So you want to be a web contractor? (Part 1: Tips for getting started)

In 2013 I left my cushy full-time job as a Front end developer to enter the scary world of self-employment. This wasn’t the first time I’d attempted to go self-employed and I was terrified that like the other times, I’d fail within a year. However this time I was doing something differently, I wasn’t attempting to start an agency or become an ‘everything under one roof’ freelancer. This time I was going to be a specialist contractor.

It was the scariest decision I’ve ever made in my life but it was by far the most rewarding, over the last 3 1/2 years I’ve learned so much about my industry, I’ve developed people skills I never though I’d get, I almost never work more than 9-10 months in a year (although that’s not always by choice) and the money I make is beyond anything I could have made as a permanent developer without joining the ranks of company directors (and even then I’d probably not have made as much).

If you are thinking of making the leap, then here is part one of my guide to becoming a contractor, this guide will not just tell you how get started, but how to flourish.

Step 1: Are you sure this is the right decision?

A blind folded man walking off a cliff as his colleagues urge him no to

Ok look. Contracting isn’t easy, even if you are good enough technically (more on that soon), going into it blind will not do you any favours, make sure you have considered the following before taking the plunge.

1: You need to be good with numbers

This one is only a half truth, in reality, you need to be good at basic maths, most of the time your accountant and accountancy software will do the work for you, you just need to make sure you are doing the basics (e.g When calculating your dividend for the month, you need to keep in mind how much tax you’ll pay on that income and if you can definitely afford to take as much as you want/need).

2. You need to be good with people

I’m an introvert, so where possible, I’d rather not deal with people. However in business, you need to be personable, when you interview for a role they need to like you as a person, when you deal with recruiters (which you will… a lot!) you need them to want to find work for you because they think you’re a great person.

Quite a lot of the time, you’ll be hired as an expert and this will often mean you need to be able to communicate with the clients. This is especially true if you are contracting in the UX or design fields. As a permanent employee I led exactly one client meeting in the 15 years of career to that point. In the 3 1/2 years since, I’ve led so many meetings with clients (many of them are major blue-chip corporations) that I’ve lost count.

On top of that, you’ll be the new person in the office nearly all the time (a lot of contracts are around 3 months), so you need to be able to fit in to the company pretty much immediately. If you can’t do that (even if you are good at your job) then it’s unlikely they will renew your contract or hire you again in the future. In fact I’ve known a few companies who have let contractors go mid-contract because they didn’t fit in!

3. You need to be 100% professional

Last year I worked at one of the biggest digital agencies in the world, on the same day I started, there were also two other contracts who joined me, one of them turned up at midday and claimed that yesterday was his birthday and he’d been out drinking all night and was hungover. The project lead forgave him and he carried on with his day. The next day he turned up at 10am, same with the day after. In his second week he turned up at 2pm and claimed that yesterday was his mates birthday and he’d been out all night drinking and was hungover. Unsurprisingly he was immediately let go, upon reviewing his work, we discovered that in the seven days he’d been there, he’d done the equivalent of about 2 days work and he’d done that badly.

I’d chatted to him a few times whilst he was there and he said that he’d been a contractor for about 6 years! This may surprise you but there are two types of contractor:

Type 1: The consummate professional. This is the type you should aspire to be, they always turn up on time, they always aim to be the best person on the team, they work quickly and diligently, they are well-mannered and know how to speak to people on all levels. This type usually loves contracting and will be very unlikely to return to permanent work.

Type 2: The bouncer. This is the type that you will find has probably changed cities (maybe even countries) if they have contracted for a while. This is because they never get hired back and eventually lose all respect in the town they are currently living in. They are lazy, they are often late, they have no quality control in their work and they often stretch out a job as long as possible to a) get themselves more money and b) keep the job going as long as possible before anyone needs to check their work. Usually this type becomes a contractor because they can’t hold down a permanent job.

Type 1 excels in the contractor market and will soon find themselves to be a valuable commodity, their day-rate will steadily rise and they will almost never be short of work. Type 2 is a waste of time and money to everyone involved, they will either not be a contractor for long or they will move cities a lot. The only way to make a living as a Type 2 is to live in a massive city (like London or NYC) and have a few mates who will lie on your reference sheet.

If you are thinking about being a Type 2 then make sure you realise you’re not only hurting yourself. Last month I was due to start a new role with a small digital agency. I was hired to replace a Type 2 contractor who they had to fire part way though the project. Two days before I was due to start I was told that the role had been cancelled as the previous contractor had screwed the project up so much that it had cost the agency their major client. I spoke to them again last week and they are currently struggling to stay afloat, that one bad contractor may have impaired the agency for good.

