Career Management

What If You Have More Than One Dream Job?

Wondering how to choose a career path if you have a lot of passions?  Watch this 2-minute video and read the short article below the video for additional exercises to help you navigate this common challenge…


“Dear Pete: I have a lot of different passions and skills, and I’m totally stuck on how to choose a career path.  How do I figure out what to do?”


This question comes up a lot and it’s one I struggled with a few years ago as well.  In brief, you can have more than one “job” and you can explore more than one passion at the same time.  In the book, “I Could Do Anything If I Only Knew What It Was,” New York Times best-selling author, Barbara Sher had a great exercise on this topic.  I have adapted her exercise, so I want to give her credit for the initial idea here. 

If you find yourself overwhelmed by too many options, ask yourself this question:“If I was 10 people, and I had a magic wand, what 10 dream jobs would I give myself?”

By asking yourself this question, you are allowing yourself to think through everything you are considering, rather than trying to pick one career from your list.  During your brainstorming phase, you don’t want to limit yourself.  I did this exercise a few years ago and came up with the following list of my 10 dream jobs at the time (in no particular order):

  1. Athletic Coach/Trainer
  2. World Traveler
  3. Photographer
  4. Motivational Speaker
  5. Author
  6. Competitive Athlete
  7. Event Planner
  8. Online entrepreneur
  9. Life/Career Coach
  10. Rehabilitation Counselor

Now you might look at this list and think, “What in the world do I do next?!”

Well, after you identify 10 dream jobs (or however many you have…you could have 3, you could have 17, etc.), the next task is to ask yourself these follow-up questions:

  • Which of these jobs could be combined?
  • Which of these jobs could I do occasionally?  (In other words, which of these jobs would I be happy doing weekly, monthly, or even less often?)
  • Which of these jobs would I be most proud of? 
  • Which of these jobs can I do without someone else’s “permission?” (In other words, which of these jobs would I be happy doing on my own without being hired by another employer?)
  • Which of these jobs fit best with my personality and my primary values? 
  • Which of these jobs are most likely to help me create my ideal lifestyle?

After answering these follow-up questions, I actually found a way to have all 10 of these dream jobs at the same time.  Here is what I came up with.  (Full disclosure: it took a few years to put all of this together.)

My Primary Career:

  • Motivational speaker (Dream Job #1): I speak nationwide to young professionals, student groups, and people who work with students about 25 times a year.
  • Author (Dream Job #2):  I wrote a book and have a blog that I post on monthly.
  • Online Entrepreneur (Dream Job #3):  I have an online career coaching program for job-seekers.
  • Life/Career Coach (Dream Job #4): This is connected to my online career coaching program.

My Primary Hobbies:

  • Competitive Athlete (Dream Job #5): I work-out at my gym 5-6 days a week by training myself as if I was a pro athlete, and I play in competitive flag football and basketball leagues throughout the year.

My Weekly Activities:

  • Rehabilitation Counselor (Dream Job #6): I volunteer one morning a week with a non-profit organization called Back On My Feet.  I found this organization by surfing around online, and I did not need any certifications to “work” for them (since I’m just a volunteer instead of an official counselor.)  Through this group, we use running/fitness as a channel to help homeless men and women rehabilitate their lives.
  • Athletic Trainer (Dream Job #7): I got certified as a personal trainer and group exercise instructor and applied to teach a boot camp class at my gym.  On Monday nights, I now run a class for 50-75 people each week.  It’s a lot of fun!

Occasional Activities:

  • Event Planner (Dream Job #8): I throw a few big parties a year for friends and host other social activities every few months for a variety of groups I’m involved in personally and professionally.
  • World Traveler (Dream Job #9): I travel a lot for work and I also take 5-10 trips a year to see family and friends or to visit new cities or countries.
  • Photographer (Dream Job #10): When I travel, I “become” a photographer, taking pictures of the places I visit and developing them when I return home.

 In other words, I have 10 dream jobs right now!  It’s taken me several years to put all my passions together, but the message is that you don’t need to focus on one passion and ignore the rest.  You also don’t need anyone’s “permission” to explore your passions. 

You might look at this list and think it’s awesome, or you might look at this list and think I’m crazy.  It doesn’t matter.  It works for me!  I’m happy and hardly ever bored and I’m proud of all the diverse groups of people I’m helping. 

It’s all about creating a lifestyle that is meaningful and exciting to you.  Maybe you just want to explore a few passions.  That’s fine too.  My goal is to open your mind to innovative ways of looking at your career outside of having one standard 9-5 job that defines you completely.

Again, if you have more than one dream job and want to explore multiple passions, here’s what to do:

  • Brainstorm all your possible dream jobs
  • Identify the jobs that can be combined (i.e. how I combine speaking, writing, and coaching or how I combine travel and photography).
  • Identify the jobs you want to focus on first/most.
  • Identify the jobs you don’t need someone else’s permission to do (i.e. my “job” as a competitive athlete).
  • Identify the jobs you would be happy just doing now and then (i.e. my “job” as an event planner).

Note: You might also choose to pursue certain “jobs” later in life.  For example, if you want to coach a youth sports team, you could wait until later in life when you could coach a team that your child plays on.

Again, you can explore multiple passions at the same time… by combining jobs, by doing jobs on your own without someone else’s permission, by focusing on some more than others, or by holding off on others for later in your life.  This exercise has been incredibly helpful for me throughout my career and I hope it serves you as well if you find that you have a lot of passions you want to explore.  You can explore all of them now or some now and some later on!

P.S. I would love to hear your thoughts in the comments below!  Please “like” and “share” this article and video as well.

Leave a Comment