Ah, the promise of a new year in your freelance business.

The world is your oyster. Anything is possible. With some careful planning.

Sure, you have to roll with it to some extent as a freelancer. But you can take back some of the power by making some strategic decisions about your business.

Here’s how I map out about the year ahead in my freelance business:

For close to 15 years (even when freelancing was just my side hustle), I’ve booked a long lunch with my husband (an accountant and my best friend) to talk through the year I’ve just had.

It’s a chance for me to take a good hard look at where I can do things better and what the year ahead might hold for my freelance business.

We book a restaurant with awesome table service and take along my laptop and financials. There’s always wine on the table.

Without a doubt, this annual 3-4 hour planning session makes me a better and more financially successful freelancer- my happiness levels as a freelancer grows every single year, as do my earnings.


Before we start, we chat about the highlights for the past year. What have we loved doing, which months were best, and whether we’ve got enough balance.

My husband prepares some financials so I can take a realistic look at how my business is performing, and look for  areas I can improve.

Here’s what we take along:

> The laptop and power cord for WiFi access.

> A print-out of the clients I’ve worked with over the previous 12 months (I like to look calendar year for this).

> My earnings for the previous calendar and financial year, broken down into project fees, day rates, word rates and hourly rates.

> A breakdown of my best paying clients so I can see how much I’m earning per hour for each client.

Here’s what we work out:

> We rank clients by best earnings and by favourite in terms of projects.

> Which quarter was the most successful financially – and we talk through why/how

> Which clients have given me the most work throughout the year – interestingly, one of my lower paying clients has bought me in the most work this past year. And while this isn’t necessarily the best financial decision, the new work leads that ARE better paid that come from this client make it more than worthwhile.

> My business costs/outgoings – including costs such as the two part-time freelancers to help me run this community and handle some of my own admin tasks.

> A breakdown of any trips I’ve taken, and whether the trips were worthwhile.

> Which clients pay late – (all my invoices were paid, but a few over the year were 40-50 days, which is too long to wait, it drives me crazy).

When you see it all laid bare on the table, it’s pretty hard to escape the glare.

I love it. It makes me accountable to myself, and helps me focus on what’s important both in life, and within my business.

I feel empowered when I know exactly what I’m earning because it gives me a clear look at what areas of my business I can improve in, and motivates me to look for ways to work smarter, not harder. This includes implementing a new digital tool or app, project management tool, and led to my decision to hire a couple of freelance specialists this past year.

I love to talk through the cool projects that came my way throughout the year.

I also talk through the clients I’ve loved working with, and whether my branding, website, socials or service offering description needs a refresh.

After a couple of wines, I daydream aloud about the clients I’d like to call mine, the other freelancers I’d like to work with, and whether I’d like to travel more or less this year.

I talk about what I can improve, and we set some boundaries for our family – when I will work, and when I won’t. (I work REALLY hard, but I’m also there for my kids).

We also discuss a holiday we’d like to take in the year ahead. And map out some goals.

I structure my freelance business in a way that gives me a few key regular clients, but I purposefully leave time in my schedule to pick up exciting projects that come along. Because as we all know, the beautiful thing about being an Australian creative freelancer is not knowing what opportunity will come along next.

Here’s some of the key decisions made about the year ahead:

> I’m happy to work five days a week during school hours if I love the work, though I will try and take every second Friday off, where I can, and do something nice for myself.

> I’ll work the occasional weekend, if the project is super cool and I’m paid really well for my time.

> I’m not keen to work with two clients I’ve worked with in the past year – one was a late payer, and one has been kind of rude in emails and on the phone. (I avoid these clients at all costs).

> I realised that I want want to work more closely with a couple of Melbourne entrepreneurs I work with (I reached out to see how I could offer greater value to their business and after an hour-long discussion on the phone and we’ll work more closely together this year as their business is going gangbusters.

> I revisited the parameters of the service I offer. I also killed off a service offering I had listed on my website, but that didn’t prove to be a real hit with my clients.

> I mapped out a new product offering that could bring in some passive income via my website, which is in the planning stages.

We left feeling excited about the year ahead, and grateful for all the things that freelancing brings us.

Bring on 2019!!

What about you?

Do you hold an annual or quarterly planning session? What’s your goals for this year?

Drop into our community (for freelancers with their own profile page on The Freelance Collective) and share what your year ahead with look like. Or, ask questions of other creative freelancers and see how they do things.

Create your own profile and get found by new clients this year here. 

Nina Hendy

Leave a Reply