Work.Life CEOs on: Early business lessons

Startup tips Business advice
Estimated read time: 7 mins
Published: 12/09/2018

We think our CEOs are pretty untouchable. They glide in each morning balancing a reusable coffee cup in one hand and a pedigree pup in the other. They grab a wholemeal bagel before catching up with their perfectly picked team and starting on their 5-point plan for the day. They formulate another mind-bendingly clever idea, all the while moulding another sparkling brick to cement into the wall of their burgeoning empire.

Right? Kinda.

Maybe we’re biased, but it is hard to imagine that every entrepreneur ever had a day one. Each one had a ‘what the hell am I doing’ moment and each one learnt some tough lessons. We posed the question to some of our CEOs: what do you know now that you didn’t know then? They shared some insight on the bits they just didn’t see coming so that maybe you will.



Sad, but true. Almost everyone we spoke to wished they’d realised sooner that although your clients are the most important thing to you, you aren’t necessarily the most important thing to them. Robin fell into this trap when setting up his consultancy business:

‘I used to get really frustrated when people didn’t get back to me, and assumed when they emailed explaining they were busy, that they were fobbing me off. Now I realise they are generally busy when they say they are- the client doesn’t necessarily know how much they need you yet’

Josh, founder of Play With a Legend, found playing the waiting game to be frustrating:

‘Everything you’re doing in the beginning seems really important and it feels like you spend so much time waiting on other people. But it’s really important to be patient and not chase people all the time, it doesn’t make them want to help you.’

The hard fact is; everyone has 101 other things on their plate besides the work they’re doing with you. Laying the groundwork to your business can be a tedious process but it is massively important to its success. Going too fast and annoying people who could help you in the future will only slow you down later.



Naturally, there’s rarely a dull moment in the life of a CEO and there’s certainly nothing as stimulating or intensely demanding as the rollercoaster that is managing real life humans. Josh, CTO and co-founder of app yulife, said he learned early on that your people aren’t robots; they don’t always act in the way you expect and that’s a lovely thing:

‘Everyone is on their own adventure. The realities of an adventure is that there will be ups and downs. Sometimes you will have to pay for their failures and that’s okay. Your job is to find the difference between a crash and a bump, allow your people to hit those bumps and account for it. Let them hit bumps in the road but don’t let them crash into the wall.’

The reality is that people don’t leave companies, they leave management. An employee who doesn’t feel valued, or trusted in their role can’t take the initiative which despite risk, may lead to real progress. The more confidence they have in their role, the more valuable they are to you as an employee. The beauty of having employees is that they can check your blind spots. More humans = more experiences = more possibility.

Work.Life’s co-founder, Elliot, said he quickly realised the importance of having the right people on your side:

Focus everything on people. We’ve been deliberate in putting together an A-team who can go above and beyond their day jobs. Having the right people around you who fit your team values is everything. Don’t compromise on this.’

Not only do you need to work alongside them, you have to trust they will consistently uphold the values of the company you so painstakingly created. Identify your weak spots and continually assess how your team is working so you can fill in any gaps before things fall through the cracks.



Early on, chances are your staff base is small. Where in future there may be a Marketing Manager, HR manager and a Head of Operations, at the beginning there is only you + a myriad of decisions to be made.

Adaptability is incredibly important as a young business and with no one else around to make decisions for you, often very important and difficult decisions fall at your feet. Stephen, founder and managing director of CodeToday, found that decision fatigue quickly became a real problem for him:

I started my own business after working in a University- a place not renowned for being nimble and efficient! As a small business, you need to be able to adapt quickly whether it’s small mundane decisions like ‘should I respond to this email?’ or ‘fix the mistake I spotted yesterday on my webpage?’ first, to more weighty decisions such as ‘should I take on two new members of staff’?’

