How to break free from the cycle of people-pleasing

The Self Salutation Newsletter

Greetings and Salutations! 

I know that people-pleasing has a bad rap in our culture–and for good reasons that I will address shortly–but I want to start out with a bit of a contrarian message here and say that I think our society on the whole could use more people-pleasing not less!

I mean, the whole American rugged individualism thing goes too far sometimes. 

Anyone who’s had the fortune to travel to parts of the world where there’s a greater focus on the community than the individual knows that we lose a dose of sweetness in life by focusing so much on the individual.

Back in my monk days, there was an ethic of selfless service that we aspired to which exalted people-pleasing in a way that I think would make a lot of folks uncomfortable.

But when you’re living in tight quarters as we did, the mood of service helped to make life more pleasant for everyone.

I’ll tell you one story about a fellow monk that exemplifies what I mean. 

The gold standard of service attitudes

In New York City I lived in a monastery where the space was tight. We lived in a couple of big wide-open rooms with lockers that lined the walls.

At night, we threw camping mats on the floor and slept in rows like sardines.

One night, around 2 am or so, I lost my pillow in my sleep, and in a groggy, half-sleep state, I groped around and grabbed it

When I pulled at the pillow, however, it required more of a tug than I expected.

I was puzzled and opened my eyes and in the dim light I realized that my pillow was on the other side of me.

I had ripped the pillow right out from underneath a younger monk next to me, an Indian guy named Harinam.

Harinam leaned over to me and whispered, “Prabhu, do you need my pillow?”

Prabhu is a term of respect we used with each other, it means “my Lord.”

What’s more is that the way he asked the question conveyed to me that he absolutely wanted me to have that pillow if I needed it – and he didn’t have the slightest hint of resentment for being so rudely woken up!

Now, I have my virtues and all, but honestly–don’t mess with me while I’m sleeping, and definitely don’t steal my pillow!

If I had to devise a method of testing someone’s authentic capacity for sacrificing joyfully for those around them, I think a 2 am pillow steal would be the perfect test–and I’m certain that Harinam set the bar at the maximum height possible.

It was humbling to be around people who had that kind of nature. 

A challenge of ashram life

The funny thing you might not expect about monastic life, however, is that in almost all the monasteries I went to there was someone around who was like, hmmm… lots of people pleasers around. I could sort out a nice situation, now, couldn’t I?

And they did.

There was always that person for whom serving others was just not part of their makeup and instead–especially if they had been monks for a few years–they maximized the opportunities the service attitudes around them afforded them.

The maximizers, as I will call them, had a steady stream of younger monks eager to serve–and a group of slightly older monks eager to keep a distance from them.

I counseled younger monks a lot, and the resentment that built up with these maximizers was a common theme.

I probably gave them horrible advice. I really didn’t have a great solution to the challenge at the time.

Three questions to ask yourself about people-pleasing

Regardless of your environment, we all have this dance in relationships between giving and taking. 

Part of that dance is learning to tell when serving and pleasing the people around you is a positive, affirming thing, and when it becomes negative.

Serving others around us in a healthy way means being generous, helpful, and, yes, sometimes even sacrificing for them. 

Mostly it means showing up for the people around you in a way that touches them, in the ways they need.

To understand when it’s becoming unhealthy, here’s a great question to ask yourself: are you resentful?

If you are, then it’s best for both of you if you take some time to examine what’s going on in your dynamic.

Sometimes resentment can be buried because we don’t want to recognize it, however, so if you answered a quick no to the first question, then you might want to ask yourself a few follow-up questions.

Here’s the second great question: Are you neglecting yourself in important ways?

Life brings us all into periods of time where it is important to sacrifice for those around us so sometimes we do set our own needs aside–so if you are neglecting yourself, the real crux of this question is… is now really such a time?

If you’re not holding resentment towards those around you and you’re not neglecting yourself in important ways then you’re probably in a healthy state!

Still, there’s one more question I would encourage you to ponder: how does the other person receive your service?

In other words, what’s the dynamic in the relationship? How valued is your sacrifice?

The unfortunate thing is that sometimes you can get caught in a dynamic of service to people who actually think less of you because of it.

Finding out how you got caught

Now we turn to the all-important part of our exploration which is what to do if you find yourself in a situation where you realize you are people-pleasing and it’s not healthy.

A lot of people just try to cut off the behavior and start saying no to the people around them but I recommend taking more time to sort out what is really going on in the relationship before you start to set different boundaries.

Once you truly understand what the need is that’s underneath this behavior, you’ll naturally find the right way to resolve that need in a different way, and then you’ll be able to start saying no in a way that isn’t reactionary.

Here are a few questions to ask yourself about your people-pleasing tendencies:

Do you engage in people-pleasing because disappointing people makes you feel bad?

Is it because you don’t value yourself and don’t think it’s worth taking care of yourself?

Do you feel unworthy in their company? 

Do you feel service is the only way you will be loved or accepted?

These are hard questions to ask yourself! If any of those questions seemed painful to you just at the onset then I recommend a healthy dose of self acceptance.

Why self-acceptance is a critical step

The key thing to understand about people pleasing is that when we engage in such activities, it is fundamentally a question of self-esteem.

And at the heart of the problem of self-esteem you will find one terrible feeling that nobody wants to encounter: shame.

So we need to start treading lightly here. The key thing to learn with shame is to know that you yourself can start to heal this unwelcome feeling by learning to go deep within your heart of hearts–something meditation is powerful at helping you accomplish–and giving yourself acceptance in the most fundamental way.

In the Self Salutation I call this the Moose mediation because Moose are thought by Native Americans to embody self-acceptance.

I know, the science is still out on that one, but I roll with it.

The beautiful thing about this is that as you learn to go deep into your heart and fill yourself with the feeling of acceptance, you are learning to tap into your own well of worth.

The more you learn to do this, the less you need to seek your worth in other people–which is, in effect, the essence of what is happening in most people pleasing. 

It’s hard to over-estimate the value of self-acceptance—not just in this one challenge, but in all of personal transformation!

Hopefully I’ve convinced you to give it a shot!

Until next week…

Peace,
Simon

P.S. Have you checked out the Self Salutation App yet? It’s up and live and you can explore it for the first week free of charge—after that, it’s only $9.99/month!