Choose the Hard Path
When choosing between options, pick the harder one because it wins whether or not it works out.
- Difficulty
- Easy
- Time to result
- ~months to results
- Steps
- 3
- Confidence
- 90%
A decision heuristic for choosing among options where the payoff structure is asymmetric. If you pick the easy path and it fails, you learned little; if you pick the hard path and it fails, you still gained hard-won skills and relationships with smart people. The hard path is a hedge that pays off in every outcome except the one where you never attempt it.
Origin
Farhan Thawar's personal operating principle, developed across his career (Waterloo minors in electrical engineering and financial engineering, chosen because 'the smarter people were in that path'). He notes it only makes sense in retrospect, Steve-Jobs 'connect the dots looking backwards' style.
Core principles
- 01An hour spent on a hard problem returns learning even in failure; an easy problem that fails returns nothing.
- 02Hard rooms are where the smartest, most motivated people are, because they're there for the same reason you are.
- 03Optimize for the learning journey, not the immediate outcome.
- 04'Hard' means intentionally difficult-but-instructive, NOT gratuitously dumb or self-sabotaging.
How to run it
- 1
Frame the choice as a payoff matrix
For any fork with an easy and a hard option, mentally lay out all four outcomes: easy+works, easy+fails, hard+works, hard+fails. Notice that easy+fails is the only quadrant that leaves you with nothing.
Pro tip Ask 'what do I keep if this doesn't work?' The hard path always leaves you with skills, work product, and relationships.
- 2
Screen for who's on the path
Prefer the harder path partly because it concentrates smart, motivated people. Thawar picked hard courses specifically to meet peers who are 'still my friends today.' Use the calibre of people as a signal that a path is worth its difficulty.
Watch out Harder is not automatically better. Joining a terrible company or building something in a dumb way is just hard, not instructive. The test is whether the difficulty teaches you something.
- 3
Produce evidence of learning, not just effort
Concrete application: a job seeker sending 10 resumes a day is on the easy path and learns nothing. Instead, build something real on the target company's platform (e.g. a Shopify app or admin extension). Even if you don't get the job, you have GitHub artifacts and demonstrated product learning.
Pro tip You can't do the hard thing every single day, but you can do it once a day and compound the learning.
In the wild
Thawar tells job seekers who send 10 resumes a day to instead look at the Shopify API and build an app or admin extension on top of the platform.
→ Even without landing the Shopify job, the person has learned the product, built portfolio artifacts, and can show them to other employers, potentially translating to a job elsewhere.
At Waterloo, Thawar added an electrical engineering minor on top of computer science, and during his MBA added a financial engineering minor, despite being a 'tech guy' surrounded by people heading into finance jobs.
→ He got worse marks but met smarter people who remain his friends and network today; the relationships outlasted the grades.
Common mistakes
Equating 'hard' with 'good'
Difficulty alone is not the signal. A frustrating job or a needlessly convoluted build is hard without being instructive. The heuristic only holds when the hard path teaches you something and puts you next to smart people.
Optimizing for the win instead of the learning
People choose the easy path to maximize the odds of a clean success, but if it fails they walk away empty. The point is to structure choices so that failure still compounds into skills and relationships.
Is it for you?
Best for
Early-career professionals and job seekers deciding between a safe, low-effort option and a stretch option that surrounds them with stronger people.
Not ideal for
High-stakes production decisions where a 'hard experiment' could cause real damage (e.g. an untested config that could take the whole system down); use guardrails there.
From the transcript
“if you do the hard path and it doesn't work actually you still kind of win because you've now done something hard you've probably worked…”
“why don't you look at the API and build something”
“I ended up meeting smarter people in those courses because they were there for the same reason I was because the content was hard”
From the episode
How Shopify builds a high-intensity culture
Farhan Thawar (VP and Head of Eng)