You frequently have the urge to stab your eyes out while sitting at your desk. It is an effort to pretend to feel alert and engaged (especially during boring meetings). Something is gnawing at the pit of your stomach each day when you walk into work (Darth Vader’s theme song plays). A voice whispers in your ear (on repeat): “You were made for greater things. This is not your destiny.”

The good news is, you are self aware enough and brave enough to know you need to make a change. But how drastic should it be? Do you even know what that “something greater” is?

If not, figure it out above all else and put your notions to the test because chances are, you’ve buried your dream under the pyramids in Egypt, and even Indiana Jones is scratching his head.

I thought I knew what I wanted to do next when I realized I had to dig deeper and delete limiting beliefs. Determining your dream before you quit is ideal but it wasn’t the case for me. I needed a clear head and plenty of time on my own to determine my calling. And if that is the case for you, EMBRACE IT.

Let’s assume you found your dream before quitting. Should you immediately start working towards it full-time or should you take another day job and work towards your dream on the side?

It isn’t an easy choice and you may feel that Option B means you are a cop-out, a sell out, or a pussy (at least that is how I felt).  Well I’m here to tell you that it is OKAY TO TAKE A SMALLER LEAP as long as it will take you closer to your ultimate dream.

Life is not black and white – there are many factors at play and many ways to move from point A to B. ULTIMATELY, YOU NEED TO FEEL READY to take the PLUNGE. You can increase your chance of escaping the cubicle forever by doing these things before you quit:

1.       Plan to NOT look for a new 9 to 5 job: Sounds like a no brainer but if you haven’t mulled over and committed to working on your own (whatever sacrifices that entails) or giving yourself 6 months of free time, you will get sucked into the “OMG. I HAVE TO FIND A NEW JOB” panic and spend a lot of energy on a new search. This is easier to do when you know your dream. Mentally prepare yourself and others with respect to your next move. Don’t just think “I need to get out”. Think about where you will go next and WHY. Then plan.

2.       Develop a personal source of income before quitting: Identify skills you can monetize (i.e. freelance writing, marketing) and begin to solicit your services for free or minor pay, while you are working, in order to build a portfolio. The income stream doesn’t have to be related to your BIG DREAM but it can give you more time freedom to pursue your dream.

Jet Blue Flight Attendant set a new record for dramatic exits. Try not to let it get to this point before you quit.


1.       How do you feel about spending most of your time at home and with limited social interaction with the outside world? The extent of this will vary based on your own situation.

2.       How much money are you comfortable making? Can you handle a drop in savings? Are you willing to sacrifice your current lifestyle? What future costs will you be faced with when you achieve your dream and do you think you have enough to weather them?

3.       Do you prefer to test out your dream on the side before committing 100%? Admittedly, this desire may be due to a lack of confidence or conviction in your dream (perhaps you haven’t proven your skills or talent to yourself yet).

4.       How important is a strong sense of purpose to you in the short term and what would give you more: Being an employed person, in a job you can tolerate, while working on your dream OR working on your dream full-time?

5.       How quickly do you want to achieve your dream and will having 100% disposable time make you achieve you dream faster? Ironically, I tend to be more disciplined and produce more quality work when I am under the gun with limited time. If I have lots of extra time, I’ll use all that time to complete the task i.e. I’ll waste time.


My answers to the above made me feel that working in a new job was the right next step for me. I am currently managing relationships with broadcasters for a Canadian service, similar but different to Hulu.

EVALUATE EACH NEW JOB LIKE A POTENTIAL MATE: will it fulfill your needs?

So you’ve decided to apply for new jobs. Be picky and put some criteria around your search.

  • Will the new job help you learn “the business” of your dream? If yes, apply! Can you find a job that will help you learn the commercial side of your dream? Even creative professions like movies and TV need to make money to flourish. If yes, apply!
  • Will the new job help you prove your passion for the industry? If yes, apply! If you are planning to apply to a program like me, gaining relevant work experience can show your commitment and determination. Look at your past experience and education and see what position you could take on that will bring you one step closer to your dream.  It could even be a volunteer position or side project.
  • Does the new office environment match your personal preferences? If yes, seriously consider it! I grilled the interviewers about the culture and values (team and company). I assessed whether I could see myself liking, trusting and getting along with my coworkers.  If the day to day is unbearable and you aren’t having fun, you may feel less motivated and energized which could impact progress on your dream.
  • When you received the offer, did the timing and your gut make you feel like you should take the deal? If something in you says take the deal (not your fear talking), then take it!

o   Was there a pattern in the opportunities you got call backs for? After applying for many jobs, I was first offered a free internship in TV and then a paid gig in TV. TV was the pattern and the fact that I also wanted to work in TV made me feel like the universe was speaking to me.

o   Imagine doing something during the hiring process to jeopardize your progress.  How would that make you feel? In my case, I thought I had truly sabotaged my chances during my interview by referencing my blog when the top post was inappropriate for a recruiter. I instantly regretted opening my mouth and thought all was lost. This made me feel more “happy” surprised when I received the offer and more likely to accept it!

o   Run the opportunity by someone who is living your dream job. Do they think it would be a good next move for you? I connected with a local HBO writer who encouraged me to take the job.

o   Are other signs at work? I ran into an old colleague of mine from a 2007 internship at an art event after I had applied to this company. He told me he worked there but I never followed up. A month later during my second interview, I saw him in the office on my very team (30 person team versus thousands of company employees). I thought that was interesting.


Remember that sometimes we take something/someone on with a specific intention or expectation and we end up getting something quite different out of it (a lesson learned or a different but still positive outcome).

You quit before and you can quit again. You want to give this new job a fair chance, do well and you don’t want to burn any bridges. Ultimately though, it is up to you to know when to pull the plug again. Have a little faith.

AND THEN GO STREAKING (metaphorically speaking).

Pin It on Pinterest

Share This