My Thoughts: #2 When setting boundaries feels unsafe—but you choose it anyway

This is part one of a two-part article on boundaries. You can read part one here: My Thoughts: What No One Tells You About Boundaries

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If you’ve read my previous article, you might have resonated with how setting boundaries isn’t as simple or straightforward as it’s often portrayed online. More often than not, our responses are shaped by past conditioning that taught us which needs were safe to express—and which weren’t.

Breaking the cycle isn’t impossible, but it also isn’t easy—especially when our nervous system interprets boundary-setting as a threat. That’s why it can feel so scary, even when we know it’s the right thing to do. In this follow-up, I’ve compiled some insights and suggestions, drawn from both my own journey and my clients’ experiences, to help you begin—and more importantly, to make it stick.

Recognising the pattern is the first step.

If you’re here because you’ve begun to recognise this pattern in yourself—let me offer you a gentle pat on the back. Awareness might sound simple, but for many, it can be incredibly hard to see, especially when the habit of self-abandonment has been normalised over time.

Many years ago, when my counsellor first suggested that I set firmer boundaries with stakeholders at work, I resisted. I told her, “There’s no one else to take over my workload. If I stop replying after hours, we might lose clients.” She gently asked, “And in exchange, what is at risk?” “My mental health... and my self-care,” I replied. And she pointed out the obvious “Are you sacrificing your own needs in order to meet someone else’s?”

That was the moment I realised—I wasn’t just allowing others to overstep my boundaries. I had been abandoning myself to prioritise their needs.

So if you’re still unsure whether you’ve been letting others cross your boundaries, try reflecting on these questions:

• What parts of myself am I putting aside to keep others comfortable?

• Do I often feel exhausted, resentful, or invisible after helping others?

• Have I said "yes" when I really wanted to say "no"?

Your honest answers may offer insight into where your boundaries are being tested—and where your healing might begin.

If you haven’t been practising boundaries, you’re likely used to seeing things from others’ perspectives—and you might not even know what your own needs are.

When I ask clients what they need or want, I’m often met with silence. Or they’ll say something like, “My father/mother/partner thinks I should…” That’s when I gently ask, “Yes, I can hear what they want. But how about you?”

The first step in asserting boundaries is actually figuring out what your needs and wants are. After all, how can we express a boundary if we don’t even know what it is?

Start by going about your life as usual, but with more intentional observation. Notice where you feel anger, resentment, or hurt—these are often signs from your psyche saying, “Hey, someone’s crossing a line.”

And for now, let go of the pressure to voice your boundaries out loud. We’ll take this one step at a time.

Start Small

Once you’ve gained some clarity around your needs, start practising with the person or situation that feels least intimidating.

For me, that meant telling a few of my closest friends that I had recently turned pescatarian and that I have a peanut intolerance. I had already assessed that these friends genuinely care about me and would want to respect my dietary choices.

But here’s the thing—when I was growing up, my father was visibly displeased when I tried going vegetarian. He told me I was making things difficult for the family. On top of that, one of my best friends mocked me when I opened up about it, saying “Siao ah” (which means “Are you crazy?”). So even though I now know my current friends wouldn’t react that way, my nervous system still flinches.

Our past experiences shape our nervous system’s understanding of what is “safe.” If you’ve been shamed or rejected for asserting your needs before, your body may associate similar situations with danger—even when your mind knows you’re okay now.

That’s why I suggest starting small. It’s a form of exposure therapy. Begin by speaking up in low-risk, safe, and supportive environments. This helps you slowly build confidence and, more importantly, teaches your nervous system that advocating for yourself can be safe.

Please don’t start with the most intimidating situations—like confronting someone unpredictable or where the stakes are high. That could re-traumatise you and reinforce the belief that asserting your boundaries is unsafe.

Let the small wins build your confidence—like tiny deposits into a safety bank within your psyche. Over time, those deposits add up and strengthen your capacity to face bigger, scarier things.

Even when someone respects your boundaries, it can still take time for them to honour them consistently

When I first began asserting mine, some people would be polite about it at first—they’d honour my request for a few days… and then slip back into old patterns. I remember venting to my counsellor, frustrated: “What’s the point? It takes so much effort for me to speak up, and things just go back to how they were.”

She gently reminded me that I had been accommodating others for so long, it simply wasn’t part of their habit to consider my needs. It wasn’t that they didn’t care—it was just unfamiliar to them. Like any new habit, it takes time (and sometimes gentle reminders) for others to adjust.

So if you're feeling discouraged, be patient. Change takes time. You’re not just creating a new boundary—you’re helping build a new equilibrium, one reminder at a time.

Forgive yourself if it didn’t come out the way you intended

When anger, resentment, and hurt have been building for years from allowing your boundaries to be crossed, your first attempts at expressing them might not come out the way you hoped.

