Recently I have received a number of emails from aspiring illustrators asking how I knew it was the right time to go solo. Perhaps you are also thinking about taking the plunge into the unknown world of freelancing and you’re asking yourself questions like, ‘Will I be able to earn enough from creative work?’ ‘What would it be like being my own boss?’ or, more importantly, ‘Will I be able to stay in my pyjamas past 2pm?’ and ’How many biscuits is acceptable to consume in one morning?’

The freedom of when to get dressed and how many biscuits to consume is not far off how I initially imagined freelance life to be – drawing one minute and watching daytime television the next. How hard can it be, really? The reality is, freelancing is not the easy life we might make light of, otherwise everybody would be doing it (and there would also be no need for blogs like this one).

It may come as a surprise that, although I always aspired to do creative work, I never wanted to work for myself – I always much preferred working in teams. The challenge came when I found myself in circumstances that meant I needed flexible working – with a six month old and a four year old just starting school, this meant juggling childcare and work was tough. On top of this I have always been extremely passionate about my vocation and I didn’t want to limit my options for career progression. I felt that the only way I could make things work financially and logistically was to carve out a career that meant I didn’t have to work solely within 9-5 office hours and where I could allow opportunity for my own learning and development. Ironically, I became a freelance illustrator for practical and financial reasons. Unheard of. The challenge of course, was that I had nothing to fall back on as my options were limited. I had to make it work. Four years in and I now earn more than any previous role which has meant myself and my partner are now able to invest equal amounts of our time into work and childcare.

So, should you quit your day job? And if so, when is the right time? Here are some things that might help you with your decision and some things I’ve learnt in hindsight.

1. What is your financial situation

Be realistic about what you can afford to live off. Don’t put yourself under excessive financial stress trying to carve out a ‘dream career’ (you’ll swiftly find out that enjoyable work will not be enjoyable if you can’t pay your bills with it). Think: how much do I need to earn a month? Then try to save at least three months income if you can, or as much as you can to use as a buffer while you’re building up work. If you can’t, then it may be wiser to focus on building up a client base before you take the leap or be prepared to take on a bit of part-time work if you need it.

2. What is your temperament?

Are you someone who thrives around lots of people or do you love your own space? Can you go for hours on end without human contact or are you on the phone to your best mate every two minutes? Working for yourself doesn’t require a specific personality type, but your personality type does require consideration. Although I love independence and the space to think up concepts, I also need the support of others. I spent the first year of freelancing working from home and felt incredibly isolated. Since then I have found a shared studio which means I get the best of both worlds, but this obviously adds financial cost. Think about what you would need if you were to work for yourself and whether those things add any financial implications. Would meeting people for coffee once a week suffice or do you need to work in an environment with other creatives? Think also about your day to day routine – would you make sure you switch off after 6pm? How would you get yourself out of bed? As much as being your own boss sounds like a luxury, having no structure in place may not be conducive to bringing in the work and paying the bills. It may also make you aware of how much you need company or boundaries.

3. Have you proved your work is profitable?

Have you already sold any of your work? Undertaken commissions? Have you put your work out for feedback from potential clients? You may not be able to prove you’ll earn a sustainable income just yet but you can test the waters. If someone has invested in your work already, who are they? How much profit did you make? How many more clients like them do you need to be able to get enough to live off? Is it a realistic goal or do you need to diversify to other types of clients? Can you experiment with charging more? You may be able to do the most beautiful work in the world but no one will invest in it if it is not pitched to the right businesses. If your work is taking you months to complete, which clients will have the budget or deadlines to fit? Do you need to find ways of working quicker or pitching to clients who may have bigger budgets? Start to market yourself now – make sure you have a good online portfolio and social media profiles. The work won’t come in by itself, you need to continually promote yourself.

4. What is your current network like?

How supportive are your friends and family? Do you have a good community who will offer advice or make you a cup of tea when you’re pulling your hair out with fees or negotiations? If you don’t, start to build one. Although this may seem initially daunting, networking is an essential skill that you will need if you work for yourself and it’s far easier to learn networking skills with people who are in a similar boat to you. Start to connect with people on social media, ask to pop into studios, go to exhibitions and events. Other creative professionals will not only come in handy for passing work around and offering help when you get stuck, but they may become some of your greatest friends.

5. What have you got to lose?

You may be leaving a job you hate, or you may be leaving one that is simply no longer a good fit for you. However, there are bound to be things you will lose by changing your work situation (else why would this be a hard decision?). Think carefully about what you would leave behind if you left your current role. Is the position hard to come by? Is it particularly well paid or does it have other benefits? These things don’t mean you shouldn’t quit, but they do mean that you need to consider what you are walking away from and how it will affect you. Aside from financial rewards, friendships may have been formed that are hard to walk away from and it may take time to readjust. That said, if you have formed genuine friendships, they should understand that your decision is not a personal one. If you do not get on with your colleagues and you have no interest in the work, it sounds like you need a better way to make money. After all, any employer could make you redundant tomorrow so security should not be the only reason to stay in a role if you are not happy.

