I think a lot of misery comes from the privilege having your basic needs met.
You stop appreciating the little things and start complaining about non-sense. We've all been there...complaining about work, the neighbor, the food we don't feel like eating. But I think that's where a lot of misery comes from.
As a VC one way of looking at a day, week, month is we're aggregating all the 💩 that's hitting the fan across all 500 companies in the portfolio. We're in the expect 💩 to happen constantly business 🤓
"Lowering your expectations isn’t about giving up; it’s about gaining freedom. It’s about realizing that the $80k-a-year version of you and the $80-million-a-year version of you are using the same brain hardware." This is such a huge lesson to unlearn. We are taught to worship more, but forget the hardware we use to perceive more doesn't compute that way.
Love this, Dennis. Also reminds me of my own steakhouse incident when I was living in Japan. I ended up being taken to an extremely high-end Japanese steak restaurant when I was basically working as an intern, not entirely sure what was going on and was sweating when the bill appeared. Thankfully a CEO of a company happened to be at the table and picked the whole thing up. Never been more grateful in a restaurant environment, and I'll always remember that guy's kindness when he could see I was clearly never going to be able to afford the bill.
LOL. Nice. Yes, this steakhouse was similarly priced... need to know going in. We have those guardian angels like that CEO everywhere... if we look around.
While I was reading about your story about the man in Armani clothing I could only think of one thing: success without fulfilment is the ultimate failure like Tony Robbins says. Great article Dennis!
Very interesting. Maybe I've laways been nonchalant but I always had goals and never been extensively disapointed if things didn't work out. Somehow, I always looked at what was and enjoyed it. My work had been done to discover something else or to learn a lesson. I guess goals and expectations were never the same for me as I don't really have expectations... Does that make sense?
Love it. You are in a small percentile who understand this. But, it's also just the human condition. We expect a result from an action, otherwise, why take action? But emotionally detatching from the outcome is maturity, IMHO.
Somehow, I never thought of expectations = emotionally attached. Thank you for clarifying this for me. To me, the emotion attached to my goals is just love. I set goals on journeys that I love. There is a downside to this as well (as some persons would say) because I'm not overly emotional when I reach them lol I just reward myself and move on.
Well, sometimes the smallest discussions open the biggest doors!
Loved this, Dennis. It reminded me of a time I was at a high-end restaurant as an intern and couldn’t afford the bill. A CEO at the table quietly covered it. I’ll never forget that kindness.
This really makes you think. The idea that our frustration comes from the gap between expectation and reality is so true. A great reminder to stay grounded and protect our peace.
Dennis, this is a precise audit of a systemic fragility that most leaders are too insulated to recognize. You’ve identified the "CEO Bubble" not just as a leadership hurdle, but as a critical failure in the intelligence cycle.
In my line of work, we view this level of isolation as "operational blindness." When the signal from the ground is sanitized by layers of middle-management ego or fear, the executive at the top is no longer making decisions based on reality; they are navigating a hallucination. In an era of exponential technological shifts—what I call the "Airlock"—this gap between perceived stability and actual kinetic risk is where most high-performance firms fracture.
You’ve done the community a service by naming the ghost in the machine.
My challenge to the readers here: Most of you believe you are the exception to this rule. You aren't. Precision is the only antidote to the entropy of leadership. If you do not have a formal "Red Team" or a sovereign intelligence vector that bypasses your direct reports, how do you verify that the "truth" on your desk isn't just a comfortable fiction?
The silence at the top isn’t peace—it’s a lack of telemetry. Fix the loop before the system corrects itself at your expense.
This silent killer shows up differently across the voices:
Nurturers might feel emotional fatigue and relational drift.
Guardians might notice standards bending to keep things moving.
Creatives might feel curiosity shrink under pressure.
Connectors might sense trust thinning as conversations shorten.
Pioneers might keep pushing momentum, sometimes past the warning signs.
Naming these responses makes the invisible visible.
I think a lot of misery comes from the privilege having your basic needs met.
