Becoming A Chronically Ill Freelancer – My Story So Far

pippa sat at desk wearing stripy shirt and silver noise cancelling headphones, writing in a diary with open laptop in front of her and books in the background

Time and time again, people ask what I actually do for a living… and I’m yet to find a concise way of answering this question. If they’re familiar with my online life, I’ll tell them I’m a writer and a blogger. If they’re aware of my health situation, I’ll tell them I work from home in digital communications. If it’s somebody I don’t know well, I’ll simply tell them I work in the charity sector. And all of these answers are true.

My Background

I graduated from university in 2016 (finishing my postgraduate diploma in 2017), and thanks to the joys of an unrelenting chronic illness, I had no idea what the future would hold. As I discuss in more depth in this post about being an ‘in-betweener’, I knew I was well enough to work in some capacity, but far from able to pursue a typical 9am-5pm occupation that involved leaving the house and being around other people every day.

Still adapting to the constraints that my health had imposed on my day-to-day life, back then I didn’t think I would have the luxury of choice over what job I went into; I thought I’d simply have to take whatever I could secure. By then, my self-worth had taken a serious battering. Everything had been overshadowed by my condition and the struggles of navigating an inaccessible society, and I was yet to realise that I still had all these valuable skills to offer.

My First ‘Proper’ Job

Truthfully, it was a series of lucky interactions that led to my first ‘proper’ job. After finishing my studies in June 2017, I reached out to a well-known UK disability charity to introduce myself and see if they had any suitable opportunities up for grabs. It was such a long shot, but it just so happened that they were about to advertise for an intern… and I couldn’t believe my eyes when I read the job description and it sounded right up my street. I’d started my blog earlier that year and this, combined with my specific degree and other work experience, meant that I was actually in with a chance.

After a successful interview, I commenced my three-month internship, and I cannot speak highly enough of the experience and the team I was part of. Alongside day-to-day work managing a thriving online community, I received support and training in digital marketing that I otherwise might never have had access to. Working alongside other disabled people, we all talked comfortably about our conditions and ensured we had each other’s backs: something utterly invaluable for somebody still contending with self-esteem issues in the world of work. Towards the end of my three months, I was thrilled to be offered a permanent, more senior role within the team. I was employed by this same charity for almost three years, working part-time (around 18 hours a week) and almost entirely remotely to manage my health, and I can safely say that this first positive experience transformed my perceptions of working with a chronic illness. My employers made sure I had the adjustments I needed to perform my role to the best of my ability, and they also invested in my career by ensuring I was developing new skills.

screenshot of instagram story, featuring pippa at recording booth tagged as bbc radio sheffield, wearing headphones and smiling whilst taking selfieBlogging Opportunities Arise

Way back in the early stages of my initial internship, I also began to receive my first freelance writing and sponsored collaboration offers through my blog and social media. Thrilled and somewhat baffled by the fact these opportunities had even come about, it was around now that I took my first tentative steps towards self-employment, and maintained these small commitments pretty consistently alongside my charity sector role.

At the beginning of 2019, however, an opportunity with another charity arose: a cause very close to my heart and again, a role that seemed almost a perfect fit for my skills and experience. After interviewing for and securing this role, I had a difficult decision to make. The new role would mean fewer hours and lower pay, but given the nature of the charity and the fact that my freelance work was continuing to increase, I made the risky decision to pursue this new opportunity. This was the first instance where I consciously modified the balance of what I call ‘work-work’, with my own personal freelance opportunities.

A few months down the line in this new job, however, I knew all too well that what I initially thought was my dream role was unfortunately rather far from it. In all honesty, I actually felt as though I was stagnating rather than growing and improving. However, the time and energy I’d invested into my freelance work was continuing to pay off, and as I’d hoped, was almost covering the reduction in my wages from accepting this new role.

It was around now when I was finally becoming self-aware enough to know that I had something to offer. I was much more confident in my ability to write a cracking article and pitch projects, collaborate successfully with brands and sponsors on my blog, and even indulge in my love of editing and proofreading to support the work of others. I began to wish I had just a little more time to really harness these skills and see how much further I could take them… and after months of agonising over the decision, requested to further reduce my ‘work-work’ hours and job-share instead. Fortunately, this request was granted by the organisation (opening up an opportunity for another chronically ill person to enter the world of work!), and once again, the balance between my ‘work-work’ and freelance work shifted. Around now, it would have been around a 60:40 split, with my freelance hours almost matching my work hours. The income split wasn’t as evenly dispersed yet, but that would come in time.

