Many years ago – another lifetime it sometimes seems – a friendship of more than a decade ended. Truthfully, it had been fading for some time by then. Still, it wasn’t me who pulled the plug when my friend took up with a married man. It was she who, underwhelmed with my underwhelm, said something like, “If you can’t be excited for me then I’m okay with ending our friendship.”

I had, quite unusually for me at that time, drawn a boundary. Instead of quietly going along with my friend’s new relationship, I expressed concern for where it might go for her, the likelihood of pain whether due to him ultimately not leaving his wife or her own guilt at her choice welling up in her; I knew her to cast current frustrations – like having been single longer than she wanted – as divine punishment for previous decisions that went against her religious faith.

She didn’t want my concerns or doubts. She wanted, understandably, unquestioning and joyful backing.

In one of the more extraordinary moments of my life, we met at a quiet bar neither of us had ever entered before. We lingered briefly over one beer each. After all this time, I can’t recall what it was that served as the conversational punctuation mark to our years of friendship.

We paid and walked to the parking lot. She had never been much on hugging and we didn’t hug then, either. We simply said goodbye and walked to our separate cars.

Though the contents of our final conversation are gone from my memory, what have stuck with me from that experience are two things:

  1. An appreciation for our calm and mutual agreement to dissolve our friendship. All other former-friendships in my life have either faded or exploded, and I often hold that experience up as an aspiration for those inevitable times when it becomes clear that a friendship has run its course.
  2. In the lead-up to my friend suggesting that we’d reached our friendship’s mortal edge, she said, “I guess I don’t know you as well as I thought I did.”

After all those years, her words stung. When I conveyed them, feeling confused and hurt, to my mom, she said, “Apparently she doesn’t.”

The secret and sneaky wish of the people pleaser is that we will ultimately be accepted as we are, for who we are. Yet, our path to achieving this aim is to contort ourselves into the shape we imagine each person will find most pleasing. Along the way, we bite our tongues bloody and eschew boundaries for our certainty that they will inevitably displease the other. We agree to all manner of things about which we feel anywhere from neutral to uncomfortable.

In our 11+ years of friendship, for example, I spent ungodly numbers of hours sitting quietly on this woman’s couch while she watched the soap opera that she recorded diligently each day onto VHS tapes.

In this way, we people pleasers make ourselves less visible in the misguided hope of being more visible. To hear her say that after so much time of saying yes to the soap operas, yes to the takeout junk dinners, yes to the occasional party with other parts of her social world where I was such a mismatch that I was once asked to leave and never return… after all of that, to hear that she didn’t know me as well as she thought was both true and painful.

I’ve made a lot of progress in my people pleasing ways since then – so much so that I’ve recently considered giving away the award ribbon-shaped keychain I bought for myself several years ago as an aspirational reminder. It reads, “Didn’t please everyone.” These big learnings always have more room to go, though. Forever and ever, amen.

Last week, I again met that growth edge when the need to set boundaries on three different fronts happened to coalesce on one day. Two were related to Rawz Coaching. I wrote the emails. I read them to Theresa. I sat on them for hours. I sent the first one and received back a relatively quick response that was entirely understanding and caring. This gave me the courage to send the second; I received back an even quicker, almost instantaneous, response that was a leaden door closing decisively on our relationship.

The third was related to a volunteer job when an interaction that should have lasted shy of an hour pushed past the timer while I reached out more and more to my shift supervisor who went to her peers as we all struggled with the increasingly aggressive insistence of the contact. After two and a half hours of interaction, I ended my shift a half-hour late, spent and doubting my ability to continue my commitment to the volunteer position.

To assert healthy boundaries requires a variety of skills that aren’t native to the people pleaser such as:

Tuning into ourselves, our feelings, our needs, our wants.

Letting this guide us as we communicate clearly, directly, and proactively.

Allowing for our limitations in choosing the outcome.

And then, of course, there’s navigating the feelings that arise when the outcome is anything other than compassionate acceptance. The self-doubt and sadness. The guilt and, all too often, shame.

It has taken me years to also engage with the positive feelings that arise like relief for no longer having to navigate the discomfort of an unspoken boundary being threatened or crossed and pride in myself for having done the best I could in that moment.

And I did. In all three of those scenarios, I did the best I could given my current abilities to tune into myself, communicate with thoughtful assertiveness, and accepting the limitations of my control.

That’s mighty nice to notice. As is noticing that where those positive feelings might have once felt to me like a lashed-together liferaft in a sea of self-punishment and doubt, it now feels like a well-built pier from which my feet dangle into that sea.

Soon, I’ll be able to pull my feet up and towel them off. Maybe, though, not today.

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