My life as a recovering people pleaser… and 5 things I’m doing to make it better

And there I was.

Alone in my apartment, a lukewarm Coors Light in my hand, sitting in people pleasing limbo. I’d missed out on doing what I actually wanted to do, and let my best mates and the girl I fancied down in the process.

How the hell did it get to this… again?!

Well, it all started with a “yeah of course, no worries at all, I’ll be there!”

While my head was saying “but there is lots of worry — why are you like this…?”

I can’t help it. How come?! Oh, that’s right — I’m a habitual people pleaser…

That was a little insight into my excitable, but overwhelmed, 21 year old monkey mind. On the outside I was happy, agreeable and stress-free. Yet the voice in my head was nagging at me saying something wasn’t quite right…

I’ve always been laid back, enthusiastic and positive (I was once described in a performance review as endlessly enthusiastic!).

Wanting to help others is part of my nature — I mean who wouldn’t want to make people happy?!

But I seemed to have a particularly hard time saying “no” to things.

But why? It probably comes from a fear of upsetting others, letting them down, or perhaps I just wanted to avoid confrontation — sound familiar?

The particular incident that kicked off this internal monologue was one from my personal life — but I’ve got 10,000 other examples from my work life too.

For example, a colleague asked for help because they were having a “bad day”. So I thought I’d be the nice, good guy and help out a “friend”. I picked up some of their work, and what happened? They have a relaxing, stress-free day and I end up overloaded, working late and asking myself “Why the hell have you just agreed to this?!”

I can see now that this happened all because I lacked the capacity to stand up for myself, say no and let someone down.

Was I trying to impress someone? My colleagues? My boss? Maybe. Fuck knows.

Why, though, did it seem that I was the only one with this problem?

The people around me seemed so confident, self-assured and would happily say “Na, I’m not gonna do that.” Yet I felt tension every time someone asked for help and it was met with awkward silence.

This pain was almost felt physical, like I could actually feel it in my skin. So what did I do? I piped up and said not to worry, I’ll take care of it…

While this might seem like a noble thing to do, it has caused me a lot of stress and internal conflict. Not to mention the “yes man” trait doesn’t have the same benefit in my personal life.

Go with the flow, bro

There’s a tendency for people pleasers like us to see everything through rose-tinted glasses. We see silver linings in the bleakest of situations!

This is such a valuable thing to be able to do naturally. Especially when others around us can suck the positivity out of the air like giant fun-sponges.

But is there a dark side to this awesome personality feature?

Arguably yes, at times there is. Particularly if your positivity is coupled with people pleasing tendencies and a severe case of FOMO…

As a people pleaser, you’re taking the easy route and robbing those around you of your valuable insights, opinions and true feelings. As well as setting yourself up to be taken advantage of.

I can’t tell you how many times I’ve done something that I didn’t want to do, or had my suggestions overlooked because someone disagreed with me and I didn’t stand up for myself and speak my mind.

This leads to things like “Na don’t worry, Jim’s chill he’ll just do whatever” or “just get Jim to help, he always says yes” — usually with zero consultation from Jim.

Nine times out of ten I am “chill with whatever” and happy to go with the flow, but there’s always that tenth time that is agonising — leaving me in no-man’s land feeling stupid, unsatisfied and stuck in limbo not actually doing anything.

Story time! People pleasing in practice.

A prime example of this was from 10 years ago. I was living in Orlando and working at Disney World on a College/University exchange program.

One particular night, I was invited to 3 different events in 3 different locations — my best mates were having a beer-pong party at a neighbouring apartment complex; the girl I fancied wanted to meet me after work for a drink; and my new roommates were having a party at ours to watch a heavyweight boxing match.

As someone who got horrendous FOMO, I wanted to do all 3 things. And as someone that was blindly positive — I thought that I could.

What I really wanted to do was hangout with my actual friends and play beer pong. So I said “Yeah, cool. See you there!”. Then I promised the girl I’d see her when she got back from work. Then finally, I told my roommates I’d be around and go get some beers before the boxing.

I was definitely least bothered about hanging with my roommates and I didn’t really care about boxing. But I wanted to be seen as a good guy, and make an effort with my roomies. At least I thought that was the “right” thing to do…

So, what happened?

Well, my best mates started their beer-pong party, and when I said I was coming “in a bit” they carried on having a great time.

My roommates and I had a few drinks, had some average chat and watched a very underwhelming boxing match.

My roomies then went to bed, so I called my mates but got no answer. One of them replied saying they’d had a great time but were all hammered and were heading home.

I texted the girl I’d promised to see to find where she was, and she replied she was pissed off that I hadn’t messaged earlier so was now hanging out with her colleagues after their shift, so I didn’t see her either.

