What I wish someone had told me about running a business.

And the mindset shift that changed the whole game.

👋🏼 Hey, I’m Anna! I’m a founder and operator in an ongoing relationship with writing. Welcome to my weekly newsletter where I share business, career and life lessons that I’ve learned over years of trying hard, failing often, dusting myself off and improving until I succeed.

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When I started out in business almost seven years ago, every moment felt like it was life or death.

The stakes were sky high in every pitch, phone call, negotiation and presentation, and I constantly felt like I was teetering on the brink. Despite having two co-founders and a strong support network, I often wondered if any other business owner experienced such heightened levels of emotion and anxiety, or whether it was just me.

Newsflash: they do, and it wasn’t just me.

My intense levels of stress were simply part of the entrepreneurial experience, and dealing with dire problems - like no money in the bank, system failures, frustrated customers, demanding clients and unresponsive suppliers - are all in a regular day’s work.

I wish someone had told me this because once I learned it for myself, my entire approach changed. Instead of acting like everything was life or death I started treating business as a game.

Business is a game you can play to win.

According to the Collins Dictionary, a game is defined as:

An activity or sport usually involving skill, knowledge, or chance, in which you follow fixed rules and try to win against an opponent or to solve a puzzle.

It becomes obvious when dissecting this definition, that business falls squarely within it:

• “An activity or sport”: Building a business is a competitive activity and therefore can be classified as a sport.

• “Involving skill, knowledge or chance”: Succeeding in business requires all three; skills (sales, marketing, logistics etc.), knowledge (product, category, industry etc.) and some luck that things will go your way.

• “You follow fixed rules”: As founders, there are laws you must follow and sadly you can’t go totally rogue (even though you might like to, lol).

• “Try”: There’s no doubt that building a business involves taking action. You can’t win if you don’t try.

• “To win”: Every business has an end game that’s self defined. Winning might be an IPO, or having total freedom over how you spend your time, or having a positive impact on those around you.

• “Against an opponent or to solve a puzzle”: For some, business is a zero sum game with winners and losers. But in my world, business is more like solving a puzzle. I think about it like this: how can I find a problem, and create and sell a solution, in such a way that the numbers add up (ie. it’s profitable)?

So if business can be classified as a game, then how can we play to win?

How I play the game.

Building a business is just like playing a game of basketball (caveat: I don’t watch nor have I ever played basketball, but let’s just run with this metaphor shall we?). Here’s what I’ve learned about how to play:

1. Play with the end in mind.

The objective of a basketball player is to score points and beat the opposing team. The way to win is crystal clear.

Taking inspiration from the Kobe Bryants of the world, when thinking about my business and career I also start with the end in mind. My personal goal is to do work with a deep sense of meaning, earn great money, have ownership over my time and impact as many people as I can. This end game dictates everything I do.

2. Develop the game plan.

An NBA team tailors their match strategy depending on multiple factors: which players are injured, whether it’s a home or away game, the team’s strengths and where the opponent’s weaknesses lie.

In business too, I build a game plan depending on what’s happening in my life. I consider things like how much money is in the bank, my sales pipeline, how excited I feel about a particular project, what gives and drains my energy, how much time I have, and what I’m trying to optimise for. When I plan for the day, week, month and year, all of these things (plus many more) factor in.

And when my plan inevitably goes to shit, just like a ball player, I dodge. I weave. I adapt.

3. Acquire new skills.

A young basketball player starts out by learning how to pass the ball. Once they’ve nailed that, they learn how to shoot hoops. Then they move onto layups, free throws and jump shots. It’s only through dedicated practice that they move from beginner, to intermediate, to advanced.

In business it’s no different. I’m a big believer in learning by doing (rather than learning by learning), and so I often roll up my sleeves, jump off the cliff, figure it out and upskill as I go.

4. Treat losses as wins.

Michael Jordan had 366 losses over his career and he was arguably the greatest champion of all time. Whenever I screw up or fail I think about MJ, and remind myself that losses are inevitable and there’s no point getting worked up about it. Instead, it’s better to view them as necessary obstacles on the road to building something great.

Many things have gone catastrophically, dramatically, explosively wrong over my career. I’ve experienced the cold, harsh, brutal truth of running a business first hand. But I’ve survived. And these days I know more. I know different. I know better.

Unserious business.

When I started viewing business as a game to be played and my progress as something to be won, everything changed.

Even the most mundane situations became exciting. Hard times became opportunities to learn new skills and a chance to move up a level. Instead of thinking my life would implode if I lost an opportunity, I rested easy knowing another would come along. I shifted from trying to solve problems for right now, and worked to solve them for good.

While I certainly still have panic inducing, soul destroying moments, I’m now entirely focused on the levers I can pull and the buttons I can press. I’m more savvy. I enthusiastically dive into the abyss because I realise that it’s not that serious.

It’s just business.

It’s game time.

As one of the greatest basketball players of all time said:

"The only way to get better at basketball is to play basketball." - Shaquille O´Neal

While playing with the end in mind, developing a game plan, acquiring new skills and treating losses as wins are all important, here’s the fundamental truth of it all: to win in business, whatever that means for you, you must get on the court. You have to dive right in. Boldly. Wildly. Enthusiastically.

So flex those muscles. Do your warm ups. Put on your game face.

Get out there and shoot your shot.

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