Navigate / search

How Playing More Can Make You More Successful

Start, Stick, and Stay at Anything!

I was destroyed in a chess game. It was Halloween 1998 when I saw some friends playing chess over a bench by the courtyard. They asked me if I wanted to play and I said yes! I thought that I was going to beat them through my “natural” intelligence. I lost. Then I lost again. The following summer, I was determined to learn how to play. I don’t know why, but I was motivated to keep playing, and losing, for about 200 more games. That translated to about 60 hours of practice before I could finally win a game! I’ve probably played over one hundred thousand games since. Today I wonder: what happened that made me start, stick, and stay at it? Let’s look at how playing more can make you more successful.

Consider that every new challenge you decide to embrace has a learning curve. On the y-axis you have learning (performance) and on the x-axis you have time (experience). Learning difficult skills, like chess, require effort over a long period of time. Luckily, the learning cycle happened accidentally for me, and I was able to learn chess. Understanding these circumstances will help you apply them consciously to embrace your next personal challenge. First, how did chess happen for me?

  • Exciting and supportive (I was having fun with friends).
  • Captivating (I felt intrigued and drawn to the game).
  • Accessible (I practiced a lot online and met other learners).

So why is it so hard to embrace a new challenge? Simply because we don’t want to make mistakes, we don’t want to show our initial struggles, and perhaps hope that we won’t need to work as hard for it. We also make unreasonable expectations about how we should initially perform, and consequently make ourselves feel bad for making mistakes. Why would we put ourselves under so much pressure before we even begin? Think about it. Why did we end up associating learning and performing with our sense of self-worth? And when did we stop playing?

In my life, the moments when I have stopped playing, I have stopped learning. And when there’s no learning, there’s no sense of progress. Why don’t we engage in learning more often? Because we often fail to approach learning with an open and positive attitude. We’re more likely to give up if we have unreasonable expectations of how we should appear smart, quick, and certain. Thus, we become risk averse and fail to move along our learning curve. On the other hand, what do you think would happen if you allowed yourself to have more fun? When it comes to learning—play is the glue that makes it all happen. Here’s how to do it:

Play to start

To begin a new challenge, usually what you do is try to control everything. You don’t want to make mistakes, because it’s painful. You don’t want to take risks, because you might lose. And you don’t want to work hard, because you might not appear smart. Instead, you need to let go of these expectations. To the degree that you let go of your initial assumptions and attachment to outcomes, you’ll be able to grasp any new challenge. Begin by shifting your focus to what feels good to you:

  • Why is learning this so desirable to me?
  • How good will I feel being able to apply this? 
  • How can I reward myself for starting?

Find a way in which you can start by being more playful. Halloween made my whole chess approach fun. Play and you will start! When you play you let go, and you allow yourself to enjoy the process. When you play it’s easier to be present, to express yourself, to make mistakes, and learn from them.

Play to stick

Playing to stick means you commit to doing it over and over again. And why would you do that? Well—why would you repeat a vacation? Or repeat your favorite song, or your favorite food? Because it makes you feel good. Repetition feels good. Repetition is the mother of difficult learning. In education there’s a concept called “Gamification” which intends to bring elements of games into non-game settings to enhance and accelerate both engagement and learning. One of these elements is the ability to be engaged by being able to quickly repeat and have feedback. Another is to assign rewards, have goals, penalties, time restrictions, etc. To stick, make sure you gamify your experience!

Culturally, being smart means you “study little and ace easily”. As you free yourself from this nonsense, you cultivate a more positive attitude, and embrace repetition. If you keep playing, you keep practicing. When the practice becomes less than fun, that’s when it’s time to spice it up again. Not sure how? Ask someone who has been where you are. Life has no final grades. Whatever new adventure you wish to stick to is not a pass/fail test. You form a vision driven by you we care about, you commit to it, and keep playing.

Play to stay

What about the moments when you feel you really need to perform? When you’re confronted by high stakes situations it’s difficult. This happens because time is not understood well (we think of progress linearly) and an obsession with results (we arbitrarily decide when the learning stops). Often, this results in self-doubt. You might even forget why you started in the first place! You must remember that what you do is something you choose to do from a place of wholeness. The only reasonable expectation from a high stakes situation is to fully show up to do your very best. Your best will be a reflection of where you are with your learning, not your worthiness. 

If, in spite of this, someone is being overly negative or critical then you can firmly communicate to them if they’ve ever heard of learning curves. All you need is constructive feedback to improve. There is always a learning curve for everyone. Every expert had to go through it, even if they conveniently forget about it. So keep learning. The learning process will continue far beyond this moment of high stakes. You can’t control the outcome, but you can shape your attitude if you:

  • Assist more, judge less
  • Mentor more, criticize less
  • Engage more, spectate less

If you open up to communicate how you feel and allow yourself to be fully present, you would definitely be having a little more fun! But it takes more than that. Staying means coming back to your why: your inner drives, your dreams, what makes you feel  good, and energized. What’s your juicy vision that propels you to move forward? If you don’t have one, create one that compels you to move. Playing to stay reminds you that it’s not about the results, but about your grit to pursue what matters.

Traditionally, we are taught to be ever more competitive. No wonder change is hard! But now, you can disassociate learning as something that’s painful or labeling of your self-worth. Sure, it can be uncomfortable at times, but that doesn’t mean you stop having fun. You play and you stay because you know it takes time to learn something well, and because eventually you want to contribute back to society. To play means to be human. You play when you learn, laugh, touch, and build meaningful relationships. Is chess still fun to me? You can bet it is—even when I end up with a headache! What’s next for you?

