Raise your hand if your parents or a high school guidance counselor ever told you that you can be whatever you want.  Anything at all. Just take your pick!

Awesome, right? What a lovely, encouraging message.  

Only it didn’t work out quite like that.  Only you weren’t told how to figure out what you want. You weren’t told that you are a highly sensitive person and that this should be a major factor when you consider your career options. And you also weren’t told…

  • how to fully explore all other sides of your personality
  • how to take into account all of your preferences and talents
  • how to separate your real wants from those voices in your head that were telling you what you should want
  • how to look for possibilities beyond that list of majors in that particular catalog
  • how it’s possible to enjoy your work and make a living
  • how it’s ok to want it all
  • how to get it all

So you didn’t get it quite right. Maybe you never really made a choice at all and just drifted into a job because of circumstances. Maybe you made the wrong choice because you didn’t have the right tools for choosing at the time. Maybe your choice was ok for a while, but not anymore…

Whatever happened, I’m guessing much of the above resonates with you, since you are reading this article. It sure resonates with me. Picture me here at my laptop eagerly raising my hand for all of it. 

When I finally came to the realization that I was terribly unhappy with where my own career choices had led me, I had no clue what to do. I had some vague ideas for alternatives, but I was terrified of making another wrong move. 

Now, I have learned a lot since those days, and in this article, I want to share with you what I know about making a career change that will lead you to work you are totally googly-eyes over. Of course, simply reading this one article will not get you your dream job. But the five steps I outline below will get you started on that path and I’ve also added some info on how coaching can be used along the way to help.



When you are unhappy at a job, the most obvious thing to do is to update your resume with your current skill set and work experience and start looking through job ads for other positions you might be qualified for. This will work just fine if your dream is to be using your current skill set and you just haven’t found the right environment for applying those skills yet. Let’s say you love your job as an accountant, but you are working in an open-plan office with an unreasonable boss, too much time pressure, and arrogant coworkers. Another job in the same or similar field might give you the change of environment you’ve been looking for.

But the thing is… If you are not excited about the actual tasks you are performing on a daily basis, you will never be fully satisfied. And by the way, it doesn’t matter if you are fantastic, mediocre, or terrible at those tasks – you will be miserable regardless. Just because you have acquired certain skills or managed to become good at something, doesn’t mean that is what is going to make you happy.

I happen to be really good at number crunching and I was paid a very comfortable salary to be a number cruncher. The only problem was that number crunching bored me to tears. So switching to a different number crunching job and expecting to like it would have been a bit like putting my broccoli on a different plate and expecting it to start tasting like chocolate.

To find work that you will actually enjoy doing, make yourself reconsider everything and start the career decision making process from scratch:

  • Pretend you are 18 again. Pretend you never got a degree in anything. Pretend you never had a real job. Your whole life is ahead of you. (And unless you are 99 years old, don’t forget that you actually DO still have a whole lot of life ahead of you!)
  • Completely ignore your current skill set for now.
  • Completely ignore your past work experience for now except as a guide for what you like and don’t like.
  • Completely ignore what the voices in your head think would be “sensible” or “reasonable” or “doable”.

HOW COACHING CAN HELP: If it’s hard for you to let go of the past and start fresh… If your mind is filled with doubts to the point that you can’t even let yourself consider the possibilities and imagine a different future, a coaching session can be a safe space to uncover the beliefs that are keeping you stuck and to work on replacing them with beliefs that will allow you to move forward.


Maybe you didn’t have the tools or the life experience to know who you were or what you really wanted when you were a teenager. And how could you? At age 18, most of us were struggling to decide whether to drink one more Mike’s Hard Lemonade and whether to hook up with that cute guy in Western Civ. It’s a bit much to ask an 18-year-old to really understand the ramifications of a career choice.

But take the second chance NOW to analyze the crap out of yourself. You already know that you are a highly sensitive person, but what else is there? Become intimately familiar with every aspect of your personality and temperament. Figure out what your natural strengths and weaknesses are. Be brutally honest with yourself. Forget about who you think you should be or who you think other people want you to be. Focus on who you actually are. The good, the bad, and the ugly parts of you all provide valuable insight into finding the best new career path for you.

HOW COACHING CAN HELP: I have a literal plethora of tools to help you with this step. 🙂 These tools range from simple value identification and passion finding exercises you can complete during a regular coaching session to formal assessments like the MBTI® and the Strong Interest Inventory®. Click here for the full list of self discovery tools available to you.


