Choose the Hard Path

Pick the harder option because you learn more even if you fail

Farhan Thawar
How Shopify builds a high-intensity culture

Choose the Hard Path

"If you do the hard path and it doesn't work, actually you still win because you've now done something hard. You've probably worked with smart people. You've learned something along the way that is valuable." - Farhan Thawar

What It Is

When faced with multiple options, intentionally choose the harder one. This counterintuitive approach creates an asymmetric outcome: even if the hard path fails, you've gained skills, relationships, and learning that the easy path would never have provided.

The framework is based on a simple observation: the easy path attracts average effort and average people, while the hard path attracts smart, ambitious people solving interesting problems. By consistently choosing harder challenges, you compound your learning and build a network of high-caliber collaborators.

This doesn't mean doing things in unnecessarily complicated ways. It means choosing challenges that stretch you, put you in rooms with exceptional people, and build skills that compound over time.

How It Works

The Asymmetric Outcome:

  • Easy path succeeds: You win, but learned little
  • Easy path fails: You lost time, learned little, didn't meet interesting people
  • Hard path succeeds: You win big, learned a lot, worked with smart people
  • Hard path fails: You still win—learned skills, built relationships, gained experience

What Makes a Path "Hard" (in a Good Way):

  • Working with smarter people than you
  • Learning new skills that stretch you
  • Building something tangible you can show
  • Putting yourself in uncomfortable situations
  • Creating optionality through demonstrated capability

What Makes a Path "Hard" (in a Bad Way):

  • Doing things in dumb or inefficient ways
  • Working at a terrible company
  • Taking on challenges with no learning potential
  • Suffering without purpose or growth

How to Apply It

  1. When job hunting - Don't just send resumes. Build something on the company's platform. Learn their API. Create a project you can show. Even if you don't get the job, you've built skills that transfer.

  2. When choosing courses or roles - Take the harder class, even if your grades suffer. Join the team with higher-caliber people. The relationships and learning outlast the credential.

  3. When evaluating opportunities - Ask "Where can I learn the most?" not "Where is success guaranteed?" Optimize for your learning journey, not short-term wins.

  4. When building skills - Put yourself in rooms where you're the least experienced person. That's where growth happens fastest.

  5. When making career decisions - Apply your personal framework of values. If a role violates your framework, resign—even without another job lined up.

When to Use It

  • Choosing between job offers
  • Deciding which project to take on
  • Evaluating courses or learning opportunities
  • Considering career transitions
  • Picking which problems to solve

When NOT to Use It

  • When "hard" just means poorly designed or toxic
  • When there's no learning potential in the difficulty
  • When the downside is catastrophic (bet the company decisions need more nuance)
  • When you're already at your growth limit and need consolidation time

Source

  • Guest: Farhan Thawar
  • Episode: "How Shopify builds a high-intensity culture"
  • Key Discussion: (00:05:43 - 00:09:37) - Why choosing the hard path creates wins even in failure
  • YouTube: Watch on YouTube

Related Frameworks

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