Do You Really Want to Start a Creative Business?


March 10, 2021


James Greenfield


Many of us dream of starting a company and being our own boss. Oh, the freedom! The control! Hmmm, maybe, but not quite. Before going full steam ahead, it's wise to do a little introspective digging. James Greenfield, Creative Director and Co-founder of branding studio Koto, poses five self-reflective questions to help you decide whether you're cut out to start a creative business. Be prepared to take some notes as you go!

A couple of times a month someone will reach out to me asking my advice about starting a creative business. Mainly from people I don't know, these requests initially feel almost impossible to answer. Not because I don't want to help, but because the topic feels too big for a simple reply to do it justice. Summing up all the emotions and learnings from running Koto, the branding studio that I co-founded,  leaves me not knowing where I would start, or which piece of the ever-changing puzzle to include. I feel the need to really think about this topic, to not be glib, but considered, especially when imagining the breadth of people out there. But I am keen to pass on the knowledge I have, in the hope that it's in some way useful and can be part of a conversation about how a great creative business can be genuinely life-changing. So the following are some thoughts on my journey, as well as plenty of learnings from others, that should suit a breadth of business types in the creative sector. Before I continue and for the purposes of clarity, I define a creative business as more than one person for this piece. Oh and maybe grab a pen and write down any thoughts you have as you read this.

Where to start

The desire to change your situation and your circumstances is the usual starting point for many considering a business of their own. Setting up shop can be the most rewarding and amazing feeling, but it can also be the most challenging life experience. So, if the idea is rolling around your head, it's best to give those thoughts some inspection. I've broken down step one into a framework of five questions I think any prospective business owner should answer before embarking on the journey.

1. What's your motivation?

To borrow author Simon Sinek's famous approach, I'd suggest starting with why. I know a few designers who've started their own business so they can design more, and others looking for more freedom in their day-to-day existence. Everyone is different when it comes to motivation: for some people, part of it is wanting to be left alone to work; for others it is about being known, to stand out. Some dream of it from an early age, others it catches them by surprise one day. All of these are good surface reasons, but what else lies deeper beyond this? Do you have something to prove? Either to yourself or others? What's your end goal? 

I had wanted to work for myself since being a teenager, but I eventually started my own business because we had a hypothesis about how the business of branding could evolve, which in turn we believed would lead to better work and hopefully a happier team. Also, after 13 years of working for others, I was ready to break from working within an existing framework that limited my ability to act in the way that best served the outcome, the team and me. It’s the best decision I ever made because the hypothesis has proved true and the speed and quality of work is better, in most cases, than it was in my previous leadership roles. 

For all my happiness and love of what I do, I don't design more and I definitely don't have more freedom.

Starting a studio is a great eye-opener to all the things that just happen day in, day out when you're working for someone else.

Suddenly, or so it seems, I am partly responsible for 50 people and that comes with a lot of day-to-day challenge and change.

When I look back I thought heavily before starting a studio, almost to the point of procrastination, spending three years on and off toying with it, but maybe this was me just being sure? Don't beat yourself up for spending a lot of time thinking about this stuff, it's time very well spent. One good framework to use here is The Five Whys, a problem-solving technique originally developed by Sakichi Toyoda of the Toyota Motor Corporation. Designed as a way to explore cause-and-effect relationships, in this case it can unearth deeper thinking. By asking yourself why five times, you will start to dig beyond the surface.

2. Where are you in life?

As I’ve mentioned, starting and maintaining a creative business requires a lot of energy. Life is rarely perfect and there will always be reasons to not start something new, but it's a good idea to be sure that you have an idea of the impact this might make on your life. You will need to expend more energy than the average job to be really successful. There are many hats a company founder has to wear and your to-do list will almost always be growing, especially at the start, which is when many businesses fail. Being distracted will make this list even harder to attack as a challenge. Having a family, existing work and other commitments can stop a lot of new ventures dead in their tracks, so you need to be honest with those around you about your plans and, more importantly, honest with yourself. Is this a business that's going to be designed to suit your lifestyle, with flexible working? Or will it be a business that's about the collective success of the team and will come with some sacrifices to your life? These are good things to note and talk about to anyone you plan to set up with.

