From Freelancer to Entrepreneur

From Wage Slave to Freelancer to Business Owner to Entrepreneur – simple, right?

Speaking as someone who’s feels like all of the above on any given day, I would say, no, it’s not that simple.


I became freelance because I didn’t like working for companies. I set up my own business because I didn’t like working for people.

I now consider myself an accidental entrepreneur as the whole process has caused a desire to try out new ventures and business ideas. And, I like the idea of helping people.

“Many believe that the age of the big corporations is past. They are simply not nimble enough to discover the new products that will keep them abreast of the market. Small businesses can now market across the world with none of the costs and aggravation of previous eras”. – Anthony Hilton

I used to be like everybody else. I used to travel on the underground train to my place of work along with millions of other people. Head down in the morning paper. Not questioning my existence.

Becoming freelance

I didn’t think twice about working for some faceless organisation, without meaning, without purpose. That was my reality.

But I hated it. I hated the pettiness. I hated the falseness. I hated the fact that other people (and, increasingly, younger people) could tell me what to do. Even worse, criticise my work!

Somehow for some reason I ended up out of that rat race. How? Going freelance was the first step.

The difficulties of going freelance

In someways becoming a freelancer was actually harder than setting up my own business. For me, becoming a freelancer really meant jumping off a cliff and hoping that I’d assemble a parachute before hitting the bottom.

But, once you’ve gone for a few years without a regular pay check and you know you can do it, the sky’s the limit.

“Why are you freelance, anyway? Why don’t you get a proper job?” This was the reaction I got from most of the people who I used to work for as a freelancer.

At times I might have agreed with them. I thought I was a bit weird as well.

But, I couldn’t understand them either. Why work your arse off for someone else? Is it an important job? Does it benefit other people? If not, then you’re faking it. Why feign the importance of your job when you’re ultimately adding value to something else while taking the value away from yourself as anyone can spot a lack of authenticity?

I’m proud to say that the last time I had a proper job Margaret Thatcher was still Prime Minister.

The difficulties of running your own business

I have to be incredibly strict on myself and not follow my new business ideas to the detriment of my client work – and, don’t forget, it’s the client work that brings in the readies.

I’m finding it increasingly hard to know what to focus on and what not to focus on. But, is it worth it? Of course it is.

“Talented people don’t want to work for anyone but themselves.” – Anthony Hilton

You can do it

You can live your life on your own terms – just don’t expect it to be simple.

There’s never been a moment where I’ve sat back and thought, “ahh, I’m happy now!” And I don’t expect there will be. I almost don’t want there to be. Of course it’s not easy. If it was it wouldn’t be worth doing.

Did this help you? If so, please share!

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  1. says

    Great article. I have been on the fence about diving into freelancing for a while now. I have been taking the odd job here and there but never took it to seriously until recently. My wife and I want to move from MI to CO this year so thing started to move a little faster lately.
    My wife and I started a LLC mainly for her custom accessory business ( so that she could write off her supply expenses, so we have a joint owned LLC (DH Creative) and a DBA (Canary Created). I have been working on starting the LLC as my own freelance business but it has been slow going. I have read lots of freelancing articles and they say to ” make sure you have at least 6 months savings before you start…” but it seams the most successful freelancers stories have all been about them being thrown into it and they were forced to make it. Any advice on when I should make the dive into full freelancing or should I wait and build some cash up. Let me know what you think.

    • says

      I’ve always said about 3 to 6 months money, Jason. But I’m not the best one to advise you on this because my freelancing made it really easy for me to set up a business as I could quite easily work as little or as much as I wanted on my freelance work. So, I would only work for two or three days a week and on the remainder of the time I’d work for my clients at home. As I made more money at home I took on less and less freelance work. However, I’d been working the freelance circuit in London for years so everyone’s situation is very different and the last thing I’d do is encourage people to leave a “permanent” position. Although, nothing’s permanent!

      There’s plenty of advise here on how to get clients from your website, Jason. Let me know if you have any questions.

  2. Oksana Frewer says

    I’ve heard too often that I should find a “proper job” ( I haven’t worked for a few months now ), and I really think I should hurry up before I find some other uninteresting low paid job, or stop believing in myself. Thanks Rob for a nice article, you ‘ve published just in time!
    @ Jason, I don’t have any savings either, so it will be interesting to hear what Rob says about that.

    • says

      Well, I hope I haven’t dampened your spirits with my answer to Jason! Not working for a while is actually a good thing because it means anything you make “off your own back” now is a bonus. The people I feel sorry for at the moment as those that are on six figures in a corporation with huge mortgages and debts because they can’t do anything entrepreneurial – or it would be very difficult – they’re stuck!

      Glad you liked the article, Oksana.

  3. says

    Hi Rob

    I’ve still got a full time job running alongside my own business which means many hours of work! However when I have enough clients of my own, paying enough to pay the bills, then I shall leave the ‘day job’. It’s hard going and many late nights but I know I will get to the point where I can concentrate solely on my own business.

    My savings aren’t great which means I can’t just take the leap now into only working for myself now but I believe a measured albeit slow approach will get me there eventually..

    • says

      Hey Lee, well done you. I don’t that this period you find yourself in can be challenging but you will get used to it. You will know when the time is right to leave (or go part time) your day job. I’m sure you’re taking the right approach.

  4. says

    Hi Rob,

    Yes, I enjoyed this article and I just tweeted it.

    You being an entrepreneur is an accident…however, me being a freelancer was also an accident. It is not something I really wanted to do. I’ve always wanted to work-for-hire where I can have benefits and have a permanent job.

    But what is permanent job so to speak? There is NO such thing as “permanent.” This is a deception of reality. You can lose a job any minute even if you work there for many years. That’s how some company does. They’ve got the power. So why give the power to them to CONTROL over you? So yeah. I’m glad I’m not working for anyone but myself.


    • says

      Haha, Angela, you’re right – nothing is permanent! I love working for myself as well and part of the reason is definitely to do with freedom. Thank you.