Let’s take a look at what people had to say (oh, and any comments I’m adding are just general advice; I’m not saying that it is right for that particular person etc).

Cole Henley:

I earned more money but struggled with the regularity of cash flow. Periods of feast and famine were tough with a small family to support and never took as much time off from work as I would have liked.

I also ultimately struggled managing my time and my expectations (of myself).

I found it difficult working in isolation so opted as soon as possible into a co-working space.

Well, Cole kicks off here with some real classics. Sure you can earn more money but you’re more than aware that work can dry up at any time; and the weight of a young family (and our own punishing self expectations) can bear down heavily.

Dan’s experiences also bear this out:

Feast and famine – A glut of work followed by a fallow period of ‘not much on’.

Having money in the bank, before the get go, certainly can help give your freelance career more runway. And you do need runway; if you’ve not got a lucrative contract from day 1 then you need time to find your feet, time to find your rhythm, time to find decent clients – but time costs money.

Matt Saunders:

I found that working alone at home was a lot more lonely than I expected it to be.

If you’re used to working in a vibrant agency office then you do need to prepare for this. As Cole says, co-working spaces can help. There are also places like Regus. Or set up an office together like Shane & Ben did.

Dan Davies

The hours were longer. The money (IF I got paid) was alright to begin with and the projects were usually amends to existing WordPress sites. When I did get to work in Starbucks, the place was too noisy and I couldn’t concentrate. When I finally got to work on the train, I never got a table.

I now work better hours but, hell, it has taken years to get to this point. In truth, I think you probably have to go through the furnace of working stupid hours for the wrong clients. Nothing teaches like experience.

As far as the working in Starbucks goes… ah yes! That catalogue perception of the carefree life; free wheeeling between web design, sipping mochiatos and attending Tai Chi classes. Whilst that may be a mirage, as you can see from Dan’s experience below; things can get better.

To be fair, I worked on some great projects near the end of my freelance time and I really enjoyed the 6 months in Manchester. Did a lot of growing up that year.

Rick Hurst

while I was a permie, I would be aware of what was being charged by my employers for the work I was producing, so my thinking was “I can just build one intranet a year, over the course of a few months, and then won’t need to work for the rest of the year – if I build two, i’ll be rich!”

I found myself working all the time, because I overcommitted to work and tried (and failed) to juggle on-site freelancing with direct client project work. In the first year I just got away with it and actually made decent money, but then lost any of the surplus money that theoretically would buy me some time off during my second year, due to a few mistakes – bad projects, sub-contracting work to inexperienced people then having to do it all again myself etc. By year three I had regained control financially but I was still working non-stop. The idea of “being my own boss” was laughable, as I found I had about 20 bosses, all more important than each other. I found that while I believe i’m capable of managing projects and writing code, I can’t do both at once, and I certainly struggle with managing multiple projects at once.

Managing client expectations is critical. Don’t pull an all nighter or work all weekend if it’s not actually necessary. My old mate Luc (who’s now had the good sense to move to Melbourne) once worked in a place where he figured out the priority scheme was CODE RED, CODE RED ULTRA & CODE RED TRIPLE ULTRA*. Basically there is no priority level: everything (according to the client) is high priority. Everything is urgent! It’s hard to work in an agency like that. It’s impossible to freelance like that. That’s a one way ticket to the funny farm.

Nowadays I always dig into why clients have the deadlines they have; remember they are their deadlines – not yours. If their deadlines are not achievable then say so. Save your midnight oil for when it is needed.

Matt Saunders

I’m not that good at touting for business or, to be brutally honest, marketing or promoting previous work. I found I was relying on word of mouth and existing clients to keep the work coming in. This meant that I didn’t really give myself the opportunity to push for the kind of work I actually wanted to do.

I enjoyed being in control of my own time but felt more pressured to deliver as everything was on my own head.

Brutal honesty. I have to say there is nothing like setting up your own business for bringing on a bout of brutal honesty. To most people, sitting in their shiny, new freelance business, “marketing” and “sales” are alien artefacts; complex foreign objects eluding the comprehension of us mere mortals.

