Another view of self-employment

I’m writing this not to counter, but to complement the perspective on self-employment by Christine Wilde published on Everyday Designer on 19 June.

I agree with all Christine says about the importance of finding enjoyment and meaning in one’s work. As I say below self-employment opens possibilities for designing a fulfilling working life transcending many of the compromises inherent in salaried employment. I’m all for stepping out of one’s comfort zone in pursuit of worthwhile labour, and I agree that fear can trap us in stunted working lives characterised by cautious, compromised mediocrity.

But it is precisely because I believe so strongly in the importance of fulfilling work that I want to caution against expecting too much of self-employment. It offers the prospect of new freedoms, but comes with its own set of constraints. If you don’t like your job you may well be better off simply looking for another one than entering the vertiginous world of freelancing.

I’ve been self-employed for 10 years now. (I prefer the term ‘self-employment’ to ‘freelancing’ or ‘contracting’, both of which seem to me a little too evocative of the image of some kind of hired gunslinger – particularly absurd in my case.)

In summary, it’s been a hell of a struggle. I dare to hope, a decade in, that I’m at last finding a mode of self-employment that works for me. But I’ve been on the verge of giving it up for the past nine years. Don’t believe the hype about how liberating it all is. You really have to work to get to that point. Trust me, there are times, lots of times, when self-employment feels like a burden one is desperate to unload. Excuse the melodrama but it can feel like a form of imprisonment, with the exception that prisoners at least enjoy a measure of economic security.

Here’s my take on the advantages and disadvantages. I’ll conclude the post with a brief account of a kind of self-employment that, in my recent experience, can work, offering a measure of both freedom and stability.

Advantages – Autonomy

First the good stuff. It’s fair to say that self-employment does indeed offer the prospect of autonomy, authenticity and dignity. The exhilirating opportunity to present yourself to the world on your own terms: here I am, these are my skills, no more, no less, this is my price, take it or leave it.

If one thinks of the marketplace as a stormy sea the act of becoming self-employed is like stepping out from the protection of the ship’s hold onto a deck buffeted by strong, purifying winds. There’s no hiding away from the rigours of the market by taking shelter within a large organisation, with the attendant compromises. There’s no being told by others what tools to use, what projects to work on, where to work, or even what clothes to wear.

All of this is particularly important for web designers and developers. You are free to develop your own brand, your own website, your own business cards, your own logo. You can chose your own software and hardware, and set up your own working processes.

Something of the initial thrill of this sense of autonomy still lingers for me, a decade on.

(All that said, let me stress that I have nothing against paid employment: self-employment will only suit a minority, there are lot’s of great employers out there, and many jobs are only possible within a corporate environment.)


Another big advantage: freelancing offers certain logistical freedoms I would sorely miss. You can choose where you want to work. That might be a home office, or, if you are fortunate to live near one, a pleasant open office space that makes it possible to get out of the house and avoid isolation.

You also have some control over your time. I have developed a schedule interwoven with my particular idiosyncracies, which would tax the liberality of the most open minded boss. I like to get up early and get a good five or six hours in before lunch. I have always found working in the early afternoon strange and unnatural – surely northern Europeans can have seistas too – so I solve the problem by simply taking a long lunch break, rarely less than two hours long.

But don’t believe the hype about self-employment facilitating shorter hours: in my experience your freedom in regard to time consists in deciding how you schedule a greater number of working hours than 9 to 5, not in how you make best use of all that extra leisure time that freelancing affords.

That said, I acknowledge that the freedom to work where and when you want are real benefits.


There’s the promise, in theory, of greater freedom as to who you work with, not just whatever clients your boss happens to land you with. And if you are an assiduous networker self-employment offers possibilities for working with a far greater variety of people on a wider variety of projects than before.

More money…

I am bracing myself somewhat as I type this, but it is conceivable, if you know and assert your worth and are able to land contracts with larger companies, of earning more than employees with comparable skills.

Certainly, you can and should be charging considerably more than the hourly or daily rate you were receiving as an employee. Well established freelancers can actually bill close to agency rates. (But don’t delude yourself that you on your own can offer a comparable service to a good agency staffed with a range of specialists.)

As I shall lovingly detail shortly, self-employment is by its nature fraught with financial insecurity. But it can offer the tantalising prospect of greater financial stability in the long term than working for an employer. The employed are wholly dependant on a single job. Losing it can be catastrophic. Freelancers can spread the risk by building a sustaining network of clients and project partners.

To revisit the nautical image, the employee takes refuge in a ship, which might seem stable and seaworthy. The self-employed are afloat on a network of rafts. But if the ship sinks, it’s all rather inconvenient. But if a raft goes down there are others to which one can move. More about that later.

Disadvantages – Financial stability

So, financial stability and self-employment can go together.

