Let me start this piece the only way I know how:

No. You shouldn’t quit your job.

You’re not ready to do that, and you know it.

You don’t have enough money saved up. You probably don’t know how to earn a buck outside of showing up to an office and seeing your bank account balance go up every other Friday.

“Doing what you love” is neither a recipe for being happy nor starting a profitable business–it’s more likely a recipe for developing animosity towards what you once thought you loved.

Working for yourself is just as difficult as having an asshole for a boss, except that boss becomes your face in the mirror–and the ensuing, lifelong game of psychoanalysis in trying to figure out what that face really wants is certain to prompt so many questions, doubts, worries and fears that your old cubicle will look like a beach-front resort.

Then again, who am I to tell you that?

I Disregarded All of This Advice When I Quit My Job Five Years Ago Today.

I was desperate. I was fighting to survive.

I didn’t care that I wasn’t “ready.” Didn’t care that I had a state job in a terrible economy that could have given me a ridiculous pension after 20 years of service.

I didn’t know what I was doing next or how I was going to do it. I didn’t know how to earn an honest dollar outside of being paid for showing up to an office. I didn’t understand that having total freedom is equally as daunting as having no freedom at all. Having “no one to answer to” is as liberating as it is excruciating when the face in the mirror is the only person to blame for your shortcomings, failures, struggles and doubts.

As an exile of the traditional working world, I often find myself in conversations with young men and women who want to know how they too can quit their jobs, what kind of money they need to have saved up, and what first steps they should take immediately thereafter.

I’ll have this sort of a conversation about once every two to three weeks with a friend, a new neighbor, a yoga teacher training peer or in an email with one of my readers.

The truth is, I’m not qualified to tell you why you should or shouldn’t quit your job.

I’m as qualified to discuss what it takes to responsibly quit one’s job as I am qualified to tell you about the mechanics of cars just because I’ve held a license for a dozen years. Let me explain why:

I quit my job before I was stuck. Before I was entrenched, on the hook, or in need of every penny I was earning.

I left a 3-month-long career at the age of 23 and was afforded the chance to spend my first two years of self-employment living off of a combination of personal savings, selling my Blu-Ray collection and scraping together a couple thousand bucks per month by doing work that I actually didn’t want to be doing (creating websites and WordPress blogs for clients and maintaining them for months at a time).

In other words, I escaped early. I could afford to. I had no credit card debt or student loans, no family or girlfriend, no bills or rent (I was living at home with my parents at the time), not a dog or a goldfish to take care of.

I had a lot in my favor when I quit my job. I was lucky to do it–not profoundly skilled or particularly brazen.

And I’ll never feel comfortable telling someone, “Yeah, you should quit your job,” even if it’s someone who is as desperate or depressed as I was.

What I do feel comfortable with is telling you that what it is infinitely more important than “quitting your job or not” is understanding why, in your heart, you want to quit it.

I can’t tell you how much money you need to live after you escape cubicle nation–but what I can do is break down the subtle workings of your mind, dissect the stories that you’ve been telling yourself and unfurl the knots of ideas and seemingly disconnected desires that you share with me when we sit down for coffee and have our “I want to quit my job” conversation.

Jalaludin Rumi once said, “I know the ways of the heart–how it wants to be alive.”

I agree with Rumi–I say, “Me too.” That is what I do.

All the experience and expertise that I’ve accrued in the last five years of my life has far less to do with writing, artistry, leadership or book-publishing than with pertaining to the ways of the heart, and how it longs to be alive.

So let’s talk about that, instead.

Why I Quit My Job

2008-ddI quit my job because I was fractured and falling apart.

In the span of one year, I had moved my life to Washington D.C. to begin a career (see me on The White House lawn on the right), watched job opportunities fall apart with a global recession, and ultimately had to take my only job offer back in my home state after 6 months of searching. I moved back in with my parents, feeling like a failure, and with few accomplishments under my belt in the twelve months since graduating college and entering “the real world” with all the go-getter piss and vinegar that we had felt wearing those caps and gowns.

