Getting Over My Addiction to People Pleasing

Jenny the chain-smoker. How did she justify her first cigarette?

My fiends were doin' it. Just one. Marlboro box cowboy has sexy abs. Innocent, right. Until 20 years later you’re 42, divorced in Sacramento. Thinking, how the fuck did I get here?

Little things, dubiously innocent, can get us off track and stuck in a bad habit. We call this addiction.

Addictions are easy to start, hard to get out of, and even harder to be aware of.

Alcoholics Anonymous has a 10 point plan out to get you out. Millions face addiction yet only the lucky ones have “aha moments” - realization that they need to change.

I had one of those. Except mine happened at the office thinking “how the fuck did I end up a marketer?"

Like any addiction, I stumbled into a job that seemed a harmless good fit, and got caught in a habit that spiraled out of control. My escalation looked like this:

  • High School: loved education and teaching people
  • High School: did not like business
  • College: needed practical skills
  • College: saw the light that business is in everything
  • College: did business school
  • College: veered towards marketing because I hated other classes
  • College: interviewed for marketing roles
  • Work: did marketing at one company
  • Work: then another
  • Work: then another, got good so was easier to get marketing jobs
  • Work: then another
  • Work: Kicked but and celebrated with coworkers

Then BOOM. Now 3 years later I am completely derailed from what is important to me.

What derailed me? A smile.

Yes, a smile.

At each opportunity, someone greeted me like Willy Wonka swinging from the fence of the chocolate factory. “You did it!” I felt affirmed, welcomed, cared for. People told me I did a good job. I got leads. I grew a user-base. I won a golden ticket. 

Whenever that little voice pried, “maybe I should do something more fullfilling?” - anxiety and ambiguity would flood me like Augustus Gloop in the chocolate pond. I’d grab for support, and when I didn’t find answers, didn’t find an alternative path to marketing, I turned to a smile for comfort.

People pleasing isn’t inherently bad. It becomes dangerous when you rely on it to feel full inside instead of relying on yourself. It’s dangerous when you put others’ interest over your own. It dangerous when hit by hit you start to find so much joy in other’s happiness that you forget what delights you. The joy of others and your own blend until you can’t differentiate the two … and that little voice in your head calling truth gets lost at the bottom of the chocolate pond.

People-pleasing addiction can contaminate your sense of what’s important to you.

It’s danger can also be subtle:

You can justify almost anything when someone is smiling at you.

Sandra Robbins is so positive she could make Oscar the Grouch smile. She’s brilliant: 23, went to Yale, wrote a 300 page novel, started a blog that without promotion got 20k views in its first weeks. She’s since joined a big company in New York… She used to beam about the characters in her book but now she tells me she’s “getting good at excel” with an expression that begs for my smile.

Here’s the thing - Sandra is so positive that she could justify ANYTHING as a good opportunity. She finds positivity in the 7/10 opportunities so she won’t reach for the 9/10s. Or even look. And with other coworkers smiling at Microsoft Excel, and people telling her she’s doing a good job and growing, she could get lost in a spreadsheet forever.

Someone smiling at us can make us feel like we are on the right track and keep us complacent.

You don’t risk for something greater because you make people happy now. 

You can fall back on smiling as a crutch.

You can stop reaching for more.




Have you given up your dreams? Do you now forget them and feel like you are just going through life. Then you don’t know what you want! If you just say I guess I’m ok in this situation, then you aren’t wanting enough.

I'm not calling for an end to people pleasing. I'm calling for people to not sacrifice their own self-interest. I'm asking people to find space and time to truly see past the nicotine-smile-blur and actually identify what they want and how to get it. 

Breaking an addiction to people-pleasing, like rehab, is an uphill battle. It can sour people’s mouthes. You may see yourself more as a Violet Bouregart (“I want mooooore daddy”) than a Charlie Bucket. But working on my addiction has helped me feel like Jenny before she picked up that first cigarette. I don't have the answers, but I do think I have some tips that worked for me:


1. Scrape your dreams off the bottom of the chocolate pond: 

Take some time alone. Go out of town, rent a cabin. You’ll be tempted to search for a smile, resist. Without distraction the loneliness may pain you, allow it. Just “be” for a bit. Journal. Reflect on elated memories. Meditate.  Let whatever arises arise. Sit in it. Notice it. Ask yourself what you desire. Ask the 5 whys. Be patient. Carve into your wants and don’t let the practicality of attaining it get in the way … you can want anything. 

[Rilke quote on value of isolation]

Read this. Focus on the 9th path. Enough said.

In isolation you forget everything and remember yourself.


2. Pursue what you want and build support to make it happen: 

Like the 10 steps in Alcholic’s Anonymous, here are my 10 steps to getting over people pleasing:

  1. Just do it. pssshh, like that’s gonna work.
  2. Put a smiley sticker on your bathroom mirror. Good reminder to put yourself first. 
  3. Beware of environments. Don’t go to the chocolate factory if you want to diet! Self control and will power are limited. Plan ahead so you don’t put yourself in high pressure situations and compromise yourself. 
  4. Say no, politely. This formula works for me “(1) Thanks so much for the offer/ask, and thinking of me. (2) I’m focused on [x priorities] and want to keep those committments so (3) nows not a good time/I can’t. (4) Thanks though.”

    (1) Appreciation - acknowledges their effort
    (2) Focus - explains why you say no
    (3) No
    (4) Appreciation - affirms their kindness
    + [optional] suggest a resource or friend who may be interested
  5. If you question “am I being a bad person” use this framework: 

    Only do quadrants 4 and 6.
  6. Don’t apologize. You have every right to pursue your own wellness and self-interest.
  7. Don’t be scared of fallout or consequences. Taking self+mutual interest approach is an important habit. If people want your time that is in quadrant 3 then you don’t want to be with those people.
  8. Ask yourself - 5 years from now what will I think of today’s people pleasing decision? Thinking of long term goals can help us make wise decisions in the present.
  9. Realize you can’t be everything to everyone. Have you mourned that thought? You can’t please everyone. And you shouldn’t be the one who loses. 
  10. Find a Grandpa Joe - a friend who can walk with you along your journey. Together, you can celebrate when you stick to self+mutual interest. Vent your challenges. Talk through habit-changing tactics. Ironically, this may be the very person you most want to please...

And when you do. Maybe you, me Sandra, Jenny and Grandpa Joe can sit by the lake and enjoy a nice bar of chocolate.