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From Passive to Assertive Mindset - Challenge #3

Better Said Newsletter 003
Read time: 7 min
Topics covered: Assertive Communication, Setting Boundaries, Soft Skills

Welcome back to this week's exploration of effective communication. If you're new here, welcome! You may want to go back to the beginning and start there as it will give you some experience to reflect on in this article. Definitely not required but recommended.

Quick Reflection

  • Which of the 3 assertive techniques was most difficult for you?  

  • What was the most difficult aspect? (i.e. finding the right words, not wanting to sound too mean, justifying why this is important to you, not overexplaining?)  

  • Why?


Making personal changes and growing involves overcoming blockers, but many challenges in communication and assertiveness are common. 

People often believe their issues are unique, but adults can hide internal conflicts well. The concerns around assertive communication share 90% similar blockers. 

Common blockers for passive communicators include cultural influences (gender norms, people-pleasing), fears (conflict, rejection, past trauma), and self-prioritization challenges (placing others' comfort over their own).

This week’s challenge (45 min)

  1. Identify Personal Blockers  

  2. Explore Origins  

  3. Write Down the Findings  

  4. Acknowledge the Challenge of Change  

  5. Initiate Positive Change

Blockers in Mindset Changes

Whenever you are making a change and growing, you’ll run into blockers. In my experience, everyone thinks their circumstances and challenges are unique to them, that their co-workers and peers don’t experience the same issues to the level they do.

The truth is, adults are just very good at masking our internal conflict so it doesn’t appear on the outside.

Of the hundreds of clients I’ve met, their concerns with assertive communication fall into 2 categories (being too aggressive or too passive), and the blockers are 90% the same within those groups.

This doesn’t take away from your struggles, and it doesn’t mean that you don’t experience them to different levels, but it does mean that most of the blockers you face don’t have to be permanent. The clients I’ve worked with who are dedicated to making a change ALL find marked improvement within 3 months of working with me.

Let’s lay out all the blockers that passive communicators tend to have:

1. Cultural Influences

It's no secret that the culture we grow up in shapes our decisions as adults. We don't think about it regularly, mainly because we stay within our cultural norms. It's only when faced with a different societal perspective that we begin to question what has been normal to us our entire lives.

Cultural influences play out on a large scale. Take gender norms, for instance. Men are typically encouraged to embody traits of speaking out, bravery, and boldness from a young age. On the flip side, women are often instructed to be polite, kind, nice, and sweet. This encouragement often leads to prioritising harmony and others' feelings over our own.

It's not about being right or wrong; it simply shapes how we perceive ourselves internally.

The term "people-pleasing" applies to both men and women. This tendency often stems from parental influence, where certain behaviours are insisted upon. It could be as straightforward as hugging a family member even when you don't want to, just because it's the polite thing to do. This repeated reinforcement can create a habit of seeking approval and avoiding displeasing others, making it challenging to assert your boundaries.

Our parents teach us how to identify and set boundaries from a young age. If a parent tolerates discomfort from grandparents due to a cultural emphasis on respecting elders or avoiding conflict, it sets our expectations for boundaries. Again, the message is that others' feelings take precedence over our own, emphasising the importance of respect. 

There's an incredible therapist who delves into this concept. Many adults are now distancing themselves from their parents due to a lack of mutual respect. Parents may feel they should be tolerated because they never distanced themselves from their own parents. Regardless of your interest or connection to this concept, I highly recommend checking her out. Her name is Whitney, and she goes by SitWithWhit on Instagram.

2. Fears

You're probably familiar with the fight-or-flight response, where our primal instincts warn us of potential harm. Back in the day, this instinct shielded us from threats like bears or predators and prevented us from engaging in activities that could be fatally harmful, such as cliff jumping.

In the present day, our fear of predators and life-threatening situations has significantly diminished. However, this doesn't mean that the corresponding part of our brain has shut off. Instead, it now focuses on contemporary situations. When it comes to fears surrounding assertive communication and what might hinder you, the fear of conflict, rejection, or abandonment, along with past traumas, play a pivotal role.

The fear of conflict might manifest as concerns that asserting your boundaries or expressing dislikes could harm your relationships or result in a negative perception. I can relate to this worry, where being too assertive might make me appear insufficiently contributing to the team, leading to concerns about potential reprimands or even termination due to issues with our workplace dynamics.

This fear is intertwined with the dread of rejection or abandonment. The apprehension that expressing an idea in a meeting, not meeting the team's standards, could lead to rejection, making others lose hope in you, and consequently, feeling inadequate in front of peers, jeopardising your standing within the team.

All these fears are connected to past trauma or abuse. It's essential to note that abuse doesn't always have to be significant to impact our current behaviour. It could stem from a distant memory of someone, whose name you may not recall, shutting you down or making fun of you. Even if you logically understand the wrongness of their statement or recognize it was rooted in their pain, it doesn't prevent our fear-driven responses. I recently had a revelation that surprised me.

