Be Freelance for the Right Reasons

How do you become a mega successful freelancer with a great quality of life?

I don’t know.

But here’s what my experience and intuition says…

For the last four years I’ve spent the majority of my time working as a freelance video producer and before that I worked in-house at a London Sports Agency.

In the final few weeks of university I was intending to chase the freelance video dream the moment I walked out of my last exam. If it hadn’t been from a chance email from a friend, telling me about an opening at a sports agency I know I most certainly would have dived in and gone freelance.

Looking back I’m so glad I didn’t.

At that time I wasn’t anywhere near ready for the big wide world of freelancing. Having the guidance, training and often brutally honest feedback from my former Sky TV producer boss during my time in house, meant I was able to get the experience and skills necessary to get to an industry appropriate standard for freelance video professionals.

When working in house I would be out on location filming at least 2 or 3 times a week and spending 70 plus hours of my week immersed in video production.


Working at the Rugby World Cup in 2015 was pretty special!

This was an incredible opportunity to work with and learn from other professionals, experiment with new kit and practice, practice, practice, all under the watchful eye of my producer and the big bosses.

Most importantly, if something went wrong, at the end of the day there was always a safety net.

I was never solely accountable for production budget, timescales and the quality of the content we were producing. The buck didn’t stop with me, it stopped much much further up the chain.

To me if you’re working in-house, as long as you show up on time and give your best effort that means you’re doing your job correctly.

It’s up to the people paying your wages to make sure what they’ve asked you to do, is feasible, the right decision and ultimately will make the client happy.


I always showed up before my boss and worked later than he did, I gave up weekends, evenings and pretty much everything else I enjoyed in life in order to be better at my job.

After a few years I felt I was plateauing and there wasn’t a whole lot more to gain from working at the agency. So after a lot of consideration, I chose to go freelance to take on more challenging projects, work with a whole range of different clients and ultimately work towards becoming a better video producer and businessman.

I am so grateful for the time I spent working in house, but the moment I walked out the London agency door for the last time, I was so excited thinking that I had escaped the so called ‘rat-race’ so many of us desperate to avoid.

The truth is, the moment I walked out on to the street, I had just started a much tougher race, the freelance rat race.

And it can be so easy to get swept up in it without even realising…


You spend your life desperately trying to produce as much as you can, whilst simultaneously chasing that next project. In order to make sure your bills are paid you take the jobs that guarantee income rather than perhaps the ones that are better for your career. And most sadly you’re scared to book any holidays or time off because it could mean you miss out on an amazing opportunity.

I don’t know whether it’s a sign or pure coincidence, but this summer I’ve very luckily got to meet and work alongside some very talented freelance videographers and photographers, and the majority of whom have said exactly this to me and that they are looking to get out the game and work on something of their own.

How do you measure success as a freelancer? Is it how much money you earn? Is it the prestige of your clients? Is it how full your diary is?

My intuition and experience tells me it’s none of this.

At the moment my immediate goal is to buy a place to live. I want to stay in the area I’m in currently which means I either need to win the lottery, rob a bank or work my face off to be able to afford even a one-bed flat.

As a freelancer you’re selling your time, and the most obvious way to earn more money is to work on more projects. For me late last year there came a point where I realised there is only so much work you can do before some serious negative consequences.

After a week straight of 16 hour days, on the final day I had another 16 hour work day, this time with a four hour drive to the location (and then a four hour drive home). I arrived to the location before 9AM, dived in to a petrol station to get a coffee and was just shaking, I felt physically sick and was genuinely unsure if I’d be able to stand up all day, let alone operate a camera with any skill or quality.

It was that moment that I realised working freelance does require you to work hard but it doesn’t mean working yourself to the breaking point.

I’ve close friends that have worked themselves far, far beyond that point and thankfully they’ve come out the other side stronger, happier and are now on a new path to be much more successful. But this game can take you is a horrible, dark place.

If you’re a new freelancer or aspiring to be, please heed this article as a word of warning. It’s going to be tough and you should be prepared to work harder than you ever have before in order to be successful. But every low point you come across, make sure to ask yourself if you’re still happy with your situation. Make sure your physical, mental and overall well-being is always your number one priority.

This leads us on to how, in my opinion anyway, you define being a successful freelancer…

Are you happy?


Photo Credit: Syzmon Nieborak

The most successful freelancers I work with are also the happiest. There are some that have so few days off but they’re also the ones that live video production. For them any chance to have a camera in the hands and be filming is pure joy, the fact they get paid handsomely for it to is just a bonus.

They work they produce is also phenomenal and there is most definitely a direct correlation between how happy you are and the quality of videos you produce.

My intuition says being freelance is not about the money. It’s about the flexibility it gives you…

Whether you use that flexibility to pick and choose the projects that are the best for your career, or plan your working life to maximise time with your family or even be able to take a holiday whenever you feel like it, those are all great reasons to be freelance.

Don’t do it for the money.

Yes, you can earn a great living being freelance, but it’s an incredibly unstable financial life.

If you’re considering going freelance, I would say go for it, but only if…

  • You’ve worked in the job you want to do for another big company for at least 18 months, and gained all that expreience.
  • If you’re willing to live a very unstable financial life and are prepared to get part time work or other odd jobs to make sure you can pay your bills and support the people dependant on you financially.
  • If you want to be freelance for the lifestyle, and to use that flexibility to either further your career, be with you family or focus time on the things that are truly important to you.

I wanted to write this blog as it’s a topic that has been on my mind for some time now. I’m most definitely not at the top of the freelance video game yet and still do want to keep my hand in to keep learning and improving.

Although I will be doing less freelancing from now on, I’ll always feel incredibly lucky for all the life and business lessons my time as a freelancer has taught me.

It feels like the right time to focus on a new challenge, one I know will be incredibly difficult and one with lots of potential to learn, improve and gain skills I need to.

If you have any questions about being freelance, I’m always happy to share my thoughts and experience, please email me at

And remember, be freelance for the right reasons.

I wish you every success.

What I’m Currently Reading…

‘Crushing It’ — by Gary Vaynerchuk — it’s a great one! Check it out here…


About Jack

I help people, brands and business communicate more effectively with their customers through visual, audio and written content.

I do this through Southpaw Sport, the sports content marketing company I’m currently building as well as on a freelance basis working for agencies and production companies.


You can follow me on YouTube where I post weekly vlogs sharing my experience and opinion on content production.

YouTube —

And my social media for behind the scenes look at what I’m up to

Instagram — @jackwrtompkins

Twitter — @jackwrtompkins

Jack Tompkins