5 Questions To Ask Yourself Before Deciding, Should I Go Freelance?

Last updated: 2021-05-28 (originally published on 2019-05-23)   — by Dominique Afacan

This lady really loves freelancing

It’s been a bad day in the office. Your boss is behaving badly, your colleagues are driving you crazy and tomorrow, at 7am, your alarm will go off and it will start all over again. Sound familiar? It’s no wonder so many people are considering going freelance.

A report by the Office for National Statistics in the UK suggested that 15% of the workforce were self-employed in 2017 and it’s been steadily climbing ever since. In theory, it sounds dreamy. With yourself as a boss (and wouldn’t you be a good one!), you can finally live without corporate shackles, you can work anywhere you please and you never have to make small talk with your team again. Bliss.

The reality, though, is often quite different – and it’s important to weigh up those pros and cons before taking the leap.

Are You Proactive and Motivated?

Yes, in your first week as a freelancer you’ll likely be as motivated as they come. Up at the crack of dawn, putting in long days and feeling as energetic and focused as you have in years. But how long will that last?

Once the initial buzz has worn off, and you get used to the idea of being your own boss, standards can start to slip. Before you know it, you’re letting things slide that you’d never dream of in a contract position, and early starts have become a thing of a past. Your office attire looks suspiciously like your pajamas and your lunch breaks have become long enough to slot in a round of golf.

For freelance to work, you need to be a naturally proactive and motivated hard-worker. If you aren’t putting the time in winning contracts and getting things done, you won’t get paid. Simple as that.

Be honest with yourself before quitting your day job – are you willing to work even harder  – often for less money – in order for this to work out? Or is this more of a pipe dream that crops up when you have a bad day?

If it’s the latter, stick with your regular job, and take a well-earned holiday (you don’t get paid for those as a freelancer). If it’s the former, prepare to get busy – and the rewards will likely follow.

There are some down sides

Do You Detest Admin?

A few months into freelance life and you start to realise that the accounts team in your old office were wildly undervalued. All of a sudden, it’s you that has to log all your work, create invoices, chase invoices (a mammoth task) and sigh… do your own tax (even worse). It’s an entirely new job role that you weren’t prepared for, and, depending on what sort of person you are – this aspect of freelance can make or break you.  

Before you jump in with both feet, try to learn some administrative basics. There are plenty of online tools now to help you (see Expensify for logging expenses, Zegal for invoicing and contracts and many more besides) so it’s all achievable with a bit of forethought.

It also helps to plan out exactly what you need to survive before taking the leap. How much do you have to earn to pay your bills and maintain the standard of living you’re used to? Ideally, you’ll be bringing that (with more to spare) every month. When you’re knee-deep in deadlines, knowing you’re on top of things in the finance and admin department might just keep you sane. Time to get back to those spreadsheets.

Have You Got Work In The Pipeline Already?

In an ideal world, freelance is something you’ll have prepared for months in advance. You’ll have spotted a gap in the market, already have a roster of clients who have agreed, at least verbally, that they would hire you – and there’ll be no ‘dead period’ while you set up shop.

Often a good way to slide into the freelance world gradually is to start working evenings or weekends while you’re still in a full-time position. Short-term pain, long-term gain. The early days should be the hardest – once you have a reputation and repeat business, weekend working should be a question of choice rather than necessity.

In the meantime, network, network, network. And if you can’t get out there and do it in the real world, at least show up online. Make a website showing off your skills, have a relevant social media presence and be on the constant lookout for new opportunities. In the freelance world, complacency is dangerous.

What should I order for lunch?

With all this considered, it’s time to get out there and follow your freelance dreams. If you can make this work, you’ll be able to enjoy the wealth of benefits that the freelance work model has to offer and you’ll join the growing group of happy people who wouldn’t dream of going back into a full-time office job. No wonder it’s been estimated that by 2020, 43% (source: Nasdaq) of the US workforce will be doing it. Will you be one of them?

Dominique Afacan is the co-founder of Bolder and a freelance editor and writer based in London. 

The opinions expressed in the column above represent the author’s own.

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READ MORE: Think You’re Productive At Work? Think Again

READ MORE: How To Select The Right Freelancer For the Job

Tags: be your own boss | freelance | z-syndicate

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