Is freelancing child’s play? - Kids' App Designer Chris O'Shea

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Chris O’Shea first started freelancing straight out of college.

After teaching himself web development with a library book, Chris had a phone line installed in his childhood bedroom in the family home. From there, 18-year-old Chris ran his own web design company in what was his first stab at self-employment.

Sadly, (or luckily, depending on how you look at it) that one didn’t work out, and so Chris went back to uni to study a Digital Art degree.

Moving to London in 2005, Chris soon found himself leading the way in the world of interactive installations.

Travelling the world, running events and managing a successful blog - all alongside doing the work in his freelance business - Chris became an authority in his field.

From building a name for himself to building a family; Chris is now a stay-at-home dad of two. Shifting to a career that allows him to work on projects he loves while still being around for his kids.

We talk about what he learnt from that early experience of freelance life, how he applied those lessons to the impressive career he built for himself in London, and how he’s now found himself scaling back a little to juggle family life with running his third business, ‘Cowly Owl’.

Chris isn’t just designing games. He’s designing a work life that fits his family.


Chris O'Shea:       I've always been working for myself really. I dropped out of college when I was 18 and I've never really had a normal job with a payslip since. I went to study for my A-Levels but I wasn't really enjoying the subjects and how they were being taught and I taught myself how to make websites from a library book and I came out of college with no A-Levels and started looking in the Yellow Pages for local companies who made websites and then when I was looking at their websites I didn't like what any of them were making so I decided to start on my own with no experience and I was 18 years old and went on a crash course in working for yourself and running a business.

Steve Folland:      Wow! Quite a...were you still living at home?

Chris O'Shea:       Yeah, I was still living at home and I have four brothers as well so I had my own phone line put into my bedroom and I started making websites for local businesses. I would get phone calls and basically have to hide from my brothers who were making noise down the hall.

Chris O'Shea:       When I moved out of my parents house, I'd also rented an office in the centre of the town and things were getting busier and busier and I looked at two friends who I was in college with and basically hired them. One was a designer and one was a developer and we basically made websites for local businesses. After about four years, I just couldn't make enough money to keep the company going and at the time there were all these big web agencies crashing and all these big dot-com retail sites were going under and also I was very inexperienced, I was 21 by that point and I had to close the company down.

Chris O'Shea:       I'd had four years of running this company and making websites for local businesses but I didn't have any qualifications so I decided to go to university. I went to university in Plymouth down in Devon, I worked hard on my degree because of failing in the business I wanted to make sure I came out this time with my qualifications and I did a digital art degree that was a combination of technology and cultural art thinking.


Chris O'Shea:       Then I moved to London in 2005, I basically found some freelance work for a company that make interactive museum exhibits. I worked for them for about 10 months, they asked if I wanted to stay on full time and go on payroll. I declined and said I wanted to go freelance so that was my first official, working for myself on my own being a freelancer from that point onwards.


Steve Folland:      What was it at that point that made you think "no, I don't want to work for you full time I want to be by myself?"


Chris O'Shea:       It was a combination of I get a bit itchy feet if I'm in one place for too long and also they were pushing me more towards the web side of their work because museum installations don't really pay very much money so the web side was a much more of a stable base to earn money from and I wanted to keep doing this interactive, experimental art stuff.


Steve Folland:      Ah, right.


Chris O'Shea:       I landed on my feet arriving in London and then I've then worked, hard work of trying to find some stuff from there.


Steve Folland:      Yes!


Steve Folland:      So how did you go about finding those next freelance jobs doing the thing you wanted to do?


Chris O'Shea:       Well, I basically, you obviously make a website, you make a portfolio but I'd only had to republish projects through them and I basically just started approaching all the companies that I knew that made these interactive installations and went to them, showed them what I'd made. I did a lot of work in a short space of time. Some of it perhaps underpaid but just to get my foot in the door. I'd also over the years built up an authority voice on this field. People know me for understanding this field and what things are out there so I'd have a blog that was popular at the time called Pixelsumo.


