I still have the journal entry. It says, in striking black pen, “I wish I could say what I mean. If I can learn to say what I mean before I die, I will die a happy woman.”
I’d written it the morning after I’d been the recipient of unwanted advances at a bar. A stranger had engaged me in aggressive conversation, peppered in flirtation, and every so often slipped his bony hand around my waist. For 30 minutes I’d tolerated his behavior with a fake smile before feeling it was appropriate to escape to the bathroom.
I could’t bring myself to say “Thank you, but I’m not interested. ’’ I’d waited in silence, hoping the man would mind-read my discomfort and give me space. My stomach had churned with discomfort. The next morning, I took my pen and articulated what I saw as my Great Frontier in life: speaking up, resisting the impulse to people-please, and not settling for less than I deserved.
My tendency to people-please at the expense of my own wellbeing manifested in all areas of my life.
It was why I worked in a job that didn't reflect my values; why I felt emotionally isolated in my imbalanced relationships with friends, lovers, and colleagues; and why I relied on external distractions and addictions to numb myself to my emotional landscape. Sometimes, my people-pleasing manifested as mildly as staying too long in a conversation that bored me, or offering to help a friend when I didn’t have the time. Sometimes, it was as extreme as sleeping with someone I didn’t want to sleep with because I didn’t want to “hurt his feelings.”
I knew that my difficulty setting boundaries was largely a consequence of a culture that encourages women to be people-pleasing, accommodating, and self-sacrificial. As Harriet Lerner says in The Dance of Anger: “Our society cultivates guilt feelings in women such that many of us still feel guilty if we are anything less than an emotional service station to others.”
Though I understood the cultural roots of my behavior, I didn’t want my socialization to define me. I wanted to develop the capacity to speak up for myself. The less I heeded the wishes and warnings of my inner self, the more her cries went unheard - and the more her anger, instead of directed outward, became directed inward, at me.
I felt like I was constantly betraying myself, constantly designing my life around others’ desires. The result was a life that felt mediocre, underwhelming, and not quite my own.
Starting At Rock Bottom
My journey setting boundaries began when I hit a personal rock bottom. I went through a challenging break-up with a longterm partner and suddenly awoke to the reality that I’d always been the only person responsible for my happiness. When I was sad, anxious, or troubled, it was my responsibility to soothe myself. In order to heal, I had to become my own first priority and recover who I was.
I was so unaccustomed to meeting my own needs that, at first, the burden felt unbearable. But I was raw, stripped to my core, and in that rock bottom state, a survival instinct took hold of me - survival of my inner self. It was now or never.
It started slowly. Friends would invite me out and I would say no because “I was having a rough night.” Clients would ask me to reschedule calls and I would say I couldn’t because “Consistency in my schedule is critical right now.” Bit by bit, as if supported by a pair of training wheels, I made the decisions that felt right for me.
Once the acute phase of my heartbreak as over, I didn’t have a universally accepted “excuse” to say no: my training wheels were gone. The reason morphed from “I don’t want to because I’m grieving” to “I just don’t want to.”
At first, setting simple boundaries and speaking up for myself in mild situations felt as monumental as running a marathon.
One night, a friend made a rude comment about my sobriety - pressuring me to have a drink - and I, flush with anger, told him that sobriety was “hard enough as it was without having to deal with those insensitive comments,” a retort that might have come naturally to some. To me, it felt like I’d tossed a 300-pound boulder 30 feet. I immediately went home, crawled into bed, and sobbed. I felt panicky and guilty, like I’d done something wrong. I felt so awful for what I’d said that I went BACK to my friend and apologized an hour later! And later, after reflecting on the exchange and feeling more righteous in my stance, I went back again and redacted the apology.
Even that experience - which I’m chuckling about as I type this - was formative. It wasn’t a seamless example of boundary-setting, but it was an exercise that built the muscle within me. It put the “Speak Truth” option in the drop-down menu of ways I could respond to uncomfortable situations.
The more I set boundaries and spoke hard truths, I watched as my friends didn’t judge me, my lovers didn’t leave me, and my world didn’t crumble.
As a matter of fact, I felt empowered, strong, and deeply right. Suddenly, being the one responsible for my own happiness began to feel empowering.
Boundary-Setting In Intimate Relationships
Then came the greatest challenge of all: Speaking truth in my most intimate relationships with lovers and family members. Telling a stranger you don’t want to get coffee is one thing; telling a member of your family that you feel hurt when they do X is another.
