I like to set my goals so I fail 50% of the time.
Chip Wilson
The meaning of the quote
In 1985, a 30-year-old Chip Wilson quit his job at a Calgary oil company to run his surf clothing brand full-time, in a province with no ocean.
He had already ticked off the first big goal on his list, running his own business by 30. The next one said he’d be retired by 40, which to him meant waking up each morning free to do exactly what he wanted.
He got there at 42.
Decades later, he summed it up in 1 short line.
“So I failed, but it got me there.”
That missed deadline is the whole idea behind the quote. A goal you’re sure to hit tells you nothing new about what you can do. If you reach every target you set, you aimed too low and you’ll never find out how far you could have gone. Wilson wants each goal to feel like a coin toss.
He explained the quote in 2021, while talking about how he learned to set goals. He picked up the SMART goals method from Brian Tracy, where the A stands for achievable. That A never sat right with him. As a young swimmer he had pushed himself to failure so often that he came to see it as a learning experience, even an exciting one. So he dropped “achievable” and aimed for goals he’d miss about half the time.
He never goes looking for failure, but when a goal slips past him, he resets it and goes after it again, as long as it still excites him.
He built this habit into Lululemon. In the back room of every store, staff posted their goals on the wall, usually 15 to 40 of them, where anyone could read them. Each goal needed a clear finish line and a “by when” date, and the team reviewed them every quarter.
Wilson noticed that about 80% of people left out the date or wrote the goal so vaguely that nobody could tell whether it got done. Many people would rather look good than be seen missing a target.
Google runs on similar thinking. In its re:Work guide on setting goals, the company says the sweet spot is hitting 60% to 70% of your goals, and anyone who keeps scoring 100% needs to think bigger. Wilson’s 50% is his own rule of thumb rather than a tested number, and Google aims a little higher. Both treat some misses as a sign that you’re stretching.
Some goals shouldn’t be a coin toss. Google also keeps a second type, called committed goals, that teams must hit in full. Paying your rent on time belongs there. Save the 50% goals for the ones meant to grow you.
Action steps
You can test the quote on your own goals in 4 steps.
- Count your hits. Look back at the goals you set last year and count how many you reached. If it’s all or nearly all, you played it safe.
- Raise one goal until it feels 50-50. Pick one goal and push it until you can’t tell whether you’ll make it. If you planned to read 6 books this year, aim for 15.
- Give it a date and post it. Write down what finished looks like and the date you’ll finish by, then put it where other people will see it.
- Reset when you miss. Look at how far you got, set a new date and go again.
Wilson missed his retirement goal by 2 years and still ended up living the life he wrote down.
About the author
At 10, Chip Wilson was a mediocre swimmer waiting to race the 100-meter backstroke. His dad, a phys ed teacher, told him to stop saving energy for a flashy finish and go full-out from the first stroke. If he drowned on the third length, his dad promised to fish him out.
The Canadian record was 8 seconds faster than his best time.
He broke it.
As a teenager, he went to work on the Alaska oil pipeline, and the money he earned there paid for his first experiments in making clothes.
In 1979 he started Westbeach, a surf, skate and snowboard clothing company he later called his 18-year MBA. It came close to going broke before he sold it in 1997.
In 1998, at 42, Wilson took his first yoga class and saw people sweating through baggy cotton clothes. That same year he started Lululemon. His goal for the new company was 1 store, the best in the world, that he could ride his beach cruiser to every day.
The money nearly ran out 3 times. Break-ins were hitting the area and he couldn’t afford the insurance, so he and his 2 sons slept in a tent inside the store every Friday and Saturday night for 6 months.
Nobody ever broke in.
Lululemon went public in 2007 and helped start the athleisure trend. Wilson left the board in 2015 but remains the company’s largest individual shareholder.
He told the full story in his memoir Little Black Stretchy Pants.
In 2021, 36 years after he walked out of that oil company, Wilson sat down with Tim Ferriss on the podcast The Tim Ferriss Show, where you can hear him explain this quote and the goal-setting system he built Lululemon on.
Resources
- Chip Wilson on building Lululemon and the art of setting goals (Podcast)
- Little Black Stretchy Pants (Book)
- The Story of lululemon, free edition (Book)
- Set goals with OKRs (Article)
- Set your course (Article)
- Chip Wilson (Wikipedia)



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