Chris O'Shea:       I also co-founded a series of events called "This Happened" which was a free event you go to where you hear someone talk about their project and the process they went through to make that project in this field. At its height, we had about 300 people in the audience. This was a free event so we wanted to make it accessible to students.


Chris O'Shea:       A combination of doing the work and blogging and running these events in this field makes you an authority on that subject so you'd often get phone calls to come in and pitch stuff to ad agencies or production companies.


Steve Folland:      Cool!


Steve Folland:      How long did that go on for? You were in London from 2005, so, suddenly we're in 2006. How long were you doing that kind of thing for?


Chris O'Shea:       I lived in London for about 11 or 12 years and I did a combination of making installations for myself, so getting commissioned to me personally under my own name by museums or art galleries or festivals chasing arts money and grants and a combination of that plus being a creative technologist. I would, some companies or artists need an installation making that has some involvement of technology and people interacting with it, I would go in and help them deliver that either through coding or production things. I did that for 11 years, got to show my work all over the world, Alaska, Tokyo, South Korea and all kinds of places and lots of conference talks and things but eventually got married and had kids and we decided we wanted to get out of London life really. With two children, one of them about to start school we thought now as good a time as any to push out.


Steve Folland:      When you were doing that work for 10, 11 years and some of it was being commissioned direct to you, were you hiring other people? Were you tempted to grow a company like you had before?


Chris O'Shea:       No. The main reason why is because of the failure of my business when I was much younger. That made me really realise how to manage money and also that I didn't want to have staff and an office again. I was quite happy going between different companies and doing bits of their projects.


Chris O'Shea:       I had some projects that were quite long, a year or two long, but other ones that were very short like you had three months to make and deliver but I never really had that desire to lead a team and run a big company again.


Steve Folland:      Yeah.


Steve Folland:      What did you learn from that very early experience? What was it that you took away from it?


Chris O'Shea:       Well, to always be projecting forwards in terms of your money, to make sure you're charging enough, to be always marketing yourself.


Chris O'Shea:       When I was doing the web stuff on my own when I was much younger, I had, I was trying to do the business side but I was a really bad salesperson so I'd hire a salesperson who was maybe much better at getting that work in that you were and this was also because it was working in a very small town in Somerset where there wasn't much work going on and local businesses didn't really want to pay very much anyway.


Chris O'Shea:       After moving out of London I decided to concentrate on my new business which was Cowly Owl, which was making games for kids.


Steve Folland:      I see. You became a Dad and that changed your outlook?


Chris O'Shea:       A little bit. I started doing this before but my outlook changed slightly with kids in that, all of my interactive installation work has been about people and play and how they play in a space together and I started experimenting, made an iPhone app that lets you turn your phone into a toy car with Lego bricks and I realised at that point if I wanted to put out more apps, I needed a brand and a company to put it out under rather than my own name and so that came first.


Chris O'Shea:       Now that my children are a bit older and we actually play video games together, it made me realise that I don't want to just make apps that keep kids occupied and busy at the restaurant or on the aeroplane, but actually wanted to make games that parents and children could play together. I've recently re-branded the company, relaunched with a new game with that as focus so the kids, having the kids has made me realise that shift in direction from making just apps for kids to making games that parents and kids can play together.


Steve Folland:      Wow! There's obviously a big change there. Going from I guess taking on a project where a client is paying you money and it could go on for a year and it's month by month and there's that security as you go through and see something through to the end. To, making your own app. Making your own product and not knowing if people will buy it or anything like that. How have you coped with that change?


Chris O'Shea:       Yeah, it's massively different and it's really hard because the mobile space is very hard to make money in and it's enough for me as an individual in a company to get by but it wouldn't support having a team of people making these apps.


Chris O'Shea:       The mindset of going out looking for freelance versus having a product that you can sell, it is a lot harder but actually the nice thing about it, is it's not passive income because obviously you work very hard to get it to that point but the apps that I released two or three years ago still bring in a little bit of money in each month so collectively all of those app sales build up.


