So last week I took a look at some of the freelancing positives that have worked for me. But as with everything, there is another side to the story.

I am not totally deluded, I realise some of the battles I have had this last year.

I don’t have the rose-tinted glasses on all the time.

Here are 5 of the main difficulties I have faced and how I have overcome them. Or at least attempted to.


1. I know bugger all about the money side of things

So I got an accountant and a financial advisor.

Two things I would never have thought I would have or would need in life. I thought financial advisors were for those earning at least 6 digits. The Wolves of Wall Street, the suited brigade. The Directors, CEOs and MDs. Not me sat here working in my comfy pants under a blanket.

I couldn’t believe it the first time I came out with “I shall check with my financial advisor” in response to one of my chap’s many questions (he loves to talk about pensions and other yawny tripe). I felt like an absolute tool and fraudster to utter those words.

But they are key to not getting myself in trouble with HMRC and explaining things to me in a language I can understand.

Sure you can research things for yourself but it takes an age to find the right info, then it is written in some kind of secret code I do not have access to. Plus with many things, you cannot be sure of the validity of the info.

So I often fire off a quick email to the accountant, this week’s entitled ’tis the season of stupid questions’ and have her confirm or clarify a few things for me.


2. I hate negotiating and discussing rates

There is no-one else to do this so there is an element of having to just suck this up. However, there is also a lot to be gained from asking fellow freelancers for advice and reassuring you that you are worth what you are asking for.

I collated all the fab advice I got in this LinkedIn article.

In reality, no customers have yet challenged my rates (except one fellow freelancer who said I am hugely undercharging, which I think for the specific project I was on ended up true).

Maybe I should increase them. Surely you should have the odd challenge here and there if you are charging enough. 😉


3. Damn those Non-Disclosure Agreements

Most of the work I do is wrapped up in NDAs so I cannot add those projects to my portfolio or website, or share the work. This makes it very difficult to show my latest stuff and is something I am currently struggling with in designing my new website.

There is not much I can do about this one other than add a note to my website about frequently working under NDA and doing as much as I can outside of these projects to give visibility to my ideas, writing and design.

A lot of freelancers and contractors have this issue, so it does seem to be fairly widely understood by those hiring.


4. Project delays, customer chaos, and unexpected ‘holidays’

One of my current frustrations is projects continually getting delayed or put back. The end clients just don’t seem to be able to keep hold of their Subject Matter Experts (SMEs).

This is always the nature of projects, especially creative ones, but I have been unfortunate that 3 have done this at the same time. So that busy December I was expecting has become fairly non-existent.

This can be frustrating enough in any job, but when in the position of (a) having turned down other projects, and (b) not working means not getting paid, this can be a real worry.

The projects were initially all slotting so well together — it was a stress-free, scheduling dream. But you can guarantee they will all start up again at the same time now and it will become a scheduling nightmare.

But that is the nature of freelancing.

Nothing is guaranteed, so you have to go with the flow.

Revel in the unexpected time off, and prepare yourself mentally and physically for the chaos to come. And just be glad the work is there.


5. It is really difficult to plan ahead

It is so hard to know when will be good to book time off for a holiday, to visit a friend, or to just have some downtime.A lot of people think as a freelancer you have total free rein over holidays and days off, but really, I am dictated by my projects.

If I plan and book some days off now, for example in February, I could find that a project I am on ends up desperately needing me at that point. An opportunity that is too good to miss may arise. Or I may be on a new project where the timing just doesn’t fit for that client.

On the flip side, you can’t just wait for a project to dictate ‘you can have time off now’, especially when working on multiple projects at the same time, as they will never all align. That is how you end up in the spiral I have had for the last 6 months where you don’t take a day off.

There is a real balancing act to be learnt.


Sometimes there is not much you can do. You have no control. The important thing for me in many of these situations is to be assertive, realistic about what I can achieve in a given timescale and ensure this is clearly communicated (verbally and written).

Many challenges can occur and they can be different for each person depending on clients, agents, communication, expectations and a multitude of other factors.

But the absolute key is to reflect during and after projects to think about the issues you faced and how you can avoid them in future, and equally to look at the successes and see how you can replicate those.

I have a little notebook in which I record all the info about each project – rates, contact details, how I got the job “(word of mouth, agency etc), highs and lows and the gist of what the project involved. I highly recommend doing this in whatever format works best for you.

So a question for you – what do you find the hardest part of freelancing or owning a business? And how have you tried to overcome it?

Write 52: Week 24
Theme: A few of my favourite things