The Art of Balancing in the Entrepreneurial Journey: Between Persevering and Giving Up

This article was originally published in a Norwegian online magazine Shifter.no focusing on entrepreneurship. The following version is an English translation of the article in Norwegian.

How often have we not heard expressions like “Go full throttle, always,” “never give up,” or “those who give up never win”? There is a widespread belief that true winners never give up. But what does this entail in the world of entrepreneurship?

Entering the realm of entrepreneurship feels like dancing to an ever-changing melody. It’s about knowing when to take steps forward when to accelerate, when it’s time to change direction, and when one should gracefully step back.

A recent video with Sam Altman on LinkedIn emphasized the importance of perseverance in entrepreneurship — to stand firm through challenge after challenge. This resonated with me and also led to deeper reflection on the underrated ability to know when it’s right to give up.

Society tends to glorify clinging onto something until success is achieved, viewing this as the only path to victory. Reflecting on my experiences, including the difficult decision to shut down my previous project, SoBo Community has taught me the value of knowing when it’s time to close one door to be able to open another. Sometimes, the bravest thing you can do is to take a step back and let go. Despite the negative view many have on giving up, I consider it a sign of strength. It’s not about giving up, but rather making a well-considered decision to pause, reflect, and find a better way forward that aligns with shifting goals and values. Even if some projects look promising, persistent effort does not always lead to success.

Unlike SoBo Community, my belief in the value of Tørn, my current scale-up project, has remained strong. Yet, navigating through this journey requires strategic timing, adaptability, and not least, complex operational decisions.

I recently came across a lecture by Annie Duke, a renowned poker player, and her insights struck me deeply. She points out that giving up is not necessarily a failure, but can be a strategic decision.

Duke highlights a common pitfall called “resulting” — judging decisions solely based on their outcomes. This can be risky for entrepreneurs. If their decisions turn out to be successful, they might become overconfident. This overconfidence can lead them to overlook the various factors behind their success, thus ignoring important details in future decisions. On the other hand, if a decision does not work out, even if it was sensible at the time it was made, entrepreneurs might become too anxious to take similar risks in the future. This fear can prevent them from seizing great opportunities.

To maneuver through the entrepreneurial landscape, it’s essential to avoid the trap that resulting represents. Duke recommends embracing uncertainty and thinking in probabilities, rather than viewing decisions as binary — right or wrong based on outcomes. By considering the spectrum of possible outcomes and their probabilities, a more nuanced decision-making process can be achieved.

In the entrepreneurial world, this insight is particularly poignant. A successful project might result from luck or timing, while a failed project does not necessarily indicate poor decision-making; it could have been the right decision given the circumstances.

Furthermore, evaluating past decisions based on the information that was available at the time they were made promotes continuous learning and development.

From Altman’s focus on perseverance to Duke’s perspectives on strategic withdrawal, a holistic framework for decision-making crystallizes. Making decisions, whether it involves sticking it out, changing course, or choosing to give up strategically, is an art; a logical and rational art. It’s about continuously asking the right questions: What problem are you trying to solve? Is it important? What’s the most effective way to add value? How can you best utilize limited resources? And so on.

Changing direction or giving up should not be seen as defeat; it’s a wise redistribution of effort and resources. Looking back on my entrepreneurial journey, I realize the importance of understanding my decision-making process and becoming aware of my natural tendencies, influences, and blind spots. Embracing uncertainty, learning from successes and failures, and seeking external perspectives are crucial for improving future decision-making.

For entrepreneurs, it’s about developing a robust framework for decision-making — making strategic choices in the face of constant challenges and opportunities, and knowing when it’s right to hold on, change direction, or strategically withdraw.

This journey is not just about surviving but thriving by understanding the balance between pushing on and knowing when it’s time to consider new paths. The greatest strength can sometimes be admitting it’s time to let go, so new doors can open.