Everyone wants to win, and no one likes to lose. Winning means getting what you want, fulfilling your needs, and finding satisfaction in your life. Losing means going without, dealing with disappointment, and maybe not even surviving to the end of the day.

When you think about your approach to solving problems, are you trying to win or not lose? Did you choose a strategy deliberately? Or did one choose you? Your choice is critical to thriving long term. Taking chances and being accepting of mistakes can be a powerful catalyst for creativity. Creativity in turn leads to better solutions and more long-term satisfaction. It leads to having more fun. In business and in life, that’s huge.

A winning recipe

I’ve always loved cooking. Being Cantonese and growing up in an Italian–American town exposed me to a wide range of foods, so I developed a diverse palate. My father is a restaurateur–engineer who expresses his love by feeding his family. He enjoys nothing more than watching children enjoy food. Eating was probably the first skill I ever acquired. Cooking was the second.

As my culinary abilities developed, I devoured cookbooks but found even greater joy in discovering things on my own. I was always trying new techniques, new flavors, and, like my father, sharing the results. Socially awkward and a perpetual outsider, I was frequently shy and insecure. Besides math, cooking was the one thing I had real confidence in. It connected me to the larger world. My creativity was endless, and the results of my efforts enriched my life. Through cooking, I was winning.

I never pursued a career in food, though I thought about it thousands of times. Instead, I found a career in data and analytics. Food remained a constant, however. Building data warehouses around the world allowed me to eat around the world: roast goose in Hong Kong, cioppino in San Francisco, and endless amounts of meze in Istanbul. My passion for cooking also deeply flavored my management approach. By finding out what customers and teammates were hungry for, I could combine my skills and creativity to wow them. 

And there were more wins to come. On our first date, my now-wife and I went to the amazing but long-gone B-Side Lounge, where we had a steaming bowl of mussels (still a favorite of ours) and goat cheese salad with arugula, apple, and candied walnut. On our second date, we went to Chinatown, where I introduced her to Cantonese BBQ and the deliciousness that is roast duck. My future mother-in-law proclaimed me a keeper after I cooked for her (we had bananas Foster for dessert). I was motivated by winning—and I was winning BIG!

What is winning?

Winning is a positive outcome that fills a need or desire.

When we win, we make progress. We make things better for ourselves and those we support. After a series of wins, we can more easily see a future where our aspirations come true. Our minds seek out additional opportunities with the belief they can be achieved. This unlocks our creativity and helps us be our authentic selves. It’s that feeling of “I was born to do this!”

Going for wins is not without cost. We risk short-term losses in return for potential gains. This is the nature of investment. But being motivated by winning unlocks our creativity and problem-solving because trying to win is about taking actions, about doing. We’re not waiting for problems to come to us. We have an idea, a goal, and we take a chance to reach it.

What is not losing?

Losing is a negative outcome that leaves a need unfilled.

When we lose, we end up in a worse place than we started. Naturally, we want to prevent that from happening. When we try to prevent loss, we are trying to stay where we are and not backslide.

Sometimes, this makes sense. When the short-term consequences are severe, the rational thing to do is play to not lose and hope something changes. But as a long-term strategy, that puts the hope of progress external to ourselves and outside our agency. A stance of loss prevention can’t improve our situation. It’s inherently passive and does nothing to stimulate our creativity. When you’re waiting for problems to occur, the future is filled with uncertainty and lacking in shape or promise. Rather than imagine what can be gained, our minds are focused only on what could be lost. Loss prevention is forgoing the potential for future gains in favor of short-term survival.

A bad taste

When I had kids, my relationship with cooking changed. Making pasta by hand was impractical. Trying to come up with an original dish every week seemed impossible. Leisurely wine dinners just didn’t gel with diaper changes. The joy of parenting brought me satisfaction but made me cautious in the kitchen.

Now, instead of trying to wow friends, I was making sure my kids were getting the food they needed to grow. Controlling sugar content was more important than tweaking flavor content. Mistakes were more costly, and there was less upside to experiments. I still cooked, and I’ll argue my family ate well, but I could feel that my creativity had dried up and my love for cooking had faded. For the first time in my life I would sometimes just not know what to cook. Dinner became a problem I struggled to solve. This was really weird, and I couldn’t help but feel something important was gone. What had changed? My motivation. I was now motivated by not losing.

The taco stand

Playing to not lose protects you in the short term but may set you up for future loss. Let’s take a trivial food example. 

Suppose you have a favorite taco stand. It’s everything you want in a meal, and you can happily eat there every day. Why would you ever try someplace else? You’d be guaranteed an inferior meal. In fact, in happiness studies, people who order the same thing to eat consistently report greater happiness with their food than people who try a lot of new things. Isn’t sticking with what works the winning strategy?

