I spent many scrappy years as a freelancer before becoming an entrepreneur. During that time, I was focused on short-term wins: get that first paying client, build a portfolio of interesting work, pay rent, repeat. This journey from zero to one—from an empty portfolio to a growing career—took years of hard work.
During my freelancer era this attitude of saying yes, then figuring things out was incredibly effective. But as I shifted into being a business owner, my short-term way of thinking became a problem.
The infinite game of business
During a recent road trip, I listened to Simon Sinek's book “The Infinite Game,” which outlines a key problem that erodes businesses, leadership and personal fulfillment. My company was coming out of our hardest year to date, so I was listening very closely to what Sinek had to say.
He argues that people adopt a finite mindset when they should be using an infinite mindset. In business, this finite mindset is commonplace. Entrepreneurs operate with a finite mindset focused on achieving specific wins or goals, like sales targets or market share.
In the book, Sinek explains when entrepreneurs approach their work with a short-term, win-lose perspective focused on immediate gains, rather than long-term sustainable growth, they lose.
Instead, Sinek advocates for an infinite mindset in business. This involves leading with a vision for a future that extends beyond an entrepreneur’s immediate goals and sharpens their focus on long-term growth.
From shortsighted to rebuilding my business
In early 2024, morale at my company was at an all-time low, due to the shaky job security and financial compromises many of us faced in the previous year. I hadn’t behaved like the money-hungry CEOs described in the book, but I realized I was caught in shortsighted, finite thinking.
I had unconsciously implemented my scrappy, freelancer mentality as our business strategy, and that shortsightedness nearly led us into bankruptcy.
So how can entrepreneurs shift from the constraints of a finite game to the many possibilities of an infinite mindset?
Sinek covers five essential practices for adopting an infinite mindset, and I’ll walk you through each one, showing how we used these principles to shift our business goals.
1. Advance a just cause, together
Commit to a cause bigger than yourself, and inspire people to work together towards a future they might not see or understand yet.
Our company creates content for other organizations. Many of us working here grew up using an internet that felt very different from the one we use today. We came together and decided that the reason we come into work every day is to make the internet a more useful place for everyone.
We only write articles people want to read—something we felt had been lost in the previous decade of longtail keywords and data-driven SEO strategies.
Our just cause is to create a useful online experience, not only because that’s what the world needs, but because that’s what talented writers enjoy writing.Casey Milone
Finding a just cause to work towards is a deeply personal thing and has to emerge from within you and your business. To find one, reflect on how your business can make the world into a place you’d like to live.
This can be as simple as offering healthy food options or as complex as developing a safe way to use AI in your industry. It can be done by a single person running their own company, or it can be the result of a group coming together to craft a vision.
A just cause should be something that extends beyond any individual, even the company’s founder. The important thing is that it’s a cause that can live on through the life of the business.
2. Build trust
Cultivate an environment where team members feel safe to express themselves honestly, admit mistakes and depend on each other.
Working with people you care about and who collectively build a structure of psychological safety is truly joyful. Our team was remote long before the pandemic, and we struggled to develop the rapport we craved.
We studied the real financial impact of low-trust relationships between our team members. We tracked the time spent by writer/editor duos who had developed a friendly relationship versus those who hadn’t. The math was clear.
It cost our company money not to prioritize trust and rapport building.
All organizations want high-performance/high-trust people on their team, but almost no organization measures trustworthiness–we only have measurements for performance.
Take a look at your own company. If you have a team of people, be honest with yourself about the real cost of poor working relationships. Are you losing your best team members due to one high-performing (but toxic) coworker?
High turnover can result in significant expenses from having to spend time hiring and training people. This was one area of business that took some vulnerability to acknowledge and evaluate.
In the end, the benefit of a high performing person who is hard to work with might not be as cut and dry, if you look at the situation through a wider lens.
3. Study worthy rivals
Learn from competitors who challenge you to improve.
There are plenty of other companies offering services similar to our own, but we’ve struggled to find one with our exact service offering. So we study potential clients who turn us down. We examine how they solve for our value proposition and learn from that to refine our services.
This perspective forces us to shift our focus from competing with our rivals to learning from what works for our potential clients—aligning with Sinek’s idea that in the infinite game, the goal isn't to win but to keep playing and improving.
4. Embrace existential flexibility
Be willing to make significant changes if they will advance your just cause, even if they involve risk.
Existential flexibility (as defined by Sinek) refers to an organization’s or individual’s ability to make profound changes in strategy or operations, in response to shifting external conditions or insights.
AI is coming for the marketing industry. The question of what we are going to be selling in 2 years continues to drive conversations at our company, and we continue to do research experiments to understand the usefulness of generative AI tools, like ChatGPT, in creating long-form thought leadership content.
By this definition of existential flexibility, any implementation of AI would need to advance our just cause and from everything we’re seeing today, AI doesn’t yet make the internet a better place for readers or writers.
Because of this, we have not adopted it in our blog writing. However, just because we’re not being forced to pivot today, doesn’t mean we’re ignoring AI altogether. We already use AI in many areas of our company, for example, we use it to write blog meta descriptions and summarize meeting transcripts.
For me, existential flexibility was the hardest infinite mindset shift to make, but taking Sinek’s definition to heart, the key is to remain in touch with your just cause.
5. Demonstrate the courage to lead, especially through crisis
Embrace these principles even when they go against traditional or short-term success metrics.
2023 was the most challenging period our company has faced since its founding. We lost our biggest client and spent 12 months in financial freefall. We made hard decisions, including converting team members on stable salaries into hourly contract roles.
That instability challenged us to adapt our company structure and make it more resilient to the uncertainties of running a service-based business. Team members who lost the security of their salaried position did not get it back. Instead, we increased their hourly rates and committed to finding a consistent workload for them.
I’m certain that the only reason we are still operating is that we took on Sinek’s principles of an infinite mindset.
They’re easy to follow when things are going well, but the true test of leadership, and the courage it demands, comes when things are falling apart. Personally, I found the strength to keep going from the relationships I had with the people who work with me.
By fostering a workplace built on trust, I felt comfortable discussing last year's challenges openly with those who would be most affected if our company failed. I spent time talking with my team and found solutions with them, rather than for them.
Where it was appropriate, I even spoke candidly with one of our clients. They went on to advocate for us within their company and dramatically increased their scope of work with us when their next year of planning came around.
As the saying goes, courage is not the absence of fear. It is doing the next right thing in the face of fear. That is a strength I would not have had on my own.
What have we (un)learned?
Being finite-minded in business can take many forms. In our case, the constant hustle of trying to build something up from nothing resulted in a growing company that was not pricing its services correctly; a team structure that demanded overhead we couldn’t maintain; and a business model that was not resilient enough to adapt to the shifting client load.
For a small business like ours, every customer can mean survival or the end of the company. And that makes it easy to believe long-term thinking is a luxury. The hard truth is that growing a business requires you to focus both on the immediate next goal and the distant horizon.
Playing the infinite game in business means recognizing that there are no true endpoints. Success is about longevity, adaptability and principled growth. It’s about leading with a just cause, building a team based on trust and having the courage to make hard decisions that align with your long-term vision.