Taking Control

Midway through 2019, experiencing ongoing frustration with ‘work-work’ and on the fringes of burnout from trying to embrace as many external opportunities as possible, I became reflective. I looked at my employment history, and I looked at my blog and freelance work, and for the first time, I really sat down to think about what I wanted from the future, not simply what I thought it would be possible to have alongside my illness. Instead of assuming my health would always dictate the direction of my career, I began to more seriously consider how I could instead chase my own goals and proactively adapt them to accommodate my illness.

By then, it was clear to me and those around me that I wasn’t happy in my current ‘work-work’, and equally as clear how much joy and purpose my writing brought to me. Heck, I’d even been secretly writing a book for the last two years; something I still can’t quite believe actually happened. I knew that the freelance opportunities were out there: as my reputation and experience developed, they were dropping into my inbox more and more frequently. So, I was left with yet another big decision to make: whether it time to risk it all and go full-on freelance.

The Turning Point

headshot of pippa in yellow jumper, holding up paperback copy of "university and chronic illness: a survival guide" book and smiling Shortly after I’d begun contemplating what steps to take next, a few timely opportunities came about. Firstly, I signed a publishing deal for my debut non-fiction book. Secondly, I entered talks with another charity, and though I was still reeling from my supposed dream job turning out to be quite the opposite, I had a really good feeling about this one. And finally, after spotting their advertisement for a local course that sparked my interest, I took my first steps with The Prince’s Trust.

After completing The Prince’s Trust’s 3-day Exploring Enterprise course, simply with the intention of improving some of my business management skills, I suddenly found myself face-to-face with the opportunity of a lifetime: the support and tools I needed to pursue the freelance route and potentially become entirely self-employed. With their support, I developed a business plan outlining my desired path to become an established freelance writer and blogger, and since then have received genuinely useful feedback, one-to-one meetings, a small grant for materials, and have been partnered with my brilliant mentor Duncan Lewis.

So, what was the business I pitched? Admittedly, my situation is slightly unique. Rather than pursuing an enterprise with a clear-cut service or product to offer, I was basing my proposal (among other things) on the hazy grey area of influencer marketing… an industry still so new that the regional team believe I’m one of the first (if not the first) person to go through The Prince’s Trust in-part upscaling my blog into a business.

So, what’s the plan?

My short-term plan is to continue to refine my skills and develop my reputation as a writer and blogger, whilst exploring other creative projects. I want to aim for more prestigious bylines in bigger publications, and produce bespoke written support and advice on topics that all too often go unspoken about. I’d like to collaborate with higher-profile brands, not only on producing relatable and informative content on living with a long-term condition, but also increasing the visibility of disability and chronic illness in more mainstream campaigns. I hope the future will hold further opportunities to write books and become a published author once more, and in the meantime, I’d also like to continue producing my own bespoke eBooks. As such, the ultimate goal would be to one day have both an active and passive income as a result of my online platform, whilst remaining true to who I am. I hope to achieve relative financial stability, so that I can continue to give as much of myself as possible to the charity sector and furthering the causes I believe in.

pippa on stage at tedx, sat on chair and making strange hand gesture whilst talking to audienceThat last point is important, because not all that long ago, I thought that my ultimate dream role would be to pursue the blogging and writing solely within the context of my ‘Life Of Pippa’ platform. What I wasn’t banking on, however, was that I was also about to pursue my favourite charity job to date. I officially began my role as a communications consultant at Astriid at the beginning of 2020, again supporting a cause very close to my heart, and can safely say you’d have to drag me away kicking and screaming now. Doing a few hours a week in a flexible, self-employed capacity leaves enough time to accommodate my freelance opportunities, and yet the role has reaffirmed just how important working in the charity sector is to me. Even if I was being inundated with other opportunities, I simply don’t think I could walk away from it: and that in itself is very telling. Sitting here now, in the middle of 2020, I feel incredibly lucky to have this shot at combining so many of the things I love and shaping a safe and accessible career out of them… perhaps even enabling other people to do the same. And I swear, I will make this count for something.

