How to stick to your New Year’s resolution to go freelance

Owen O'Leary
7 min readJan 10, 2020

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This Time I Know It’s for Real!

Photo by David Iskander on Unsplash

Have you had a festive break and are still coming to terms with the culture shock of being back at work? This year the resolution to go freelance might just be the one you follow through on. If it is here’s a few things to consider before starting out:

You better have a good reason for doing this and know clearly what it is

Ask yourself why am I doing this? Get the root of what you want from freelancing. Freedom? To earn more money? To get to do more interesting work? Maybe you don’t have a choice or that you die a little every time you walk in the door at your current work.

Knowing the driver is vital and being clear on it will guide your next steps. When things are difficult, that “why” will help get you through the tough times and see the bigger picture. So go on, write it down and tease it out. Clarity brings you closer to reality. It will also be the compass that helps to steer you in the right direction when a rush of distractions come in. These can be anything from networking to training courses to the requests for free consultancy.

It is also ok for your Why to develop over time from one thing into another. You might start out wanting to become CEO of everything but in the pursuit you realise that making a small difference using your unique blend of talents is more than enough. For that reason it is worth checking in with yourself every few months to ask why you are doing this. It helps rekindle that all important flame.

Start from a position of strength — Find out what you need to have in place before you go freelance

If you’re transitioning from a full time job to a freelance practice you’ll want to start from a position of strength. This will look different for everybody. You might like to keep it loose and think: “If I build it, they will come” and just open for business. Perhaps instead you are particularly cautious and want to have a certain amount of savings stored up or guaranteed work waiting for you as a freelancer. There’s no right way but a little planning can make all the difference.

This is not an exact science. The aim is to recognise if you are becoming over cautious by putting up barriers to going freelance whilst at the same time getting your ducks lined up in a row so it feels like you are in a strong place starting. You should feel energised working through your requirements before going freelance full time. This will bode well for the future. Know too that the transition does not have to be absolute. I secured a short part time contract when I started freelancing and it was just enough to give me the security I felt I needed to make the change.

These preparations aren’t all financial by the way, they could include making plans for childcare, moving house, organising a place for work or anything else you feel needs to be in place before you become a freelancer. Find out what that is and do it.

Get to know your numbers

  1. Find out the minimum you need to earn to cover your living costs comfortably.
  2. Name the figure you want to earn.
  3. Work out the number of billable days you would like to work in a year taking into account weekends (104 days) and holidays (15 -30 days maybe) and admin / marketing days (2 a month perhaps).
  4. At this point also be mindful of the daily rate you want to charge (depending on sector, experience and more…).
  5. In an ideal world the daily rate you charge X the number of days you want to bill should be greater than the amount you would like to earn. If it turns out less than the figure you need to earn to live comfortably then it is time to adjust either your day rate or the number of days you’ll need to work.
  6. Don’t forget to put around 20% of this income aside for tax!

Being clear on these numbers is super powerful. Apart from the benefit of having a target to aim for it also helps inform so many business decisions.

  • Can I afford an office?
  • Do I have to take this job?
  • Do I need to change client sectors to hit my income targets?
  • If I hit my targets early can I go travelling / fishing / home to binge on Netflix?

Spending time on your numbers pays.

Hustle

There is branding. There is marketing strategy. And there is hustle. All of the above have their place but nothing happens without hustle. To win work you must ask for work. This does not mean you have to turn into a stereotypical used car salesman. Being extroverted is not a requirement. You just need to be able to clearly articulate your offer and be willing to share the benefits of working with you.

I totally understand people reading this who might say: “I have no problem promoting other people’s work but not my own. Talking about how great I am just doesn’t feel right.” The good news is it’s not about you and when you focus on the potential client it becomes about them and what they need. So the pitch becomes about asking if they need what you can provide with a polite reminder of what you can do, what you have done for others before or any other useful back up info.

Approaches vary from industry to industry but here’s how I like to approach this. Following some in depth client research to make sure I am talking to the right person I like to ask to meet because it is harder to ignore a request for a meeting than to just ignore an email enquiry. At least you might get to go on a call or get an email reply. Follow up preferably with a phone call.

Cold calling can feel intimidating but treat it as a fact finding mission. If someone responds with a no down the other end of the line then ask how they work with freelancers, what sort of work do they usually outsource to freelancers and are there times they review their budgets when you could check in with them in the future. Turning the request from asking for work to asking how a potential client work changes the dynamic and energy completely. I have found people who were brusque to the point of rude open up when it comes to talking about how they like to work.

Hustle is just a numbers game. It’s not personal, it’s a process so crack on and good luck!

Focus on the place where money changes hands

Of course freelancing is about your Why. It is about sharing your unique blend of talents. It is about living the life you have always dreamed of. But before all of those things it is about getting paid. Cashflow is the lifeline that allows you to exist not just as a business but to eat too.

In the rush of excitement while winning and delivering work the needle of an unpaid invoice can be too easy to ignore but getting that money into your bank account is everything. You owe it to all the effort involved to make sure you get paid and paid on time. That is why it is super important to facilitate and understand as much as possible about the process of getting paid.

This means knowing who signs off your invoice for payment, who actually pays it, whether your client has a payment policy. These could be anything from:

  • 30 days payment terms
  • invoices only paid on the last Friday of the month
  • invoice needs a Purchase Order Number to be paid
  • invoice must be approved by the board, delivered on a full moon or worse!

Try and avoid surprises by finding out what the situation is up front and share your own payment terms at the point of hire in a contract and reiterated on invoices. There’s a great blog by Freeagent on getting paid on time here: https://www.freeagent.com/blog/take-the-detective-work-out-of-getting-paid-on-time/

Finally please please please double check the details on your invoice. The wrong date or invoice number is unfortunate. The wrong company name, unprofessional but for the mother of all mistakes don’t do what I did and put the wrong bank details on there. Reliving the phone call where I chased the client for payment and discovered the mistake still makes me shudder! On my first ever invoice too. It took weeks to recover the money from whoever got it and much longer to recover a reputation as a professional publicist with that client.

The most important thing I learned though from that mistake and others is that it is going to be ok. There will be ups and downs but no more challenging than in a full time role. Be kind to yourself, support and look for support from fellow freelancers and embrace the knowledge that you have the skills to pay the bills!

May the road rise to meet you and the money be in the bank

Owen

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Owen O'Leary

Writing on freelancing, making mistakes, learning on the job and things that make me go Oh Really!? www.ohreally.co.uk