4. You need to be experienced and highly skilled

This one should be a no-brainer but you’d be surprised at how many junior developers I’ve spoken to who want to start contracting. Whilst it is possible to start contracting as a junior, I would strongly recommend against it, freelance Junior roles are rare and the pay isn’t much better than you’d get as a perm. If you are thinking of pretending to be a middle-weight or a senior, then forget that too, this will just result in you biting of more than you can chew and getting a bad reputation.

My advice is to stay as a permanent developer, work at a few different agencies (and work client-side at least once) to get a feel for how our industry works and to gain enough experience that you will know how to deal with the common pit-falls that web-developers come across, you won’t learn this stuff from books, it’s the sort of skill that only comes with experience. A good rule of thumb is not to become a contractor until you are a senior.

Having said that, your job title is often dependent on the whims of your employer when you are a permanent member of staff (despite having 15 years experience, I ended my permanent career as a middle-weight due to a boss who had a chip on his shoulder) so use your own judgement when it comes to determining your skill level. Just make sure you are 100% honest with yourself, if you don’t think you can be, then ask your colleagues and close friends in your industry what they think of you.

5: You need survival income

The market is often brutal to new contractors, even ones with loads of experience. It took me almost a month to find my first role and then I had to wait two more months before I got paid (I worked a month, then invoiced at the end of it and got paid 30 days later). This nearly killed my contracting career before it started as I’d only saved 3 months of survival income. My story isn’t even the worst I’ve heard. A friend of mine was very unfortunate in that he started contracting the same week as the Brexit vote, that vote killed the contractor market (it’s still not completely recovered), it took him almost two months to find work and only managed to scrape by because he was lucky enough to find an agency who paid fortnightly.

I would recommend saving at LEAST 3 months survival income, if you are joining the market during its annual quiet period between November and February (which is a bad idea) then you should probably double that as work is nearly impossible to find at this time (unless you are happy doing bug fixing roles for a pittance).

Step 2: Getting yourself ready

Scar from Lion King during his 'be prepared' song.

Assuming you can check off all the above, you’ve probably got what it takes to be a successful contractor, so now you need to make some crucial first steps:

1. Get that CV up to scratch

A contractor CV isn’t the same as a permanent CV, your summary is a lot more important and your educational history is a lot less important. Whilst mine is probably not the perfect example, I’m often complimented on it and it’s definitely one of the reasons I get offered so much work. So I have included it here for you to use, feel free to edit it to suit your own goals.

Note: This is a Microsoft Word document.

2. Get a portfolio site online

It doesn’t have to be perfect but it does have to show off your skills to the best way possible. Also link to any social networks which show your work off as well (eg, Github, Behance, Dribbble etc…) and definitely include a link to your LinkedIn portfolio.

Another tip is to include your availability and a link to your CV on the home page, quite a few recruiters have thanked me for making this information easy to get access to from the start.

Again, I offer my portfolio site as an example, it’s not the shining beacon of all things portfolio-y but it might give you a good jumping off point.

3. Polish up that LinkedIn profile

LinkedIn is by far the best way to get contracts, even if a recruiter doesn’t find you on LinkedIn, they will nearly always ask for a link to your profile, so make sure that it sells you to the best of your ability, make sure the profile completeness indicator is at 100% and use your status to show your availability, your location and what sort of roles you are looking for. I could write a whole article on improving your LinkedIn profile but it’s been done to death already so I suggest googling that one.

4. Get on the job sites

I practically never look for work anymore. If the recruiter market is even slightly busy then my phone rings at least 3-4 times a day, at really busy periods, my phone pretty much rings off the hook. Last year it got to the point where I had to set up a separate number just so I could disconnect it when I was unavailable, otherwise I’d spend all my time either answering the phone or deleting voicemail (more on this in part two).

The secret to this is simple. Follow the steps above and then post your swanky CV to the following sites (assuming you’re in the UK):

Make sure you fill out every single detail they ask for and don’t forget to set your availability, location and desired rate on any of the sites which ask for it. Another tip is to update your CV every week (Do this on Monday for the best results), the reason for this is that most of the sites above are linked to a central recruiter database which puts the most recently updated profiles at the very top, you don’t have to actually change your CV. I normally just change the date in the title (e.g. Alex_Ward_UI_Developer-28-09-16.docx) and then re-upload it. You can do this daily if you like but I haven’t personally noticed any increase in calls/emails above one update per week.

Keep your eyes peeled for part two, which will cover the sort of equipment and software you’ll need to get, things you can do to stand out more to recruiters,  and a few insider tips to make your contracting life as easy as possible.

Are you an IT contractor too? If you have any tips and tricks you think would be good to include then please let me know in the comments!

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Alex Foxleigh
Freelance UI Developer at
Freelance User Interface Developer, Aspiring novelist and ill-informed political writer from Sevenoaks, UK.

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