Freelance Web Developer Q&A: Ross Wintle, Oikos


(This is the third in a series of interviews with freelancers, telling us their stories on how they went freelance. The aim is to help others who are thinking of becoming freelance learn more about what it takes, as well as get advice and inspiration so they can get the confidence and understanding to find out if freelancing is right for them. If you want to take part in the series, simply head here to tell us your freelance story.)

Name: Ross Wintle
Freelance area: Web development and technology consultancy, for charities (large and small), communities, and small, local businesses
Freelancing since: 3 years
Twitter: @magicroundabout

What made you decide to go freelance?

Wanting to: develop myself personally; learn new things; stretch myself technically; work with smaller clients; give something back to the world; be more myself!

What steps did you put in place before you went freelance?

I had a reasonable financial buffer, which helped, because I’m naturally a cautious person. I’d done some work up-front in my spare time on a voluntary basis, or for smaller fees, just to get some projects on my portfolio. I set up a website and did some initial branding. I read lots of blogs, learned what I needed to know, and followed loads of people on Twitter. I can’t stress how valuable contacts and help from other people have been. I’d thought a lot about what I wanted to do and why. What the principles and values of the business would be. That’s been crucial to the ongoing execution of my work. I sought advice from friends, family, other business people. I prayed like crazy!

How did it feel before you went freelance?

In the question ‘what made you decide to go freelance’ I tried to be as positive as possible. But here’s the negative stuff that pushed me to go freelance. I was working in IT for a big corporate and was totally fed up with the big corporate world. Lack of personal development; inability to change and embrace new tools and technologies; money being wasted; constant re-organisation; little job security. Outside of my immediate team and my boss (who was brilliant) I felt like I was a little-valued number on a balance sheet. And, ultimately, the only thing that mattered was shareholders getting value: not respect for people, not doing a good job, not long-term investment. Just making the balance sheet look good and making a quick buck. Not all corporates are like that. But the one I was in was. I wanted out, and was looking for a way.

How does it feel now you are freelance?

It’s amazing. I have amazing clients. I get to do amazing work. I love what I do. I have freedom and flexibility. But, as was said to Spiderman, with great power comes great responsibility. I don’t have a boss to escalate issues to. The success of what I do is almost entirely down to me. That creates pressure, and I set my own expectations high. About two weeks after leaving my employment, my wife discovered she was pregnant, so there’s also the responsibility of providing for my new family, and it’s pretty scary at times.

What are the positives of freelance life?

For me I love running a business that is generous. I love helping other people achieve their goals. I love the fact that my work benefits me, my clients, and wider society too. I love that I can constantly learn, try new things, be agile in what I do without the need to take hundreds of other people in the same direction. And I love that I can be with my family. I work in the room next to my son’s nursery. I can pop downstairs to see him when I make coffee. I can take every Wednesday morning off to spend time with him while his mum works. It’s great!

What are the negatives of freelance life?

Cash flow. Cash flow. Cash flow. And the fact that just running a business takes so much time: pitching for work, networking, accounts, communication with clients, and generally staying on top of everything. Don’t think you can do 7 or 8 hours paid work every day. It won’t happen. Oh and taking holidays is really hard. It’s a double hit of both spending cash and not earning cash.

Any advice for others looking to go freelance?

I see lots of people saying ‘go on…do it’, but I’m slightly more risk-averse. In fact, it’s a wonder I’m freelance at all. I say put work in up front and make sure this is the right decision. Build contacts and a portfolio in your spare time. Make sure people want your work and like your work and you can get recommended for more. Build a financial buffer. Have an exit plan if it doesn’t work out. Be prepared to fail, learn, change. Find a mentor who can advise you on running a small business. And pray like crazy!

Thanks for taking part, Ross, and for sharing your tips and advice. Make sure to check out his website at or follow him on Twitter at @magicroundabout. If you want to take part in the series, simply head here to tell us your freelance story.

More from the How I Went Freelance series:

  • Ruth Walters, Let Her Eat Clean
  • Matt Collins, Charity Chap
  • Ross Wintle, Oikos
  • Sam Phillips, Freelance Digital Strategist
  • Damien Clarkson, Social Chic
  • Nick Nicolaou, Freelance Web Designer
  • Art Anthony, Freelance Copywriter
  • Sean Hargrave, Freelance Journalist

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