This is further echoed by a touching, anonymous comment:

Probably my fault, I’m not much of a salesman, I just want to make cool things.

No, it’s not your fault. People don’t just erupt from their mother’s equipped with all the business skills of P.T.Barnum, they are learnt. In some shape or form, we have to market ourselves – and when we are dealing with potential clients, we are selling. So, like it or not, we have to make our peace with the demons of sales & marketing. And making your peace doesn’t mean you’ve got to turn into Gordon Gecko.

Matt Hill

Love Matt’s comments; so typical and so eloquently written:

I thought it would certainly be easier than it turned out to be! I had no idea it would be basically three full time jobs in one.

Perhaps the biggest shock was being completely unprepared for the amount of sales work I’d need to do. I was doing both full web design & build for small business sites, and also doing front-end work for agencies. While I got some lucky breaks through word of mouth, I still had to promote myself every where I could think of and that rarely yielded the quality jobs that I was looking for.

The day to day running of the business was something I hadn’t really considered in great detail. Managing cashflow, tracking time, doing tax returns: all the paperwork was quite onerous and not something I particularly enjoyed. I eventually got some decent systems in place, but it took me far too long and I made a lot of mistakes along the way.

I was also very naive about being able to take flexible days. There *were* times I could do so, but on the whole I’ve never worked so hard, often late into the night. The reality for me was that I had to work considerably harder to make ends meet, although I later realised this was partly due to me undercharging for my work.

Many points to be made here but allow me to focus on this: the biggest thing which people fail to prepare for is the fact that we are not productive and billable 40 hours per week. Hell, anyone who has worked anywhere already (secretly) knows this: come in with a hangover, mess around on a bored afternoon and you’re productivity is already down to 75%.  And that’s with you NOT having to worry about running a company!

Now factor in these ‘running the company‘ tasks; perhaps do a time & motion study on yourself. Find out how many hours you can realistically bill per week; and let that dictate your per hour cost (rather than an idealistic world where you are billable 100% of the time). Oh, and with time take a look at tasks which you can outsource; as you get busier you may as well pay someone to do that bookkeeping when you could be billing your hours (at a higher rate), investing in learning (which makes you more billable) or playing with your children.

Benjy Stanton

I thought I would be able to pick and choose some ‘cool’ projects like designing posters for bands. I also thought it would be easy to sell stuff like t-shirts and icons to generate passive income.

Profitable work doesn’t always come from the places you expect.

I thought finding clients would be the hardest part of freelancing, I don’t particularly like selling myself.

The concern about selling shines through again here; we really don’t like having to put ourselves out there do we! However, the point I want to talk about here is this “Profitable work doesn’t always come from the places you expect.“; aint this the truth. As true as bad clients lead to bad clients, a truth I’ve found is that good clients recommend you to other people who also turn out to be good clients. Don’t treat that website you are working on simply as a widget traversing your web design factory conveyor belt; it’s part of your oeuvre – be proud of it; tell Twitter about it, blog about it. Let the work become part of your marketing. Don’t by shy now.

Andy Davies

I had a runway of savings and picked up my first client just before I actually made the jump so I had cashflow very early on, this client also produced a lot of repeat business.

After a while clients came in through recommendations and reputation so attracting clients eventually became much easier.

Balancing client work against research and speaking was harder as essentially the latter are non-paid activities (they could be counted as promotion but…) and client work seemed to be most busiest when I had speaking engagements due.

I’ve found “word of mouth” (WOM) to be crucial, even in this world of social media (social media just puts WOM on rails). Reputation takes time to build so, again, you need plenty of runway to allow for this. Also, being backwards in coming forwards when telling others about our good work will not make ourselves easily discoverable; don’t make it hard for people to pay for your services.

Closing Thoughts

Thanks to everyone for their honest thoughts about their experiences and I hope this helps if you are also experiencing some of the scenarios described above.

If you too have something to share, I’d love to hear what you have to say in the comments below.

Oh, and don’t forget we’ve got a conference coming up in July next year in Cardiff which is just about the business side of web design. Perhaps follow on Twitter or sign up to the monthly newsletter to make sure you stay informed.

