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Thinking of starting your own business? Be prepared...

(it's not for everyone)

I left the cubs when I was 7 years old - having been mercilessly mocked by the Akela’s son, Ian, for being the only person in the 2nd Basford Pack without a solitary achievement badge (I’ve been perpetually under achieving ever since). But I’ve thought about their motto a lot over the last two years.


In late 2018 my (now) business partner at Harbour, Mick Mahoney, pulled me to one side and uttered the now fateful words “You can stay in a cushy, safe, well paid network job for the rest of your life Kev. Or you can chuck in all that safety and salary & come and join me”. Actually, thinking back on those words now, I’m not sure if Mick was trying to persuade or dissuade me from joining a fledging start up called Harbour with him & Paul Hammersley.

I’ve noticed that there has been a flurry of new start-ups over the last six months. I don’t know whether the pandemic has shifted many people from the slumber of salary-land (voluntarily or not), but 2020 seems to have been a catalyst for many to decide to start their own thing. Starting up or running your own business isn’t for everyone. It’s like writing a book - a lot of people say they’re going to do it and very few do, and even less succeed at it. I was very grateful to many friends for good advice on ‘starting up’ whilst I was twiddling my thumbs on garden leave from my last job (Special thanks to Andy Nairn, Jen Smith & Graeme Douglas, amongst other generous souls).

So, I thought, just over two years on from the launch of Harbour, it would be a useful thing to pass on some advice to anyone who is even thinking of starting their own business.

Two words. Be prepared.


Be prepared to be scared.

It is genuine scary to cut the cord to corporate life. Every four weeks for your whole career a magic fairy has come along and filled up your bank account with money. All your spending behaviour has been predicated on that repetition, that surety. And it stops. Almost immediately. Now it’s down to you. Every penny. Scared yet? Want to get off? No? OK, let’s carry on.

Be prepared to be tired.

It’s not for everyone. It’s very (very) tiring. Long hours, and if you’re the kind of person who is driven to succeed then you’ll be the worst boss you ever had. Want to go home early on a Friday to stick it to the man? Oh, you are the man. Or woman It’s down to you & a small group of partners. It’s the hardest I’ve ever worked in my life. After all, every hour you’re not working is an hour when your business isn’t being built. It’s quite tempting to fill every single one. Bank holidays? Ha!

Be prepared to be surprised.

It’s like that old story about Mike Tyson – “everyone has got a plan until they get punched in the face”. Have a plan, have a strategy, and be prepared to change it. I think we’ve pivoted 3-4 times on the plan in the last two years at Harbour – and that was before the arrival of a global viral pandemic just around our one-year anniversary! Nothing you expect to happen will. Brilliant things will show up. Nailed-on certainties will fall through. That’s why you need to….

Be prepared to be flexible.

Know what your objective is. Know what your ambition is. Most importantly know what your values are & what the core purpose of your business is. I’m not talking about silly mission statements or trying to pretend that (like a lot of start-up agencies) your product is so unique when you (and everyone else in the industry) knows that it isn’t. I’m talking about knowing what values and value system you share with your founding partners. But you have to be prepared for what comes around the corner. Go with the flow a bit. It’s as joyful as it is scary. Now it helps that Harbour is pretty unique (a brilliant idea by Paul Hammersley in the first place), but we still had to be prepared to change things about how we worked based on ‘first contact with the enemy’.

Be prepared to go all in.

It never stops. I once heard Charlotte Semler, the founder of Votary, say that the reason running your own business was so tiring was because “everything that is going right is not your priority today”. That’s it. So much can be going right but you need to focus on fixing what isn’t, and ‘the next’. You have to be all in. According to the latest data 60% of new businesses fail in the first three years. If you want to be in the 40% then you’d better be prepared to be committed. Remember bacon & eggs. The chicken was involved, the pig was committed.

Be prepared for the emotional roller coaster.

