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10 Mental Health Questions You Should Ask Yourself Before You Go Freelance

Ten important questions to ask before you make the leap to self employment. We don’t always have the answers, but sharing and talking helps, and just because you work alone, doesn’t mean you are alone.

In the last decade, there has been a 66% rise in the number of 26-29 year olds opting to make a living from freelancing, and many more are set to choose this career path in the future.

This flexible way of working is particularly attractive because it offers opportunities to make appointments, meet friends and exercise at one’s leisure. This humanising aspect of freelancing is regularly cited as beneficial to the mental health of individuals who may otherwise feel stifled in the traditional office set up.

However, when you’re stepping away from the support of a team, there’s a risk to your wellbeing, with money, stress and loneliness high on the list of ongoing issues. If you’re thinking of taking the leap, ask yourself these questions:

1. Why are you leaving your current role?

Freelancing isn’t going to solve all your problems. If you’re sick of your boss then leaving your job may certainly help. But if the real issue is that you don’t like being told what to do then you might not enjoy having multiple clients to answer to. Maybe you want a job with more creative control, but if the real problem is that you hate paperwork then you might not enjoy handling your own taxes.

2. What are your triggers?

Think about what stresses you out. Maybe it’s commuting, noisy colleagues or money worries. Consider whether freelancing is going to make these stresses more or less frequent, then put measures in place to react positively to these triggers when they occur. If you worry about money, set up a savings fund. If isolation affects your mood, rent a co-working space.

3. How do you deal with rejection?

In a regular job you simply apply, attend an interview and then once hired you’re relatively safe. But with freelancing, you might find yourself pitching for new work on a daily basis, and chances are you’ll hear ‘no thanks’ more often than you’d like. This can be disheartening if you’re not in a good headspace, but the good news is that failure is proven to build emotional resilience. Or as psychologist Suzy Reading puts it: ‘It is not evidence of us lacking as human beings…. Embracing compassion and kindness allows us to bloom and grow in the aftermath of failure.’

4. Do you have healthy coping mechanisms?

If the answer is no then it’s time to start working on your wellbeing toolkit. This is a selection of activities or behaviours will help you cope with whatever freelance life throws at you. When I’m feeling annoyed about something I call one of my mates to have a rant. Being part of an online community like Leapers can help with this because you’re instantly connected with people who understand the nuances of being self-employed. Other healthy coping mechanisms that might work for you include running, journaling, yoga, getting more sleep or eating healthier.

5. What gets you out of bed in the morning?

If you find your day job mind-numbingly boring then there’s no doubt that freelancing will inject some excitement into your life. But to pay the bills, you’ll probably have to take on some boring tasks now and again. What will motivate you to get out of bed then?

6. Can you say no?

Saying yes is the easy part, especially in the beginning when work is thin on the ground. You’ll probably charge a little less in the early days and be grateful for the money, but this is an unsustainable model which can lead to burnout. Eventually, you’ll need to learn to say no. No to discounts, answering emails at the weekend, late payments and maybe even your dream project if the price isn’t right.

7. Do you like people?

It’s easy to turn to freelancing as a way to rid yourself of all the idiots you’ve suffered over the years. But if you have a plan to run a profitable business from your bedroom without ever connecting with another human being, it’s unlikely to come to fruition. Anxieties become heightened when you isolate yourself, and with no one forcing you to socialise you’ll have to take the lead.

8. Can you set boundaries?

Aaah the old work-life balance. Has anyone ever truly achieved it? Unless you rent out an external office space then you’ll need to make a conscious decision to separate your work and home life. One gripe for many freelancers is the inability to fully switch off from work. Having a set workspace and a separate work phone can help.

9. Do you worry about the future?

The reason some people shy away from freelancing is the lack of security. Whilst your income might fluctuate month to month, there are some who say it actually increases job security in the long run. If you don’t want to worry about where your next wage packet is coming from then maybe freelancing isn’t for you. But if you want to build an empire that you can’t be made redundant from, roll up.

10. How’s your self-esteem?

If you don’t value yourself and your abilities then neither will your customers. Freelancing is competitive, and often it’s the most self-assured people who get the most work. This doesn’t mean having an aggressive sales technique. It’s about being confident that you can deliver the goods. Seek out client testimonials before you make the leap. Add this to your website so that customers can see how amazing you are, and stick the best ones above your work station as a daily reminder.

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