Can. But I don’t know a single self-employed person who doesn’t worry about money pretty much all the time, regardless of their skills and experience. Perhaps I just need to get out more.

Some may be in the fortunate position of having another source of income, perhaps shared with a significant other with a ‘proper’ job. Others might live in one of the few remaining countries that provide decent social security to tide you through difficult times (oh to be Scandinavian).

But let’s assume that you are self-employed in austerity Britain, on your own, or, like many of us, in a household reliant on dual incomes.

Consider what you’ve taken on. Your industry and ingenuity are all that stand between you and the financial abyss. The self-employed receive none of the benefits enjoyed (at least for now) by most employees. No paid sick leave or holidays. No maternity or paternity provision. No pension contributions. No redundancy pay-off. No company car. You will pay exactly the same tax as the employed, despite your receiving none of the same benefits.

There’s virtually no support from the state if the work dries up: indeed once you’ve registered as self-employed it’s hard to re-qualify for social security. It’s significantly harder to get a mortgage.

You don’t have any career ladder to climb. That might not seem a big deal when you are starting your working life and your employed peers are at low rungs in their organisations. You’ll probably be on a par with them. But they have the opportunity to progress through an organisation and – eventually – accrue the substantial pay and benefits available at senior management levels. It’s easy to mock the corporate grind but it can bear fruit quite spectacularly later in life.

As I’ve said, there’s a certain stark joy when the reality of all this hits for the first time. Pride in having had the courage to seek to map your own course through life, and not having wobbled down a well-trodden, safe, established path for want of imagination. It’s all quite exciting for a while, and your commitment to making a success of it will be intense.

But, believe me, that sense of euthoria passes. The realisation grows that the same pitch of intensity must be maintained at all times. The bills never stop coming. Unlike many employees there’s no possibility of coasting from time to time (as I certainly did) secure in the knowledge that a pay cheque will be there at the end of the month whether honestly earned or not. I can honestly say that I have worried about money every single day since becoming self-employed, even when things have been going well.

Moving from employment to self-employment is, if I may get philosophical about it, an existential decision. It’s not a simple adjustment in one’s economic arrangements. Everything looks different when you’re self-employed. The windows are open, and a brutally competitive market economy, with all its opportunities and dangers, confronts you at all times.

The anxious search for control

The absence of that regular pay cheque has a profound impact on poor old worriers like me. I try to manage my sense of insecurity by looking for ways of establishing some kind of control.

I find myself working at breakneck speed to try tick off projects and get money coming in as soon as possible. I hope clients will be impressed with my industry and timeliness and will be similarly motivated to meet their deadlines, and bring the project to a speedy and efficient conclusion.

After all this time I really should know better. In reality you can only go as fast as the client. And even good clients tend to be bound by organisational strictures that make it impossible for them to move anywhere near as fast as you.

This is the classic cycle:

Just like it says in all the articles and books extolling the virtues of self-employment I draw up a contract at the outset of all my projects, specifying my and the client’s obligations, and the project milestones we solemnly vow to observe.

Contracts are essential. But I have to say I no longer expect them to make too much difference to how projects actually pan out.

As I’ve said, clients can’t move anywhere near as fast as freelancers. Most work for large, slow, conservative organisations, with set ways of doing things that they won’t change just for your benefit.

When they first get in touch with you clients inevitably ask that a project be completed ‘as soon as possible’, and are usually sincere in their belief that they will have time to focus on the project when it gets underway. But things change. They get busy with other demands, or realise soon after getting started that they’ve underestimated how much time the development of a worthwhile website takes. They may take weeks, indeed months, to respond to requests for feedback and content, and project milestones soon recede into the haze of an obscure horizon.

It’s essential therefore to keep taking on new projects to maintain cash flow. Quite appalling bottlenecks can develop, successive projects colliding into each other like rudderless oil tankers. When a client is finally ready to move a project to the next phase you need to respond quickly before that window of opportunity closes, and they are submerged under a new wave of competing demands.

These frustrations are of course common to all modes of employment, self-employed or otherwise. But it is particurarly stressful for the freelancer, whose very livelihood is on the line, at the mercy of processes beyond their control.

All of the most efficient clients I have worked for have been other self-employed people. They keenly appreciate how important it is that projects be completed on schedule, and invoices settled on time. But most clients are employees. And the unvarnished truth is that employees simply do not have the same sense of urgency as me. They have a wage. They are not indifferent to deadlines, and, as I’ve said, are often constrained by processes beyond their control. But they will get paid at the end of the month whether deadlines slip or not, and they won’t be working evenings and weekends to go the extra mile to make sure a project is completed on time just for my benefit.

Worse, when a project grinds to its conclusion don’t expect ready payment. Clients will pay in their own good time. Contracts and upfront payments certainly help, but large companies and organisations hold are the ones with the power, not the freelancer.

