Career & Side Hustle Coaching For High Achievers

3 Career Struggles All People-Pleasers Will Face 

For a long time, I didn’t think of myself as a people pleaser; I thought of myself as a rule-follower, a “nice” person, a “hard worker” and “initiative-taker.” 

Basically, I used to think of myself as synonymous with a “people pleaser” but never thought about it as having negative connotations or consequences.

I just saw myself as a hard worker and someone who really “rose through the ranks” because of it. I gave that person’s pleasing side of me so much credit for my success without really evaluating the consequences.  

I never spoke back, but that also meant I never stood up for myself.

I always followed the rules, but never questioned them.

And anytime that I did something wrong, or disappointed myself, I would beat myself up more than anyone around me because of my own internal standards. 

This was especially prevalent when I was in my 20s and younger in my career because I didn’t really know how to manage this “people-pleasing” side of me. However, as I’ve grown in my late twenties and really evaluated what success means to me, I see that this has come with a lot of consequences that I’ve had to learn to manage.

So today I wanted to talk about the 3 career struggles all people pleasers face in their careers….let’s get started!


1. Taking On More Work To Prove Yourself

It has taken me literally years to get comfortable with the fact that I deserve to be where I am. In almost every single job I’ve ever worked at, I’ve often felt “lucky” to be there, and thus I always felt the need to prove myself. 

And because of that, I’ve always taken on more responsibilities. Now, under some circumstances, this type of strategy can work to develop your career. However, in my case more often than not it is just people taking advantage of those people pleasing nature and my high standards for work that I would do 2, sometimes 3 jobs….and only be paid for one. 

One of the consequences of this was also that I was scared to stand up for myself and create work-life boundaries, even when it was 100% within reason. 

I also think there is a hint of first-generation immigrant mindset sprinkled in there so I’m not going to completely blame my people pleasing nature for this one. Because my family came from a developing war-torn country, I have always felt a sense of gratefulness for my opportunities because this was above and beyond anything my parents had.


2. Being More Successful In Careers You Don’t Want 

As a high achiever, I know I could basically pursue any career path I want. And I don’t say that in an arrogant way, I say that in an honest way. 

Because I’m a hard worker and a people pleaser, I know I could work hard enough to achieve any career path. However, most of the career paths in the world don’t interest me.

But acknowledging that difference is sometimes harder than I think because I could be good at them if I wanted to be. The lines for this get blurry when I start working in a career path and getting good at the job to the point where I start getting promotions…but it’s not a career path I really want to be successful in. 

This has happened a few times, particularly because I have every quality required of a really good assistant. I’m organized, I’m a great people person, and I follow instructions really well. And I have no doubt I would make a fantastic executive assistant. For a few years, I was actually an assistant to politicians and I was really good at that job, but the more I learned about the job and the path, it just didn’t have the fulfillment I needed or utilized the skills I really wanted to develop and utilize. 

One of my clients recently also came to this realization as well. She was a good manager and would receive really good feedback about her management skills, but deep down she knew that’s not the job she wanted.

The thing about this is that when you are a people pleaser, you really have to take the time to also ask yourself what you truly want and how you define success. And extracting that can be more difficult than you anticipate because it’s not only about the career development piece, but also the execution. 

As a people pleaser, it can be easy to stay on certain paths because you don’t want to disappoint others, especially if they have given you certain opportunities and feedback. In my past career, I was actually getting promoted. My employer was also paying for me to get a university certification, and I didn’t want to let anyone down. So that people pleasing nature came out in different ways, not just in the career planning, but the career execution. 

And if this is something you need help with, I really invite you to book a free Career Clarity Call to really uncover what is holding you back in your career and how to achieve your dream by overcoming obstacles like people pleasing and the resulting consequences. 


3. Overwhelm and burnout. 

When you are a people-pleaser you will inevitably take more than you can chew off, not only when you feel like you have to prove yourself but also because you can’t say no. 

And this work will lead to more than just overwhelm, it will lead to burnout because of your internally high standards. As people pleasers, we thrive on helping others and get that dopamine kick every time we do a job above and beyond what was expected. Even though we don’t seek praise, we love the rush of obtaining perfection. 

This is not only unhealthy, but it’s also completely unsustainable. No one can keep up that type of pace of doing 2-3 jobs (I’ve been there, done that); the responsibilities of those roles are divided into 2-3 jobs for a reason…no one person should be doing them. 

Inevitably, this burnout will take a toll on your mental and physical health and even before it reaches that point, it tends to bleed into our personal lives. Trust me, I’ve been there too. I’m not proud to say I used to take the stress of my work out on the people around me, and when it came down to it, it was because I couldn’t advocate for myself. 

One of the most important things a people pleaser needs to do is really understand that having this habit of taking on more and more is not only a detriment to yourself, and your personal life, but also to your work. No one can do 2-3 jobs at 100% all the time sustainably. You reach a breaking point eventually and then the burnout actually impacts more than you

It can be so hard to separate ourselves from our ego as a people pleaser at work, but how self-important is to have everyone depend on you to the point that everything crashes a long with you? This is something I am actively working on and which is why I truly believe that you are not your career, you are more than that. And to be successful in your career, it’s important to get your fulfillment and sense of value from other sources so you can show in the best space for yourself and your work. This can be in the form of something intangible like throwing a surprise party for a friend or for your own career development like starting a side business alongside your full-time job.


The struggles of people-pleasing are not fixed overnight because, for a very long time, these habits and tendencies served us so well. That’s why I’m so passionate about helping women mid-way through their career, because yes you can keep this up in your twenties, but as you get older you learn that your career is not worth sacrificing yourself or your priorities. There is so much more to life, I promise. And again if you are looking to really take your career to the next level while creating true work-life balance so you can be the version of yourself for your career and your family, make sure to book a free Career Clarity Call to see if we would be the right fit to work together to achieve your dream career and balance!

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