12 tips for quitting your job to be an artist (or whatever you want to be...)

How to quit your job, Part Two: FAIR WARNING.

If you read Part One: My Story, arose from your cubicle chair, pushed the wall down ala Office Space, gave your ugly plant to your secretary, told the annoying girl in the corner that you really don't give a damn what stupid fucking flowers she picks for her bridesmaids' nosegays-not-bouquets and walked out the door with a big old middle finger in your boss' direction, I commend you. You much bigger proverbial kahonays than I do.

But you might want to get a plan.

As promised, here's my advice on how to actually quit your job.

1. As I said earlier, don't think it's going to go away.

I mean this in a bigger way than you might think. Say it bigger than you think you need to: I am not THIS job. I will go be THAT instead, and I am still me, regardless of it all. "I am" is a complete sentence in and of itself - the labels that follow are up to you, and only you can identify them.

2. Accept and grieve the loss of what you might have achieved in your current job.

The reality was not that I was a dumb insurance broker or that I was capable of "doing" the job. In fact, I was, and am, pretty darn smart. I could have gone pretty far in it. We're somewhat conditioned in high school and college to steer toward the career path that makes the most possible money while still falling within the range of our intelligence, talents and range of tolerancy. I wanted to be an artist. But I was smart enough for and could tolerate (at least for a while) an MBA and insurance. I could be making a lot more money, drinking Stoli-Doli's at the Capital Grille in Pencil Skirts, and talking to hot little businessmen from Underwriters' offices every day. But I made the wrong decision. So I had to go back and make the right one.

Truth be told, I can't say that I don't walk by commuters in Center City, sing Dolly's "9 to 5" in my head and feel a pang of jealousy sometimes. They can afford Starbucks - with an extra shot. They get conversation with adults. They get built-in feedback from all kinds of people while I second-guess myself. If they mess something small up, they don't run the risk of not being able to pay the rent. The list could go on and on.

But do I bottle that jealousy up and cover it up by getting on my high horse to scream to the world about how they're "sheep" and that their lives aren't tolerable in the "corporate slave" world? No. I'll leave that to the thousands of hipsters running around this city crying at Dashboard concerts. I had to admit to myself that while I wanted to be what I am more than anything and was willing to sacrifice what I needed to, it didn't mean that I couldn't miss certain parts of my former life. When you go through such a big change, it is quite literally like a death. You have to let that person go - but it doesn't mean you can't remember the good times.

When you acknowledge that you will have those pangs from time to time, you'll be better tuned into whether or not you regret things or whether or not you just have natural human envy. The envy passes, I assure you. While I'd love to sip fancy cocktails in cute little suits from time to time, I know that I don't really want the whole corporate shebang ever again.

3. Figure out how much you are willing to give up - then double it and triple it.

Or halve it or third it - whatever. The point is that it is harder than you think. When you have that amount of money - because let's be honest, it comes down to money sometimes - that you are, bare minimum, willing to live on, cut it again and figure out what you can do for supplemental income. More on this later.

4. GET YOURSELF INSURED.

I pay $483 a month for health insurance under COBRA. I consider this a travesty in the world's most developed country, who considers expression of one's self to be a founding principle, but that's another blog. My point is that you can NOT risk getting sick in this day and age. Take it from me. When I had zero money, I developed an ear infection, went to the doctor, and found out that because of lifelong frequent ear-nose-throat infections, I needed surgery within months or I risked losing my hearing. I was in surgery for nine hours. Yes folks, that's pricey. I was unable to commute ten feet into the studio for two weeks. Had it not been for that Cobra coverage, I could have literally gone deaf - there just wasn't the money available to go pay for surgery on my ears and sinuses. Furthermore, when you are hurt while working for an employer, you are entitled to Workers Compensation benefits that provide for your care. If you are self-employed and therefore not subject to the Workers Compensation Act and/or have dependents, it is all the more essential to find and keep health care coverage - that policy is your only source of health care. While chasing after your dreams is a wild adventure, it just doesn't mean you should risk life and limb just to prove that you're a starving artist.

The details:
You are allowed, under the Consolidated Omnibus Budget Reconciliation Act, to elect continuation of your current coverage for up to eighteen months after you have left your job. If you have access to equivalent coverage (if you get a new job or are covered under student insurance if you go back to school), you may be required to pick this up instead. The catch: you may be required to pay UP TO (yeah, they COULD charge you more in other cases) 100% of the premium. You can find coverage for you and your family - even with the SAME or better coverage - for much less through sites like this. Please read the fine print - mental health coverage is excluded, as is ANY and ALL preexisting conditions (except pregnancy) in most of these policies.

Please note that I have used my experience as my basis for this statement. While I am licensed in insurance in Property & Casualty Insurance in the Commonwealth of Pennsylvania, I am not, nor was I ever, licensed in Life & Health Insurance. I do not have the moral or ethical authority to counsel you on insurance matters. Your HR representative will answer any of your questions or point you in the right direction for further information.


4. Go on a "stuff" diet.

I didn't even say "spending diet" like Oprah's gurus say to do or whoever. Welcome to the Wild West, because you're headed for LEAN TIMES, settler. Spending, saving, selling, reusing, robbing Peter to pay Paul - you name it, I can do it. This is such a big topic that I'm going to address in a later post, but do yourself a favor and sit down and take inventory - of everything. Everything you have, everything you owe, all of your ongoing bills, everything. If you have access to your bank statements, go through them for the past year and sort through by LOCATION. Put all the Starbucks, all the Targets, all the Krogers, all the CVS' together to get an idea of what you're spending if you have no idea. We'll get to work later on this.