This part of the process required a great deal of trust on my part. I had to trust that those closest to me would be receptive to my wanting what was best for myself. I also had to to trust that my relationships could weather the storm of change and disagreement.
Often, I referred back to this quote: “The only people who get upset about you setting boundaries are the ones who were benefiting from you having none” - Unknown
Over the course of many months, I terminated romantic relationships that weren’t meeting my needs; unpacked old childhood hurts with my parents; and told best friends and partners when their actions upset me. These difficult moments of truth rarely took the form of a single sentence; often, they were a conversation, or two, or three, over the phone or over coffee. After each conversation - even if it had gone rockily, with tears or with anger - I felt like a weight had lifted from my chest.
The hard truths I had never spoken had been stored in my body as physical stresses that weighed me down.
In some instances, my honesty prompted my loved ones to share their truth about my actions or behaviors. It’s never easy to hear how you’ve upset someone, but I was grateful for the opportunity to have a transparent conversation with those I loved. I knew the ultimate goal of our conversation was to build a stronger relationship founded on mutual trust and compassion.
Sometimes, after speaking a particularly challenging truth, I would have a similar experience to the one I described earlier: some panic, some tears, and a deep sense of guilt. In those moments, I called on my rational mind to remind myself that speaking up for myself was not only my right, but my duty to my inner self if I wanted to navigate this world as boldly and fully as possible.
It is a massive upheaval for the mind and heart, to uproot patterns in relationships that have been years in the making. The pain was a growing pain, and the more it hurt, the more I grew.
The Wide-Reaching Benefits of Boundary-Setting
This work is ongoing. It is never “done.” I still take a deep breath and give myself a mental pep talk before I say “I don’t agree”, or, “I feel hurt”, or, simply, “No.” But speaking my truth has become eons easier than it was when I wrote that fateful journal entry.
Becoming better at setting my own boundaries has made me more receptive to the boundaries of others. In the past, when loved ones told me that me they needed space, or that they wanted to postpone a plan, or that something I’d said upset them, I quickly internalized their feedback and responded accordingly - usually with anger or by being overly apologetic. I had unrealistic expectations and got offended when they didn’t sacrifice their own boundaries the way I would. In arguments, I would taut my self-sacrifice as an act of love, when in reality, it was anything but.
People set boundaries to protect their wellbeing. To challenge or disrespect another’s boundaries is to place your own desires above their wellbeing - something I’d never want to do to any friend or partner.
By learning to speak my truth, I’ve gained a sense of self-trust and empowerment. I’ve enhanced my relationships with friends, lovers, and family members, and feel more myself in those relationships than ever before.
The following five techniques were critical in my journey towards speaking my truth. I hope they’re helpful to you as you embark on this critical work.
Radical Transparency: When I first started this work, I used a radical transparency approach. Before anything came up with friends, family, or lovers, I would say: “I want you to know that I’ve been working on speaking my truth and setting boundaries. It’s still challenging for me, but having those difficult conversations is an investment in my wellbeing and my relationships.” This disclaimer paves a pathway for compassionate conversation.
Cheerleaders: If you’re anything like me, boundary-setting is going to be some of the most important - and most challenging - work you’ll ever do. I knew I would need additional support from loved ones. I told two close friends about my plan and let them know when I set a boundary that I was proud of. They understood how important this work was to me, cheered me on, and celebrated my successes.
Harriet Lerner’s The Dance of Intimacy: In my opinion, this book is the ultimate guide to setting boundaries and changing old habits of people-pleasing in intimate relationships. I read this book with a pen in hand, highlighting the passages that resonated with me (hint: almost all of them), and referred to it when I was having a difficult time in my practice. My most important takeaway from this book was the concept of relationships as a “dance.” When one partner changes deeply ingrained, years-deep habits, it’s natural for the other partner to attempt to restore things to the way they were. The key to creating long-lasting change is to hold firm to your boundaries even when it’s hard.
A Practice Buddy: I attribute a great deal of my growth in the boundary-setting department to a partner, Matt. When we met, he had just emerged from a break-up and was clear about his need for healthy space. Immediately, he was a person who communicated openly about his own boundaries and needs. His openness felt like the permission I needed to practice my own openness, which I did with gusto. We responded to each other’s boundaries and truths with compassion, patience, and curiosity. To this day, we have a deeply caring and communicative relationship that has helped me realize that radically honest relationships are not only possible, but preferable.
Journal: Track your successes. When you set a boundary, write it down. There will be days you struggle and falter, and in those moments it will be critical to reflect on all of the important work you’ve done so far.
Get these blog posts directly to your inbox by signing up for my monthly newsletter here.