Maybe, but what if your taco stand goes out of business? Now you need to find a new place to eat, fast. If you had invested in finding new wins, you’d be in a safer, more secure place.

Let’s apply this concept to our occupations. When you lead a team, the most important task is communicating the vision. Why does the team exist? What problem is it trying to solve? Maybe your job is to maintain some essential business system, such as a financial reporting system. The first of every month, senior management depends on your reports to plan the next 30 days. An absolutely critical function. In the short term, you might be delivering a lot of value. Sometimes, we refer to this as “Keep the Lights On” (KTLO). Maintaining such a reporting system requires a tremendous amount of knowledge and skill. But if that is all your team can do, what happens when this reporting system is replaced by a new application? You’re facing obsolescence. This underscores the danger of focusing only on existing solutions rather than underlying need. Our senior management team needs to plan effectively. Is supporting a legacy reporting system the best way to meet that need? 

The point is, by playing ONLY to not lose or being overly content with what you already have, you may be creating future risk for yourself. Only by achieving new wins can you create the margin to handle future loss. Sort of ironic, huh? By playing not to lose now, we may lose more in the future. 

This raises the notion that the difference between winning or not losing is a matter of delayed gratification versus immediate returns. It might be a matter of timing.

The marshmallow experiment

In the famous Stanford marshmallow experiment, psychologist Walter Mischel offered children the choice between an immediate treat now or two treats at a later time. In follow-up studies, the researchers found that children who were able to wait tended to have better life outcomes, as measured by SAT scores, educational attainment, body mass index (BMI), and other life measures.

The children who were able to wait were playing to win! They demonstrated an ability to invest in better outcomes. A small investment in time led to a doubling of reward, and the risk of failure was moderate compared to the potential gains. This was a not a foolish bet.

A winning strategy

I believe the marshmallow experiment, fun as it is, actually illustrates something profound: the optimal sustained strategy, the one that leads to the best aggregate results, is a strategy of steady, incremental wins. This strategy is conservative enough to avoid serious risk and bold enough to secure future gains. We may not have the math to prove this, but our intuition and experience tell us there is a sweet spot, a the-porridge-is-just-right strategy for taking calculated risks. By pursuing steady improvement, you maximize the odds of long-term success.

Does fear of losing make you less likely to win?

All of the above sounds reasonable, right? But what does it mean for us? Well, what if we’re using a strategy of loss prevention and we don’t even know it? And what if by doing so, we lose some of our ability to win, like I did when my cooking creativity evaporated? What if fear of loss is ironically leading to more loss? Vicious cycles are…vicious.

Why did I lose my creativity? It wasn’t because of losing. It was the fear of losing. 

I was worried my kids weren’t going to eat—that we’d have a bad meal and mess up the whole evening. And if that happened, well, I was a crappy parent to my children and a terrible partner to my wife. My children would be physically stunted and suffer from a host of metabolic diseases. While there is some truth to these concerns, looking back, I realize they were grossly magnified. My fear told me I could not afford to lose, so trying to win just wasn’t an option. Goodbye creativity and goodbye to something that had been a huge part of my identity. Ouch. 

So there it was, the big revelation: fear kills creativity. When I was in a situation where losing was relatively costly, I literally lost my ability to come up with new ideas. It was so strange to not know what to cook. However, if I had been aware of what was happening, perhaps I could have found ways to temper my fear of losing and reawaken my creativity. How? By making winning easier and losing less daunting.

We can have our cake and eat it, too

Let’s tie this back to business objectives and analytics. 

The purpose of analytics is to make better decisions. We derive insight from data and take actions based on that insight. Analytics helps us choose the best possible action. But what constitutes best? Well, if the consequences of being wrong are severe, then the best choice would be the one that minimizes the impact of failure. However, if we’re looking for a lot of upside, analytics can guide us to the big bet. Analytics burns away unknowns and helps us plan more effectively, tilting the balance toward winning. The right insights take the guesswork out, magnifying our wins and blunting our loses at the same time. We get to have both. Analytics enables a strategy of playing to win.

Tilting toward winning

If we want to pursue a stance of playing to win, our monkey brains have to believe this is the right choice. How can we convince ourselves?

Create a habit of pursuing steady wins.

Make wins easier.
Formulate immediate goals that you can visualize. In soccer, aspiring to score five goals is fine. But focusing on making every kick count is how you get there.

