Three Questions I Constantly Ask Myself as a Freelancer

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As a freelancer, it is up to you to keep business momentum going. It can be a tough, but constantly asking myself these 3 things really helps my business development…

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Taking the leap from a full time job into freelance work can be scary. There is no job security, no weekly pay packet and none of that oh-so-handy ‘sick leave’ and ‘holiday leave’. There are some pitfalls to freelancing, but the freedom and variety of work you get as a freelancer is unbeatable. I wouldn’t change the set-up I have for the world.

One of the hardest things about going out on your own is the business development side of things. You can’t just open your computer and hope that there is a heap of work sitting there waiting for you. It takes a whole lot of hustle to keep finding and securing the work you need to make ends meet. Complacency can’t and shouldn’t be a thing in the world of freelancing.

After around 3 years of freelancing, business development is now a natural and normal part of what I do. It has gone from being a scary and awkward part of my job, to something I actually enjoy doing. If you are thinking about making the leap into freelancing, or you just starting out on your freelancing journey, perhaps these 3 questions I constantly ask myself will also help you when it comes to building up your work as a freelancer.

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What is the worst that can happen?

It sounds so obvious, but asking myself ‘what is the worst that can happen’ has got me through many overwhelming situations.

Take – for example – all those times I had to email people back with my rate card. Or the time I emailed a new publication with a pitch for a piece that wasn’t the right fit for any of the publications I already wrote for. Both were instances where I was putting myself out of my comfort zone. I found myself putting off sending those emails out of fear.

The only reason those emails got sent was because I sat and thought about the worst case scenario in each situation. The worst case scenarios were that people refused to pay me, that I never heard back from the new publication and that my ego was a little bit bruised for a few days until I forgot about the exchange.

None of that is life threatening.

In fact, most of the things that fear stops you from doing really don’t have any huge negative implications attached. Most of the time, the worst that can happen is you get a ‘no’. Maybe you won’t hear back from anyone, or maybe you just have to keep trying.

The best case scenario? You actually get what you were asking for (as was the case for the two examples I gave). And this really is the best case for a freelancer!

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What will I be losing/will I be losing a job if the negotiation doesn’t go well?

I had this question posed to me by an older friend and mentor when I told him an amazing brand had contacted me to promote one of their dresses, and I didn’t know what to do about the email. I was so excited to be contacted by them, but it had come across very clearly in the email that they had no intention of working with me for any sort of valuable remuneration, let alone monetary remuneration.

He looked at me and asked me why I didn’t just go ahead and send them my rates. When I told him I was scared I would lose the job, his response was ‘you aren’t losing a job if they were never going to pay you in the first place’.

This comment has stuck with me ever since.

Am I really losing ‘work’ if someone doesn’t want to put any money behind my worth? In my eyes, no. Not only does completing these jobs for free totally devalue my work, it devalues the whole industry and takes work away from my peers. I can also generate my own ‘free’ work. There is absolutely no need for me to be writing 800 word articles or promoting someone’s pretty maxi dress if I don’t get something of enough value to me out of it.

It might sound harsh, but asking this question has helped me so much.

Note: This doesn’t mean you should only work with brands that will throw money your way. You still need to think critically about who you are working with. Think about the messages you want to get across. These working relationships reflect on both yourself and the brand.

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What am I worth?

Ah yes. The all important question that a lot of people stumble on.

Over the years I have had countless people ask me what they should be charging for certain jobs. The best advice I can ever give when it comes to trying to price a job is ‘how much would I be happy doing this job for?’.

Everyone’s time is worth something and everyone values their time and skills differently. I constantly ask myself what I am worth on each job and how much would I be happy to do a particular job for? My answers always vary, but that is what happens when you work with different clients with different needs.

This question and the previous question work hand in hand. It is important to sit back and ask yourself what you are worth on the regular. When you know your worth, you will find that the ‘am I really losing a job’ question will become much easier to answer.

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