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When the Obstacle is Showing Us The Way: A Stoic approach to business strategy

What do Southwest Airlines and ancient Stoic philosophers like Marcus Aurelius have in common? They both share an uncommon view of life's impediments and limitations. Instead of seeing a deterrent like many would, they viewed obstacles as opportunities, as signals to a hidden, undeveloped virtue.

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius, Meditations

In life and in business we are taught to avoid obstacles. To go around them, wait them out, or bypass them entirely.

But what if the obstacle isn’t something to escape from? What if it’s pointing to the exact path we need to follow?

This ancient Stoic idea has guided some of the most resilient individuals and companies to greatness. And it’s more relevant than ever for businesses navigating today’s uncertain markets.

David meet Goliath

Take Southwest Airlines as a case in point.

In the early 1970s, they weren’t just another airline—they were an underdog with 4 aircraft, a shoestring budget, and intense competition from established carriers.

Most businesses in this position would have looked for ways to mirror the big players. Cut corners, find investors, and try to survive by following the industry norm.

Instead, Southwest leaned into its limitations.

They saw the obstacle, not enough resources to compete conventionally, as the very thing that could shape their strategy.

Game time

Here’s how Southwest transformed constraint into competitive advantage:

  • They operated only Boeing 737s, which reduced maintenance complexity and training costs.
  • They eliminated seat assignments, which sped up boarding and allowed for more flights per day.
  • They didn’t serve meals, cutting down on turnaround times and overhead.
  • They rejected the hub-and-spoke model, instead flying point-to-point, giving passengers more direct, efficient routes.

This wasn’t just cost-cutting, it was engineered simplicity.

And it paid off:

  • 47 consecutive years of profitability (1973–2019), a streak unmatched in U.S. airline history.
  • At their peak, operating over 4,000 flights daily with around 800 aircraft—impressive numbers for a domestic carrier.
  • #1 in U.S. domestic passengers, built on a foundation of customer loyalty and low costs.

Southwest didn’t succeed despite their challenges. They succeeded because of them.

What are you waiting for?

So, what obstacle are you facing right now?

  • A small team?
  • A limited budget?
  • A competitive market that feels impossible to break into?

Maybe you don’t need more resources. Maybe you need a better perspective.

I’ve personally been able to reach over 30,000 people with an ad budget of just $30, not because I had more, but because I made the most of what I had.

When we stop fighting obstacles and start working with them, we unlock new levels of innovation, efficiency, and focus.

Don’t avoid the hard thing.

Use it.

Because more often than you think, the obstacle is the way.

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