Win more often.
Small wins go hand in hand with frequent wins. Try to deliver as often as possible. An office goal might be to do something for your customers or co-workers every morning. A home goal might be knocking off those small, well-defined tasks. Software engineers pursue a tactic of steady wins through Continuous Development/Continuous Integration (CD/CI). By setting ourselves small, achievable goals, we make wins more frequent and more habitual.

Expect wins.
Be purposeful in your work and understand why you’re doing something. How will what you’re doing right now lead to a win?

Lessen the fear of failure.

What if we try to win but fail? Going for it could leave us in a worse place than we started. No argument there, but what we are trying to avoid is an unconscious or default state of playing it safe. As we saw, no progress can be made without taking some chances.

So how do we get okay with occasionally failing?

Prepare for emotional loss.
Explore what it would feel like to fail. Some of the greatest fears are the ones we’ve never confronted. If I make a presentation to the senior leadership team, what’s the worst that can happen? What would that feel like? Am I overweighting that?

Prepare for actual loss.
We all lose sometimes. It’s inevitable. Given that, we should prepare for it and blunt the impact. If I want to try out a new meal that my family might not like, I can prepare for loss by having a backup meal in place. Yes, it’s a bit more effort, but it helps me avoid disaster. Prepare for loss by investing in insurance.

Practice losing.
If we want to get really good at something, we need to practice. That includes losing. Baseball players spend endless hours in the batting cage. By simulating the game, they are practicing loss, so when actual loss comes, they can deal with it. 

Reframe losses as wins. 
When you lose, is it really all for naught? Can you reframe a loss as a partial win? What did you learn? Did you get stronger or wiser? Did you eliminate bad choices, making future wins more likely?

Be aware of the consequences of NOT going for it.
What’s the cost of not trying to win, of not taking action? What’s the missed opportunity? Sometimes by playing to not lose, we lose even more.

Bring future loss into the present.
Imagine the worst-case scenario. What would the consequences be? Knowing that, how could you prepare for and mitigate the damage?

Turn inaction into action.
When blocked from going forward, think about how you could overcome the blockage. Turn this into a mini opportunity to win.

Evaluate workplace culture.

Rightly so, companies are bringing new focus to workplace cultures. For too long, the view of humans as autonomous machines dominated. There was little regard for people’s personal motivations and no focus on unlocking group creativity. Today’s tech giants are all based on vibrant corporate cultures—ones where innovation and collaboration are rewarded and failure is welcomed as a learning opportunity. These cultures foster winning.

How can we tell if our workplace culture supports winning? Perhaps these questions can help. 

Are teams clear on what their mission is? Is it obvious what winning would constitute?

How does your mission support the company mission? 

Are people given credit for hitting their goals? Conversely, are some rewarded for unspoken or subjective goals?

Are you, your coworkers and your boss aligned? Can they win even when you lose…or even because you lose?

What’s the role of gender or race in perceived success?

When’s the last time you saw someone celebrate failure as a learning lesson?

The right ingredients

As tends to happen, my kids got older. And lucky for me, they became more adventurous in their eating. I’ve got an appreciative audience, and the consequences of a stinker are less serious now. I’ve been able take more chances and try out new ideas. We’re eating gumbo, ebelskivers, smoked duck confit, African peanut stew, hand-pulled biang biang noodles, and more. I’ve developed a habit of recording my recipes and taking notes so I can improve them. We even have “The Top 50.” If we ask, “Is this dish a Top 50?” and the answer is yes, then it’s more than just something to make again—it’s something to build upon that will lead us to future winners. And if the answer is no… Well, I try to have a backup meal in the freezer just in case. 

The point is, once I conquered my fear of loss, my creativity returned. Dinner is no longer a problem I can’t solve. Cooking is fun again. That fun drives a virtuous cycle of making it easier to take chances, which in turn creates more wins, which in turn creates more fun. When my older daughter really likes a new dish, she says, “Dad, this is slap!” I’m back to being motivated by winning. 

Analytics alone isn’t the recipe for success. It needs to be paired with a culture that rewards wins and turns losses into learning experiences. By getting value out of losing, we lessen the emotional burden of taking chances.

If you’re at a growth company, you should consider how much risk, how much experimentation your teams are engaging in on a daily basis. Do they have the information they need for solid bets? Does the culture provide psychological safety? Is occasional failure acceptable? Or do your teams play it really safe so as to not make mistakes? Are they rewarded for their wins or punished for their losses? Are you giving your teams good planning tools to derisk their situation? Are you providing them with the insights that help them take chances and go for more audacious goals?

The theory of constraints tells us that we are limited in our achievement by a small number of things holding us back. If your strategy is holding you back, why not try another? Choose to be motivated by winning. Let your creativity loose.