7 questions to ask yourself to work out whether freelancing is for you

Published by nedmortimer on

You are teetering on the abyss. Thinking of leaving your full-time job, not completely satisfied with the 9 to 5 (or downright hating it). Wondering whether there are more fulfilling and inspiring ways to spend your time and earn money.

Firstly, well done! You’ve overcome the first challenge, i.e. not just ignoring the problem and pretending that you love your job, but putting some genuine thought into whether it’s the right lifestyle for you.

These 7 simple questions will serve as a guide, to direct your thoughts and help you work out whether you should take the plunge and become a freelancer!

Question #1 – Do you like fresh challenges?

If you enjoy that adrenaline rush triggered by the unknown – that feeling of stepping into something that will seem overwhelming at first but extremely rewarding as you begin to wrap your head around it – the freelance life may well be for you!

Of course, administrative tasks like doing your taxes, saving up for a pension and planning your own meetings etc, will all seem very daunting as you begin your journey.

But mastering the admin side of freelance will bring you joy in itself – the feeling of accomplishment as you achieve something you had previously thought was out of your reach.

Question #2 – Do you envy people that work for themselves?

If you look at those people who work for themselves – running their own companies or working on independent contracts they’ve secured themselves – and think “how did they get so lucky…?” then stop!

You need to flip the question on its head – how can I MYSELF carve out that style of working?   

It is not the case (for the vast majority at least) that they have some rich, Dickensian uncle bankrolling their lifestyle while they pretend to work. These people have recognised that there is far more money out there to be earned, far more opportunity to carve out a living from their niche than people assume.

The world is pitted against you seeing this opportunity, and an epidemic of pessimism can deter even the most talented of self-starters from taking the leap into freelance work.

Why? Because the negative people are telling everyone just how difficult it is to do anything but the status quo, and the positive people are either believing them, or already DOING the exciting, more fulfilling work and not necessarily wanting to share the space with more people.

Question #3 – Do you like free time?

There is no denying that the majority of regular, full-time jobs involve a lot of wasted time.

Meetings are the largest culprit, but you can also throw in all the time you spend checking emails (so that you look busy), chatting to people by the kettle or even travelling to and from the office. These are minutes and hours EVERY SINGLE DAY that add up to a huge amount of wasted time throughout your working life.

With freelance, every minute counts, and so you’re encouraged to use your time more effectively, so that you can either earn more, or spend more time on other non-work activities.

Question #4 – Are there things you’ve always wanted to do, but don’t have time for?

As we have just hinted at, the opportunity to explore those things that you “never have time for” because you spend a huge chunk of your waking hours at the office is a big attraction to the freelance life.

If you feel that itch to make more of your time, you should strongly consider freeing up more of it and going independent.

Question #5 – Do you enjoy your job?

This is a big (and obvious) question.

If you love your job, then maybe you shouldn’t be reading this article. 

But if you have any dissatisfaction with it at all – whether financial, or working style, or you just don’t believe in the purpose you’re trying to achieve in your job – then stepping away from it and working for yourself can help you gain perspective on what WOULD make you love your job.   

Question #6 – lie-ins – yay or nay?

If you like lie-ins, then unless you’re lucky enough to work for a company that doesn’t care what time you rock up in the morning, you would LOVE freelance lifestyle.

There’s nothing wrong with sleep – sleep is actually very healthy – and as long as you have a good morning routine to get you up-and-running, it doesn’t matter if you do it in the early morning, late morning or early afternoon, as long as you’re happy and getting the necessary work things done.

Question #7 – If you look back on your life, having worked in your current job or work cycle for several decades, would you feel happy?

This is a broader, philosophical question about life’s meaning and the idea of regret.

If you are perfectly content with your work situation and get your meaning elsewhere – your evenings and weekends and the social life you lead during that free time – then there’s no strong reason to change it.

But many people take the leap into freelance because of a broader dissatisfaction, not just with the specifics of their current job (Question #5) but because of a missed opportunity to lead a more interesting, ambitious life.

The culmination of these various questions is that, if you feel any doubt whatsoever about your current employment, balance of hours or general lifestyle, there are lots of ways out there to make money independently, working for yourself.

You free up your time, your headspace; you control your own life. As long as you’re thinking about it, not just settling for the status quo, you are on the right path – and we’re here to help you if and when you do decide to take the plunge.

As always, thanks for reading and please leave comments! Have you thought through any additional questions about whether the freelance life is right for you?


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