The 'Quit Your Job' Checklist

Here are what I think are the major things to be considered before you make the big decision to follow your dreams. There are many more variables to consider and every situation is different, but if you choose to follow in my footsteps, review each of these steps carefully and honestly.
03/27/2014 05:30 pm ET Updated May 27, 2014

I've written here before about how I quit my six-figure corporate job a decade ago to follow my dreams of being a writer and performer. My decision was based on this idea of the Third Metric years before I even knew what the Third Metric was. I chose to take my life in a new direction that wasn't driven by money and power, but by fulfillment and happiness.

Over the years, many people have reached out to me looking for advice. These folks were all in the same position I was in -- stuck in a job they hated and wishing that they too could quit to pursue their dreams. When I was in that situation, I felt like I was the only one. It was eye-opening to hear from so many people who were in the same boat. When it came to their requests for advice, I felt a great responsibility in encouraging people to choose the right path, but also urging them to be realistic before making any huge, life-changing moves.

Here are what I think are the major things to be considered before you make the big decision to follow your dreams. There are many more variables to consider and every situation is different, but if you choose to follow in my footsteps, review each of these steps carefully and honestly.

1) Why do you want to quit your current job and try something else?
Don't quit because your boss is a jerk. Don't quit because you don't want to work that hard. Don't quit because you THINK you'll be happier doing something else. It always surprises people when I tell them I didn't leave the corporate world because I hated it. Truth is, I didn't really care for it the whole 16 years I was in it, but that wasn't enough to get me to leave. I eventually made the decision to quit when I realized that I'd achieved a higher level of success than I'd ever dreamed of, yet it still wasn't satisfying. If your job is as good as it can be and it still isn't making you happy, that's when it's time to think about choosing a different path.

2) Can you test the waters of your new career from the safety of your old one?
If you can live in both worlds for a while, do it. Once I realized that what I really wanted to do was write and act for a living, I didn't quit right away. I did both. I worked my day job for three more years while writing on the train and auditioning on my lunch hour and doing stand-up at night. It wasn't easy, but the success I had in those early years is what gave me the confidence to dive into the creative life full-time. If I had failed right out of the gate or realized I didn't like it as much as I thought, I would have still been able to carry on down my corporate path. Luckily, I didn't have to. Whatever passion you want to follow, whether it's writing, or music, or opening a bakery -- whatever it is, make sure you know that you can do it full-time and be happy. Otherwise, you're just going from one job you hate to another, with a lot of extra risk thrown in.

3) Do you really have what it takes to make it in your dream career?
Don't go all in on a shaky hand. If you've been following a passion on the side and not getting anywhere, that may not be the leap of faith you want to take. It's great to have conviction, faith and confidence in yourself, but if you've been struggling at your side project for ten years, there's no guarantee that doing it full time will make you any better. Chances are it could make you even more miserable. This is where feedback from others comes in real handy. This can't just be friends and family members -- of course they're going to tell you that you're amazing, that's what they're supposed to do. What do others think? I'm not saying give up entirely if the first three folks you encounter don't dig what you're doing, but if hundreds of folks over a span of time tell you no, then maybe it's time to reassess and make a new plan. You don't have to give up, but it might be time to step back see what's not working and start again.

4) Do you have a road map?
If everything is telling you to take the plunge and you decide to quit your job, make sure you have a plan. What will you do that first Monday morning after you quit? Where do you want to be in three months? A year? Five years? Having a game plan is the most important part of what a lot of others will see as a reckless move.

The huge caveat here is: Don't expect things to go the way you plan. Some things will go much better than you expect, others will go terribly worse. Shit happens. Once you actually take the leap you have to be ready to go with the flow and handle any opportunities or adversity that comes your way. My road map since my adventure began 10 years ago is filled with massive blunders, miserable defeats and unforeseeable successes. I took each in stride as best I could and re-calibrated my plan along the way.

5) Do you have a solid base of support?
You need someone who believes in you unconditionally. It doesn't even have to be someone who believes in what you're doing 100 percent, it just needs to be someone who will support you as a person whether you succeed or fail. For me, that support came from my wife. I knew she had my back regardless of where this journey took us. Breaking out into the void isn't easy, and your confidence and faith in yourself is going to be shaky at times. Mine sure as hell was, and occasionally still is. You need the trust and faith of those around you to prop you up when the going gets rough. Conversely, make sure you are being that support system for others as well. No one likes a taker. Plus, being there for others during their struggles can have a huge effect on how you feel about your own endeavors.

6) Can you afford it?
I'm the first one to say that it's not all about money, BUT it is a little bit about money. We all need dough to survive. You can't have so much faith in your future that you use it to bankroll your present. Make sure you can cover the basic necessities of life for as long as it takes to succeed. It is impossible to do your best work when the Sword of Damocles is hanging over your head. If you need to book an acting job to pay this week's rent or need your new business to make money right out of the gate to succeed, that just adds an insane amount of pressure to what you're trying to achieve. Even if you're one of those people who thinks they thrive in stressful situations -- "I'm like Michael Jordan... I do my best work under pressure!" Just remember that while MJ was succeeding under the toughest of circumstances on the hardwood, he still had a loving family at home and more money than he could spend in five lifetimes backing him up if he missed a clutch shot.

If you do decide to make the leap and pursue your dreams, the most important thing to remember is that success comes in many forms. You may never make as much money on your new path as you did before. I certainly don't. It's the quality of life and how you live each day that is the true measure of success. After all, isn't that why you're thinking of quitting your job in the first place?

I wish you well with your quest. Drop me a line and let me know how it goes. We're all in this together.