How I Made the Leap into Freelancing (and Made it Work)

Today, I'm more content than I've ever been with my job, and I'm earning enough that I am able to live comfortably, travel the world as a digital nomad, and save money for retirement and other big expenses.

But the road to get here was long and bumpy, especially at the start.

My journey to freelancing started in 2008, when I graduated from Emerson College in Boston with a degree in Writing, Literature, and Publishing. I wanted to write for a living - a tough dream during that year of financial turmoil.

But I managed to find a job at an agency called Brafton doing something called Content Marketing - I had no idea what it was, but I knew it was money for words, so I took it.

I didn't know it at the time - but that would become my career. Over the next decade, I worked at 3 different agencies in Boston and Sydney, Australia. At my last job, I was director of content, and I had some great mentors along the way that taught me SEO.

But frankly, I HATED my life at agencies. 😖 😖 😖 😖

I hated being chained to a desk. ⛏

I hated having no choice in the clients and accounts I worked on. ⛓

I hated working with colleagues that I didn't enjoy spending time with on a personal or professional level. 😩

The straw that broke the camel's back came in 2018, when my company made the fatal mistake of giving me access to all of the revenue figures.

I took a look at it and realized that I was pulling in A LOT of money for the company... but most of it wasn't ending up in my pocket. 💸

So I decided it was time for a change. I made a promise to myself that I would quit my job and start my own business. commence freak out

I originally set a deadline of 1 year, but due to my dissatisfaction with my job, I ended up putting in my notice after a few months.

My company's other big mistake: I had a 3-month notice period. Which meant I had 3 months where most of my duties had been passed on to my replacements... and no obligation to the company besides showing up. I was annoyed at first, but this was a blessing in disguise, because I used those three months to start preparing.

Here's what I did in those first crucial months:

First, the beginning of my freelance journey (and the journey of most of my freelancer friends), required a huge time investment. There's no way around it - there's a lot to get into order. My schedule looked like this for a while:

5am: Wake up and go to the gym/eat breakfast

6:30 - 8:30am: Spend 2 hours working on my freelance business

9am - 5:30pm: Go to my job, and secretly work on my freelance business whenever I could

6pm - 8pm: Free time with my boyfriend/friends/family

8pm - 11pm: MORE work on my freelance business.

Rinse and repeat. It was exhausting, but by the time my 3 month notice period was up, I was feeling really prepared.

A big chunk of that time was dedicated to setting up my business. I built a website. I filed all the legal paperwork.

I revamped my LinkedIn and Twitter accounts.

BTW, I've put together a few ebooks about how to set up a freelance business. It's written for Australians, but there's info in there that's useful for everyone, and it's free: https://resources.rounded.com.au/start-freelancing-guide

The next thing I did was start asking questions to anyone I knew who was already freelancing.

I had a head start here, because a big part of my job at my agency was managing freelancers. I also found a few good Facebook groups (I didn't know about Slack then - but a group like this is KEY).

I asked questions like:

1. How did you get started? (That's what this thread is for!)
2. What were the unexpected challenges you faced?
3. How did you get over your fear?
4. What would you have done differently?
5. How do you charge your clients?
6. What apps/software are you using?
7. Where did you find your first clients?

My favorite quote from a freelance friend:"Starting out as a freelancer is like walking into a dark stairwell. You have no idea how far down the first step is, and it's terrifying to put your first foot down. But once you do, you realize it's not that far, and your eyes adjust quickly until you're running down those steps." 🪜

This was so true. I was sh*tting myself when I started, but once the ball was rolling, the momentum got much easier to keep up.

If I could recommend one thing all freelancers do as they're starting out, it would be this:

Tell EVERYONE what you are doing. Tell your friends and family.

Tell your former colleagues and clients.

Tell strangers on the bus and the waitress and the street performer and anyone else who will listen.

🗣 Word of mouth is by far the most popular and common ways to get your first clients, and it's still my most successful form of marketing.

But Word of Mouth only works if people KNOW what you're doing.

Other important things I learned at the start:

1. Don't wait until your website/profiles are perfect (or even live) to start looking for clients. It takes forever to make a good website, and I'm still constantly working on and improving mine 3 years later.
2. Create a space that you really enjoy working in. Put your desk by a window. Get a comfy chair. Buy a second monitor for $50. You're going to be spending a lot of your time sitting there, and if it's uncomfortable, your motivation will tank.
3. Save everything, and turn them into templates and processes to save you time. I am still building off the quote template and content calendars I had when I started out.

And finally, don't let your finance-phobia stop you from doing the admin stuff that MUST be done. You'll be better off if you begin your freelance journey with a trusted financial management system. I recommend Rounded if you're in Australia/NZ. I'm in the US now and use QuickBooks self-employed, and I've also heard good things about Bonsai.

Don't fall into the tax trap that many freelancers experience. These programs tell you exactly how much money you need to set aside for taxes. Put that money in a separate account and DO NOT touch it.

They also help you track your business expenses, which is by far the best way to save money as a freelancer.

There will be ups and downs as you go through your first few months of freelancing, but over time, things smooth out. (Especially if you take my advice on the lessons I learned!)I'm going to wrap it there, but if you want more tips, check this out:

My full blog on how to start freelancing

And if you like that, here's my one-year-later update.

I share lots of tips on my LinkedIn and Twitter, so please come connect with me and say hello!

Last but not least, I'm always happy to chat with people who have questions about starting out a freelance career. I'm also happy to share my financial tracking template, or show you how I quote and charge clients.

Oh, and you can get my best tips delivered via email if that's your thang.