I’m used to waiting several months for payment for certain projects. When the money does arrive it will more likely than not come in the form of a cheque (online banking hasn’t come to all that many organisations yet), causing further delay. Organisations will follow their established payment processes, regardless of payment terms specified in contracts and invoices. All this sounds rather cynical, but I promise it’s how, in my experience at least, things actually work.

Quality of life

Clearly, all of this can and does damage quality of life, the very thing that prompted the decision to enter into self-employment in the first place.

As I’ve said, I find myself working very long hours: it takes discipline to take evenings and weekends off, even when it’s possible, and it can be very hard to switch off properly during holidays. Before I go I find it helps to write down all the reasons why I have permission to take time away like anyone else, but sometimes one’s worst fears can come true. During a recent break I checked my email after a couple of days to find that four client websites hosted with a particular hosting company had gone down the day after I left. The knowledge that my clients were – shall we say – keenly awaiting my return with the expectation that I would deal with all of the problems immediately on arriving back in the country made it quite hard to enjoy my remaining time away.

Some other problems. It’s hard to find the time and mental energy required to engage seriously in other interests that might be wholly unrelated to work. One can expend so much energy working and worrying that time spent not working can degenerate into little more than vegetative recuperation, rather than proper leisure time during which other interests can be pursued.

Relationships with family and friends can be affected, as you disappear into your work.

You may find yourself becoming quite resentful of those enjoying the security of full time employment, especially those for whom you are working who may be taking their time to pay you.

And there’s the problem of loneliness. Not necessarily isolation: as I’ve said, there are opportunities to find shared office space and attend networking events and conferences, where one can build up a good support network. But there’s a certain kind of loneliness borne of shouldering a financial burden on your own. Employees at least have the sense of all being in the same boat.

Complexity of modern web design and development

Everything I’ve said thus far applies to self-employment in any field. But I want to mention briefly an additional concern that’s specific to self-employed web designers and developers.

In a nutshell the escalating complexity of contemporary web design makes it increasingly hard – in my view impossible – for one person to do everything.

I’m aware that many self-employed designers and developers often work as part of a project team, and so have an opportunity to specialise. That’s good, and I’ll say more about that shortly.

But until the past couple of years or so it was possible for a single designer/developer to handle all aspects of a moderate project, from planning, through to design and delivery, and client training. A lot of us are still doing that, me included.

Those days, I contend, are rapidly coming to an end. I’m shocked at the amount of work it takes these days to develop even a simple website, at least if there’s the least concern with quality.

Consider everything that’s involved in developing a responsive website: Content strategy. Project management. HTML5. CSS3. JavaScript. Graphic design. Photo editing. Responsive design. Copywriting. Browser testing. Device testing. Content management system integration. Client training.

(Here’s a rather more comprehensive checklist.)

If you can do all that for two or three thousand pounds – the best most designers can charge for a medium sized job – you are a much more organised and skilled designer than me. Client budgets, understandably in today’s economy, haven’t gone up much, if at all, over the past few years. But the skills required to develop a good website have multiplied exponentially. I’m not ashamed to admit to making all kinds of compromises just to get projects out of the door and get paid.

In particular the issue of device testing seems to me a serious problem for self-employed designers. I test on real devices so far as possible, but rely heavily on emulators. I just don’t have the budget to afford a test suite necessary to check performance on all but the most popular two or three devices.

At least I can say I’m upfront with clients from the outset as to what I can and can’t do. In a word, not everything. Not even close. Enough to get a reasonably good looking and functional site out there, that will work on mainstream browsers and devices. And that’s it. I think it’s only possible to deliver a first class website these days if designers and developers are prepared to pool their expertise by working as a team.

Flexible networks

Which brings me to my concluding, and slightly more positive, remarks. I’m now convinced that a preparedness to specialise and work more often than not with others is the most sustainable model for self-employment, more so than ever.

Trying to do everything yourself is a pretty joyless business. Too much work, too much financial uncertainty. It makes much more sense to be honest with oneself as to where one’s strengths lie, and consider how those might fit within a network of complementary talents.

That doesn’t necessarily mean giving up self-employment and looking for an agency role (although it may well make sense to take a suitable job). It means doing a lot of networking with one’s peers, on and offline, and letting them know what you can and can’t do. After a time, if you’re any good at all, there will be invitations to work with others, as part of teams assembled for the specific demands of particular projects. If you do a decent job other opportunities will follow to work on new projects with different casts, with familiar and unfamiliar faces. And so it goes on.

It sounds quite precarious, but it actually feels quite secure. As I’ve said, like being afloat on a network of ever shifting rafts. The burden of responsibility is shared, there’s companionship, and the pooling of talents assures a quality service adequate to the demands of contemporary web design.

