The Before: My Life as a People-Pleasing Machine (And Why I Thought It Was Working)
Let’s be real: for 20 years of stand-up comedy, I was the human embodiment of "I’ll do it!" I’d say yes to every open mic slot, every "just one more" podcast, every friend’s "urgent" request at 2 a.m. while simultaneously working a 9-to-5 as a corporate lawyer (yes, I was that person who wore power suits to open mics). My internal monologue? “If I just do more, I’ll finally feel like I deserve to breathe.”
Here’s the thing nobody wants to say out loud: I treated my life like a hostile takeover. I was earning my worth through achievement. My metric for success wasn’t “Did I laugh today?” but “Did I avoid disapproval today?” I’d cancel my own therapy appointments to say yes to a client call. I’d down three espressos before a set to “power through” the anxiety that made my hands shake. I was a people-pleasing machine fueled by caffeine, panic, and the quiet terror that if I didn’t say yes, I’d be found out as a fraud.
And it worked. For a while. I got the corner office. I got the “Most Promising Associate” award. I got my mom’s approval (which I’d been chasing since I was 12, when she said, “You’re too sensitive for this world, Sheila”). But the cost? I’d wake up at 3 a.m. with my heart pounding, convinced I’d messed up something I hadn’t even done yet. I’d cancel a date because I was “too tired” (read: too anxious to risk someone noticing I wasn’t “perfect”). I’d laugh at my own jokes too hard on stage, just to prove I was “fine.”
Then came the year I turned 42. I was booked for a 7 a.m. court appearance, a 2 p.m. client meeting, and a 7 p.m. comedy show. I’d been surviving on cold brew and sheer will. At 6:30 a.m., I sat in my car outside the courthouse, paralyzed. I couldn’t move. I couldn’t breathe. I couldn’t even think about the case. I just sat there, tears streaming, realizing: I’d been hollowed out for years, and now I couldn’t even get out of the car.
I’d been in therapy for 15 years. I’d analyzed my childhood, my parents, my entire emotional DNA. But nothing clicked until I stumbled on The Courage to Be Disliked while scrolling through a bookstore’s “Self-Help for People Who Hate Self-Help” section. I was skeptical. “We create our own neuroses? Trauma isn’t a life sentence?” I’d spent decades building a narrative of being done to. This felt like someone handing me a bill for a restaurant I didn’t eat at.
The “Insulting” Part: Why Adlerian Psychology Made Me Want to Throw the Book
I know, I know. You’re thinking, “But Sheila, isn’t that just toxic positivity?” Here’s the thing nobody wants to say out loud: It’s not about ignoring pain. It’s about owning it. Adlerian psychology says: Your feelings aren’t caused by what happens to you—they’re caused by how you interpret it. So when my mom called to say, “You’re so quiet on the phone, are you sick?” I’d think, “She’s worried about me. I must be failing as a daughter.” But Adler says: “You chose to interpret her concern as judgment. You chose to feel unworthy.”
Oof. That felt like a personal attack. I’d spent years saying, “My childhood made me this way!” And here was a book saying, “Nope. You’re the one who’s been holding the remote control to your own brain.” I almost threw it in the trash.
The Exercise That Made Me Want to Scream (And Then Laugh)
But then I tried the book’s exercise: Imagine a conversation with someone who triggers you, and respond as if you’re free from their approval. I chose my mom. Not because she’s the worst—she’s just the one who’s been my emotional punching bag since I was a kid.
Her: “You’re not really a lawyer, are you? You just do comedy because it’s ‘safe’.” My old self: “No, Mom, I’m a real lawyer. I just also do comedy. It’s not ‘safe,’ it’s my thing.” (And then I’d apologize for being “defensive.”) My new self (in my head): “Mom, I hear you’re worried. But I’m not ‘just’ a comedian. I’m a lawyer who also does comedy. And I’m not asking for your approval—I’m telling you how I choose to live my life.”
I did this in my head for a week. Then, one Sunday, she called. “You’re not eating enough, Sheila. You look tired.” Old me: “Sorry, Mom, I’ve just been busy.” New me: “Mom, I’m not asking for your approval on my eating habits. I’m a grown woman who knows my body. I’m not asking you to worry about me.”
I didn’t yell. I didn’t cry. I just stated it. And the silence on the other end? It was liberating. Not because she agreed, but because I didn’t need her to.
Why This Isn’t About “Being Nice” (And the 3 Biggest Mistakes People Make)
Here’s the thing nobody tells you: Boundaries aren’t about making people like you. They’re about making you like yourself. I used to think, “If I set a boundary, I’ll seem rude.” But here’s what I learned: People-pleasing is the real rudeness. It’s rude to yourself. It’s rude to the people you’re actually trying to help.
Common mistake #1: Thinking boundaries = being a “jerk.” I used to say, “I can’t do that,” and then immediately add, “But I’m sorry!” No. You don’t owe people an apology for protecting your energy. Try: “I can’t take that on right now. I’m focusing on X.” (No “sorry.”)
Common mistake #2: Setting boundaries with people who won’t respect them. My mom still says, “You’re too quiet!” but now I just say, “I’m not asking for your opinion on my quietness.” Then I hang up. It’s not about changing her—it’s about not letting her drain me.
Common mistake #3: Thinking you “should” be able to do it all. I used to say, “I’ll just do it this one time,” to avoid saying no. Stop. The “one time” is the start of the cycle. “I’m not doing that.” Period.
Building My New Operating System (One Awkward Boundary at a Time)
This isn’t about being perfect. It’s about choosing. Now, when I feel that old urge to say yes to a gig I’m not ready for? I say: “I’m not doing that.” And I mean it. I’ve canceled 3 comedy shows this year because I needed to rest. My agent was furious. I said, “I’m not canceling because I’m lazy—I’m canceling because I’m not lazy. I’m choosing to be present.”
And it’s not just work. I’m a mom of twins. I used to say yes to every playdate, even when I was exhausted, because I thought “I’m a bad mom if I say no.” Now? I say: “We’re doing quiet time tonight. I’ll call you next week.” My twins still ask for playdates, but I’m modeling: “Your needs matter. Your energy matters.”
Practical step #1: Name the old pattern. When you feel that people-pleasing urge, say it out loud: “This is my old operating system. I’m choosing a new one.”
Practical step #2: Start small. Say no to one small thing this week. “I can’t grab coffee today.” “I’m not taking that project.” It’s like flexing a muscle you forgot you had.
Practical step #3: Forgive yourself when you slip. I said yes to a podcast last week. I felt awful. Then I remembered: This isn’t about being perfect. It’s about choosing to try again. So I texted the host: “I’m not doing that. I’m choosing to rest.” And I did rest.
The After: Not “Fixed,” But Finally Free
I’m still a high achiever. I still get booked for shows. But now? My success is intrinsic. I do comedy because it makes me feel alive—not because I’m trying to prove I’m “good enough.” I’m not “cured” of anxiety. I just don’t let it run my life anymore.
And the best part? My mom called me last week. “You seem… different,” she said. I didn’t say, “I’m sorry I’m not the same.” I said, “I’m me. And I’m good.”
She didn’t understand. But she listened.
That’s the shift. It’s not about making the world fit your old model. It’s about building a life that fits you. And yeah, it’s messy. I still cry when I say no to my mom. I still overbook myself sometimes. But now I know: My worth isn’t up for debate. It’s already mine.
So here’s my challenge to you: What’s one tiny boundary you can set this week? Not to be “better,” but to be free. Because you don’t have to earn your worth. You already have it.
— Sheila Bishop, laughing so I don't cry (and sometimes both)
— Tracy Carlson, saying the thing since 2018