The Path Through
Facing Obstacles Head-On
We spend so much of our time trying to sidestep pain. We avoid difficult conversations, steer clear of confrontations, and make decisions that minimize discomfort. In the moment, it feels like we’re being smart, protecting ourselves from needless suffering. But here’s the thing—eventually, that approach catches up to us. No matter how much we try to avoid it, some obstacles need to be faced head-on, because the longer we dodge, the harder they are to overcome.
In both personal and professional life, it’s tempting to believe there’s always a way around an obstacle. We convince ourselves that if we finesse a situation just right, we can avoid pain altogether. But as every leader, entrepreneur, or even soldier knows, there are times when the best path is straight through the obstacle. Trying to avoid suffering often leads to greater challenges down the road, and the cost of avoidance can become greater than the pain of confronting the issue head-on.
Avoidance Comes at a Price
We live in a world where comfort is often seen as the end goal. From career decisions to interpersonal relationships, there’s a tendency to opt for choices that promise the least friction. This avoidance of discomfort, however, often leads to stagnation. When we refuse to face pain, we also refuse the growth and progress that come with overcoming obstacles. Just like muscles build strength through strain, leaders and teams grow through adversity.
Take the lessons from history, where conflicts—when avoided for too long—have festered into larger, more devastating wars. We see this now with the growing tension between Iran and Israel. A regional war is threatening to unfold, and while this conflict comes with historical complexities, one can’t help but feel that decades of trying to dodge the core issues only made the inevitable more explosive. The geopolitical atmosphere is already tense, and as often happens in life, the more we try to skirt around a problem, the more potent and uncontrollable it becomes when it finally hits.
The War Within: Our Reluctance to Face Pain
On an individual level, the same dynamics apply. We avoid having difficult conversations because we fear confrontation, only to find that unresolved issues build into larger conflicts. We dodge challenging decisions at work, hoping the situation will resolve itself, but eventually, it spirals into a bigger mess than it ever needed to be.
In The 33 Strategies of War, Robert Greene talks about the concept of the “counterattack,” which can be applied here. Instead of retreating from difficulty, we counterattack—we move toward it, not away from it. While war strategies may seem harsh in everyday life, there’s truth in the idea that confrontation is often the only way to disarm a problem before it grows too powerful.
Sometimes, the best way forward isn’t around or over the obstacle. It’s straight through it.
Lessons from the Battlefield
Leaders like Omar Bradley, who served as a General during some of America’s most harrowing military moments, knew that there are battles you can’t win by flanking the enemy. In his autobiography A General’s Life, Bradley reflects on how sometimes, you have to face the enemy directly and with full force. There’s no avoiding the pain of combat, but through it, victory is possible.
The same applies to us. Whether in leadership, entrepreneurship, or daily life, the battles we avoid will eventually find us. We can either run from them or prepare ourselves to march straight into them with resolve. And here’s the crucial bit—when we face challenges head-on, we’re not just dealing with the obstacle. We’re proving to ourselves that we have the strength, resilience, and courage to handle what life throws our way. Every obstacle becomes a building block for future success, instead of a lingering shadow that haunts us.
The Pitfalls of Delaying Conflict
Gary Kasparov, in his book Winter Is Coming, makes an astute observation about global politics. He reflects on the fact that delaying conflict with adversaries often leads to greater disasters. He describes how the world allowed authoritarian regimes like Putin’s Russia to fester, thinking that engagement and diplomacy could avoid outright conflict. But by not confronting the real issues, the problem grew. What could have been solved early on spiraled into a full-blown crisis. We see the same principle at work in our own lives. When we avoid small conflicts, they tend to metastasize into much larger ones.
This isn’t to say we should go looking for conflict. Rather, it’s about recognizing when an issue needs to be addressed directly and then summoning the courage to do so. We can learn a lot from history, geopolitics, and war strategies, but at the heart of it, the lesson is simple: some problems only grow worse when left to fester. Sometimes, the best solution is to meet the challenge head-on and push through it.
Finding the Courage to Move Forward
Facing obstacles head-on is never easy. It requires clarity, courage, and often, a good deal of discomfort. But it also brings something valuable—growth. By moving through difficulties instead of around them, we learn, grow, and ultimately come out stronger. Whether in business or personal life, our most significant wins come from the moments we dared to face adversity without flinching.
It’s in those moments of conflict that we become the leaders we’re meant to be.
So, the next time you find yourself trying to avoid a difficult decision, ask yourself: what will the cost of avoiding this be? And then, with clarity and resolve, remind yourself that sometimes the best way forward is to walk straight through the obstacle.
In doing so, you might just find that the pain you feared wasn’t as great as the victory waiting on the other side.