Every cliché you’ve heard about start up life is true. The highs are higher and the lows are lower. I genuinely thought that I knew the highs of winning business until I won business at a business I owned. I had no idea – the rush is better than anything I’d enjoyed before, in work at least! I also thought I’d experienced disappointment until it was someone saying ‘no’ to something I had a genuine, literal stake in. Don’t let anyone tell you it isn’t personal. When it is someone saying no to something that might mean YOU having to say no to your children about something then it can’t feel like anything else. In the film Erin Brockovich, Julia Robert’s character says when experiencing an office knock-back: “That is my work, my sweat, my TIME AWAY FROM MY KIDS! If that’s not personal then I don’t know what is”.  Now I know people don’t mean to personally harm you or your family, it just doesn’t feel that way when you’re in the middle of it.

Be prepared to be delighted by people.

People are great. They really are; most of them, anyway. I have experienced some amazing generosity from people in the last two years, inside and outside the company. And I’ve been humbled by the commitment & energy people have put into Harbour - especially since March 23rd 2020. I’ve been delighted by the amazing clients who’ve been courageous enough to take a chance on a genuinely new model of doing things. I’d especially call out Miruna Constantinescu at McCarthy Stone, Barney Harrison at The Gym and Joanne Savage at Fitbit EMEA. People are great when they’re great - and all businesses are just collections of the right people. The right personalities build business success. Choose wisely. Both colleagues and clients. The good bit about owning your own place is you get to say NO to people.

Be prepared to be disappointed by people.

This one is hard, and I don’t want to be negative about anyone. When or if you set up your own place, you’ll get a lot of people who make you a lot of promises. My advice is not to rely on them. Lots of people will tell you to make them your first call when you set up, or they’ll promise you all sorts of ‘jam tomorrow’ on briefs that will never appear. People will genuinely want to help you. All these promises will come from a place of genuine goodwill. But in my experience? They’ll all be Jackanory. None of the things I thought would be part of our present & future on day 1 ever actually came off. Back to being surprised and flexible!

Be prepared to be brave.

'Can a man still be brave if he's afraid? ' 'That is the only time a man can be brave,' – I’ve thought a lot about that exchange from Game of Thrones over the last two years! There will be times when you’ll doubt. There’ll be times when the four weekly salaryman world will seem very attractive. There’ll be times when you think you’ve gone mad. Stay on target. Remember why you did it in the first place. This really helps if you’re doing this with partners you love and trust. It’s a big risk. You shouldn’t ever take a risk with someone you don’t trust or love. Choose your companions wisely. The other test of your bravery (and self-confidence) is it’s now all down to you. You can’t blame your failing, failures or those of your company on “New York” or “the leadership team” or “the network” – it’s you and only you. No big boss man or lady to ask, or to shift the blame onto. It takes quite a lot of bottle to go it alone. I’m not sure I really appreciated or anticipated that bit.

Be prepared to be happy.

The last two years have been the longest, hardest, funniest, most rewarding and happiest of my twenty -five -year career. Genuinely - even leaving aside the arrival of the biggest economic & public health tsunami for one hundred years - it’s still been brilliant and long may it continue. If you’re prepared for the nine things above on this list you’ll succeed (with that little bit of luck that we all need, just ask Andy N). I wouldn’t want to be doing anything else.

I’ll finish where I started - it’s really not for everyone. Think long and very hard (and think even more) before you decide to the leave the warm bath of monthly salary-fairy land & set sail in a boat that you’ll have to build yourself to an unknown destination across uncharted seas. But if you do decide to do it, I can promise you it’ll never be boring. I can promise you that the joy of watching something you’ve invested time in grow & succeed is more rewarding than all the discretionary bonuses or pay rises you’ve ever had (or might get in the future) from a corporate boss put together.

I wish nothing but success to every brave soul who decides to set up something new. Unless I’m competing with them of course. When I hope they’ve failed to prepare.

Dib dib dib.

Kevin Chesters
Kevin Chesters


This article was first published in The Drum in February 2021 and has been replicated here with Kev's permission.

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