The Bow Wasn’t Big Enough

Issue #23

By Debbie Lawrence

Read Time: 7 minutes

I am a people pleaser in recovery.

Before I was a hard core people pleaser and it looked like this. I was in a leadership role, and November through January was one of our busiest periods of the year. Early one December, my boss called me into her office and asked for a favour. Her sister had a large memory trunk built for her daughter, a Christmas surprise, and she wanted something hand-painted on top like a Christmas scene along with a big bow.

I was an avid tole painter and my boss knew it. She told me there wasn’t anyone else she could imagine asking to take this on but me. She also said that of all people, I “could pull a rabbit out of a hat” given it was mere weeks from Christmas Day.

I hesitated. I told her I had a lot on my plate, that it was the holidays, and there were a hundred things already stacked up. But I didn’t say the word “no”.

“Well,” she said, “why don’t I just have the trunk delivered to your house and you can take a look at it?”

You know what happens next. That trunk landed in the middle of my living room, because that was the only open space I had. “Just size it up,” she said. “If you can’t do it, we’ll come and pick it up.”

Nobody ever came to pick it up until close to Christmas Eve.

I designed and painted the top of a 4-foot-wide, 3-foot-tall barrel-shaped trunk lid, night after night, into the early hours of the morning, for weeks on top of everything else that month. When her sister finally came to see it, she looked at the hand-painted bow and said, “I hate to ask, but could you maybe make it bigger?”

I was already neck-deep into this commitment so saying no was not an option I felt I could entertain and reworking the bow required another full night of painting.

I remember being tired and cranky and resentful the whole way through. There was absolutely no joy in it. And the only person I blame for that entire episode is me. My boss had positional power over me, sure, but I was in a leadership role and I could (and should) have said no.

The pattern revealed

There is a silver lining here, a gift of sorts, as that trunk was the beginning of a turning point for me. Over the holidays I decided I was never going to put myself in that position again.

Looking back I could see how I thought I was being nice and kind and helpful. What I was really doing was avoiding an uncomfortable conversation that resulted in living through a miserable month instead.

I’ve heard it said that people pleasers can’t be trusted, because they aren’t being direct and honest with you. The first time I heard that, I couldn’t argue with it and that was uncomfortable to admit to myself.

If you genuinely want to do something, believe in it, and know you’re the right person for it, that’s not people-pleasing. That’s just doing the right thing. The trunk was never that. The trunk was me saying yes so I wouldn’t have to sit in the discomfort of saying no to my boss during our busiest season.

Why smart women do this

I’ve watched a lot of capable women who lead say yes the same way I said yes to that trunk. What tends to be underneath it is any number of things.

Worry starts to feel like loyalty. I’ve talked about this angle before in a different context and here it shows up again. You tell yourself that if you stop worrying about disappointing someone, it feels like you’re saying their feelings don’t matter so the worry keeps running, as proof you still care.

Saying yes feels safer than finding out what happens if you say no. Most of us have never tested this, which is why we’re people pleasers. We just assume the relationship can’t survive our honesty, so we tell ourselves we’re protecting it by hiding or suppressing what we really think.

Being asked feels like being chosen. I know this one really, really well. My boss told me there wasn’t anyone else she could ask. That line did more work on me than the trunk itself as flattery is a very effective delivery system for an unreasonable request.

And underneath all of it we see how time and again people pleasers default so quickly to saying yes. There’s often no pause between the ask and the answer and without that pause, all you’re doing is reacting rather than making a thoughtful decision.

What building trust requires

If you want to build trusting relationships as a woman who leads, you have to be willing not to people please. That starts with being able to say no.

A client of mine who was invited to join a panel discussion at a business association event ran straight into this. The audience wasn’t her primary sector but the friend organizing it was someone she genuinely cared about, and she’d also been offered a 15-minute solo presentation as part of the event. Fortunately, the request came in a text message and my client had done enough work with me that she immediately flagged her tendency to default to a quick yes. Wanting to disrupt this pattern, she reached out for support.

When we broke down what saying yes would cost her, we started with the reality that public speaking wasn’t her strength to begin with. She’d need real time to research an audience she didn’t know well and she’d be away from her business for the better part of two days once travel and the full conference attendance were factored in.

The opportunity cost to her business was bigger than the opportunity loss of skipping the event. That became obvious once we quantified what saying yes would mean and put it on paper. The only thing left was the emotional cost of potentially disappointing her friend.

She said no. Here’s roughly how she approached it: “I’m so touched you thought of me. I know you want this event to be the best it’s ever been, and I’ve decided to decline. I’m confident you’ll find someone who’s a better fit for this sector, and I know it’s going to go well because you’re the one running it.”

Her friend’s response was to thank her. She added, “I didn’t want to decide for you, which is why I asked. I genuinely respect your decision.”

That was it. My client told me afterward that the old version of her would have said yes, resented every hour of prep, and driven home from the event ruminating about why she keeps doing this to herself. Instead, she said no and found out the friendship was exactly as solid as it looked.

The sequence that works

When a request lands, don’t answer right away. Instead, buy yourself some time. “Let me check my calendar and get back to you by tomorrow morning” works wonders. So does asking to put someone on hold for a minute during a call so you can refrain from giving a knee jerk response you might later regret. The point isn’t the delay itself. It’s the space it creates between the ask and your answer.

Use that space to reflect on two questions. Do I actually want to do this, or believe in it enough to be the one who does it? And if I say yes to this, what am I saying no to? The reverse question works just as well: if I say no, what am I saying yes to?

Then decide, and say it directly. Not “I’ll try” or “let me see what I can do.” Make it a clear yes, a clear no, or a real counterproposal.

What I do differently now

When I notice myself starting to say yes before I’ve thought about it, I stop and ask myself (ideally out loud if I’m in a space by myself): Debbie, do you really, really want to do this? I’ve even learned to pause, close my eyes, and just check with my nervous system. It always has the most honest answer for me, and with practice and discipline I’ve learned to listen to it.

If the honest answer is no, I say no. I don’t dress it up with six reasons, and I don’t over-apologize. I’ve learned that a clean no, delivered with warmth, does far less damage to a relationship than a resentful yes ever does.

I still feel the pull of flattery. I still notice the instinct to say yes so fast it beats my own judgment to the punch. The difference now is I catch it before I answer, not three weeks in, painting a bigger bow at midnight.

Your turn

The next time someone asks you for something this week, big or small, don’t answer in the moment. Buy yourself an hour, or a day. Then ask yourself what you’re really saying yes to, and what you’d be saying no to instead.

Comment below and tell me: what’s the trunk sitting in your living room right now, the thing you said yes to that you’re already resenting? I want to know what it is.

I read and reply to every response. And I love hearing from you.

P.S. You can also listen to this issue on The Compassionate Leader School podcast episode, which drops the same day on Apple Podcasts, Spotify, and all major platforms. Click here to explore all the episodes.