Juan F. Diaz

Thank you for stopping by the Insightful Bean! I hope you found the insights enjoyable and the content useful! Want to make my day? Subscribe to my mailing list to receive future articles straight to your inbox. It really does help! Lastly, If you like this post please give it a like!


Hector Rodriguez

As i was reading the article i couldn’t help but think on my last learning experience. Tennis. And everything fits together.
I always thought it was a fun sport to play, and it is, i would spend some time watching on the TV the pros that tend to make it look so easy, even when it is not ! i was thinking to myself “How hard can it be? It’s all about hitting a ball with a raquet over a net”
My surprise when i started to play was humiliating, not just that i lost the game, but i couldn’t do something i thought i could easily do. I couldn’t answer a single point.
Then i understood that tennis (like any other sport) is a matter of practice and learn just like playing the guitar, playing chess, learning advanced math or building a relationship.
Just like you, i thought that just because of my natural speed and skinny complexion i would be able to win. Then i lost, not once, nor twice, but dozens of times and still counting !
Now, aplying this insight :
Play to start
Why is learning this so desirable to me?
It’s such a fun sport, also making excercise is healthy for the body and the mind plus it was a new challenge to me.

How good will I feel being able to apply this?
So good as it is a sport i find passion in, a sport that in some measury will contribute to my health and a sport i enjoy playing.

How can I reward myself for starting?
Investing time in something you enjoy is a reward itself. With the fun of the game, the joy of learning something new and the challenge of the learning curve.

As you said, the more you play the better you get.
I’d also like to add something : Since we’re all human, we are made of emotions and these play a huge role in us. Sometimes it just isn’t your best day and you will fail even if you had everything to win, and it is normal because we are not perfect. We can also learn alot from this.

As an example (Using tennis as i have done in the whole post) :
I remember one day making amazing serves, with some aces here and there. Such an amazing game it was.
Then, the next week on another game, i just couldn’t make a fine serve and i was thinking to myself “What is wrong with me? I was making the best serves i had ever made just a few days ago!” so i tried to focus, but it couldn’t help. I gave a poor game and poor techniques that i did amazing on previous games (backhand, serve, etc.)
After the game was over (clearly losing it) i had a mix of sadness and anger for my bad performance with no apparent reason for it. When i was in bed ready to sleep i kept thinking “Why did that happen?, i wasn’t sick, nor tired, nor dehydrated” trying to find an answer that i couldn’t find.
And i learned that sometimes it simply is not your day, and even if theres no apparent reason and it’s your fault, let it go, tomorrow is another day to perform.
-Assist more, judge less
-Mentor more, criticize less
-Engage more, spectate less
Be present,possitive, give the best attitude, enjoy the game and learn the most you can on everything you make.
At the end of the day not everything in life is a pass/fail test, but a ride to enjoy.
Great article Juan!

Hector Rodriguez.

Juan F. Diaz

Hi Hector! Thanks for the amazing comment. Glad you found the article useful and see some principles reflected as you learn how to play tennis. Initially, we become aware of our incompetence at new skills and that’s when we tend to get frustrated. But of course, that’s an indication that we’re being too cognitive. Check out this link: Let me know how Tennis evolves for you!


Great article! The timing could not be better as the World Chess Championship just recently concluded. The soon to be 46 year old challenger Vishy Anand and the former World Champ lost his second match in two years against the much younger reigning champion Magnus Carlsen (23) who retained his title. Having just suffered his second match defeat, Anand was asked if he planned to retire and his answer was a firm “No”. These days chess is considered a young man’s game, however, we can all learn from Anand’s resolve to continue to play and learn. In fact, this same question came up last year when he lost the first match and even a few years before that. It’s funny how the expectation of the media is that since you must not like losing, why not just give up already?! I guess this simply externalizes the question we wrestle with whenever we have to face the possibility of failure. However true growth is not possible without failure and Anand would not be the great player he is today without the thousands of defeats he turned into growth opportunities.
A few year ago Anand was asked about the secret to his longevity and Anand said, “First of all if it is a secret, I would simply say that it is keep playing the game of Chess. I keep forcing, I keep learning new things in the game and so far I have been taking challenges as they come.”
This topic of failure also came up in recent article on bigthink:
So once again great article and I’m glad to see it finally ties into one of our shared passions of Chess. By the way one possible thing you could do to improve this article would be to include a diagram to better illustrate the learning curve graph. Also, a good book that discussing at learning and practice is Mastery by George Leonard.

Best regards,

Juan F. Diaz

Hi Ted! What a fantastic comment! This adds so much value to the article. The bigthink link is fascinating. You bring a great point about media. Somehow the belief is that as soon as something gets tough- we feel we must give up. In part, that’s because it’s hard for anyone to continue when the expectation is that it can’t, won’t get any better (more fun, more growth). Anand said he won’t retire, a firm no, but he also said that “Carlsen is the most stable player”. It’s hard to be an optimist when you place such a label on the identity. Performance is an effect of applied effort over time under different learning methods. Perhaps Carlsen proved to have better stable methods! I included a link (in blue) for “learning curves” in the beginning that directs to Wikipedia for amazing diagrams. Thank you so much Ted!

Leave a comment


email* (not published)