A letter from Robert Glazer Founder & Chairman of the Board, Acceleration Partners From United States to me
Friday Forward - Playing Up (#481)
If you feel like the most capable person in the room, it might be time to find a new room
Robert Glazer
Apr 25
READ IN APP
A few months ago, I played in a pickleball tournament at a business conference. I’m a decent player and can hold my own, but in this setting, I was frequently the weakest of the four players on the court.
Despite that, I played some of my best pickleball.
The pace was faster. The shots were sharper. I had to adjust quickly, stay focused, and play at a higher level, rather than relying on my usual strategies. I didn’t dominate, but I didn’t embarrass myself either, and I left a better player.
That experience reminded me of the importance, and the discomfort, of playing up.
In sports, we often tell young athletes to seek out stronger competition if they want to improve. The same principle applies in every area of life. Growth happens when we surround ourselves with people who are a little bit better, sharper, or more skilled than we are. It’s not always comfortable, but it’s how we stretch our limits.
We are tempted, of course, to do the opposite. It feels good in the moment to play down; to be the smartest in the room, the most experienced on the team, or the person others turn to for answers. It’s easier and safer, but it often leads to stagnation.
When we’re in groups where the thinking is sharper, the conversations move faster, and lazy arguments fall flat, we’re forced to level up. We prepare more thoroughly, listen more carefully, and realize we can’t get away with half-baked ideas or untested assumptions. That pressure and higher standard makes us better.
I’ve noticed this in business meetings, leadership groups, and even casual debates. When I’m in a room where everyone is operating at a high level, I leave sharper, even if I don’t say much. Being challenged in this way helps us grow, as long as we’re willing to face the initial discomfort and remain open to learning.
This kind of growth also requires humility. It’s not always enjoyable to be the least experienced or least informed person in the group. It can stir up self-doubt and imposter syndrome. But it also creates opportunities that familiarity and comfort rarely provide.
In a popular previous Friday Forward, I wrote about the Safety and Comfort Matrix:
When you’re playing down, you’re in the Limiting Quadrant—safe and comfortable. When you’re playing up, you’re in the Magic Quadrant—safe and uncomfortable. It’s called the Magic Quadrant for a reason: it’s where your best learning and growth will happen.
If you always feel like the most capable person in the room, it might be time to find a new room. Seek out situations that stretch you.
Playing up doesn’t mean pretending to be something you’re not. It means seeking out environments where you’ll be challenged and may even struggle. Over time, those challenges become less daunting, and you become more capable than you ever could have by playing it safe.
Growth usually doesn’t come in big leaps. It happens when we consistently choose challenge over ease. Each time we do, we build confidence, and that confidence increases our capacity. Eventually, we come to appreciate the value of the discomfort that once held us back.
So whether it’s a court, a boardroom, or a conversation, seek out the people who push you to be better. Spend more time in places where you feel a little behind, or even a bit intimidated. It might not feel great in the moment, but it will move you forward.
Where in your life are you playing it safe? And where might you benefit from stepping into a situation that forces you to play up?
Quote of The Week
"Growth and comfort do not coexist." – Ginni Rometty
Have a great weekend!
-Bob
robertglazer.com
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New Article: Why You Can’t Have Breakfast With Me
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© 2025 Robert Glazer & Elevate Meda Group, LLC
548 Market Street PMB 72296, San Francisco, CA 94104
Friday Forward - Playing Up (#481)
If you feel like the most capable person in the room, it might be time to find a new room
Robert Glazer
Apr 25
READ IN APP
A few months ago, I played in a pickleball tournament at a business conference. I’m a decent player and can hold my own, but in this setting, I was frequently the weakest of the four players on the court.
Despite that, I played some of my best pickleball.
The pace was faster. The shots were sharper. I had to adjust quickly, stay focused, and play at a higher level, rather than relying on my usual strategies. I didn’t dominate, but I didn’t embarrass myself either, and I left a better player.
That experience reminded me of the importance, and the discomfort, of playing up.
In sports, we often tell young athletes to seek out stronger competition if they want to improve. The same principle applies in every area of life. Growth happens when we surround ourselves with people who are a little bit better, sharper, or more skilled than we are. It’s not always comfortable, but it’s how we stretch our limits.
We are tempted, of course, to do the opposite. It feels good in the moment to play down; to be the smartest in the room, the most experienced on the team, or the person others turn to for answers. It’s easier and safer, but it often leads to stagnation.
When we’re in groups where the thinking is sharper, the conversations move faster, and lazy arguments fall flat, we’re forced to level up. We prepare more thoroughly, listen more carefully, and realize we can’t get away with half-baked ideas or untested assumptions. That pressure and higher standard makes us better.
I’ve noticed this in business meetings, leadership groups, and even casual debates. When I’m in a room where everyone is operating at a high level, I leave sharper, even if I don’t say much. Being challenged in this way helps us grow, as long as we’re willing to face the initial discomfort and remain open to learning.
This kind of growth also requires humility. It’s not always enjoyable to be the least experienced or least informed person in the group. It can stir up self-doubt and imposter syndrome. But it also creates opportunities that familiarity and comfort rarely provide.
In a popular previous Friday Forward, I wrote about the Safety and Comfort Matrix:
When you’re playing down, you’re in the Limiting Quadrant—safe and comfortable. When you’re playing up, you’re in the Magic Quadrant—safe and uncomfortable. It’s called the Magic Quadrant for a reason: it’s where your best learning and growth will happen.
If you always feel like the most capable person in the room, it might be time to find a new room. Seek out situations that stretch you.
Playing up doesn’t mean pretending to be something you’re not. It means seeking out environments where you’ll be challenged and may even struggle. Over time, those challenges become less daunting, and you become more capable than you ever could have by playing it safe.
Growth usually doesn’t come in big leaps. It happens when we consistently choose challenge over ease. Each time we do, we build confidence, and that confidence increases our capacity. Eventually, we come to appreciate the value of the discomfort that once held us back.
So whether it’s a court, a boardroom, or a conversation, seek out the people who push you to be better. Spend more time in places where you feel a little behind, or even a bit intimidated. It might not feel great in the moment, but it will move you forward.
Where in your life are you playing it safe? And where might you benefit from stepping into a situation that forces you to play up?
Quote of The Week
"Growth and comfort do not coexist." – Ginni Rometty
Have a great weekend!
-Bob
robertglazer.com
Share
Leave a comment
Upgrade to paid
You May Also Like:
New Article: Why You Can’t Have Breakfast With Me
Keynotes: Book Me To Speak
New on the Elevate Podcast: Giftology’s Sara Hardwick
Like
Comment
Restack
© 2025 Robert Glazer & Elevate Meda Group, LLC
548 Market Street PMB 72296, San Francisco, CA 94104
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