Why

Every difficult journey needs a reason.

I was talking recently with a colleague about a challenge he has been working on for quite some time. Let’s call him “Andrew”.

Andrew had been facing a series of significant business setbacks. The kind of challenges that were draining his energy and making him start to question whether the effort is worth it. By the time we spoke, Andrew was seriously considering stepping away from the project entirely.

At one point in the conversation, I asked him a simple question, “Why did you take this on in the first place?”

His answer was… a little shallow. Sorry Andrew, I’m just calling it like I see it.

His answer wasn’t wrong. But it didn’t feel like the kind of reason that inspires someone through the inevitable difficult challenges that come with any meaningful endeavor.

I thought about out conversation for a few days afterward. Not because Andrew’s situation was unusual, but because it’s actually really common. Leaders often begin difficult journeys with reasons that make perfect sense and seem deep enough at the time. But when the work becomes harder than expected, and it almost always does, those initial reasons sometimes aren’t strong enough to inspire the continued effort.

That’s where clarity about why becomes so important.

Why, “Why”?

In his book Start With Why, one of Simon Sinek’s main arguments is that individuals and organizations are far more resilient when they have a clear sense of deep purpose. When the “why” is well understood and meaningful enough, the endeavor stops feeling like a collection of difficult tasks and starts feeling like part of a larger impactful mission.

Similarly, but in a much deeper context, Viktor Frankl wrote about the same topic in his book Man’s Search for Meaning. After surviving Nazi concentration camps in WWII, Frankl observed that people who maintained a strong sense of meaning were often better able to endure unimaginable hardship. While our leadership challenges are obviously not even remotely comparable to the experiences Frankl described, his underlying insight is still relevant.

Purpose changes how we experience difficulty.

Consider something as simple as training for a long-distance race. Early in the process, motivation usually comes easily. The training plan looks manageable. The race itself feels exciting. But somewhere along the way, on a cold morning, a steep hill, or a run when you’re tired, the question inevitably appears: Why am I doing this?

If the answer is shallow, the commitment is often tenuous. But when the reason is deeper, like health, discipline, community, growth, or honoring a promise, those difficult periods tend to become part of the journey rather than reasons to stop.

Leadership challenges often follow the same pattern. Founders encounter market setbacks and pressure to extend the runway. Leaders face difficult decisions or complex trade-offs or challenges with the team. For a variety of reasons, the work becomes more challenging than expected.

That’s when a clear and compelling “why” becomes so important.

Purpose doesn’t eliminate difficulty, but it can help reframe it. Challenges become part of the mission rather than obstacles to it.

Which brings me back to Andrew. The real question he was facing wasn’t whether the work had become difficult; it was obvious that it had.

The real question was whether the reason he started mattered enough to keep going.

Because every difficult journey eventually asks that question. And the answer often determines whether we stop or continue.