Outside of the hours required, another important consideration is: how much experience do you have? Have you just graduated from college or have you been working for others gaining valuable insights? A lot of great businesses are started by very young people because these people often have the energy to go out there and really stick at, combined with lower costs of living and fewer responsibilities. But these businesses can often have a much higher rate of mistakes and the lack of management experience can make working with others tricky. I think some experience is incredibly valuable because even if you work for people you don't rate,  you will have something to compare it to. This is especially useful if you plan to employ other people: you’ll have an understanding of people’s desires and motivations for work. This experience might also allow you to accelerate through some of the early days of starting and growing a business.

A forensic look at where you are in life and whether everything is working in your favour can be really beneficial. That said, there is no perfect moment to start something. 

3. What are your limitations?

The complete person does not exist. All of us have strengths and weaknesses, things we excel at and things we suck at. Some of us are great at starting things, full of energy, but bad at finishing. Many of us are great at fooling ourselves that we can do anything if we put our minds to it. But this is a bad path to take and can lead to frustrating others you manage. Instead, have a look in the mirror – do some self analysis in order to offset future issues. Are you a big picture person or more about the detail?

My number one suggestion here is to find a partner – a problem shared can be so helpful and make the ride smoother.

Finding someone with complimentary skills can be one of the biggest strengths any business can have. If you don't have that person then do a SWOT analysis on yourself. Draw out a list of each bucket and see what you come up with. If you're feeling brave, ask others for their input, but only ask objective people whose opinion you trust. Consider finding a mentor, too, someone who you’ve had a good working relationship with in the past, be they more senior or not. Set some time aside with this mentor and let them build up a fair picture of you. Ask them to write up some thoughts about you, your strengths and weaknesses, attributes they think you bring to a new venture and areas for development, an objective report of sorts.

Putting your ego to one side is also really useful at this juncture. In Ryan Holiday's Ego is the Enemy he argues that our greatest opponents are often ourselves. The book is a thorough investigation into reining in our pride and becoming better at delegation and decision-making. Reading about great leaders, companies and innovations can really help shape the kind of person you are.

For me, the work of the ancient Stoics really helps me frame the problems I see day in, day out and helps me deal with them.

A traditional weakness in creative businesses is money and its management. Find someone else to do the money part of the job from the start because unless you trained on the side as an accountant, this will never be your priority and it's best to delegate this. Reach into your network and find someone that people you know trust. All businesses have a cash squeeze at some point or another and you want to be prepared. There is a famous adage that any agency is only ever three phone calls away from going bust. Try and learn from the mistakes of others here, hire experts early in your weak spots and soften the inevitable squeezes all new businesses go through.

4. What type of work do you want to do?

Think about a perfect day in your new company. What are you doing? How are you spending your time? This isn't wild daydreaming but solid forecasting about making this new world a reality. If you can share that vision then others will buy into it, but first you need to know what this destination looks like. But you also need to acknowledge it won't be like that day every day. In fact, it probably won’t be the majority of the time. Creativity can be hard work, you'll have to get up every day and want to do it. There will be emails, project management, repetitive tasks that keep things moving. Muhammed Ali summed success up well when he said "The fight is won or lost far away from witnesses – behind the lines, in the gym, and out there on the road, long before I dance under those lights."

All those emails and drudge tasks are the things that make your world go round. You can’t ignore them.

