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freelance = freedom

September 17, 2026 Darren Caveney

“You have to be comfortable with being uncomfortable”

“Comfort zones are great, but nothing ever grows there”

This is just some of the advice from a ‘Going Freelance’ call I was a part of this week.

by Dee Cowburn

Going freelance is not a decision to be taken lightly.

People come to it for different reasons. Change usually always drives it.

Difficult work conditions, or need for a work life balance.

Not feeling supported, developed enough, or just wanting to try something different and strike out on your own.

There’s clearly a lot of people considering the switch right now.

Being part of a network has helped me enormously and I can’t say that enough.

Feeling part of something and less alone. Knowing others in similar positions had done it and excelled. Knowing I would have to be brave and be comfortable with discomfort.

Speaking to Darren about it while I was still in-house, he showed me an eight-point plan he had drawn up. That’s on a previous blog HERE.

So I figured, two and a half years in, how about outlining eight things I have learned in that time? I’ve probably learned a lot more than eight things, but I know some jump out more than others.

1. Having to tolerate discomfort

You might know your current role inside out, I know I did.

Freelance, I thought to myself, would be me just doing the same but not in-house.

It might work like that for some and that is great, but it hasn’t for me. I have sort of done a bit of everything, mainly crisis comms, but a lot of things in between.

To pushing out of my comfort zone to deliver training in a different country, to speaking at the PRCA conference and delivering webinars on policing, crisis comms, devolution and media training for parents of children in hospices.

None of that would have happened without accepting being scared, or out of your comfort zone, a bit of imposter syndrome thrown in, and doing it anyway. Susan Jeffers wasn’t lying, Feel the fear and Do It Anyway. There is a reason why that book is a best seller!

2. People aren’t lying - getting an accountant might feel like an expense, but in my opinion an essential one

Especially if you are a limited company. Even if you’re not, I would have an accountant.

Ask for recommendations, and go with your own feelings, I had a shocking first one and changed. Which felt painful at the time but is so much easier now. I just do my day to day and they look after the tax scenarios.

3. Get business insurance 

It’s pretty cheap, but essential. Make sure you have the right cover for the jobs you are doing. I had to increase my personal and professional liability to work abroad and change and tweak my insurance.

This and the accountant one were on the 8-point plan Darren drew up, but they still are as important now as they were then.

4. Ask questions and network

Ask people who are already working for themselves, scout about, and become aware of networks. You’ll be amazed once you start freelancing, and focusing on making connections in that world they really do appear.

What membership bodies do you want to be part of? Why? Who do you know who knows someone who is freelancing? Which old contacts can you connect with?

Don’t be afraid to ask questions. I’ve had people contact me out of the blue and ask about how I went freelance and what areas I work in. I think collaboration and shared knowledge is important, because supporting people is a good thing to do. And why not?

5. Be brave

Just do it. That call you want to make, but your critical voice just stops you from doing it. Just do it anyway.

That business you wanted to approach and keep finding excuses not to? Just approach them. I’ve done that and felt so worried, and its worked out sometimes, and other times it hasn’t. And that’s okay. But unless you are doing it, and putting yourself out there, you are never going to know. It’s a cliché but you have to be in it to win it!

6. Clear boundaries

Knowing your personal boundaries is essential. Knowing your professional boundaries is also essential. 

Because you are responsible for your own work, your own relationships, and your own motivation and discipline. But the same as being in the workplace, or at the school gates, or part of a sports team, or whatever. People are people.

Some freelancers might be like people you work in-house with. What I mean by that is some you gel with, some you don’t, and that’s okay.

Janet Street Porter (bear with) once said a third of people you will get on with, a third will be indifferent, and a third won’t like you, and that’s okay.

As Advita Patel said, you won’t be everyone’s cup of tea, otherwise you would be a mug.

So, accept that some times people come into your life, and then they leave, and that’s okay. Know your values, know your boundaries, and be comfortable with them and the decisions you make in line with them. This was one of my steepest learning curves, but most valuable.

7. Freedom

You are responsible for your time, get to know yourself and what motivates you, what tires you, what bores you, what your energy levels are like. When do you work best, do you want interim, fractional, freelance, a mix of all?

This is your business, your responsibility, and you are accountable to yourself.

That might seem slightly terrifying at the start, but then you sort of grown into the responsibility you’ve given yourself if that makes sense.

You look back and think the decisions you made that didn’t feel that big at the time, but they really were.

Keep the path clear, think about things with an open mind, take opportunities where you find them, and be flexible. You might start doing work you never thought of and that’s great too, who says you have to be defined by one thing.

8. What is your value proposition?

Now I’m slightly contradicting my last point by saying you should know what your offer is. You don’t have to be defined by one thing. However having a clear value proposition, which is what your offer to organisations is, can help you.

Someone told me this and it stuck.

What is your offer that can meet an organisation’s pain point? What problem of theirs do you solve?

So it isn’t about your services, it’s how they solve a problem for a specific organisation.

Having a paragraph of your distinct offer, that can be tweaked depending on who you are approaching.

Who are your contacts you can ask to make intros on your behalf, or let you mention them in intros to their own network?

Who have you worked with before who may need your services? Make a list

Know your value, know your worth. Enjoy it.

Also, be clear on what you DON’T want to do, as Darren said on the freelancer call this week, that is just as, if not more important. Knowing what you don’t want to do. And you get to choose.

Get that last bit right and it helps.

None of this is easy, or comfortable, but its hugely rewarding and a new way of living, that shows you actually how possible things are and what possibilities lie before you. You can literally create whatever you like with the skillset and network you have. And, if that isn’t there for you, create it.

Dee Cowburn is owner of Dee Cowburn Communications Ltd, a media and crisis communications consultancy. You can say hello on LinkedIn here.

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In research + evaluation, resources + good stuff, training + development Tags freelance = freedom, You have to be comfortable with being uncomfortable, Comfort zones are great, but nothing ever grows there, Top tips for going freelance, Going freelance is not a decision to be taken lightly, The pros and cons of becoming a communications freelancer, Dee Cowburn, comms2point0 comms best practice, public sector communications best practice
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