I think that the simple reason many of us end up in careers we don’t love is because we settle. We think it’s not possible to find work we love. We think we are not good enough. We think we are not supposed to love the work we do (duh, that’s why it’s called work!). We think we don’t deserve to love the work we do. We think it would be too hard to make a change.

But I’m going to ask you to stretch yourself. Let yourself dream. Let yourself want it all. The higher you set the bar, the better the outcome. Even if you only get 80% of “the all” that you want in the end, it will be much closer to your ideal than not letting yourself dream and not going after your dreams at all.

As a starting point, I would suggest that your dream career should meet at least the following criteria:

  • The work has to let you use your gifts as a highly sensitive person and the strengths of your personality type.
  • You have to be comfortable with the work environment. Even if you love the work itself, it’s hard to be satisfied if the people you work with, the commute to reach the work, or the setting in which you spend a majority of your waking hours stress you out.
  • The work has to be meaningful to you in some way.
  • You have to be able to make an income you feel comfortable with. Money doesn’t bring happiness, but constant worry over being able to meet your basic needs brings stress.

HOW COACHING CAN HELP: This is another step where self doubt causes many people to get stuck. Again, a coaching session can be a safe space to uncover the beliefs behind those doubts and to work on replacing them with beliefs that will allow you to take action and make your ideal vision a reality.


Most of us have done a whole lot of adjusting and compromising and settling to force ourselves to fit into a career. But to achieve career satisfaction, just the opposite needs to happen. You need to find work that fits YOU just as you are. And just because you haven’t encountered it yet, doesn’t mean it doesn’t exist. There are thousands of careers out there, many that you’ve probably never heard of.

Start collecting a list of potential careers that fit most or all of your criteria. Err on the side of including too many, rather than not enough at this point. Don’t rule careers out because there are some obstacles.

Once you are satisfied that you have explored all the possibilities, pick the best fit for you, taking all your criteria into account.

HOW COACHING CAN HELP: The coaching process can be helpful with both identifying career options as well as with choosing one to proceed with. Many HSPs find great benefit in taking assessments like the MBTI® and the Strong Interest Inventory® which allow you see actual job titles that people similar to you are satisfied with. As for making the final choice… Decision making can be extremely difficult, especially for highly sensitive people who like to process deeply and really think things through.  Sometimes decision making is so difficult that people get stuck and stop making progress toward their goals. If this sounds like you, we can talk through the issues in a coaching session or even use formal decision making tools to help you pick the best path forward. 


When you finally figure out what your dream career is, you’ll be on a happy high flying around in la-la-land clouds.

For a while.

Until the shit that is reality hits the fan and throws you back on the ground. Until you remember that there are all kinds of obstacles on the road between here and dream-career-country. There are fallen trees and big-ass rocks and police-check-points on that road. There are mortgages and kids to be fed and degree requirements. There are time constraints and judgmental mother-in-laws and will-powers that have gone missing. Thinking about it all hurts your brain and just makes you want to go to sleep. And it makes most people want to stop right there.

But guess what? You don’t have to. Every single one of those obstacles can be dealt with and crossed over in turn.

HOW COACHING CAN HELP: My goal as your career coach is not only to help you identify the career that will keep you excited to jump out of bed in the morning, but to make sure you feel confident and resourceful enough to actually make the change. In successive coaching sessions, we’ll address whatever is holding you back and formulate strategies to overcome any obstacles. You will also have the accountability and support to conquer the fears and doubts that keep you stuck in procrastination.


If you’d like support navigating the HSP career change process, please click the button below to schedule your free introductory session! We will talk about creating a coaching package that is tailored to your needs. Some of my clients start with me from zero, having no idea what they want to do. Others have already figured out at least some parts of what they want, but need support with making their vision a reality. So please know that you are welcome regardless of where you are in the process. 🙂 Your geographic location doesn’t matter either. My coaching services are location-independent with all sessions conducted online via Zoom.

About the Author

Hi, I'm Anni! I'm a life and career coach for stressed out highly sensitive people. My mission is to help you discover your true self and create a life you ACTUALLY like.

Related articles

3 Reasons Why HSPs End Up On The Wrong Career Path
5 Reasons Why HSPs Stay On The Wrong Career Path
Worst Jobs For The Highly Sensitive Person
Best Jobs For The Highly Sensitive Person
Upsides And Downsides of Self-Employment for Highly Sensitive People
7 Ways Self-Employment Helps Me Meet My HSP Needs
Schedule your free introductory session!

In this 30-minute Zoom-meeting, we'll work on clarifying your goals and discuss how coaching might help you reach them!