“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 help and, 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 a subtle (and insidious) form of people-pleasing .

(Men do it too, of course: “John Cleese once told me I would never be happy unless I stopped “being so f***ing polite all the time,” British actor Stephen Fry has said. “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 disturb the status quo. To avoid doing what might offend or disappoint.

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. We’re apologetic when we haven’t done any harm. And we don’t live the life that we really want.

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, there’s something we’re getting 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 seeing the look of 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. Acknowledging someone’s feelings is also powerful: “You seem disappointed,” you can say, 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 honouring their wishes and pursuing his own dream. I suggested he start by trying to understand where his mother was coming from: what were her real fears and concerns? 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.