Career & Side Hustle Coaching For High Achievers

4 Hidden Ways You’re Sabotaging Your Own Career

Self-Sabotage is the obstacle that we least expect in our careers. Because doesn’t it sound so contradictory? Why would we sabotage our own career?

When we think about career development, it’s really easy to think that it is only influenced by external factors like what the job market looks like, if there are promotional opportunities at work, how supportive your team/manager or work environment is like, but sometimes all of these things can work out and you still don’t reach your career goals.

When it comes to personal growth, it’s important to understand that a part of this behaviour is because your brain and body are trying to serve you, it is trying to keep you safe. 

Self-sabotage is your career can stem from a lot of reasons, but at its core, it’s when your internal narrative regarding career goals and career actions are in conflict. And this conflict creates a tension that causes self-doubt, procrastination, impostor syndrome and a host of other feelings to stop acting in a way that achieves our career goals. 

So if you are a high achiever, who has always been used to being successful in school but are struggling to apply it in your career, then these are 5 ways you might be self-sabotaging your own career: 


1) Pressuring Yourself To Choose “The Perfect Career” and Have “The Perfect Plan”

I am a firm believer that you are not your career. This is one of the first things I tell my clients whenever they get stuck in their career direction and choices. 

One of the most common self-sabotaging behaviours in career development is not choosing a career path or choosing to change it because of fear of failure and fear of disappointment. 

Fear of failure and disappointment is self-preservation and it’s your brain and body trying to keep you safe. 

However, when you are looking to choose a career path, you have to remember that a dream career can and should not be a singular path for the rest of your life. Your career path will change because your life priorities and circumstances will change and once you release yourself of this pressure, it’s easier to make a decision. 

Furthermore, as a high achiever, it’s important to remember that you will excel at anything you work hard at and that hard work has been the biggest factor of your success. As high achievers it can feel tempting to think that gifts are “natural” but if you continue with that belief, you will self-sabotage yourself when choosing a career because you aren’t a “natural” at it. 


2) Not Practicing Your Job Search Skills (Including Rejection!) 

Job search is a skill all in itself. Not only the tangible skills but also the rejection process. 

Many high achievers are not used to the rejection, because it wasn’t normal. We strived for excellence all our lives so we didn’t have to practice the feeling of “not being good enough” which is how many people misinterpret the job search process. 

When you get rejected from a job search, there are so many factors involved behind the scenes. You could have been a great candidate, but they may have been looking for something slightly different. 

…..Or one person on the hiring team might have really wanted to hire you, but the team decided on something different.  

…..Or there may have just been someone who was so completely overqualified that they decided to move in a different direction.

,…Or, you might have been the perfect candidate but didn’t market or present yourself in the best way for the position. 

There are so many reasons that you might not have gotten a job. This was a really interesting conversation I recently had with my fellow Career Coach Amber Chow from Crossroads Surrey who sees a lot of the same things. However, learning to separate yourself from the job search from your sense of worth is so important. Because if you know you would have been perfect for the role, but didn’t get it, it might discourage you from applying for more jobs. 

Fear of wasted effort is a huge self-sabotaging habit for high achievers because we don’t want to be discouraged. If we apply for many jobs and no one gives us an offer, it can be easy to interpret that as “we are not good enough” which is a fear we don’t want to face. 

This is something I see a lot in my clients so if building a personal, marketable personal brand, developing your job search skills, and developing the personal growth skills to stop self-sabotaging in your career, make sure to book a free discovery call for my 1:1 coaching program! 


3) Not Healing From Past Career Trauma

Self-sabotage happens when your subconscious starts interfering with your rational, conscious mind.

And as high achievers, we have very high standards for our work so when it doesn’t produce the result we want, we blame ourselves. It might not be so apparent at first, but this can be something severely holding you back and something I really uncover with my clients. 

Without knowing it, there are many career experiences that have shaped my clients and how they proceed with their careers. For example: One of my past clients was extremely hesitant to apply for jobs she didn’t feel qualified for or list herself as an expert in software she knew really well because of a past boss and said to her face that she didn’t have what it takes to be successful in a certain position. 

Not only was that experience really traumatizing but because she subconsciously believed it, it severely impacted her job search, confidence, and how she marketed herself because she kept self-sabotaging herself.  Instead we worked to uncover the beliefs about that situation, namely that this was not a very good boss and this information was not valid. I really dive into my clients on how to transform our beliefs, including how we view our past experiences, and that’s why if you are truly looking to advance in your career, it can be so helpful to work with a coach to help uncover these past beliefs. 

Blaming yourself is a huge habit of self-sabotage because it’s something we do in our mind and if we believe it enough, it can become our reality. 


4) Overthinking What Other People *Might* Think

As a high achiever, it’s extremely likely that you are also an over-thinker.

And as an over-thinker, it’s easy to get into analysis paralysis in decision making, especially when it comes to situations we can’t control like when we are around other people. 

Self-sabotage in your career can also look like letting your fear of what other people think or how other people might act stop you from taking actions like speaking up in a meeting, negotiating your value, applying for a job, or even starting a side business alongside your career

These are all things I help my clients with because this is something I also really struggled with. I can so easily go into the worst case scenario of everything, and 99.99% of the time it doesn’t turn out as badly as I think in my head. Even when I say something embarrassing or applied for a promotion at work that everyone knew I was applying for and didn’t get,…the end result has never been that bad. Most of the time, the consequences were higher when I didn’t speak up at a meeting, negotiate, apply for a job I felt unqualified for or start my side business. 

Feeling like “I can’t control this situation so I’m not going to take action” is one of the worst self-sabotaging habits that high achievers can make because as perfectionists, we excel at so much and have so much contributed….but are holding ourselves back because of what *might* happen.


One of the biggest mistakes I see high achievers make is they solely rely on the employer for their career development and the job search skills we were taught in high school. However, career development is an ongoing process and it’s important to catch ourselves in these self-sabotaging habits in order to ensure we are not letting our past beliefs from our subconscious affect the future trajectory of our career. 

Lastly, if you are ready to stop these self-sabotaging habits and take control of your career make sure to book a discovery call for 1:1 coaching!

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