Is freelancing right for you? The resources to help you decide


The number of self-employed workers is on the rise. If you’re thinking of leaving your in-house role to join them, these resources will help you work out whether you’re equipped for being your own boss

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Living the dream? Credit: Death to Stock

Living the dream? Credit: Death to Stock

Colin from accounts was on your back again this morning because you still haven’t sorted that invoice out. The boiling tap has broken down for the third time this week so there’s no chance of tea. And you swear to goodness you’ve been working on this same project in 39 different iterations for four years.

If you’re thinking of heading out from an in-house career to join the 15% of the UK workforce who are self-employed, some or all of that might sound familiar. You might also be fed up with doing the same commute every day and frustrated with the presenteeism that means you sit at a desk for eight hours every day, or maybe you just think you’d be a better boss to yourself than any you’ve met so far. Whatever the reason or reasons, moving away from in-house work usually stems in part from some dissatisfaction with the status quo, as well as the positives that come with self-employment - variety, flexibility, more time in the outdoors, more time for life. I certainly felt those frustrations feeding my desire to be my own boss leading up to that move in January 2018, and to help me suss out whether my feelings were fanciful or formulated, I used - and continue to use - a few different resources.

Career coach

The coach I worked with helped to clarify the jumble of emotions, needs and pressures. She would say that I did all the work - and I did - but she is the one who managed to steer me on that path. She had the clarity, distance and professional training that my friends didn’t. Save your discussions with them to fanciful imaginings about how you’re going to spend all your time in coffee shops and do yoga every day. Here’s how to find a good one.

Online course

I worked through Seth Godin’s Freelancer Course because I wanted to learn from someone who’s been making this work for many years how I would continue to work at my relatively senior level in a freelance capacity. If you’re heading out of house, you might be feeling the same. He covers in detail how to ensure you’re providing the value that is your worth, rather than delivering on anything that is asked of you.

Financial formalities

Once you’ve set up as self-employed in the UK, HMRC will send you lots of useful guidance on filling in your tax return and what’s classed as business expenses. In the meantime, the fundamentals of what they class as ‘working for yourself’ are important to know now to see how practically and economically viable it is for you.


Now that I work for myself, I’m more motivated than ever to keep learning and developing because no one else is going to force me to sit down for half a day in a formal training session with an A4 folder of slide printouts and my Myers-Briggs results. I read at least one chapter of a business or career book every day and take a day off in between titles to think critically about the insights I’ve read. These are the books that motivated me to go freelance - and keep going.

On my wishlist

Maybe one day my feet will itch to go back in-house, maybe they won’t. What I do know is that I feel stronger and better equipped to take on any work challenges because of facing down decisions and development with these tools. If you decided to take the plunge into self-employment, I’d love to hear what helped you get there.