Two Ways to Win. No Way to Lose.

Back when I was in college, I was fascinated by the billionaire college dropouts like Bill Gates, and Steve Jobs.

I was foolish enough to contemplate dropping out of college myself. I actually thought that it would be cool. Tomorrow when I start a business and it becomes successful, it would feel damn good to say that I’m a successful college dropout.

It would be an interesting story to tell. This way, I thought, I’ll inspire many other future entrepreneurs to dropout as well. Yeah I was very immature!

It was only after my dad had put some sense into me that I started seeing the complete picture. “You don’t yet know what your ultimate career is going to be, but a degree would give you lots of ways to win while vastly reducing the number of ways to lose. There are lesser homeless engineers than homeless college dropouts,” my dad advised. It actually made sense. And I dropped my ideas of dropping out immediately.

But I don’t think I fully appreciated his school of thought back then. I got what he meant, but I didn’t fully grasp the overarching strategy there. Not until Scott Adams, the famous cartoonist of the Dilbert comic strip, talked about a technique to explain one of Donald Trump’s persuasion manoeuvres. The Two Ways to Win, No Way to Lose manoeuvre.


In January of 2016, Iran briefly detained ten American sailors for entering Iranian waters.

The then-candidate Donald Trump announced that if Iran didn’t release the sailors soon, he would make Iran pay for their treachery when he becomes president.

On the surface it looked like a classic Trumpish way of handling things. But if you look deeper, you slowly begin to understand that only one of two things could have happened:

Iran would have either kept the sailors in custody throughout the election, later on allowing Trump to use it as an example of why American voters needed to elect the badass Trump to deal with Iran and other future perpetrators.

Or, Iran would have released the sailors before the election, and Trump could claim it was so because of his tough talk. And therefore the American voters should definitely elect the badass Trump to deal with future perpetrators like Iran.

Two ways win for Trump. But no way to lose. What a move!

Back in the 1990s Microsoft made tremendous profit specifically because they employed this same manoeuvre. Microsoft made billions by licensing their Windows 95 OS.

Here’s how it worked. If a business that got the license for Windows 95 failed, Microsoft still got to keep all the licencing payments that had already been paid. It typically included a large upfront payment.

Or, if the business succeeded, Microsoft made even more money because the licence continued to pay out as a percentage of profits. Two ways to win. No way to lose!

This strategy can also be coupled with Confirmation Bias to make it even more effective. Take this example.

Your performance review is coming, and you know that despite your efforts the reviewer doesn’t favour your much, and that you might not make a good bonus.

Here’s what you can do. A standard tactic would be to make everybody, including the reviewer know that you think they are biased against you.

Now, only two things can happen. Your accusation of bias would either cause the reviewer to overcompensate to avoid the appearance of bias, thereby give you a lofty bonus.

Or, you don’t actually get the bonus, but now you can claim that it happened precisely because the person was biased. And, due to Confirmation Bias, others would agree with you.

If this person is actually biased, you can now rally the support of your colleagues and take it up to the higher officials.

Student protesters regularly employ this tactic when they fight against school or college authorities. But I would heavily discourage you from actually trying something like this at your workplace. Unless, you really want to sabotage your office relationships. The above example was just a thought experiment; not an advice in any way.


A good way to implement this strategy is by thinking about an upside in the downside. Invert the problem. Ask yourself, “If I lose, how can I still gain from it?”

The upside in the loss may not be huge, but this thought experiment forces you have a plan for all contingencies. This is a good hygiene in strategic planning.

Adams wrote, “When Trump dabbled in running for president in prior election cycles, he also had two ways to win and no way to lose.”

“If he didn’t get any traction in the polls, he still raised his profile and the value of his brand. In his earlier flirtations with running for president, you didn’t see him being so provocative with his policies as he was with his successful run in 2016.”

“The earlier efforts were low-risk, high-reward plays. By “losing” early in prior election cycles, he still put his name in everyone’s mind for the next time. He was literally winning by losing.”

Two ways to win, and no way to lose is a bold step towards the path of achieving antifragility.

But in the interest of clarity, I want to acknowledge that no way to lose isn’t an absolute. Life can always find ways to trip you up. But if you are playing the odds, always try to look for situations that give you two ways to win and almost no way to lose.

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