People Pleasing Will Kill Your Future: Chasing Greatness Requires Self-Determination

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Who determines your life? If you’re like most people, you’ll say, “I do.”

But the evidence is that most people don’t truly believe that, and certainly don’t act like it. 

The results aren’t there. 

While a lot of people I work with struggle with a variety of things, one thing that people at the very top don’t really struggle with is people-pleasing. I’m not talking about people who are quite successful, where this still occurs - I’m talking about the .01%. 

They are not callous, but they are not malleable. They don’t bend or change themselves to appease others - not in the same ways many others do - and they have internal reference points, not external ones. 

There is a sense of internal grounding that relies on no one’s approval for the hardest moves in their career. I’ve seen it across multiple industries, age groups, and experience levels, and - while I’ve changed some details to protect identity - here are some examples from those I’ve spoken with: 

• An athlete who gave up a full-ride scholarship for an advanced degree to play pro. Despite family concerns. Gets on the pro team to sign a significant contract.

• A guy running a billion dollar ecomm company who cut an entire product line, after giving it a good shot. A large team, and a million dollar mistake. No sunk cost bias.

• A founder who *had it all* after a couple of successful exits, but feels they still have more in the tank & wanted to take a very big swing…and runs for it. 

A lot of ultra-successful people receive judgment for how they move in the world. They can seem indifferent, disconnected, and this is both true and untrue…as you’ll read below. We misattribute these traits, and miss a very big distinction if you do - between how they operate, and how many others operate. 

People pleasing is a plague. It comes from the very best of intentions and deep care - but the baggage you’ll drag around, and how it will pull you off course and leave you lost, is very real.

Being externally focused comes in many forms, all of which you want to avoid.

You have to know who you are, dig into that, and be resolute and firm. If you are not, it will impact everything - your career, your business, and even your relationships. You will severely limit the scope of what you can do, and your own happiness along the way. 

The internal reference point should always be what matters most. This is what it requires, and the flags to look out for and correct early…as you take on whatever comes next.