Despite being an outspoken, friendly, and, I like to think, well-liked person, I often find myself questioning my interactions with friends who aren't exceptionally close. I worry about saying the wrong thing, laughing too loudly, or doubting the authenticity of their friendliness and positive interactions with me. It's odd because it's been a long time since someone expressed dislike towards me. 

Yet, a lingering fear traces back to elementary school when, at the age of 12, I faced unexpected hostility. Looking back, the person was expressing hurt and rejection from another situation, entirely beyond my control. However, I bore the blame, internalising it into a persistent fear. Now, at 33, I still worry that positive interactions may be insincere, and that someone secretly harbours dislike for me. Understanding the origin of this thought process allows me to catch and dismiss these thoughts more easily, knowing their source.

3. Self-Prioritization

There's this prevailing notion in our societal mindset that individuals who lean towards passivity lack self-love, that they don't harbour affection for themselves, and that they need to cultivate self-love to find the courage to assert themselves. 

In my interactions with numerous individuals identifying as more passive, only a handful expressed a disliking for themselves as a person. More often than not, the individuals I worked with exuded a quiet pride about themselves. They didn't feel the need to boast to others about their accomplishments, but it didn't mean they weren't proud of what they achieved. They would gladly share stories of how they assisted someone or engaged in activities they genuinely enjoyed. So, I find that narrative to be somewhat misconstrued.

It's a positive quality because individuals who appreciate themselves tend to extend kindness to those around them. 

However, what I frequently observe in passive individuals is not a lack of self-like; rather, it's a tendency to deprioritize themselves. They are inherently giving, kind, and always seeking the best for others. 

Even if it entails some discomfort for them, they rationalise it by thinking, "I can handle it. It might not be enjoyable for me, but it's a minor inconvenience. I know it would benefit someone else, so why not?" 

Alternatively, they avoid causing discomfort to others and absorb it themselves. This is not to diminish the admirable nature of this trait; in fact, it aligns with my belief that our world needs more people willing to help and be generous.

So what’s the problem?

The main challenge I see here is a lack of self-prioritisation. Passive individuals often prioritise others' comfort over their own due to their resilience and ability to endure discomfort. However, this imbalance requires adjustment because both their discomfort and that of others are equally significant. Consistently prioritising another person's comfort over one's own is not sustainable.

It's essential to consider this from their perspective. If you perceive someone as kind and generous, assuming they can handle your discomfort without giving them the opportunity to do so is unfair. This behaviour is often rooted in ignorance, as people are generally unaware when they make others uncomfortable. Engaging in open conversations and expressing your feelings fosters mutual understanding.

It's possible that you are overestimating their discomfort while they may be underestimating yours. Honest dialogue and sharing more information can lead to alignment and viable solutions. Even if it means prioritising your discomfort, it promotes understanding, effort, and the best possible resolution. This perspective is about embracing challenges without regret and making intentional decisions.

One of the clients with whom I worked on these aspects started initiating more candid conversations both in the workplace and at home. This led to her receiving more support and assistance, both domestically and professionally. Despite feeling fatigued and managing a demanding workload, she felt acknowledged, and the burnout she had previously experienced dissipated. She found a deeper sense of fulfilment, and even when exhausted, she described a profound satisfaction.

This Week’s Challenge (45 min) 

As we conclude today, I encourage you to explore your personal blockers. 

  • What hinders your assertiveness? 

  • Could it be some of the factors mentioned earlier, or is it something else entirely? 

  • Why do these fears exist? How have cultural influences shaped you? 

  • Can you recall specific instances where external factors played a role?

Instead of merely contemplating, jot it down. Whether in bullet points, a poem, or a journal entry, putting it on paper helps you approach it objectively and reduces internalization.

Bear in mind that you've invested numerous years thinking, practicing, and engaging in communication a certain way. Now, as you embark on change, be prepared for the initial challenge. The first few attempts may feel unfamiliar, akin to wearing a new pair of shoes. Although you recognize they are the right fit and offer comfort with great arch support, breaking them in is necessary to make them feel like a second skin.

Remember, you're not just reading this newsletter for enjoyment (though I hope you found it a bit enjoyable). You're committing to change, and change requires action. So, go ahead, give it a shot, and see the positive impact these techniques can have on your communication and boundary-setting skills. Keep communicating effectively, protect your time, and embrace the positive change you're initiating!


Thanks for reading issue 003 of my weekly Better Said newsletter. For those of you who are new to my newsletter, Better Said, discusses the following three goals: (1) Elevating crucial soft skills, (2) Reaching career milestones, and (3) Creating ethical leadership.

Here’s how we can stay in touch:

1. You can find me on LinkedIn and on my website,  

2. If you are curious about working with me, you can book a free consultation where I will help you outline your goals and co-create a growth action plan with you whether or not we decide to work together.


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