You stop appreciating the little things and start complaining about non-sense. We've all been there...complaining about work, the neighbor, the food we don't feel like eating. But I think that's where a lot of misery comes from.
Love that. And absolutely true. I've been on both sides of it. I'm not pure. I eventually woke up, but caused a little wreckage along the way.
As a VC one way of looking at a day, week, month is we're aggregating all the 💩 that's hitting the fan across all 500 companies in the portfolio. We're in the expect 💩 to happen constantly business 🤓
Yes, those are another type of expectations. I guess we can call those entrepreneurial expectations.💩🤣
Exactly. Happiness isn’t about what happens, it’s about managing the gap between expectation and reality.
"Lowering your expectations isn’t about giving up; it’s about gaining freedom. It’s about realizing that the $80k-a-year version of you and the $80-million-a-year version of you are using the same brain hardware." This is such a huge lesson to unlearn. We are taught to worship more, but forget the hardware we use to perceive more doesn't compute that way.
Love this, Dennis. Also reminds me of my own steakhouse incident when I was living in Japan. I ended up being taken to an extremely high-end Japanese steak restaurant when I was basically working as an intern, not entirely sure what was going on and was sweating when the bill appeared. Thankfully a CEO of a company happened to be at the table and picked the whole thing up. Never been more grateful in a restaurant environment, and I'll always remember that guy's kindness when he could see I was clearly never going to be able to afford the bill.
LOL. Nice. Yes, this steakhouse was similarly priced... need to know going in. We have those guardian angels like that CEO everywhere... if we look around.
Expectations can quietly drain joy faster than pressure ever does.
While I was reading about your story about the man in Armani clothing I could only think of one thing: success without fulfilment is the ultimate failure like Tony Robbins says. Great article Dennis!
Amen to that. There is no success greater than inner peace.
Inner peace and gratitude.
Very interesting. Maybe I've laways been nonchalant but I always had goals and never been extensively disapointed if things didn't work out. Somehow, I always looked at what was and enjoyed it. My work had been done to discover something else or to learn a lesson. I guess goals and expectations were never the same for me as I don't really have expectations... Does that make sense?
Love it. You are in a small percentile who understand this. But, it's also just the human condition. We expect a result from an action, otherwise, why take action? But emotionally detatching from the outcome is maturity, IMHO.
Somehow, I never thought of expectations = emotionally attached. Thank you for clarifying this for me. To me, the emotion attached to my goals is just love. I set goals on journeys that I love. There is a downside to this as well (as some persons would say) because I'm not overly emotional when I reach them lol I just reward myself and move on.
Well, sometimes the smallest discussions open the biggest doors!
Thanks for taking the time to answer.
Loved this, Dennis. It reminded me of a time I was at a high-end restaurant as an intern and couldn’t afford the bill. A CEO at the table quietly covered it. I’ll never forget that kindness.
This really makes you think. The idea that our frustration comes from the gap between expectation and reality is so true. A great reminder to stay grounded and protect our peace.
All about few wants but not settling for mediocrity. Really well put together, Dennis!
Dennis, this is a precise audit of a systemic fragility that most leaders are too insulated to recognize. You’ve identified the "CEO Bubble" not just as a leadership hurdle, but as a critical failure in the intelligence cycle.
In my line of work, we view this level of isolation as "operational blindness." When the signal from the ground is sanitized by layers of middle-management ego or fear, the executive at the top is no longer making decisions based on reality; they are navigating a hallucination. In an era of exponential technological shifts—what I call the "Airlock"—this gap between perceived stability and actual kinetic risk is where most high-performance firms fracture.
You’ve done the community a service by naming the ghost in the machine.
My challenge to the readers here: Most of you believe you are the exception to this rule. You aren't. Precision is the only antidote to the entropy of leadership. If you do not have a formal "Red Team" or a sovereign intelligence vector that bypasses your direct reports, how do you verify that the "truth" on your desk isn't just a comfortable fiction?
The silence at the top isn’t peace—it’s a lack of telemetry. Fix the loop before the system corrects itself at your expense.
Yes, non emotional attachment to outcomes is real maturity and emotional intelligence.