How to Fit in at Work? What To Do When You Feel Like The Black Sheep of the Office

My client Jess logged onto our session beside herself. “I try so hard to stick to my values and ‘bring my whole self to work’. But I always feel at odds with the prevailing culture of ‘move fast and break things’ and ‘push harder and harder’.


I know I’m meant to be a leader and show other women that it’s possible to work in a more sustainable way, but being the black sheep can feel so draining”. 


I totally knew what she was talking about. As women in the workplace, it’s so common to feel at odds with a prevailing Patriarchal work environment, however that manifests. 

If you are feeling out of place and wondering how to fit in at work, know that you’re not alone. 


The desire to belong in our workplace is deeply ingrained in our DNA, a fundamental aspect of our human nature. However, the real challenge emerges when our desire to fit in pushes us to sacrifice our authentic selves. 


In this blog, we’re not just exploring the typical advice on how to fit in at work. Instead, we’re confronting the less discussed but crucial aspect of this dilemma. Let’s dive into this complex issue and redefine what it means to truly belong in a professional environment, both to ourselves and to our workplace.

When "How To Fit In At Work" Requires People Pleasing

The term gets thrown around a lot, so let’s first define people pleasing.


As defined by Choosing Therapy, “People-pleasing involves speaking and behaving to accommodate the emotional needs of others, typically to the detriment of your own well-being. Common signs of a people pleaser include poor boundaries, struggling to say ‘no,’ and constantly apologizing”​​. 


When we are struggling to know how to fit in a work, it’s easy to pursue likability and agreeability as a strategy to win favor and belong. But ultimately people pleasing always ends in your own resentment, and loneliness, making you feel even more isolated. True belonging is never possible when we betray ourselves and our own needs to meet the needs of others.

Belonging is a Human Need

All humans have the need for a sense of belonging. Belonging in the workplace leads to greater psychological safety, productivity, and engagement.


Research from Berkeley emphasizes, “Humans are psychologically wired to need to belong… having meaningful relationships and networks means others have your back, and can protect or support you when you most need”​​. Thus belonging and inclusion isn’t a ‘nice to have’, it’s a need to have in the workplace. It makes sense why we continue to ask yourselves about how to fit in at work.

The Masks We Wear at Work

Brené Brown, in her book “Braving the Wilderness,” states “True belonging doesn’t require you to change who you are; it requires you to be who you are”​​. This idea challenges the often-accepted narrative that we need to mold ourselves to fit in at work into preconceived notions of what is acceptable or expected within a professional setting.


After coaching over 5,000 women, I realized that there were 5 common masks or strategies that high achieving women take on in order to fit in and extract success at work.


You can take this quiz to find out what your unique mask is and how it’s specifically stealing your fulfillment and your true belonging. 


In reality, true belonging is about bringing your whole, authentic self to the table. It’s about shedding the mask that we often wear to meet external expectations and, instead, showing up as we truly are. This authenticity fosters deeper and more meaningful connection with our colleagues and creates a workplace environment that values diversity and individuality.


True belonging in the workplace doesn’t mean everyone agreeing or being the same; it means respecting and valuing the unique perspectives and backgrounds each person brings. This diversity of thought and experience is what drives innovation and creative problem-solving. It’s what makes a team not just functional, but exceptional.

how to fit in at work for corporate women

Confronting the Success Wound™

The need to fit in and the resulting people-pleasing behavior often stems from a term I have coined, known as the Success Wound™. This is a deep-rooted belief that our worthiness is tied to our achievements and how we are perceived in terms of success. It’s a conditioning that begins in childhood and often carries into our professional lives, driving us to adopt behaviors that align with external expectations rather than our True Selves.


From the early stages of our lives, we’re taught to value achievement as a measure of our worth. Whether it’s getting good grades, winning competitions, or being acknowledged for our talents, these milestones are often framed as the benchmarks of our value as individuals. This mindset, although it may initially drive us to excel, can also become a trap. It leads us to believe that our worth is something to be earned through success, rather than an inherent part of our being.


As we transition into our professional lives, this conditioning doesn’t just vanish; it transforms and adapts to the new environment. In the workplace, it manifests as a relentless pursuit of success – not just for personal or professional growth, but as a means to validate our existence. The Success Wound™ pushes us into a cycle of people-pleasing, where we continuously strive to meet or exceed external expectations, often at the cost of our own authenticity and well-being.


Healing the Success Wound™ is about breaking this cycle. It’s about redefining success on our own terms, recognizing that our worth is not contingent on our achievements or the accolades we receive. It’s about understanding that true success is multifaceted and deeply personal – it’s about inner fulfillment, authenticity, and alignment with our values.

Breaking the People-Pleasing (How to Fit in at Work) Cycle

If you find yourself people-pleasing while attempting to answer the question “how to fit in a work” or forsaking your values for belonging, here are three steps to break the cycle:

1. Recognize Your Patterns

Begin by closely monitoring your behavior in various work scenarios. For example, during a team meeting, do you find yourself agreeing to tasks that overload your schedule just because you don’t want to disappoint your colleagues? Or perhaps in one-on-ones with your boss, do you notice that you’re reluctant to share your true opinions on a project? Keeping a journal can be incredibly helpful here. Every time you notice a people-pleasing tendency, write it down. This record will help you identify patterns and triggers, making it easier to address them.

2. Set Healthy Boundaries

Once you’re aware of your people-pleasing habits, the next step is to establish boundaries. Let’s say your colleague often asks for help with their tasks at the last minute, causing you to work late. Setting a boundary could be as simple as saying, “I’m happy to help when I can, but I need to be informed by midday if you require my assistance, so I can manage my workload effectively.” This approach respects both your time and your colleague’s needs. Remember, setting boundaries is not about being uncooperative; it’s about respecting your limits and communicating them clearly.

3. Self-Validation

This step involves internalizing your worth and not basing it solely on external achievements or validation. For instance, after successfully completing a project, instead of waiting for praise from your boss or peers, take a moment to acknowledge your hard work and skill. Say to yourself, “I did a great job organizing and executing this project. I am proud of my dedication and creativity.” This practice of self-validation helps shift your mindset from seeking external approval to appreciating your intrinsic qualities and contributions.

4. Take the Quiz for Deeper Insights

As a practical step towards breaking the people-pleasing cycle, I encourage you to take the “Why You’re Unfulfilled According to Your Personality Type” quiz. 


This quiz is designed to offer you deeper insights into your professional personality and how it aligns with your current work environment. By understanding your unique personality type, you can gain clarity on why certain situations at work might trigger your people-pleasing tendencies. 


The quiz results will provide you with tailored recommendations to help you create more fulfillment and meaning in your career. It’s an effective tool for self-reflection and can guide you in making informed decisions about your professional journey. 


​​1.  People Pleaser: Definition, Signs, & How to Stop. (2023, December 14). Choosing Therapy.

​​2.  Belonging is a fundamental human need: Why it’s lacking at work & how to enhance it. (2022, July 25). Berkeley.

​​3. Brown, Brené. Braving the Wilderness: The Quest for True Belonging and the Courage to Stand Alone.