Reflecting On The Journey

All this time, I thought that the transition from employed to self-employed status would be akin to stepping off a cliff: a sharp, sudden descent into the unknown. In reality, however, the whole process has developed much more naturally. Yes, there have been little leaps of faith made along the way, but essentially it was a case of building up my freelance portfolio and slowly shifting the balance of employed and self-employed work as my skills and experience developed accordingly. I felt in my gut when it was or wasn’t time to make a change, and (luckily for me!) my instincts haven’t let me down yet.

As such, it’s difficult to give concrete, step-by-step advice to other chronically ill people hoping to pursue freelance work. Individual circumstances vary, but I personally think there’s power in that. You know better than anybody what your skills are, and what you need in order to thrive. There’s no set path to becoming freelance, particularly when you have a long-term condition, so keep on taking baby steps forward and test the waters: see how things feel to you. Build up your confidence and reputation, and I really do think you’ll intuitively know when the time comes to take those little leaps of faith of your own. And most importantly, never ever forget your worth.

selfie of pippa in red jumper, holding up small wood "best chronic illness blog" award and smilingEvery job has pros and cons, whether you’re employed or self-employed. As easy as it is for me to sit here and harp on about the benefits, I don’t mind telling you that I’m often experiencing self-doubt, and fretting about the future. There are whole chunks of time where it feels impossible to squeeze words out of my foggy brain, and days where I end up in tears of frustration because I’m scared my health will prevent me from performing at the top of my game. It’s important to acknowledge that I’m privileged in having the safety net of my family to fall back on, in the worst-case scenario: if I didn’t have this, it could be game-over if my health were to decline again. I worry that my disability and the stigma around long-term illness prevents people from seeing my potential… the potential which I’m finally, finally seeing for myself.

I sacrifice so much in order to pursue my career, and there’s so much I’m yet to learn. I’m constantly paranoid that people look at my social media and think that I have it easy, that everything gets handed to me, when that’s far from the case. The simple fact is that I’m a hard worker who’s learned to get a little creative in finding and pursuing opportunities. When amazing things happen, I want to feel that I’ve earned them.

All of that said, I really do love my work. I’m excited to check my emails and delve into new projects, and being able to do so in a way that works for me and my health is more than I ever could have hoped for. Given the current climate in particular, I’m not naïve to what a privilege that is. I only hope more chronically ill and marginalised people are able to pursue similar paths in the future, and rest assured, I’m doing what I can to help make that happen. If you’re currently seeking work, you may find my blog post on finding accessible work with a chronic illness a helpful starting point.

I don’t know what happens next or where I go from here; none of us do. All I know is that I’m so thankful for the way things have played out so far, and I’ll never not be grateful for what I have. The real test now is seeing whether what I’m doing is sustainable, and whether I can make it work over the long-term. There are always going to be new challenges and issues to iron out, particularly with a fluctuating health condition, but I can’t help but feel that I’m exactly where I’m supposed to be. And to anybody in a similar position to where I once was, I hope this gives you hope, without minimising the struggles you’re going through. You deserve to have your potential recognised.

So, what do I actually do? I’m a freelance writer and blogger, who also works in the charity sector. I want to make the world a better place for chronically ill people, so we can live our very best lives. If you’re curious, you can find out more about working with me within these pages. Boom.

Amongst everything else that I’m doing, however, I want to open doors for people. I want to make sure that other chronically ill individuals also have a fair shot at chasing their dreams.

It’s time the world realises just how much we have to offer.


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3 Responses

  1. Very inspiring! I think your sentence: “Instead of assuming my health would always dictate the direction of my career, I began to more seriously consider how I could instead chase my own goals and proactively adapt them to accommodate my illness” really addresses the dilemma so many chronically ill people have – do I dare pursue my dreams, or must I just take whatever I can get? (I can’t think how the latter would boost someone’s self-esteem – already at rock bottom because of the limitations of their health). You’ve done SO well.

    1. This is so kind, thank you so much Caroline! There’s so much further we have to go in opening up the world of work for chronically ill people who choose to pursue it, but here’s to the future. Thank you again for putting the biggest smile on my face!

  2. It’s so helpful to hear how others balance work with chronic illness. I appreciate how you outlined how going to full-time freelance was a gradual process. I’m definitely prone to all or nothing thinking, so this was helpful for me as I think about what’s next. Thank you for sharing Pippa!

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