A New Way To Look At Optimism’s Role In Success

Why focusing on the percentage rate you need to succeed instead each individual success or failure is key to not losing faith.

A New Way To Look At Optimism’s Role In Success

General Stockdale was held captive for eight years during the Vietnam War. After being tortured 22 times and losing many friends in prison, he eventually made it out alive.


A few decades later, Jim Collins, author of the famous book Good to Great interviewed Stockdale about his experiences as a prisoner of war. Stockdale gave lots of insightful answers about how he managed to survive torture, starvation, and other horrible conditions.

One line that stuck with me more than anything after this encounter, was his answer to the last question of the interview. It was a fairly obvious one that Collins asked: “Who didn’t make it out alive?”

Stockdale’s answer was blunt: “Oh, that’s easy, the optimists. Oh, they were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.”

I couldn’t help but be deeply moved by this. I had always considered myself an optimist, as anyone out there striving for greatness might. But was I setting myself up for failure?

The Stockdale paradox: Faith trumps optimism


The answer, I discovered from Stockdale, is that it isn’t really about optimism versus pessimism. It’s about faith. Stockdale says:
“I never lost faith in the end of the story, I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.”

There is a very clear line between keeping faith and plain optimism that everything will be okay. The last words that Stockdale shared with Collins stress that more than anything else: “You must never confuse faith that you will prevail in the end–which you can never afford to lose–with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

The mirage of silver bullets in business

Stockdale’s story is insightful and entertaining. But how does this help us with the day-to-day challenges we have in our jobs, as entrepreneurs and people trying to succeed?

Answers to how Stockdale’s experience translates into business comes from ConstantContact CEO Gail Goodman. In a recent presentation, fittingly titled “The long, slow, SaaS ramp of death,” Goodman explained the hardships of the near-decade it took her company to build a great business.


Here is the long, slow, SaaS ramp of death:

At one point in the video, Goodman reminded me of Stockdale, just in the business context:

“What I hear today, when I talk to a lot of startup folks, is that they are looking for that silver bullet: “free,” “viral,” “network effect.” Maybe one in a thousand of us entrepreneurs will find that “flick-the-switch” solution. The rest of us actually have to work. For three years, I went into the boardroom and said we are about to sign ‘x,’ and it’s going to change everything. And it never happened.”

It brought to mind Stockdale’s optimists, the ones who eventually died of broken hearts. Goodman goes even further and lists the three most common mirages businesses fall for and often die pursuing:

Partners: No matter how many partnerships you manage to create, you always have to figure out yourself how to market your product.
That one next product change: Adding that one new feature, one extra item, is going to make all the difference. Unfortunately, it doesn’t.
Going “viral”: A lot of people building businesses (including me) have a hard time understanding what “viral” actually means. At the core, the definition is that through the very act of using your product, more people will learn about it, like sending emails via Hotmail that tell others to use Hotmail.


Over and over, they have fallen for “just that one more thing” that is going to turn everything around, similar to Stockdale’s friends waiting for “just that next Christmas.”

Goodman concludes with one of the best tips for any business out there: “We’ve basically learned that there are no silver bullets. There is going to be no one thing, unless you get really lucky.”

Learning to work with the law of averages.

Over the past two years, during which we’ve worked to build Buffer to a humble 600,000 users and into a profitable company, I found one strategy that worked better than anything else.

It is what Jim Rohn called the law of averages. Rohn explains the parable of the sower and the reaper. First, the seed being sown falls on good ground, but the birds get it. Then it falls on shallow ground and can’t grow. Then on thorny ground, where it withers away. And only with the last attempt it falls on good ground and the seeds grow.


So we must shift our focus. We don’t want to look for which seeds thrive and which don’t. We want to know what the rate of success is.

To give you an example where this has worked extremely well for us, consider this:

When I first started our content marketing strategy at Buffer, I was always very frustrated when I didn’t get a response from a blog I wanted to write for. I would fuss about the email I had sent, about the person I contacted and so forth. Only when I accepted the failure rate, I was ready to move on to success. I found that I had to send 10 emails to get 3-4 responses for successfully submitting a guest article.

The same was true for press coverage. I found that only one out of five emails I sent to writers would get a response. And out of those responding only one out of three would do a story about us. That was the moment when I knew to get one article about Buffer in the press, I had to write 15 emails.

Partnerships? Same thing. Only one out of three attempts to create a partnership would actually work out. And I used that number to get however many we needed.


Whatever you do, try and find the percentage rate you need to succeed, instead of trying to succeed with each individual attempt.

It’s a small change in thinking that made huge difference for Stockdale, Goodman, and our company so far. If you have faith that you will eventually succeed, by changing and trying over and over, without being frustrated after each individual setback, that’s when things work out.

Then the fact that optimists lose (most of the time) isn’t so bleak, after all.

[Image: Flickr user David Fulmer]

About the author

Leo Widrich is the co-founder of Buffer, a smarter way to share on Twitter and Facebook. Leo writes more posts on lifehacks, efficiency, and customer happiness over on the Buffer blog