“This feels too nice and polite to come from a ‘mental toughness coach,’” was my coach’s feedback when I asked him to review an email I had sent introducing myself to a high-profile entrepreneur.  

“Well, yes,” I thought. “I am asking for his time and attention, I want to be respectful.”

In fact, I was reaching out with an offer to be of service. In the process, I was tripped up by what Jean Tang describes in “Sorry, Not Sorry,” as women’s “age-old, primitive drive to avoid taking up space: in physicality, in intellect, in will, in complication.” My obsequious attempt to minimize the “intrusion” was an insidiously subtle form of people-pleasing.

(Men do it too, of course. In coaching Navy SEAL candidates on leadership, I see them opt to gain consensus with their boat crew when projecting authority and taking command would be more effective. And British actor Stephen Fry has said, “John Cleese once told me I would never be happy unless I stopped “being so f***ing polite all the time. I have spent much of my life trying to please people, trying to be what they wanted me to be rather than what I actually wanted to be.”)

As usual, it stems from biology and societal conditioning. In the days of our cavemen ancestors, displeasing others could mean being thrown out of the tribe. And as children, reliant on our parents/caregivers for survival, we instinctively have the same fear — and do what it takes to get smiles, not frowns.

So we learn not to offend, disappoint or disturb the status quo. To avoid conflict and confrontation.

Jerry Hicks tells a story from his days of being a circus acrobat. One afternoon, he walked by the lion’s cage and, sticking his hand inside, began petting the lion on the back of the neck. The lion purred and reveled in the attention. After a few moments, however, wanting to get on with his day, Jerry realized his dilemma: the lion was not going to be happy when the petting stopped. In the same way, we create a conditional relationship with others: as long as I maintain the conditions that please you, you’ll approve of me.

So we don’t speak our truth, watering down our opinions to meet approval. We’re apologetic when we haven’t done any harm. And we don’t pursue the life that really excites us.

How can you wean yourself off people-pleasing?

– Ask yourself, “What’s the payoff?” Because no matter how much we think we dislike a situation, if we’re choosing to let it continue, we’re getting something out of it. One of my clients, a CFO, had her hands full managing a high-profile organization, a growing team and her husband’s serious health condition. And yet she couldn’t say “no” to the neighbor’s request to take care of his cat while he was on a business trip. When she thought about it, she realized the payoff was the gratification of being needed — of being the one to come to the rescue.

– Pinpoint the “moment of dread.” Is it seeing someone frown, their expression of disappointment? Is it the feeling of conflict when someone tries to talk you into doing something? Identify the specific moment — when I was selling health insurance, it was the look of scornful annoyance when I said “health insurance” — and have a plan for what you’ll do when it happens. For me, it was a matter of understanding it wasn’t personal and habituating myself to it. Simply acknowledging someone’s feelings is also powerful: “You seem disappointed,” you can say, or even “You seem disappointed in me,” without caving in or reverting to people-pleasing mode.

– Find out what they really want. One start-up entrepreneur asked me for advice on how to handle his parents’ opposition to him starting his own software company. They were not happy he had left a high-paying job at Airbus – something they reminded him of by posting his last pay stub on the refrigerator — and he was torn between honoring their wishes and pursuing his own dream. I suggested he start by understanding where his mother was coming from. Most people are more comfortable criticizing what they don’t like rather than saying what they want, so ask: “What did she really want? Why is it important to her?” Once she felt heard, they could begin to have a more productive conversation.

Pleasing others is a conditional game. If it means constantly putting aside your own desires and self-expression, the price is too high.