

14. Have a self-employed best friend

I have a self-employed best friend. We call each other every week. We rant about things and celebrate small wins - from getting out of bed in the morning to getting a rejection email from someone we didn’t even think would bother reading what we had to say. We also provide the space for each other to throw around ideas and get advice. This has had a drastic influence on my motivation and inspiration.

I also have a Google Sheets with the girl above and another. We right down our revenue goals and our revenue actuals, we write down our business goals for the month and our personal ones. We keep our To Do lists in there, and little diary entries about our week. It’s a great way to hold yourself and your friends accountable, and a great motivation tool when you see how your friends are spending their working hours, and how much cash they’re pulling in as a result.

15. If you’re a writer, use Medium

Medium is a blogging platform, but it’s also kind of like a digital publication that you don’t need to pitch to. A yearly membership costs $50, and every time you read an article, or ‘clap’, or comment on one, some of that $50 goes directly to the writer. 

I keep a blog for my own enjoyment. I have been blogging since I was 14, and it has drastically improved my writing. It has also taught me how to write and position stories in a way that may engage a larger or more specific audience. Often I don’t follow this, because a blog is also a space where I can experiment and write things for myself, but the learnings I have been able to take elsewhere.

With the blogs I have already written, and would have written whether I was getting paid to or not, I pop them behind the paywall on Medium. This takes about 3 minutes to do, but allows me to earn a little extra coin while introducing my work to new readers. Of course, this is not enough to live on. I’m not active on Medium, and I only earn between $30-$50 USD a month. But it’s money that I wouldn’t have had otherwise. 

16. 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.

17. 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.

18. 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 (small to medium enterprises). Deduct tax, deduct super, deduct HECS payments, reinstate your years of experience, reinstate how much they’re saving by hiring you as a contracter as opposed to hiring someone on the books, emphasise how much money you’ll bring to their business. Stress your flexibility and (if true) your out of office hours access. 

19. 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.

20. Message brands you love

You know what value you bring. You know that your value can increase the revenue of another business. But let’s be honest, it’s 10x more enjoyable doing this for a business that you believe in. One whose products you buy, or whose stories you read. Big companies have strong internal hiring processes which are difficult to penetrate through creative means. But that small business? The one with a few thousand loyal followers? They might be looking. Or they might not know they should be looking. 

I have reached out to a bunch of brands I love over the last two years. I email them about how I found their product and why I loved it. Then I might tack on the end, “I’m a digital marketer if ever you need anything! I love working with brands I believe in, and only work with those who have a positive social impact”. Yes, you’re kissing arse. But you’re not lying about it. You love their product. They want to know that people love their product. You’re alluding to your skills a way that doesn’t require a response if they’re not interested. The emphasis is on their product, not on you expanding your portfolio of clients. You’ll continue buying their product and supporting their business either way.


I have learnt a lot about business since freelancing, but I’ve learnt a lot about myself too. I have discovered just how little money I need. I live in a coastal town where there’s no social pressure for house-buying, no weekly dinners at restaurants. It’s home-cooked meals and backyard fires, ocean swims and book clubs. I have learnt how to slow down. I have learnt that just because I’m self-employed, it doesn’t mean I need to be building a Big Huge Money Making Machine. I’m just want to Thrive on my terms.

Shoot me an email if you want to chat. hello@rubyclaire.com.au