Citywealth boss Karen Jones on the ups and downs of being a CEO

Karen Jones

Business: A Battle Worth Fighting?

Let’s start with a scene: the Luddites raging against the machine, plug-pulling protestors, the endless battle of business in a world that rarely plays fair. If you’ve ever been in business, you know this fight intimately. It’s a game of endurance, resilience, and—let’s be honest—a touch of madness. As I celebrate twenty years as a founder, it felt time to deconstruct the mirage that it’s all fun at the top.

The Pool of Hell: Why You Shouldn’t Jump in the Deep End

You wouldn’t leap into a pool if you couldn’t swim, would you? Yet, time and time again, bright-eyed entrepreneurs hurl themselves into business ventures without the lifeline of deep pockets or even a basic understanding of cash flow. I can attest to this being me.  And so, they drown. The survivors? They learn the discipline of business, that the tax man is all powerful, that paperwork can gather dust, but it won’t go away and that preparation along with permanent, risk horizon scanning helps. As well an acute awareness that even those with deep pockets can lose it all. Fearlessness, unreasonable and unfounded positivity and a large dose of stupidity also help.

Business is War: Prepare Accordingly

In the words of Mike Tyson, “Everyone has a plan until they get punched in the face.” It is a famous and perhaps throw away quote now but being in business sometimes feels like being repeatedly punched in the face. And business will punch you. Hard. The key? Get up. Again and again, wipe the blackboard clean and prepare a new set of chalk. You learn to structure your business like a military operation and learn to know when to retreat – you can’t win ’em all, and understanding that “collateral damage” often means staff morale, failed products, or investments that should have stayed ideas. A sound bit of advice a coach once charged me a lot of money for was “have less ideas.” I only wish I could have listened.

The Unseen Battle: Psychological Warfare

Malcolm Gladwell and Thucydides knew it—humans love a good story, especially if it justifies failure. Sales not happening? It must be the product. Database is wrong? No, it’s the software not the lack of care. No one asks, “What if it’s me?” Instead, blame is shuffled like a deck of bad poker cards. The truth? Sometimes the problem isn’t what you think. Instead of assumptions, just say, “I don’t know. Let’s find out.” I read a book called The Tools some time ago and it was eye opening in that humans have a predilection to find an answer to every situation – to fit a round story into the square hole. Once you know this, it means research and investigation into almost everything as well as “ask the client” feedback forms, then, actually doing something about it, not just listening to another set of stories to maintain inertia. How anyone actually makes any money in business can sometimes be one of life’s great mysteries.

Endless Tech and Broken Promises

Ah, the siren call of innovation. Businesses pile up software, systems, and shiny new tools like dragon hoarders, convinced they’ll use them all. They won’t. The mirage of the CRM system, the analytics, the payment software, all golden ground to improve your business. Well, that would be the case if they didn’t have downtime; such complicated ways of working that expensive talent and skills are what you really need, not more software and integrations that rarely work together. The nonsense that some of the software systems present as fact is also one of life’s great mysteries. You realise that they, as you, are indeed, just running a business with all the punches that it entails.

The Loneliness of Leadership

You start with wild dreams, JV partnerships that never materialise, and a belief that funding is the answer. But soon, you’re just another worn out business leader, chasing money, battling taxes, and realising that cash flow is a cruel mistress. Feast and famine cycles drain creativity. Even your accountant, who should be an ally, simply asks, “Are you doing this again next year?” (Translation: Do you still have the stomach for it?). Founders are cool right? Well, get a bunch of them in a wine bar and they all sing from the same song sheet entitled ‘it’s lonely at the top’. There are not many people who understand the balancing act, the plates spinning and how to catch them when they frisbee off. Clue, it usually entails scraped knees.

The Art of Letting Go

Business is personal. Shutting down a product people love? Heartbreaking. But some things don’t work, and sentimentality is a luxury you can’t afford although often afford it you do, for way longer than makes any sense. The same goes for some staff ideas—brilliant on paper, costly in reality. Worse still, when things go wrong, responsibility is rarely claimed, but pay rises and bonuses are still expected. I read an interesting article in Harvard magazine some years ago which nailed this exact problem. The essence was that once an investment in a product hits a tipping point it’s hard to turn back because of the money that will be ‘lost’ and emotional investment, but they recommend, losing it immediately, cut your losses and get out as fast as you can. Take the hit and get over it. Fine to say but relighting the fire in a team who see it as personal failure, takes a lot of pushing the rock up and over the hill again.

