People-Pleasing, Perfectionism, and Ten Reasons to Reschool

I’ve been drafting an official project proposal for Reschool Yourself bit by bit for months now, and intensively for the last week. As hard as I’ve worked, I’ve been unable to craft my countless notes into a cohesive, inspiring proposal. The very reason it’s taken me so long to craft a full project proposal is evidence for why I’m reschooling myself in the first place.

I have invested hours and hours detailing measurable goals and outcomes, doing research to support my arguments, and shaping the proposal into the format that most funders require. The result? Writer’s block in the attempt to communicate my ideas perfectly. Several drafts of lifeless rhetoric devoid of the passion that fuels this project. Exasperation with my inability to speak from the heart when I know I’ll be evaluated. School has trained me so well that I can’t stop behaving like an overachieving student even when it doesn’t serve me. And in adulthood, it doesn’t serve me very often at all.

In fact, the two qualities that were keys to my success in school have limited my success as an adult: people-pleasing and perfectionism.


Early in childhood, I learned to sense what people – especially authority figures – wanted from me, and that I would be rewarded for giving it to them. Now, as an adult, the rewards for people-pleasing aren’t so great. I often say yes to commitments just because I’d feel guilty saying no. I regularly sacrifice my own well-being for the sake of others, a story shared by many fellow nonprofiteers and educators. I unconsciously seek a “Wow” factor in the things that I do to replicate the affirmation that I got in school.

I know that I could be more effective, and generally happier, if I could just determine what I wanted to do, and then do it. It sounds simple, but after spending around 20,000 hours* in school doing what was expected of me, I’m out of touch with what I actually want to do.

* A very rough estimate of time I’ve spent in school from kindergarten through college, based on an 180-day average school year during K-12 and a quarter system in college.


The need to do everything perfectly, or not at all, is paralyzing. I have a hard time making decisions, small and large: what to order on a restaurant menu, or whether to go to grad school. I don’t want to make the wrong choice, so I avoid making any choice at all. If taking action requires risking failure or rejection—as with an application, assessment, or interview—I freeze up.

Accustomed to following a clearly defined set of guidelines, I also have trouble creating my own boundaries and structure. As a student, I learned to master the school game by closely adhering to its rules: do your assignments, and don’t make any trouble. As an adult, when it’s up to me to make up the rules myself, I tend to spin my wheels for months, not knowing where to start. When I finally do accomplish a task I’ve been delaying, I often berate myself with “You should have done this a long time ago,” instead of congratulating myself. Consequently, I feel disappointed in or frustrated with myself literally most of the time. As my own harshest critic, I simply can’t win.

I’m reschooling myself this year in order to break through people-pleasing and perfectionism, to be more effective and simply enjoy life more. These are ten things that I’d like to be able to do:

1. Infuse a sense of fun or play into every activity, remembering that most matters really aren’t all that serious.

2. Set myself up for success every day with a realistic number of achievable goals.

3. Do things for enjoyment instead of for self-improvement.

4. Welcome mistakes, big and small, as a key part of the learning process.

5. Make decisions easily, confident that I can change direction if something doesn’t work out.

6. Meet my needs for sleep, exercise, nutrition, and relaxation before doing anything else.

7. Erase “I should” from my vocabulary and replace it with “I could” or “I’d like to.”

8. Be fully present and focused on the activity at hand, knowing that it’s exactly what I want to be doing at the time.

9. Take more risks and have more adventures.

10. Be as patient and compassionate with myself as I am with other people.

The most important of these is the last one: learning to treat myself as I do others, sort of like the Golden Rule in reverse. In Eat, Pray, Love, Elizabeth Gilbert describes a time when she rushed into an elevator, mistook her own reflection for someone she knew, and excitedly stepped forward to embrace that person before realizing her mistake. Later that night, she wrote down a reminder to herself: Never forget that once upon a time, in an unguarded moment, you recognized yourself as a friend.

That passage has stayed with me because I want, more than anything, to recognize myself as a friend. And come June, after an intensive year of reschooling, I hope to be able to say that I do.

In future posts, I’ll describe how I developed people-pleasing and perfectionism in school, and what I’m doing to reschool myself.


Your Two Cents: Leave a Comment

How have people-pleasing and perfectionism affected you? What have you done to change these things?

Comments (8)

  1. djschwin

    One time I was riding down an escalator and caught my reflection in the mirrored glass and thought, “That guy looks pretty cool” for a sec before I realized it was me.

    The empowerment of creating our own structure and boundaries is something I struggle with every day. Your ten points are great reminders to me as I try to balance my work with having a good time, and hopefully make the two converge as much as possible.

  2. Ben Cannon

    “Never forget that once upon a time, in an unguarded moment, you recognized yourself as a friend.” – wow, powerful stuff.

    “I have invested hours and hours detailing measurable goals and outcomes, doing research to support my arguments, and shaping the proposal into the format that most funders require. The result? Writer’s block in the attempt to communicate my ideas perfectly.”

    I’ve struggled with this constantly myself; in a way perfectionism has always been the single biggest thing holding me back, but also one of the strongest assets I have (if I could just learn to control it like a lightswitch 😉 I’m making baby steps… but as I sit here working on the new website for our oct 1 launch myself (which I vowed I’d never do again) I realize I may have furthur to go than I thought!

    Melia, I had a thought throughout reading this entire post and I thought I’d share it with you: the more you let go of what reschoolyourself ‘should be’ and write about what it ‘is becoming’, the more I for one am enjoying it. (and I think it’s getting better 🙂

  3. carol

    one thing that I’ve been thinking about is how some decisions don’t matter. like, if I wear this dress or that one, order this food or that one — it doesn’t matter. I’ll have another opportunity to dress up; I’ll eat again. Thinking like this really frees me from the decision of having to make the perfect choice for a rather meaningless and temporary decision.

  4. Melia

    Just so everyone knows, Darren’s story is true. I aspire to have such a crush on myself.

    Ben, wouldn’t it be great if you could be a perfectionist only when it served you? Yes, I’ve definitely had some revelations lately about creating expectations about what Reschool Yourself should be, and I’m dedicated to just letting it unfold as I’d hoped I would from the beginning.

    Carol, I thought of you when deciding what to eat at an Italian restaurant the other night. Tuna melt or turkey & avocado? I like to tell myself, “This is not a cosmic crisis.”

  5. Margaret

    “Tuna melt or turkey and avocaco? Ohhh, nooooo!” lol.

  6. Melia

    Ohhhh, nooooo is right! I swear that I use that phrase at least ten times a day, still.

  7. Devi

    Dear Melia….i found your blog accidentally….and gosh, most of the thing you posted here are soo true….like your blog so much…

  8. Melia

    Hi Devi, thanks for the sweet note! I’m glad to hear that the blog resonates with you.


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