Being realistic about what running a company entails will stop you from being dissatisfied and keep your energy levels up. Will you be remote or in a studio/office? What hours will you keep? When do you work best? I have worked for people that came and went as their lifestyle dictated and as much as it worked for them, it didn't work for the team and caused issues. Humans like routine and to understand what we are collectively aiming for. Structure, clear parameters around work and good communication is key. At Koto we work 9:30am- 6pm five days a week as that’s the time our work needs. We put extra hours in, but that’s to the discretion of the team, as and when we think the work needs it. Creativity can sometimes require that extra push. I lead by example and am in the studio for those hours, unless I am at a meeting or travelling for work.

5. How do you feel about people?

There's no getting away from it, managing people is tough, they will challenge and surprise you in equal measures. For any new business you start the work will always be the priority – since what the company produces will define it – but its culture is a close second. My experience is that people will always want more, however much you give them. More money, however well you pay; more projects, however good the existing ones are; more of your time, however much you give. You can't underestimate the effort this part of running a company takes. If you plan to scale the team to more than a handful of people then it is never too early to be thinking about your approach and team structure. Going from working for yourself to hiring and managing a team is a big leap. It requires a whole change in mindset and an honest conversation about whether you really want to do that. Anecdotally, the founders I know often find the managing of people the most tiring part of the job.

Start by investigating how good you are at managing people. If you have no experience of it then this is a vital area to learn about. There are a lot of great resources out there, to suit all types of management, with some great books and plenty of podcasts and other resources. Rather than recommending one, it's best to find one that suits you.

Remember, you don't have to be a charismatic cliché to be a good leader. Look to the world of sports, military, tech, music and business and you will come across something that clicks.

I believe that people management can be learnt, as long as you accept it needs to be and won't necessarily just come naturally, however talented you are in your business area. 

The next thing to work on are values. Values-aligned businesses will naturally be happier, more harmonious places in their day-to-day existence. I am not talking about hiring a bland single style team. Diversity and inclusion is vital in a modern workplace and that should include all areas like neurodiversity. Work on what your values are, write them down and make sure they really resonate, then they are real and something to live by. Use them to gauge suitability of candidates, to explain your vision for the culture and to guide appraisals. This will set the tone of the business. Koto has three brand values; Uncompromising Positivity, Just Cadance and Relentless Hustle. All intentionally different, they work individually or as a set and are relevant to all people within the business.

Beyond values, think about how you could build bonds between team members. Shopify uses a system called 'The Trust Battery'. The principle is the battery is charged to 50 percent when you meet someone, each positive interaction charges it more, each negative drains it. There's a good deep dive on it here. It's never too early to think through this stuff. 

For me personally, I find all the challenges in managing people are worth it as I take real pleasure in others' creativity. 

Ready to go

So, with a document on your laptop or some Post-it notes in front of you and some questions answered, you'll have probably more questions and a lot to think about. This method isn't perfect and won't be for everyone, but luckily the internet is full of amazing resources, you just have to go out there and find them. 

Finally, this quote from author and ex United States Navy SEAL commander Jocko Willink sums up running a creative business very well:

“Don’t expect to be motivated every day to get out there and make things happen. You won’t be. Don’t count on motivation. Count on Discipline.” 

Coming up: ‘How do you start a creative business?’

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About the author

James is the Creative Director and Co-Founder of Koto. Leading the strategic and design efforts across three studios, James has led the team working with Airbnb, Coca-Cola and PayPal. James has over 20 years of experience working at some of London’s leading studios, for the world’s biggest brands. He delivers talks globally and writes regularly for Creative Review about all things branding.


March 10, 2021


James Greenfield


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How Do You Grow a Creative Business?

In his third instalment, Koto's creative director and co-founder James Greenfield shares some sage advice on how to grow a creative business with grace.


How to Start a Creative Business: Setting Up for Success

From finding a co-founder to building your reputation and voice, James Greenfield shares some solid advice on how to set up a creative business - the right way.


Do You Really Want to Start a Creative Business?

Are you dreaming of starting up? Ask yourself these five vital questions every budding entrepreneur should consider before embarking on the journey.

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