And there I was. Alone in my apartment, a lukewarm Coors Light in my hand, sitting in people pleasing limbo. I’d missed out on doing what I actually wanted to do, and let my best mates and the girl I fancied down in the process.

At that moment, my positivity persona told me it was still a good night and I’d had fun! The silver lining was that I bonded with my roommates (kinda). But in reality it was eating me up that I missed an opportunity to see people I cared about, and who actually wanted to see me.

I know this is literally no one’s fault but my own. People pleasing had become a habit and it took me until my mid-to-late 20’s to go on my own self-improvement journey and realise that maybe it’s not just “kindness”, and I can actively work on becoming more assertive, and set healthy boundaries.

Even now, this is still a massive work in progress, but I’m getting there.

So finally, what are the practical things I’ve been trying to implement (with varying degrees of success) to help overcome this habitual people pleasing?

The Honesty Appraisal

This requires some self-reflection. It’s not always easy, but stop and take a moment before committing to something. Take a deep breath and think; is this something I actually want to do? Is this what I really think? Or am I agreeing out of guilt because it’s the path of least resistance?

Tim Ferriss says that guilt can serve as a useful diagnostic tool — it shows us where our morals and values are and helps us draw a line in the sand. For me, if there is any tension in my body when asking myself these questions, then it’s probably not right.

Just remember, you can be honest, give your opinion or say no, and not be an asshole about it. It also doesn’t make you an asshole to speak your mind and stand up for yourself. Just don’t be a dick. Read the situation, give an opinion (if it’s required) or just remove yourself from the environment.

Think Like A Chess Master

Now I suck at chess, but it does give us a valuable lesson in strategising, and strategising quickly. Chess masters are always thinking a couple of moves ahead — so why don’t we do the same?

Quickly think to yourself, if I say “No” now, what will happen next? Will anything bad actually happen if I say “no”?

Most of the time, a hard “no” now will save you a world of pain later and set a healthy boundary moving forward — no matter how painful it feels at the time, this can save you from prolonged excuses and internal conflict, stopping you from doing something you don’t want to do because you’re people pleasing.

If a hard “No” is too much, start by giving yourself some breathing room. Change the habit from “yeah, sure” to “Let me get back to you”. This will give you some time to evaluate, strategise and figure out the next move (which will hopefully start to become a “no”, or a considered “yes”).

The “Yes” stamp card

Reminding yourself that you only have so many “Yes’s” to give in a certain time frame will force you out of the habit of agreeing for the sake of agreement.

Give yourself 10 “yes” stamps for the day/week/month, whatever. And before you commit to anything, ask yourself “Is this necessary?”. If it is, then great. Say yes and stamp it off your card. If not, say no and move on.

The idea is to be more mindful about your time and energy. Warren Buffett suggested this approach when considering investing in companies, and it works just as well when investing in yourself!

FYI — This one felt REALLY cringey to do at first, but if you put your ego aside and lean into the cringe, I promise it’ll make a difference!

Perhaps implement the Mark Manson if it’s not a “Fuck Yes” it’s a “No” approach to decision making for one day a week. After all, Manson is the one who reminded us that we only have so many fucks to give in our life — so choose them wisely.

The last 2 are more “Reminders” than tips, but they’re potentially the most important…

People Sometimes Suck

No matter how much you might want it, not everyone will like you, and you won’t like everyone. AND THAT IS OKAY!

In your work life — once you realise you don’t have to like absolutely everybody to do your job well, it becomes much easier to deal with. You will clash with people. You will think someone is an idiot. Someone will think you’re an idiot. Let it go, people sometimes suck.

In your personal life — remember you’ll occasionally be disappointed by your friends and family. You’ll fight, you’ll get ignored, and you’ll feel a bit shitty. Let it go, people sometimes suck.

As long as you’re not an asshole, have a bit of patience and most importantly stay true to yourself — then you’ll be fine. No one gets through life without picking up baggage, so practise patience and kindness. Everyone is going through something.

Which leads us to our final point.

You’re not that important

Sorry to tell you, but the world doesn’t revolve around you. You’re a side character in everyone’s life but your own. Literally everyone else is so preoccupied with their own shit that it’s highly likely they’ve moved on from whatever it is you think you’ve done.

If you let someone down, or say no, they have probably forgotten about it. The importance of that “event” lives in your mind and your mind alone. While others might be temporarily annoyed or upset, they’ll get over it because they’ve got their own shit to worry about.

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Remember to take care of yourself first, because if you don’t… no one else will! You are the only superhero in your life, so act like it.

Proudly wave a massive “No, not today” flag in the face of others because now you’ve joined me on the road to recovery. See you later, People Pleasing! Next stop, healthy boundaries!

Jimmy Hills

From “Confessions of a Recovering People Pleaser” blog