Chris O'Shea:       The hardest thing at the moment is the shift in the market. Parents are a lot less likely to buy premium mobile games which means you pay up front for a game versus downloading something of free that might contain advertising or in-app purchases. It's trying to keep up with the times but also I still want to be ethical in a way that I approach my work and not just put out, I'm not putting out games just to make money I'm trying to put out high-quality products that I'm proud of and people can trust aren't going to try and steal or upsell from their kids.


Steve Folland:      You've always got your designer hat on, your creator hat on. Presumably, a lot of work has to go into getting the word out there for it?


Chris O'Shea:       Yeah and it's...I sell my games on Apple, Google and Amazon on the mobile stores and by far the biggest factor in your sales is getting featured by those platforms and having those relationships but that's getting harder and harder to have now and the changes in the app stores, the front pages of the app stores which is where most people look for their products, those changes change over time.


Chris O'Shea:       On the Apple app store, for example, there's a "Today" tab now. The front page is the "Today" tab that will change every day as opposed to having a feature for a week. Beyond that it's getting people to play the video on YouTube that young children might watch, you know, six-year-olds might watch, sending it in to bloggers and reviewers but that's becoming much harder because those sites aren't reviewing apps as much anymore so it is a definitely constant uphill battle when a single person with a low marketing budget, it's very hard.


Steve Folland:      Hmm.


Steve Folland:      You said you stepped away from London for the life reasons, rather than the work reasons. How's your work/life balance looking?


Chris O'Shea:       Yeah, I mean, I definitely used to work way too many hours when I was in London. I used to take on all the projects that I could, not that I could find but that appealed to me even if they weren't the best paid, that with the blogging and events I was just working ridiculous hours.


Chris O'Shea:       Now my wife is working full time, I basically work four days a week between nine and three so between school hours. Take the kids to school, take the kids to nursery, pick them up, take them to the club or the lessons or whatever they're doing after school, play dates and I'm trying to discipline myself to do a little bit in the evenings a couple of times a week but by the time you've had the kids and done the school run and everything you're a bit too exhausted to carry on so I'm finding that transition hard.


Chris O'Shea:       When I was living in London and we had our first child, when he was 10 months old, my wife had returned to work full time as she had to finish her teaching qualification so I basically became the stay at home Dad so I was still freelance but I was a stay at home Dad and that year obviously I didn't get any, very, very little work done and I tried to work between nap times and evenings and it made me really appreciate how hard it is to look after children full time. I was doing a project for them, an installation for the Royal London Hospital and I'd have to take him with me and I was travelling to Shoreditch to the company for meetings, then I'd go to Whitechapel and I'd take my one and a half year old, two year old toddler with me and just say "look, this is the situation" here's my child and go prepared with enough snacks and colouring things and toys to sit him at the table for an hour and it never really works because they always want attention and they never sit still but you have to make it work don't you and that's how you do it.


Steve Folland:      That is great though that you could say that to the people that you were working with.


Chris O'Shea:       I think I couldn't do it if it was a new client, if you went out straight for the first client I think it would be very hard but because I'd already started working with them and this production company it's an easier thing to do. It's either that or I don't do the project.


Chris O'Shea:       I remember lugging the pushchair up a flight of stairs in Whitechapel and then rushing to the hospital there and it was a tough time. It's definitely got a lot easier as they've got older. We've got one child not in school yet so once they start school then obviously I'll get a bit more freedom over those five days.


Chris O'Shea:       It's definitely a lot more chill down here now and we can walk to school, it's very close 'cause you're in the countryside and I'm not worried about having to work so much because of the price of rent in London, makes it a lot easier.


Steve Folland:      What do you do when it comes to school holidays?


Chris O'Shea:       Thankfully my wife is in education so she's off during summer holidays so I'll take two weeks off and then the rest of it I'll work those five days a week.


Steve Folland:      Yeah, God that's handy!


Chris O'Shea:       Very handy, very handy!


Steve Folland:      There can still be that feeling of guilt in the half term that you feel like you should be doing something with them even though you know this is a great opportunity to do work.


