3 Steps to Defining Your Dream Job

Dream Job Cartoon

If you are like most people, you probably get asked every once in a while what your dream job is. For some, it’s an easy answer. For some, it doesn’t exist because they are always content with whatever they are doing at the moment. And for others, you aren’t quite sure what it is but you definitely know it’s not what you are doing now.

If the latter describes your situation, then I have three easy steps to help you define your dream job. But before I start, let me share this quick note: I find it easier to help people define their dream job when they allow themselves to think outside of a specific career or position. What in the world does that mean? Well, instead of thinking in terms of your dream job being something like a veterinarian or school teacher or accountant or CFO, think of it in terms of the aspects of a job that make it your dream. For instance, working behind the scenes vs. having front line exposure to customers, working for a company with a social cause vs. one that is transactional in nature, working at a desk vs. being out in the community, etc. Understanding what makes a job your dream job will open you up to possibilities you may not have even known existed.

With this in mind, here are the three steps.

  1. Assess your work history.

The first thing I do with my clients is to engage in a discussion where we cover job roles they have had in the past, specific skills sets, and desires for their future. This can easily be done by starting with the first job you ever had and ask yourself these types of questions:

  • What did I love about this job? (Did it challenge you intellectually, did you learn new things, did you have an involved supervisor, was your supervisor hands-off, was it collaborative, did you work with really cool people, did you love the office space, did you love its predictability, did you love its flexibility?) You get the point. It’s more about the aspects of the job rather than the actual functional role you had – although that can’t be completely ignored either.
  • What did I dislike about this job or what could have made me like this job more? Again, think along the same lines as the previous question. (Was the commute too long, did you desire more communication, would you have rather worked completely by yourself instead of on a team?)
  • What were the tasks I liked to do?
  • What were the tasks I was good at?

After completing these questions for your first job, work your way through each role to your present position. This should give you a pretty good list of your likes and dislikes. And, don’t forget to include any volunteer work you do. How you choose to volunteer your time will shed additional light on the things that matter most to you.

As you are going through the history of your job roles, also spend time analyzing when and where you have felt in alignment with your career, where you have felt out of alignment, and what was going on during each of those times to make you feel that way. This is also a good indicator of what really matters to you.

2. Visualize your dream job.

Pretend you are being interviewed by a reporter doing a story on people who have successfully attained their dream job and they want to include you in their article. They begin to ask a series of questions that go something like this:

  • I understand you have the most amazing office. Describe it to me.
  • Describe your ideal day to me.
  • It sounds like you work with some really great people. Tell me about them. (Think of your ideal co-workers, customers, employees, boss, etc.)
  • I’ve heard that you are working on some very interesting and exciting projects right now. Why do you think you enjoy this type of work?

Note: Don’t filter or put any restrictions on your answers. Allow yourself the freedom to really dream – even if some of it doesn’t feel realistic or feasible.

Answering these questions can be pretty enlightening. Take a look at your office description. Is it in a large corporate building or in a house? Is it downtown or secluded? What is the décor? Where does your desk sit and what is your view? These questions will give you a clue as to the type of environment you prefer to work in. Just as the third question will give you a clue to the type of people you want surrounding you. Or, maybe there aren’t any people surrounding you!

Close inspection of this list will start to shed light on the intangibles that are important to you so that you can be mindful of this ideal when evaluating or creating your dream job.

3. Develop a litmus test.

After completing these two exercises, start to prioritize those things that create your ideal or dream job and use the information to develop a litmus test for determining future job openings to pursue or consider. You will actually walk away with a check list against which all future job opportunities, whether they already exist or you decide to create, will be measured.

Usually my clients who have been in the workforce for a while can get through these exercises fairly easily – especially once they give themselves permission to dream. Those who are newer to the workforce don’t have as much experience to draw their likes and dislikes upon so we try to find other life experiences that can be used.

While these steps may not necessarily lead you to exactly what your dream job is it will certainly define for you what you are looking for in your dream job, what you are good at, and what you like to do. Hopefully you will find some overlap where someone will actually pay you for these things! From here, you can begin to design the plan that will fully flesh out and help you attain that job of your dreams. Life is too short not to do something that you love.


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