The Winning Checklist: Five Sun Tzu-inspired questions for developing a winning strategy in life

"Those skilled warriors of the past won where it was easy to win. Therefore, the victory of a skilled warrior is neither 'brilliant' nor 'bravely achieved.' Thus, his battle victory is without error. Being without error, his execution will succeed, having already won against the defeated enemy."
- Sun Tzu

In our society, we tend to praise individuals who have shown "genius" in their work, who have braved great risks in striving for their achievements, who never gave up in their relentless pursuit of success.

While these attributes (brilliance, bravery, persistence) are certainly admirable, surprisingly, for Sun Tzu, they are not what truly make up a winning strategy. For him, true victory in warfare is not the result of clever tactics, brave soldiers, or relentless persistence in the face of adversity. Rather, it is the result of executing a simple, well-calculated, and well-timed strategy.

In life, the same is true. The ideal winning strategy - one that allows you to overcome challenges and brings you greater control over your life - does not require incredible brilliance, courage, or grit. It doesn't require more education or taking huge risks or getting out of your comfort zone or never giving up, even if the path forward seems impossible.

Rather, it requires asking five simple, yet critical questions:

1. If successful, will the strategy be profitable (li)?
2. Is the strategy protected (bao)?
3. Is the strategy easy (yi) to execute?
4. Can you execute the strategy quickly (su)?
5. Is the strategy surprising (qi)?

You can think of these questions as a checklist to help keep you evaluate your ideas or strategies. 

Let's look at each question in greater depth.

Question 1: If successful, will the strategy be profitable (li)?
For Sun Tzu, a winning strategy must be profitable. In other words, there must be real, substantial, and clear benefits or gains from achieving the victory - otherwise the whole affair is pointless. These gains do not need to be huge, but they should be significant - that is, it should be clear how the gain will move one forward in achieving one's larger goals or aims.

For example, let's say you are considering a new diet/fitness approach. Before trying the approach, you have to do your research and determine if the benefits are worth it. Will they lead to the results you are looking for - e.g. lower body fat, more energy, bigger and more defined muscles, etc.? It doesn't matter how effective the new approach is if it doesn't produce the results you particularly are looking for.

Question 2: Is the strategy protected (bao)?
For Sun Tzu, a winning strategy is strongly protected against risk. That is to say, if the strategy were to fail, the losses should be minimal and easily manageable. Just as the profitability should be significant, the potential cost or downside should be low.

For Sun Tzu, the best way to make a strategy protected by keeping it concealed. The winning army guards itself by keeping its situation hidden from the enemy. It travels to places the enemy does not care about and presents itself as innocuous to the enemy.

With the diet/fitness example, ask yourself: is the cost of implementing the approach low? What is the downside? If I fail in using the approach, will I be fine? 

Question 3: Is the strategy easy (yi) to execute?
For Sun Tzu, the more steps involved in carrying out the strategy, the more complicated the strategy becomes. The more complicated the strategy becomes, the greater chance for error, since there is more risk to manage. And thus, the less easy carrying out the strategy becomes. A winning strategy is uncomplicated. The number of steps are minimal and the execution is simple and clear, so as to be "without error" (bu te).

With the diet/fitness example above, you must ask yourself: is the approach simple? Or is it complicated? Is it clear how and why it works? Are there a lot of steps involved in making it work? If it's complicated, requiring a lot of steps, the less likely you will be to stick with the diet/fitness plan.

Question 4: Can you execute the strategy quickly (su)?
Being simple, a winning strategy shouldn't require a ton of effort or steps, and therefore, one should be able to move quickly and unhesitatingly to execute it. For Sun Tzu, a quick victory is infinitely more preferable to a long drawn-out one. As he tells us, "[I]n warfare one hears of 'clumsy yet swift,' but I have yet to see 'skillful yet drawn-out.' No nation has yet to benefit from a drawn-out war."

With the diet/fitness example, ask: can I start applying the approach quickly? Will it take a long time to execute? Can I start right away? The longer it takes to start implementing or executing, the greater the likelihood you won't go through with it.

Question 5: Is the strategy surprising (qi)?
For Sun Tzu, a winning strategy always goes beyond other people's experience. It surprises one's enemies, catching them off-guard. Achieving this effectively in war requires two things. First, one must conceal one's positioning and movements (See Question 2). Sun Tzu calls this being "formless" (wu xing).

Next, when the right moment arrives, the army takes simple, quick, and coordinated action at a key weak point, catching the enemy off-guard. This will upset the enemy, causing panic and chaos and ultimately defeat.

Returning to the diet/fitness example, will I be able to achieve surprising results? Will I be able to see results quickly (e.g. in the next few days or weeks, as opposed to months from now)? Will I be impressed by what I see in the mirror, or with my energy levels? Will it help carry the momentum I need to stick with it over time? The less surprising the results, the less likely you'll be to stick to the plan.
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So there we have it: a winning strategy is profitable, protected, easy, quick, and surprising. In developing a plan for your next move or life change (e.g. getting a new educational degree, acquiring a job position, jumping on a business opportunity, starting a diet and fitness plan, etc.), you must ask yourself the four questions above to make sure it has these qualities. If they don't, you have some more work to do.