With the best will in the world, overuse of any muscle leads to fatigue. Similarly, overusing your willpower in making decisions wears away at your strength of will. This can lead to you being unable to make any decisions at all, and you may make the easier choice rather than the right one. Stephen’s solution was to trust his gut:

‘My solution to it has been, perhaps unexpectedly, to make decisions quickly without dwelling on them too much. Once you have all the information you need there is no point in overthinking it, as the quality of that decision will not increase significantly the more you think on it. With time your brain gets better at making those “instinctive” decisions. And, of course, you need to accept that you will be wrong from time to time. That’s just the way it is.’

There’s lots of ways to beat the beast that is decision fatigue. Everything from breaking down your decision into smaller parts, to eating before tackling your problem, can offer relief from indecision. Ultimately, it’s about finding your own technique that allows you to maximise your willpower to its full potential. And, not to toot our own horn, but Jorgen, founder and CEO of Link Humans, said if he could do it all again he’d start out in a coworking space rather than renting his own office:

‘From computers to recruiting to a stable internet connection to employee development to coffee machine maintenance: if you’re in a non-serviced office you have to spend a lot of precious time on things that aren’t making your business any money.’

Coworking spaces take the hassle out of running a business and when the basics are taken care of, you can get on with conquering the world completely uninterrupted.



Although it’s daunting and stressful being in the driver’s seat, the nature of being a founder means it’s a role only you can do. There is no one better suited to sell, market, run or shout about your brand than you, the clever sausage who thought it up. Of course, you’ll need to recruit people to fill these roles for you but there’s a joy to be found in all the responsibility. Darren, who recently founded his LGBTQ focused digital advertising company, Othervox, said that one of the biggest lessons he has learned is that there is no bigger advocate for your business than you:

‘No one can tell your business’s story better than the founder(s). So, while delegating certain tasks is imperative when you have limited time on your hands, try to keep as much of the story-telling aspects under your direct control or prepare to be disappointed.’

People will be able to facilitate your vision but Darren advises having as much creative input as possible at the beginning, to ensure what you put out to the world captures the essence of your business and brand perfectly. Then, it just comes down to showing the rest of your team exactly how it’s done… easy…



Being your own boss takes balls. Knowing what your services are worth and staying true to it is hard to do when you’re alone and people are regularly undervaluing your talent. Claudia is a conference interpreter and translator and often came up against this problem:

‘I would tell my earlier self to not let the simple prospect of paid work deter you from asking for appropriate rates for your services. Not only do you devalue yourself and your services but you also run the risk of destabilising your industry’

When you’re a one-man band, it’s easy to forget the true worth of what you do and you can end up selling yourself short. The value of your worth is a reflection of the quality of what you produce and how satisfied your clients are; it pays (literally) to remember this. In the early days- likely a time when you have few or no clients- it might seem counterproductive to say no to a paid gig but you can find value in the slow periods. Claudia said for her it was important not to be afraid of the quiet times:

They happen, especially at the beginning. Use that time for other things like business development, marketing, honing your skills, taking courses, or even (groan) getting ahead on your tax return.’

Growth at any rate is difficult to attain and is only made more difficult by a failure to charge people correctly for your hard work. Look at having time on your hands as an opportunity to grow your skills and networks. You can go looking for the big jobs that are going to pay you right and do the admin that will make life easier for yourself when the busy times come, of which they will.



What was it Springsteen said? ‘Those were the best days of my life’… It’s a tough nut to crack but try to enjoy the bumps in the road. Be it the small victories, the missed opportunities, the early finishes or the late ones. Our co-founder, Elliot, said if he had his time again, he wouldn’t take things so seriously:

‘Events or risks at the time can seem insurmountable but when you look back on them, they all merge into small bumps in the bigger picture.’

It’s not always going to go smoothly- otherwise everyone would be doing it- but, as with most things in life, taking stock and acknowledging how far you’ve come once in a while is important. Hey, in a few years you might even miss your old problems! As Elliot put it:

‘Enjoy the ride as much as you can, it only gets harder!’

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