6. Re-define success

Many creative professionals have jobs that support their creative work and, if it’s giving you the space to be creative without financial burden, why change it? If you are feeling a sense of pressure to quit a job just because it would make you seem more ‘successful’ in the eyes of those around you, this is a total farce. There are many artists who take on part-time work to support their creative work and this does not make them any less of an artist. Even as a full-time artist there may also be times you’ll have to take on commissions you are not passionate about in order to pay the bills. It’s worth considering what it means for you to be successful in your career. Is it having lots of money? Creative freedom? A balanced life? Re-define your own success and don’t be forced into a lifestyle that may be hard for you just because it’s an obvious path to everyone else. It’s only if you feel that there is currently no outlet for your creative work and it’s frustrating you that something has to give. In fact, if this is the case, I’d urge you to find new options, even if that means cutting down your hours or finding a part-time job that puts less pressure on your mental health. Think about how much you can afford to live off. If your current job is taking all your energy and not allowing any creativity, find one that allows you more opportunities to explore new avenues. I initially took a pay cut to work for myself, but being able to have flexible hours was worth its weight in gold during a challenging stage in my life. I have now built up enough work to earn more than previous positions.

7. How are your problem solving skills?

If you work for yourself then you need to get good at problem solving, so start now. Think of solutions around the challenges you are currently facing in your situation. Have you approached your current employer with your concerns? Is there a way of making your aspirations tie into the company’s goals? If not, how are you going to search out for the kind of work you want and how are you going to support it? If you’d like to work for yourself but are concerned about financial security, think about offering monthly services to companies that tie you in to a certain period (I managed social media accounts for a number of companies when I started freelancing, which meant I could have guaranteed income each month whilst still being in control of my work and time). Other freelancers work regularly in-house at studios and agencies to support their other work. Find out what work is out there that can be your ‘bread and butter work’ to compliment the more creative work while you’re finding your feet as a sole trader. There are no guarantees – styles go out of trend easily and marketing budgets may fluctuate, so how will you continue to adapt? Can you develop skills that compliment your main service? If you’re an illustrator, can you learn animation or design skills too? Having other skills is a great way of offering additional services to clients who you have a good working relationship with. People deal with people, so try to find out where your clients are investing money and how you can tailor your work to be more beneficial to them.

8. Give yourself time

For me the first three months were very hard, not purely financially, but simply finding my feet in something so new. I realised that the challenges of freelancing weren’t solely money related. I had to allow myself time to adjust to a completely new lifestyle – to set my own routine, learn how to promote my work, manage client expectations, deal with negotiations, and so on. I also had to adjust to life without colleagues. All this was a lot to take on and, while on the surface there was much excitement about ‘going it alone’, on the inside I felt very different. I look back on that time as incredibly challenging (but worth it for what was to come).

9. Be intentional with how you launch

Whatever you start advertising about yourself or your work will become hard to shake. Becoming known for something can definitely be a benefit to you, but it could also be a hindrance later down the line so just make sure that the work you are promoting is in line with the type of work you want to get more of. I did a lot of food illustration when I started and, as much as I love it, there were other areas of work I wanted to explore. I found it hard to approach people with new work as they had known me for something else and so I was only ever commissioned for the same sort of work. It’s fine to take on work solely for financial reasons, but don’t advertise this publicly unless you want more of the same. It may be harder to steer your work in different directions later down the line. Working independently, you need to continually evolve and re-invent yourself. Be intentional about the direction you want your work to head in and think about how that fits in with current trends and markets.

10. Be prepared to swap challenges for others

Ok, so you no longer have to have someone telling you what to do all the time (hooray!), but you now have to tell yourself what to do (boo!). You never really get rid of challenges, you just swap them for others. Some of those challenges may be more rewarding (no matter how hard you find it to run a business, you are now doing work you love, right?). However, it’s worth considering that autonomy brings additional pressures – you now not only have to promote your work but you also have to maintain client relationships, chase money and deal with a never ending stream of admin. It’s easy to think the grass is greener, and it may well be, but that grass still needs to be watered (and watering it may not always be the most enjoyable task). There will continue to be difficult decisions and challenges, so it’s important you are working towards goals that matter to you. That makes the hard stuff worth it.

11. Do you just need to jump?

You’ve saved some money, you’ve got a few clients under your belt. You’ve designed and redesigned your logo eighteen times. You’ve asked every freelancer you know for explicit details about life as a freelancer. You’re working evenings and weekends. Use your intuition before you end up burning yourself out – only you can know if the time is ever truly right to jump. Think about what the worst is that can happen versus the best that can happen. At the end of the day, jumping is often uncomfortable and sometimes a little bit of discomfort will push us further than we’ve been before.

12. You are already an artist

One of the most important things to realise is that you are already an artist and you don’t need to earn fifty grand a year to call yourself one. Start calling yourself what you want to become. If you are creating illustrative work you want to sell, then you are an illustrator. You might work 30 hours in retail, or you might work evening shifts at your local pub, but you, my friend, are a creator, an inventor, a designer… so start telling people what you are. Get it on your social profiles. Tell your mates. The point is, you do not have to work full time at something for it to be valuable or for it to be your main focus. Don’t let the negativity of others tell you that your work is not worth pursuing. In fact, remove yourself from people that put down your passions and tell you that you have your head in the clouds. Pursuing creative work is no mean feat and it certainly doesn’t mean you don’t have a good head on your shoulders. You are already an artist, so go find a way to create, with or without the day job.

Are you thinking of going solo? If so, what are your concerns? If you’ve made the leap from employment to freelance, what challenges did you face and how have you overcome them? Feel free to leave comments below!

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