Chris O'Shea:       Exactly. It's, I guess if I was a lot richer then I could just say I'll take off all the school holidays as well but it's hard when you've got those limited hours during the working week to get enough done. You miss them and you want to be able to go out and do things and go out on those days 'cause it's the only days that you have with them to go and do day trips. Obviously, there's weekends but there's so many birthday parties and things to go to as well, it's tricky.


Steve Folland:      At what point did you stop doing the events? Was that when you became a Dad because that sounded like a pretty big thing?


Chris O'Shea:       Yeah. The event was called "This Happened" and because it was free event and we were putting it on every couple of months and it became a huge amount of work because we'd have to then find sponsors to cover the venue and the bar and things and I just found there was a pressure point where I was doing all these things and I had to say "right, I'm going to stop blogging and I'm going to stop running this event," so, that then gave me more time to free up and basically look at what work I wanted to be doing. This was before we left London so we managed to find some other like-minded people to take on the event and keep it running so it still runs in London now.


Steve Folland:      Ohhh.


Chris O'Shea:       The event has also spread to other countries and other cities. They've taken that format of the 10-minute talk about one project, they run their own events around that as well and you can go to the website and watch all the videos.


Steve Folland:      That's really cool! Good for you! Something you created spread and still lives on.


Steve Folland:      Was there a point where you think "I kind of want to kill this" but at the same time everybody's finding it valuable and yet I don't have enough time-


Chris O'Shea:       Exactly. Especially when two other founders of that event as well, it does become a point where you have too much on and you have to look at all the pans you're trying to keep boiling or juggling, yeah.


Steve Folland:      Was it easier running something though in a collaboration like that?


Chris O'Shea:       Yeah, definitely because you could, between you, you could decide what you're doing to be doing and you already have a much bigger reach as well in terms of their audiences and people who follow them and I wouldn't want to do it on my own, definitely.


Steve Folland:      Yeah.


Steve Folland:      How did you manage the business side of things? Obviously it's almost like three chapters to this. It's your web business but we've covered that. Then there's when you were doing all those freelance projects for 10 years, let's start with that bit. How were you dealing with it then?


Chris O'Shea:       Yeah, I always, I would never have worked without a 50 percent deposit or splitting it up 20/20 something and making sure that I got some upfront so that if I was late paid or if there was an issue I'd at least have something there from it and this is from understanding how that worked previously and not getting paid.


Chris O'Shea:       Making sure I forecasted forwards to see when I might have a dry spell in work or a gap in work and therefore no money to make sure that I was then going out to find companies. I would go and freelance a company for a week and then make sure I'm scheduling in meetings 'cause a lot of projects take a long time to get off the ground. They might do six months, nine months between meeting somebody and actually getting any work so, not leaving it too late until you've got no work and got no money before you start trying to find the next job, basically.


Chris O'Shea:       Of course, it's not changed that instead of selling myself as a service I'm trying to sell my products to parents and I've got my paying customer so to speak or my supplier is Apple, Google and Amazon so they take 30 percent of a sale of an app and you get 70 percent roughly and you get your sales reports but then you get paid about a month or two after the month end of that month of the sales report so you know if you've had a low month in sales that in a month and half's time, that's the money you're going to receive on that specific day and it's very regular. You can put it in your calendar so then I can therefore look at it and say "I need to find a little bit of freelance to help me" and that's what I do now.


Chris O'Shea:       Days here and there of consulting for different companies and going on site. Going up to London, going up to Bristol, which is tricky because on those days it means I then have to find family or friends to help with the children outside of school hours.


Steve Folland:      Yeah.


Steve Folland:      That's good though, not the childcare bit but the, which is always a nightmare, but more the fact that you might have a bad month of sales with an app but you know that in advance of when that money will be coming in, that's quite useful.


Chris O'Shea:       Yeah, but there's not much lead time to that so I can see that for example at the moment, sales are trending downwards because I need to release new products but I then will do freelance work to get money in so that I can then pay freelancers to help me make those apps.


Chris O'Shea:       Whilst I do all the design and the code and the marketing, I hire illustrators and animators and sound people to do those parts of the app so that they're good games but obviously I need money to be able to pay those people so it goes in waves of me doing freelance for other people to get money in to pay other freelancers to help me make more games.