5. Banish the phrase "Backup Plan" from your vocabulary. I'm not kidding. It's amazing how quickly you can get what you want when you make what you WANT your full-time job. I'm not saying you have to quit the gig now - I'm just saying to change your thinking. Do not say "I'm an executive assistant right now, doing the acting thing on the side until I can afford it full-time". If you don't think you're an actor, no one else will. Say "I am an actor." You may have a part-time gig that consumes 40-80 hours a week for extra cash, but you're an actor. One of the most valuable lessons I learned in business school was that Plan B is almost always devised for people and businesses who truly believe they need them. Solution? Work harder on Plan A. If you happen to need money along the way and there is no possible way your bills will be paid by your passion that month, then by all means, go find a way to make ends meet.

6. Seek advice.

Find people who know you, know your field, know what it's like to have experienced such a job change, and know the ins and outs of how to make this thing work. People who are good at something innately have a desire to mentor others that remind them of themselves or their experiences. I've called my grandmother for advice on acrylic paint more times than I can count and I've asked the advice of many artists - never once have I had someone tell me "I don't have the time to talk to you." Likewise, talk to your friends and family that know YOU the best. You'd be surprised at how many of them want you to succeed and are willing to help. I am not kidding you when I say that without exception, every single person who knows me has said "I know you made the right decision" at least once throughout this journey. Finally, find people who know the sheer logistics of how to make it work - and think outside of the box. On a lark, I called a friend in the financial business and simply said "tell me how I can quit my job." I was surprised to find that he gets a lot of people calling and asking the same question - how they can continue some semblance of their lifestyle while pulling in less income. News flash: they do this for a living - it's called retirement planning. Inventory your personal resources - and use them.

7. Forget about #6 - Don't pay any attention to advice. At least some of it.

There will undoubtedly be some people who think this is the dumbest idea you've ever had. I find they fit nicely into three categories:

a) people who wish they had the balls to do it as well
b) people who don't know you very well
c) assholes.

Criticism is part of life - and at the end of the day, I'd rather listen to the critic known as ME rather than one of the above characters. When my younger brother and I spoke right after I had made "the big announcement" to my family, he said something that proved invaluable -

"I want to see you do it - because I think you have the talent and skills to do it - and I want to see you do it on your own, if not for anything else than just to prove to people 'look, I did it, and you didn't think I could. So fuck you.'"

I know, we swear a lot in my family.

My point is this: yes, it is entirely possible that the critics could be right. I could die penniless. But I'd still be dead, and I don't see any armored cars following hearses of rich people either. Neither of us can take it with us. But I'd die knowing that I did what I loved and listened to myself rather than taking the advice of people who I never even liked to begin with.

8. Stop shopping for that crystal ball.

Yes, you could die penniless. But you could also hit it HUGE. That's the great thing about pursuing what you love - you just don't know. You DO know one thing for sure, however. No one is going to come barging down your door begging you to do this, and you will never know what you're capable of until you try.

9. Work your ass off at this.
One of the things that truly pisses me off about celebrities is that they always seem to give this song and dance of "I'm just so blessed. I'm so lucky to have ended up where I did."

Shut the eff up.

Though I appreciate their bad attempt at humility, it's just not the whole truth. There is an element of luck involved with their success, but rest assured - they worked their asses off to get where they are. Even - God, I can't believe I'm giving her a compliment - Paris Hilton works her tail off at being famous for being famous. This country was founded on entrepreneurs and The American Dream, and it's almost never achieved without a huge amount of good old-fashioned elbow grease.

10. Meditate.
Every day. Non-negotiable. You can think I'm new-age and full of shit all you want, but even Dr Oz agrees - it works. It spurs creativity, allows a better outlook on life, and creates an environment in which you will find what you need.

Don't tell me that you don't have the time - five minutes is all you need. It doesn't have to involve chanting or incense or anything, it just involves you letting go of your mind. In that great book I mentioned before, Eat Pray Love, the author went to India to learn the spiritual side of herself in an Ashram after learning the pleasurable side of herself in Italy. She talked about how difficult it was to meditate at first - like me, she was raised in a Protestant home in typical American fashion. You are not turning your back on any faith that you hold dear, I assure you, you are simply listening to God instead of talking to God in prayer. If you are Atheist or Agnostic, it still works - you are recalibrating your body to prepare it for another go-round of this crazy world.

I highly recommend Eckhart Tolle's The Power of Now if you'd like further information, and there are numerous resources in your community and on the internet surrounding effective meditation.

11. Cut the excuses.

Dr Phil haunts me every time I come up with one, because he puts it very plainly when a guest gives him excuses on why they can not get toward a goal. No time, family obligations, financial constraints, the list is endless. While they're all perfectly logical and reasonable excuses, to use his words...

"and how's that working for you?"

For a more upbeat and inspiring take on it, watch Dr Randy Pausch's Last Lecture video .



It's over an hour but worth it. This man is dying of cancer as we speak and he speaks volumes on the importance of following dreams. One of the most important points he makes is regarding the obstacles that generate these excuses:

"Brick walls aren't there to stop us. They're there to make us prove how badly we want something."

Godspeed, Dr Pausch. I couldn't have said it any better than that.

12. Finally, enjoy the ride.

Every so often, I can not pick up a paintbrush or look at my laptop to write as I truly think it's driving me insane. I go get a cup of coffee. I walk the dog. I go to the Art Museum. I go have a beer with an old friend. I call my mom. And I always remember why I got into this insanity in the first place.

Sanity is overrated, but happiness is not. Find the happiness.