Joel

*Luc has mentioned that codes actually continued: CODE RED MAGMA, CODE MAGMA MEGA CATASTROPHE, THE END OF THINGS, and finally BORIS JOHNSON

I first went freelancing/contracting in 1998, when I was working on OS/390 IBM Mainframe kit (old skool!), plugging holes in the Y2K bug. I loved contracting; the money was better for starters. But, more than that,  I’d always hated working for other people…and that seems to be a common thread.

Some people fell into freelancing though, redundancy or a simple lack of full time positions:

“Thrown into it when was I made redundant from my agency job in 2011.” - Cole Henley

“The company I was working for went pop” - Darren Beale

“the decision for me going freelance was not made by me but the company where I worked. - Dan Davies

“Freedom. Fed up working for others.” - David Goodwin

“It just sort of happened” - Dan Dineen

“I would say I fell into freelancing.” - Victoria Jones

“I was very unhappy where I was” - Matt Saunders

And I can certainly sympathise with the anonymous soul who simply said:

“Hated my job.”

In the early 2000′s I was contracting and working at places that I really, really disliked. The travel was a grind and the work was soulless; so I know how the above person was feeling. There is only so long you can put up with the pain of hating your job, at some point something has to give; you are in charge of your career – take the necessary steps to get to where you want to go.

“I imagined that with the ludicrously high rates I could earn freelancing that I only needed to work for a few months a year to match the salary I was on as a permie.” - Rick Hurst

Ah yes! The lure of money! What does Del Boy always say? “By this time next year Rodders my old son, we’ll be milllllionaires!“. I’m pretty sure that it was money which first lured me into contracting in the late 90′s; I’d hear the hourly rate some hired hand was on and think “but, I’m better than you and earning a lot less?!“. But it’s never that simple of course; a full time role has other perks (aside from your monthly wage). And being a freelance/contractor also means you have to make hay when the sunshines – you don’t know where your next project may be coming from.

“It turned out that I loved being my own boss and the new found sense of control and freedom that came with it. What had been a stop gap became a full-time freelancing career for the next 6 years.” - Matt Hill

The above echoes a common theme of stumbling in to freelancing; perhaps that’s the nature of the beast but part of me wishes/hopes that people can increasingly take a long hard look at what they want out of their careers and plan a path which suits them; and not simply get dragged along in wake of circumstance.

“Freedom to work on more interesting / different projects.” - Joshua Marshall

Freedom to work on more interesting projects is a cracking reason to freelance but, for the majority of people, you have to put in the hard yards before you get to the stage of being picky with your clients/projects. If you’re smart, you’ll have a few clients ready & warmed up when you do decide to go solo (as Benjy below did); I did not – I had to create a parachute after I’d jumped out of the plane – not always the best plan (but sometimes the only option).

“I worked for a small web design agency, but one of the directors was leaving, so I decided to make the leap into freelancing. I was able to take all of our design-work clients with me.” – Benjy Stanton

“I didn’t plan on doing full-time client work but also wanted time to do research and talk about performance at conferences, I also wanted to be able to take the school holidays off and spend time with the kids.” - Andy Davies

Ah! The dream of the freelance life! Sipping a cool margarita on an exotic beach, the kids playing in the surf, whilst running your business via a shiny new Macbook Air! For most people, the initial reality of freelancing is a blind panic to get in as much work in as possible; hanging over you, the shadow of next month’s mortgage and a fear of letting yourself and your family down (why don’t I get a proper job?!). Andy is spot on here with his aims for freelancing; be warned though – it can take a while before you get the work/life balance that freelancing and running your own show can offer.

Closing Remarks

A lot of folks seemed to stumble into freelancing, as I’ve mentioned above, that concerns me a little. Hell, if I could speak to my 25 year old self again I’d give him a stern talking to – try to plan it out a bit more. What’s that saying? The longest journey begins with a single step…

Many thanks to everyone who generously shared their experience in the creation of this article (and the series to come).

Next time we’ll explore the answers to the following question:

“What did you think freelancing would be like?”

Joel

p.s. don’t forget we’ve got a conference coming in Cardiff next year (18th of July) which is solely about the business of freelancing and running your micro-agency.