How to Quit Your Job and Live Your Dream

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Hi, my name is Phyllis and I’m a lawyer.

Technically, I’m a “recovering” lawyer but like Marines, alcoholics, and Catholics there’s some stuff you just can’t ever shake. After 16 years of litigation, I quit being a lawyer about four years ago and I’ve never looked back. I’ve quit other jobs and professions too and I’d like to tell you about it so that you can dig up that high school dream you had of owning a bakery or being a river guide and make it happen. My dream was always to live in a cabin in the Colorado mountains and ride horses. Guess what? I’m a cowgirl, doing just that.

I can hear you already, right through the pages of this site, nay saying and yakking about your mortgage and the kids. Can we put all that aside for a minute? Can we just fantasize about quitting the job you hate? Can we just throw caution to the wind for a sec and have a little fun? Thanks, you won’t regret it.

I know about the nay saying right off the bat because when I decided to quit my lawyer job every other lawyer I knew was green with envy. Most attorneys hate their work and with good reason. It’s stressful, contentious, unrewarding, deceitful and about as much fun as a colonoscopy. But my brethren all quaked with fear when I made my announcement:

“Geez, ” each said, shaking his lawyer-head, “Wish I could do that. ”

“Well, you can, ” I said in my overly simplistic way.

“Nah, ” sigh, “There’s the two mortgages, college tuition, my spouse’s shopping habit. No. I’m doomed. ”

I never felt sorry for these guys. Anyone can leave anything. You just have to have courage, a vision, a plan, and the desire to be happy. This last one is likely the hardest because we’re so enamored of “hard work” and achievement. Hard work is just hard. Two four-letter words that spell aggravation.

It took me 16 years to leave the law though I knew after about six months in law school that I was doomed. I wanted to give the gig a fair shot, so I worked for three different firms thinking that a change of scenery would quell the restlessness inside me. Come to find out all law firms are generic. They are like a tube of toothpaste: you have to squeeze the bottom to ensure abundance at the top. This, in fact, is the paradigm of American business in general. Are you tired of being squeezed yet? Or maybe you’re the top of the tube, gooping “abundance” all over the place and you still ache inside. I have a surgeon friend – prominent, highly successful guy with more money than God – who dreams of being homeless.

“I’d eat at a restaurant and then leave without paying, ” he says wistfully as his wife opens more Perrier in the wall-to-wall marble kitchen, “I’d keep all my stuff in a backpack and hitch rides around the country. ”

A surgeon fantasizes about homelessness and a lawyer turns into a cowgirl. Life is weird folks, and it’s not a dress rehearsal. This is it. This is your one shot. You want to spend ten hours a day in a job that makes your chest hurt? Not me. I’m a weenie I guess. I’m not into suffering and I’m pretty much a bum. A solid citizen, I pay my taxes and take care of my kids. But at heart, I’m a bum. You probably are too.

Most lawyers are literally married to their money. I suspect this is the case with doctors, CEOs and others who make a lot of bucks. They build a lavish and unmanageable lifestyle, collect people who love to sponge off them, then have to continually work harder to make more. If you’re one of them, I hate to tell you but that whole thing is pretty dumb don’t you think? Life can be simple and easy and you don’t have to work hard. But if you’re into status, “achievement” and lots of stuff you’re just another lawyer. Sorry, that’s pretty harsh.

So the first thing you need to do to in order to quit your job is change your mind. If you really desire to simplify and change your life you can do it. Don’t let anyone or any negative thought stop you. I know, I know. The kids, the money.

For the most part, I have been a single mother raising three boys. Truthfully, when I was married it was harder to control the financial end of my life. When I got divorced (both times) it would be hard for a few years but inevitably I’d downsize, get control of my money, and be much better off. As an attorney, I always kept my salary on par with that of a teacher (my college profession of choice) so that I could make a lateral move at any time. This stunned the partners, of course, because the drill is that everyone wants to make a lot of money as fast as possible. I didn’t mind making $45,000 a year and taking a cost of living increase. But by the time I was at my last lawyer job I was making $80,000 – too much for what I needed and it still wasn’t worth the misery of being a lawyer. When I quit and went back to high school teaching I took a 50% pay cut and hardly missed a beat.

I never bought a new car; always (or mostly) a Honda, used, which I would drive until it stopped dead in the six-figure mileage area. Material stuff doesn’t interest me too much at all. I like to ski and would save up every year to take the kids to the mountains for five days. That was my extravagance. I invested wisely in real estate that was bound to appreciate. I didn’t mind moving every couple of years if the market was going to give an enormous return on my investment. My kids weren’t crazy about it but sometimes you don’t need to listen to them.

My kids went to public schools. Private education is, in my mind, about the biggest waste of money you can find. Might as well flush it down the john. What you’re paying for, when you pay $15,000 a year in high school tuition, is the privilege of telling all your buddies, “My kids go to Snob Academy. ” Good for you. Nobody learns much of anything in high school. Did you?

Same thing with college. Middle age parents strap themselves financially to send Suzy to Notre Dame for $35,000 a year, mortgaging the house that’s almost paid off, so that Suzy can get drunk. Waste of money. Unless your kid’s a genius (he/she is not. Really), take that same money and go to a casino. Same odds it will pay off. By the way, if your kid is really that smart he’ll get a scholarship.

Two year community colleges are the best-kept secret in America. They provide your kid with the basics and a bargain rate. Little Johnny can get drunk every night for $6,000 a year instead of $30,000.00. Then, if he makes it through and gets his associate he can go finish up for two years at a state college. The next best college deal. But if you’re into status and you want your child to go to “the best” then hang on for your myocardial infarction because you can’t quit the job you hate.

After the kids and the money comes the saga about how the family has gotten used to a certain lifestyle, whatever it is. How about this? Too bad. Toughen up, buttercup. Daddy’s tired of being a workhorse. Truly, if folks love each other (as family’s profess they do) then they would do anything to support the happiness of the members of the clan. If, however, you’re easily intimidated by people having hissy fits about “stuff” they “need” I can’t really help you.

So if the first thing you need to do to quit your job is change your mind, totally rethinking the way you manage your life and your money, the next thing you need to do is dream. Remember that? Do you remember how to have a dream? Probably you are so absorbed in the daily grind of “making it” (as you see it) that you have forgotten what you are born to do. I was born to be a cowgirl. By circumstances of birth, however, I was a Philly girl, then a Jersey girl, a lawyer and a teacher before I finally donned my chaps. But I never let the dream die. I talked about it and fantasized about it and made my plan. And when my youngest son graduated high school I sold everything, packed my Honda CRV with clothes, , books, and camping equipment, and went West.

Now I live in a one-room cabin with Cowboy Bob, my partner and best friend who was never really part of the decades-old fantasy but who happened to appear at the right time. That’s what happens when you start to really “follow your bliss” as Joseph Campbell would say. Once you leave the trappings of the life you’ve constructed, which is someone else’s idea of who you are, and you follow that creative impulse that’s been deep inside since you were a kid, benevolent forces will come out of nowhere to make it happen. Trust me on this one. The hardest part of this whole process is learning to be true to yourself, to pay no mind to the critical and harsh voices of those who would like you to stay miserable.

Change your mind. Start dreaming again. Don’t be afraid. Make a plan that begins with your decision to be happy. Then when the time comes to say good-bye to the job you’ve never liked, you’ll do it with joy and not anger. Good luck friend. See you on the range.

Phyllis Coletta is co-owner of KB Mountain Adventures where she and Cowboy Bob (another “recovering” attorney) help people remember how to have fun. Visit them at


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