Steve Folland:      How do you find being not a boss, but a leader of those people?


Chris O'Shea:       It's good, I always think that I'm probably not a terrible client to them but I put a lot of love into the products that I make so I don't keep going back requesting loads of changes but I do spend a long time trying to get the detail right in the thing I'm making.


Chris O'Shea:       I make sure to try and say "can you do this bit more for me" but then how much is it going to cost me, so, it might be that they have to do extra work for me on it beyond what I'd asked for but I make sure to compensate for that having been a freelancer and knowing what that's like. They've remotely, working for me so we use Slack or we use Skype or we use DropBox and all of these things to try and keep organized.


Steve Folland:      Yeah. You said about topping up your income by taking on freelance consultancy and other projects. How are you marketing yourself to those people though? Is that just like a historical web of connections that you've built up?


Chris O'Shea:       Yep, exactly. What I need to do realistically is have a new portfolio that says "I do freelance this, this and this now" and be a bit more proactive about that whereas at the moment, because of busyness I've basically gone back through to old connections and people who I've worked for in the past or people that I've met at events or people who have been interested in me previously and have said "I'm available for short-term projects" and then I'll go in and help them on their pitches or brainstorming work in the field that I was in previously or looking at kids game markets and what people are doing.


Steve Folland:      Yeah.


Steve Folland:      Mostly now you work from home I'm presuming in that bit or do you work out of the house?


Chris O'Shea:       I work from home at the moment. I did have a desk at an office in the town, I've used various co-working spaces over the years. I do find it a bit of a mixed bag. Sometimes I like the focus of being on your own and being quiet with your headphones on and other times I really like the social side of being able to chat to people but that's what I do miss about London. You can go to a co-working space that's full of people that might be like-minded and work in similar fields whereas when you move out into the countryside, people in this office could be in completely unrelated fields. You can't really ask them specifics of "what do you think about this design?" Or "what do you think about this?" If they all work in property or insurance or if it's a very unrelated non creative field.


Chris O'Shea:       At the moment I'm at home because then it also takes off the pressure of having to pay for a co-working space so therefore I have to work less on the freelance side but who knows, that might change if I'm getting a bit cooped up here.


Steve Folland:      Yeah.


Steve Folland:      Now, if you could tell your younger self one thing about being freelance, what would that be?


Chris O'Shea:       I would say be as productive as you can and make as much money as you can before you have kids. You will never have more time or more money to yourself than before you have children. As lovely as they are, that's what I would say to someone.


Steve Folland:      Do you know, it's a curious thing though. You will never have more time, you will never have more money but, do you find that perhaps you're more efficient now that you have less time?


Chris O'Shea:       No.


Steve Folland:      Ahhh! Interesting!


Chris O'Shea:       I am still a terrible procrastinator and I've come to learn to use that procrastination time to step back from a problem to think about something else. Whilst I work from home, I might go and do some laundry, household bits and bobs then come back to the problem.


Chris O'Shea:       I'm trying to be more efficient and I understand all the things of eating the frog first thing in the day and doing all these productivity things but yeah, it's, the kids can get, very young children at least, can be quite exhausting so it's all got to get back and it takes a little while to decompress and get into work mode before I can crack on with it.


Steve Folland:      Yeah.


Steve Folland:      That sounds like you're getting to know how best you work. It can almost be frustrating when you have children that you can't do what you're trying to do or what you're wanting to do but maybe you've been through that phase of frustration and come out the other side thinking "no, I just accept that now and I know my way around how best I work."


Chris O'Shea:       Yeah, exactly. I now try and say to myself, like on a Friday for example when I have my daughter who's not a school, instead of thinking to myself "oh, I've got all this project due and I can't get this done" and I'm really frustrating, I try and say "hold on a minute, this is the only time you're going to get with your kids before they go to school, you should enjoy it and stop trying to do everything at once."


Steve Folland:      Chris, thank you so much for talking and sharing your story and all the best being freelance!


Chris O'Shea:       Thank you very much, Steve. Good to talk to you!