Feel like a loser?

My daughter sucks at drawing.


It’s not her fault. She’s two. But you can tell she’s getting frustrated her skill doesn’t match what she wants to accomplish. Yesterday, she wanted me to color alongside her. She ordered me to color inside the lines. She wanted to see how it was done, and then wasn’t happy when she tried to imitate me.


Robert M. Sapolsky a professor in neurological sciences at Stanford University wrote recently in the Wall Street Journal about the “Winner Effect” (paywall). Whether you look at fish or humans, research keeps finding the same thing. When you win, you win more. When you lose, you lose more.

Losers don’t just lose more, they don’t even bother to come back to compete again.

Winners on the other hand, even if their win was faked (their opponent lost on purpose), gain the confidence to keep competing. For example a mouse who wins a fixed fight where the other mouse was sedated (i.e. forced to lose), has greater odds now of winning his next fight.

Robert brings up the unfortunate side effect this has. Acts of aggression against the weak become a coping mechanism.

But is there some upside we can find in this? Is there a way to hack the “winner effect” for our gain?


In 1985, Melissa and Doug Bernstein were planning on making their careers on Wall Street and Madison Avenue. But after a few years of feeling miserable in the jobs they had after college, they quit and created their own toy company: Melissa & Doug.

If you’re a parent in the US, the odds are pretty good you have a Melissa and Doug branded toy at home. They are an incredibly successful seller of toys.

We have multiple Melissa and Doug products in our household. One of our current favorites is the Water Wow.


The Water Wow has white pages with illustrations outlined in black, beckoning to be colored in.


But it comes with just a single “marker” which contains no ink. Instead, you fill it with water. When you draw, the water soaks through the white pages, showing the colored background hiding just underneath.


When it dries, the page goes back to white.

In other words, it’s like a coloring book. But it’s fake.

It doesn’t take any creativity. You just brush water on it, and out come the beautiful illustrations. My daughter loves it.

And so there lies one example of hacking the “winner effect”. The Water Wow gives my two year old daughter the experience of drawing. Of painting. Of creating something that her two year old hands and muscles can’t actually do just yet. Instead of settling for loss after loss as she tries to learn to color, Melissa and Doug’s toy gives her a tiny win, building her confidence to keep struggling with the real thing. Even if it’s just a little bit fake.


We aren’t two. But learning how to succeed at a new skill, running a business for the first time, or even learning a new software program all puts us back in my daughter’s shoes. (Trying to teach myself video editing feels a lot like failing to color inside the lines.)

For product and business design, I think it’s important to recognize all the areas where our customers feel like that. Can we give them an experience like the Water Wow right now? Can we fake a piece so it feels at least like a little win?

At Highrise for example, we’ve been sending a series of onboarding emails like a lot of companies do. Welcome -> Here’s how you do this important thing -> Did you see this other important thing -> etc.

But we’ve changed that Welcome email recently to ask right up front: “Do you need to import a file of contacts? Most of our customers do. If you want, just reply and send the file our way and we’ll help.”

From all the customer support we do, we’ve seen importing contacts from another system can often be a deep struggle for our new users. So why not try to make it feel like it’s easy as magic? Send us the file. We’ll help or even do it for you. We have more experience after all. We can most likely figure out that customer file; we’ve seen enough of them.

It’s important to remember from a personal and team perspective too. I’ve been running businesses now for over 12 years. It can be really stressful. The startups where no one cares about you yet. The setbacks. The turnarounds.

Highrise was bleeding customers when we took it over 2.5 years ago — everyone thought they heard a rumor it was shutting down. So it was important to celebrate our small wins. One thing we did was add Buzz and Signup channels to our Slack team chat. Most tweets about us are wins so instead of keeping those closed off to just a few of us, everyone sees the nice things people say each day. The Signup channel just shows a running series of new accounts as they’re created so now everyone can see when someone new just “walked in our door” and is trying out our stuff.

Those channels helped showcase our little wins, giving us small but important boosts of confidence, even when other things weren’t going all that well.


How have you tried hacking the “winner effect” in your own life or for your customers?

P.S. If you enjoyed this article, please help spread it by clicking that below. And if you are interested in more, you should follow my YouTube channel, where I share more about how history, psychology, and science can help us come up with better ideas and start businesses.


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