I now spend most of my time working on projects like these, navigating from network to network. I think I can now discern a way of making self-employment work, of continuing to enjoy its benefits while minimising (certainly not abolishing) its drawbacks. I no longer take on jobs that involve my going solo (although I continue to support long standing clients).

I’m now doing what I probably should have been doing all along. Self-employment doesn’t really work when you try doing things on your own. Done right, it seems to me, it requires doing exactly the opposite: the humility to realise that you can’t do everything yourself, the willingness to specialise, and to realise that true freedom requires the support of others.

  • Heather Burns

    Superb piece, Justin.

    Perhaps one of the perverse ironies of our current economic landscape is that when it comes to financial stability, freelancing is no longer a leap. It’s more of a hop.

    For me personally I came to self-employment with ease because I had no perspective from which to feel any sense of loss. I had been doing a lot of temporary and contract work, which meant that I never had sick pay or holidays in the first place. As I had been on short-term contract roles whilst expecting my child, I had to rely on the bare-bones state maternity pay without a job to go back to when the payments were up. My last employer was such a dysfunctional hellhole that, amongst other things, I was never signed up to the company pension plan. The worst example of my second-class status came in the contract role I held whilst expecting. I slipped and fell on the office’s wet stairs. I sat down frozen in terror for a few moments thinking that I had hurt my baby. I immediately reported the incident to the health and safety manager, who felt no need to record the incident because I was a contractor and not a regular salaried employee; my accident simply did not count.

    In a culture where employee rights do not exist, self-employment is a form of empowerment, not struggle. It is taking control back, not giving it away. You cannot miss what you never had.

  • Jason Hunt

    Thanks Justin, great article – very insightful and honest.

    I also agree in the ‘network’ approach to larger design jobs – it’s how I work too.

    Love your analogy of the rafts – being self-employed is just having lots of jobs, as opposed to one – which in my experience, tends to liberate and inspire – both really important for any (creative) person.

    It’s not exactly job security, but that is really just a myth – and no one person can put me out of a job except me!

  • Justin Reynolds

    Thank you very much for your comments Jason and Heather. The grass is always greener I suppose, and it’s easy to envy what one might perceive to be on the other side, in the case of the self-employed the prospect of a nice stable income and an end to financial worry. I had such a job 10 years or so ago, and, while I well recall the bad bits – somewhat boring, an encroaching sense of meaninglessness – I was in it long enough to appreciate the good things too. Perhaps – given Heather’s experience – I was lucky. Having experienced both states I’d just want to caution those considering self-employment to weight the scales carefully. There’s too much – can I say propaganda? – about the joys of working for oneself.

    We hear a lot about the importance of developing an ‘enterprise culture’, about encouraging people to try self-employment and set up their own businesses. I like the idea of all that but if policy makers are serious about it I think there need to be adjustments to the economic frameworks within which we work. Heather has talked about better child care support, which is sorely needed. And people need to know that if they fail – and most businesses do fail – that there’s some meaningful economic support available to allow them to try again. I’m in favour of exploring the idea of something like a ‘citizen’s income’ or ‘basic wage’ that provides subsistence support while trying to get a business off the ground. Sounds radical, but countries that have something like this have a livelier entrepreneurial culture than we do.

    I discussed some of this in a blog post some time ago. Certainly many of my friends and family think I’m totally mad for choosing self-employment with all its attendant risks. We need to think about changing that mindset through concrete policies, I think, rather than just exhortation.

    • Heather Burns

      > There’s too much – can I say propaganda? – about the joys of working for oneself.
      Oh absolutely; and the propagandic nature becomes particularly suffocating in some of the startup and networking groups specifically for women, where great pressure is placed on you to spin the low points of self-employment into a heroine’s saga of ambition and self-determination. I’m reminded of the brilliant interview with Madonna where the journalist was determined to spin a romanticised success story out of the formative time she spent living in a grotty bedsit while trying to make it big. Rather than colluding with him, she stared at him blankly and said: “I just wanted to get the hell out of Michigan.” And that’s the truth of self-employment.

      Self-employment has been the making of me, but it’s been the hardest thing I’ve ever done. Still, I love it, and wouldn’t trade it for anything.

  • Jason Hunt

    Of course good (and affordable) childcare is vital to so many self-employed workers – it is vital to me and my 4 children! But the inherent flexibility of working for myself was the driving force to make the final move three years ago. I had to make my work really work around me and the needs of my family. Not many UK employers would afford me the ad-hoc daily flexibility I need. This does however mean that I don’t (want to and can’t) take on ‘traditional’ on-site freelance or contract gigs. I operate a sort of micro design agency, setting my own working hours and prioritising work and projects on that basis. It works well, pulling in other resources when needed. Obviously not all self-employment can work like that, and it is a compromise I guess and certainly shapes the type of work I do and who I work for, but that’s OK – it works for me and mine.

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