When someone starts a business, it’s natural to think about the business plan, marketing strategy, website, sales and finances. We spend countless hours figuring out what we’re going to sell, how we’re going to sell it and how we’re going to stand out from the competition. But what about the brain that makes all of this happen?
After 18 years of running Cucumber Marketing and working with business owners across different industries, I’ve come to appreciate something that doesn’t get nearly enough attention: the way a founder thinks has a tremendous influence on how their business operates and grows.
I’ve seen businesses grow faster, become more profitable and develop stronger relationships with their customers. I’ve also seen businesses with excellent products, great ideas and substantial marketing budgets struggle to move forward. While there are many factors behind business success, I’ve noticed three thinking skills that make a significant difference in how founders approach their marketing, their people and their decisions.
These three skills are cognitive flexibility, tolerance for risk and the ability to act under uncertainty. And they fit naturally into our philosophy at Cucumber Marketing: Think Fresh. Keep It Cool. Grow.

1. Cognitive Flexibility: Think Fresh
Everyone wants their marketing to be different. We want to be authentic, creative and memorable. We want our businesses to stand out and offer something our competitors don’t.
But how can your marketing be different if you're unwilling to think differently?
Cognitive flexibility is the ability to adjust your thinking, consider alternative perspectives and adapt when new information challenges what you already believe. It’s an essential skill for entrepreneurs, particularly when markets, technology and customer expectations are constantly changing.
Imagine a business owner who has been selling the same service in the same way for 15 years. Their customers are changing, their competitors are changing and their marketing results are declining. Yet every time someone suggests a new approach, their response is, “We’ve always done it this way.”
Compare that with a founder who is curious. Someone who asks why customers are behaving differently, welcomes feedback from their team and is willing to question their own assumptions. They don’t abandon everything that has worked in the past, but they’re open to discovering what might work better tomorrow.
That's what it means to Think Fresh.
Creative marketing doesn’t start with a creative agency. It starts with a business owner who is willing to explore new possibilities, understand different perspectives and occasionally admit that their original idea wasn’t the right one.
2. Greater Tolerance for Risk: Keep It Cool
Starting a business is a risk. Hiring your first employee is a risk. Introducing a new service, increasing your prices or investing in an advertising campaign all involve some degree of risk. There are no guarantees in business, and there are certainly no guarantees in marketing.
Yet many business owners approach marketing as though there must be a secret formula that guarantees success.
I remember a prospective client who specifically asked us for the “secret sauce.” They wanted to know exactly what would work before committing to the process. I understand the desire. Nobody wants to waste money, particularly when it’s their own money and their business is on the line. But that expectation can become an obstacle to growth.
Marketing is an ongoing process of developing hypotheses, testing ideas, collecting data and making adjustments. You launch a campaign, observe how your audience responds, learn from the results and decide what to do next. Sometimes your assumptions are correct. Sometimes they aren’t.
When a business owner has a low tolerance for risk, they may hesitate to experiment at all. Or they may launch a campaign, become uncomfortable when it doesn’t produce immediate results and switch to another agency, platform or strategy before there’s enough information to make an informed decision.
They keep searching for the secret sauce instead of developing a process that allows them to learn.
Greater tolerance for risk doesn’t mean making reckless decisions or spending money without a plan. It means understanding the difference between a calculated risk and an unnecessary one. It means setting a reasonable budget, establishing measurable goals and giving your strategy enough time to generate meaningful information.
This is where Keep It Cool becomes important. Can you stay focused when a campaign doesn’t perform as expected? Can you look at the data without immediately interpreting disappointing results as failure? Can you remain open to learning instead of reacting emotionally and changing direction every time something goes wrong?
Your ability to manage risk influences not only your marketing investments but also how consistently you lead your business.
3. Acting Under Uncertainty: Grow
You can have a solid business plan, a carefully developed marketing strategy and access to excellent data, but you will never have all the information you need to make every decision with complete certainty.
That’s simply the nature of entrepreneurship.
Think about how often you have to make decisions without knowing exactly what will happen. Should you hire another employee? Introduce a new service? Expand into a different market? Increase your advertising budget? Sometimes the information is incomplete, the market is shifting and your competitors are doing something unexpected. Yet the business still needs to move forward.
This is where the ability to act under uncertainty becomes essential. It’s not just about tolerating risk. It’s about making thoughtful decisions when you don’t have all the answers.
In marketing, we use data to identify patterns, understand customer behaviour and make informed decisions. We look at what’s working, what’s changing and what might happen next. But data alone doesn’t make decisions. People do.
I’ve seen business owners spend so much time looking for more information that they never actually take action. They want another report, another opinion, another proposal or another month to think about it. Meanwhile, opportunities pass them by.
I’ve also seen the opposite: founders who make quick decisions without examining the information already available to them. Neither approach creates a particularly effective environment for sustainable growth.
The goal is to develop the ability to recognize when you have enough information to make a reasonable decision, take action and remain willing to adjust as you learn more.
That’s how businesses grow. Not through perfect decisions, but through a continuous process of making decisions, observing results, recognizing patterns and improving.
Here’s what I find particularly interesting about these three skills: you don’t necessarily have to be equally strong in all of them.
You might be naturally creative and open to new ideas but struggle to make decisions when the outcome is uncertain. Perhaps you’re comfortable taking risks but find it difficult to change direction once you’ve committed to a particular strategy. Or maybe you’re excellent at analyzing information but hesitate to take action until you feel completely confident.
The good news is that these are skills you can work on developing. Research on entrepreneurial cognition suggests that experience and learning play important roles in how entrepreneurs think and make decisions.
And that’s why I believe business coaching and marketing strategy belong in the same conversation. We can create an excellent marketing plan, establish clear priorities and identify the right opportunities. But we also need to consider the person responsible for making the decisions and following through on that plan.
Your marketing strategy might need to change, but sometimes your thinking needs to change first.
Think Fresh. Keep It Cool. Grow.
These three principles aren’t just about marketing. They’re about how you approach running your business.
- Think Fresh means developing the cognitive flexibility to challenge your assumptions, consider new perspectives and recognize opportunities.
- Keep It Cool means learning to manage risk, regulate your emotional responses and remain focused when things don’t go according to plan.
- Grow means putting those skills into practice. Make decisions, take calculated risks, learn from the results and keep moving forward, even when you don’t have all the answers.
After 18 years in business, I’ve learned that growth requires more than a good product, an effective marketing strategy or a talented team. It also requires a founder who is willing to keep learning and growing alongside their business.
Before you invest in your next marketing campaign, ask yourself: Is my thinking supporting the business I’m trying to build?
At Cucumber Marketing, we work with business owners to connect their business goals, marketing strategy and the decisions that move their businesses forward. Because sometimes the most important part of your marketing strategy isn't your next campaign. It's how you think about it.


