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From Freelancer to Business Owner: How do you get there?

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We’ve advised and helped many candidates make the switch from a permanent position to freelance when the right thing has come along and vice versa. We’ve previously shared some first hand advice for both, the switch from freelance to permanent and also from permanent to freelance.

However, there may be another option and it’s a big one. The boundary between being an incredible contractor/ freelancer to suddenly realising that you’re on the cusp of becoming a business, needing to employ people to help deliver the workload. For some an exciting prospect, for others a daunting turning point with the responsibility that comes from owning and managing a business.

We caught up with Simon Winter aka Winter Design, who has done exactly that. We asked him about his career journey so far and why he decided to start a business. He also kindly shared some pieces of wisdom and a practical set of tools that could help you along your own journey. Here our chat:

ADLIB: What has been your career journey so far?

Simon Winter: I graduated in graphic design from the University of Brighton 2008, and was lucky enough to get picked up by the Guardian at my degree show – my first job fresh out of university was an exciting infographics project, where I had to take statistics from the US Elections and make them visual.

From there I had a thirst to experience creative agency life, so I decided to go freelance. Looking back, this was quite a naive decision as I hadn’t planned it at all, but being a people person I made some good connections and was fortunate enough to gain a few regular freelance slots in London. I did a lot of work for KentLyons, for example, working for a range of clients including BBC, Penguin Books, Taschen, Film London, the Design Museum, Foster & Partners, LV, etc… I then deviated from graphic design…

I love innovation and iconic design, and I also love bikes. I was given the opportunity to help a McLaren F1 engineer with a startup project called Gocycle – the world’s lightest electric bike. I helped grow the Gocycle brand and business over an 18 month period – an experience which gave me a huge desire to start my own business.

I decided I wanted to build my own business; to take what I’d learned and combine it with my love of graphic design. I had loads of contacts, I knew how to communicate, and had lots of drive to make it work.

I set about creating a design service offering for clients in the South West that was aligned with that of the top London agencies, a really refined visual communication service. Beautiful graphic design, inspired by the likes of old Swiss designers Josef Muller Brockmann and Armin Hofmann. Initially I created brand identities, worked on existing brands and designed for print, but in 2012 a particularly intriguing web developer followed me on Twitter. I’d already had lots of clients asking if I could provide websites, so I decided to explore the idea of creating websites.

From there things just grew organically. I’ve been able to adopt a ‘grow slow, grow strong’ philosophy (inspired by the clothing brand howies actually). Today Winter Design, whilst still a small operation, is running brilliantly. We design, build, host and maintain bespoke websites for clients, and we also offer the refined branding services we set out to offer from day one. The business consists of myself and a full time web developer, then a pool of various freelancers: designers, illustrators, developers, writers, social media people, and marketeers.

ADLIB: Why did you decide to start your own business rather than continuing as a freelancer?

SW: I think there are a number of reasons:

  1. Building and maintaining client relationships is massively rewarding, but you don’t really get to do this as a freelancer, it’s just ‘head down and get the job done’.
  2. As a designer I like to do things my way because I believe it’s the right way, and therefore best for the client. If I’ve listened to the client’s requirements it’s my responsibility to ensure the brief is answered properly. Working under another designer just doesn’t appeal to me as there’s less involved when you’re just being told what to do. You kind of feel a bit disengaged from the client and thus their requirements.
  3. When people ask for your services directly, it’s a huge compliment. This is much more fulfilling than doing it for somebody else.
  4. Running a business is an exciting challenge – you’re not just grafting away on a mac; you get variety every day! You get to go out and meet people, you have to set targets and manage projects, you have broad responsibilities, financial commitments, and a reputation to look after.

ADLIB: What three pieces of advice would you give those wanting to also turn business owner, starting out as freelancer?

SW: I actually have five here…

  1. The best place to start a new business is from within a secure job. If you can’t put in the hours to do that, then you can’t put in the hours to get your start up off the ground. Startups require a lot of time and energy; more than your current 9–5! So don’t jump ship and then start planning; you plan first, then move. And commit to it.
  2. Define who your clients will be. Look at the market you want to be in. Consider the competition. Is your offering unique enough? Define your competitive advantage.
  3. Every day is a networking opportunity. Talk to different people about your business every day. Word of mouth will always be a reliable form of marketing.
  4. Respect your clients. Listen to their requirements, quote properly, and don’t de-value your proposition by giving away freebies; being overly generous won’t help your clients, it’ll just delay their project.
  5. Don’t employ the wrong people. Hiring staff is the biggest thing you’ll do, so they have to be the right people. I favour using freelancers over employing full time staff as it gives me flexibility.

ADLIB: Practically, during your journey and especially the early stages of founding your business, are there any tools, apps or resources you could share with those wanting to take a similar path?


  1. I use Xero accounting software which makes life so much easier. Don’t do DIY accounting. Not worth the faff.
  2. The guys at Realmac software made an app called Clear, for To Do lists. It’s a brilliant little app. Simple, but useful.
  3. The IPO website is useful for Trademark information. Don’t start an idea if someone else is already using it!
  4. An Adobe Creative Cloud subscription is a must.
  5. I use an application called Timing (for mac) which tracks how much time you spend working. It tells you which applications you were using but also which files you were working on. Being able to measure how you spend your time helps you become more efficient.

Thank you for sharing!

This piece previously appeared on the ADLIB Blog.


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