A Mirage of Success

Ever wonder why artists are remembered but business people aren’t? Perhaps because success in business is a mirage, constantly shifting, never truly within grasp. The assumption that money flows endlessly—ask Al Pacino or Muhammad Ali—has seen even the greats go broke. And women? They face a different battlefield almost, it could be called modern-day slavery while they are apparently ‘having it all’ – working all hours God sends and then balancing the burden of home with children, animals and elderly relatives, and still with unequal pay. Founders of course can create their own schedule but paying yourself does come with ups and downs as you ride the business pony and sometimes have to tighten your belt. It can also kill relationships, make you exhausted and never seem to have an end point. I always say, ‘it will still be there in the morning’ of working late. And if that work isn’t then, sure enough some other work will soon arrive.

Reputation, Structure, and the Good-Enough Point

So, what’s the key? Structure. Reputation. A ‘good enough’ point, where perfection gives way to practicality. I learned that at London Business School and it is something I live by. Don’t endlessly fiddle with projects, get them out and refine them along the way. When dealing with staff, listen—not just to the loudest voices but to all. And always remember to laugh at yourself, even I think physically laughing can reset a mood. Make friends with fellow business owners in the same boat for morale support and to provide key advice that you can trust implicitly at key moments of frustration or difficulty. Have long lunches with them with plenty of good wine so that the boat rights itself. I also flip a coin if I find myself procrastinating. A decision is a decision, it is off the desk and you can always revisit it, if the decision was crap. Celebrate. It’s easy to get too much tunnel vision, to feel like you are always in the weeds. A walk outside to the local park, a few hours in a bowling alley or on a mini golf course can really change the atmosphere and help you see people in a different light – it lifts the darkness.

The Art of Lunch

I have found women, generally, not to be very good at lunch, always late to arrive, leaving early and eating not very much. They can really learn a lesson from men who have generally thought they’ve had a very good day in business if they have a long lunch with a few glasses of something. They really know the marathon not a sprint phrase. Problems are natural in business but giving them plenty of time is also helpful. What do I mean by that? Buy time, say you will investigate and double any response time so instead of tomorrow say next week and usually the problem will have the heat taken out of it or solve itself in a way that you can accept. I did exec’ management at Said Business School and was always fascinated by their classification of problems in three ways. Small, medium and large. Small – you can solve it. Medium, you need a third party to solve it and large, you probably will never solve it and nor will anyone else. Third parties or suppliers can create their own problems, but I find sticking to them generally a better method than the Goldman Sachs idea that you change all your advisors every 5 years. Strength in family. Although I am not Goldman Sachs, nor never will be, so best not listen to me.

Business: A Battle Worth Fighting?—Final Thoughts

After twenty years in the trenches, one thing is clear: business is not for the faint-hearted. It’s a relentless cycle of wins and losses, highs and lows, breakthroughs and breakdowns. The mirage of success shifts constantly, and the reality is often far grittier than the polished surface suggests.

But if you’re still standing—if you’ve learned to take the punches, adapt to the chaos, and let go of what no longer works—then maybe, just maybe, it’s a battle worth fighting. Not for the money, the title, or the illusion of control, but for the challenge itself. For the sheer, maddening, exhilarating test of endurance. Because at the end of the day, the only real victory in business is the ability to keep going.

It’s a relentless cycle of survival, from forgetting friends and family birthdays to battling bills, fighting fires, and navigating the unbearable weight of responsibility. A key moment not to mention here, of course, was the Covid shut down – throwing a totally unreasonable set of extra problems at one’s business.  But, despite that and all my complaints, if you’re still in the game, you’ve already won the first battle: you’re still standing.

And sometimes, that’s good enough.

Karen Jones, CEO, Founder, Editor, MLRO, Citywealth