I always intended to be calm, direct, and empathetic—but sometimes, it came out as a tantrum. I raised my voice. My tone became sharp, sarcastic, even hurtful. I’ve said things I wish I could take back, and I’ve hurt people I care about.

For a long time, I held deep shame for not being able to express myself “properly.” But over time, I came to realise: that kind of intense reaction doesn’t just come from nowhere. If something has been repressed for so long, how could I expect myself to be calm and measured the first time it finally spills out?

Your psyche is trying to protect you. It’s yearning to be seen and heard.

If you've hurt someone in the process, take responsibility—apologise with honesty and care. And then, forgive yourself. You’re learning. You’re growing. And that deserves compassion too.

Know that not everything will go your way

Setting boundaries—like any relationship dynamic—is a bit like a game of chess. You get to decide where your pieces go, but when it’s the other person’s turn, their move is up to them.

You can choose to speak up for yourself. But how the other person receives it—and what they choose to do with it—is out of your hands. You might be met with frustration, guilt-tripping, silence, or even the end of a relationship—whether it's with a family member, partner, friend, or job. That part, you cannot control.

What you can do is be mindful. Ask yourself: If they say no, what might I have to face? Is that something I can live with? And just as importantly: Am I giving in again and again to avoid discomfort—at the cost of building resentment, hurt, or burnout within myself?

There’s no perfect answer. I’m not here to tell you what’s right or wrong. What matters most is that your decision is a conscious one. If it is, then I respect it—no matter what you choose.

Don’t expect everything to be perfect

Everyone has their own needs—and sometimes, those needs will clash. Some of us may have more emotional or mental capacity than others at different times, which is why relationships naturally involve a lot of give and take. We offer more when others have less, and we lean on them when we’re the ones who need support.

There will be times when others cross our boundaries. And there will be times when we unknowingly cross theirs. It won’t ever be perfect—but we can always strive for balance. We can aim for the middle way, where both sides are seen and respected.

At the heart of it all, most of us want the same thing: to feel safe, valued, and connected. And even when we get it wrong, we can return to that intention—with compassion for ourselves and each other.

The Promised Land is real—but it might not look the way you expect

The promised land is real. But it doesn’t arrive quickly, and it doesn’t come without its shadows.

When you first start asserting your boundaries, it can feel terrifying—especially if you're surrounded by people who don’t have your best interests at heart. The pushback can be painful, even traumatising. Sometimes, the people you hoped would understand respond with blame or withdrawal. And that hurts.

It’s especially difficult when people leave—and make it seem like it’s your fault.

But here’s the truth: once the people who disregard your boundaries begin to fall away, the right ones will slowly fall into place. Still, this doesn’t happen overnight. There’s a period of filtering, shifting, and healing that may stir up past wounds you’ve avoided for a long time—because they were too painful to face.

In my own experience, it wasn’t a sudden transformation. Setting boundaries didn’t bring instant peace, like a rainbow after the rain. But gradually, clarity emerged. The skies weren’t always clear, but I learned to weather whatever came. I found strength in my ability to stay grounded—even in storms.

Today, setting boundaries remains a work in progress. I’ve gone through many rounds of letting go and recalibrating. I’ve learned to regulate myself when I feel triggered. I’ve found people who respect me, and my family has slowly come to understand my needs. I’ve also created distance from those who continue to disregard my worth.

It’s not perfect. But it’s real. And it’s worth it.

Seek a Counsellor

Of course, you can absolutely try to work through this on your own using the insights and suggestions above. But here’s why I often recommend seeking support from a counsellor:

• It’s easy to take the other person’s side – especially if you’ve been conditioned to do so. Sometimes it’s hard to even see your own patterns without someone gently reflecting them back to you.

• It can get messy and confusing – If you’ve rarely (or never) spoken up for yourself, it’s normal to feel overwhelmed. You might not know where to begin, how much is too much, or what a healthy boundary even looks like. Your nervous system may go into overdrive just thinking about asserting yourself, making it hard to think clearly or follow through.

• It might trigger old trauma – Setting boundaries can stir up painful memories or feelings from the past. Without the right support, you might find yourself retraumatised—and that can make it harder to pick yourself back up and try again.

A therapist can help you untangle the confusion, find your starting point, build a clearer picture, and offer support when things don’t go as planned.

Leave a comment if this resonated with you. Book a discovery call or session if you're ready to be supported on your journey toward empowerment—and the freedom that comes with learning to assert your boundaries.

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This is part one of a two-part article on boundaries. You can read part one here: My Thoughts: What No One Tells You About Boundaries

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Hi, I’m Jasmine—a counsellor and Reiki practitioner. If you’re ready to start working on your boundaries, or explore support for your healing and self-discovery journey, I’d be honoured to walk alongside you.

Let’s chat—scroll down to book a free discovery call.