Throw in another youthful heartbreak and a ton of, “Is this really what I’m supposed to be doing?” questions and just a few months later I developed mild depression and was having anxiety attacks.

The body will give you queues that your life needs to change–so I started to listen.

I fell so sick twice in the span of three weeks that I couldn’t move from bed. My immune system was faltering–signs, for me, that have always been indicative that my self-belief was faltering.

If desperation was the driving force that helped me quit my job, I knew that I would have to replace desperation with an undying self-belief to carry me through the unknown that lay ahead.

But self-belief had always been my saving grace. With it, I felt capable of finding my way.

Ultimately, the reason why I quit my job was because my head, my heart and my entire body were simultaneously giving me signs that I was falling apart and that I wouldn’t put myself back together unless I would finally choose to escape the environment and conditions that were causing me to falter.

Why Do You Want to Quit Your Job?

Put words to the feelings. Give expression to the sentiment. Use the words.

  • Do you see quitting as a salvation from the life you’re living?
  • Does the idea of telling off your boss make you giddy?
  • Do you equate escaping from cubicle nation with winning the lottery?
  • Does quitting your job seem like the ultimate salvation, entering the promise land, discovering the key to a locked door named FREEDOM?

If you said yes to any of these questions, I will tell you this–you probably shouldn’t quit your job.

Quitting your job is not an end goal. It’s a means to an end.

Quitting is the start of an entirely new and unknown journey.

Leaving your job may indeed may represent your escape from an unhealthy lifestyle, or freeing yourself from a set of social mores that you don’t agree with, or avoiding a corporate culture that sucks the life and joy and inner peace from you. Whether or not you’re in survival mode like I was as I battled depression and a complete crisis of identity five years ago today, just understand this:

Quitting this job is not going to save you–but the act of quitting might be how you make the decision to finally save yourself.

But quitting your job, itself, is not a salvation.

It’s not a key to “endless freedom.”

Quitting your job demands a level of responsibility to self and responsibility to others that is profound, powerful, undoubtedly good and absolutely a challenge.

Quitting your job to pursue self-employment or entrepreneurship or some unconventional means of work means choosing ownership over your actions, decisions, abilities, desires, choices and non-choices, income and expenditures, habits and routines, self-care and self-harm–in other words, you take total ownership over your all-encompassing life.

There’s no one else to blame. No one to finger-wag at. It’s yours to own, kid.

If you decide you want to quit your job to “do your own thing,” I need you to understand that you will be forced to go full tilt into completely changing your life from top to bottom:

  • You will find times in which you need to put yourself on a tight and responsible budget.
  • You will become the sole owner of your mental-emotional makeup and become either a close friend or spiteful neighbor to your behaviors, habits, routines and patterns or “samskara.”
  • You will have to put your nose to the grindstone and get very good at skills that require thousands of hours of work.
  • You will have to learn how to earn ten bucks before you can make ten-thousand.

Maybe that’s what you want. Maybe it’s what you need–a complete life redesign, to start over, to begin anew.

I did.

Do you want to quit your job because you see it as the ultimate salvation–like winning the lottery of freedom, only better?

Think twice. The “four hour workweek” is bullshit.

You won’t run away to a beachfront villa and start earning easy money thanks to an Internet connection and gullible suckers who click-to-buy silly shit online.

But if your self-belief is faltering, if your body is falling apart, if you feel desperate and like you’re fighting to survive… who says you couldn’t figure out your way like I did?

Let’s keep going deeper.

3 Reasons You May Want to Quit Your Job

1. You may be unhappy.

Your job is causing you unhappiness, so you want to quit it. It seems like a natural enough reaction. But the truth is that happiness is not your ultimate goal. I don’t believe that we can embody an ongoing and unstopping emotional state of happiness–and so we ought not pursue it.

Pursue joy, not happiness.

Joy is a living state of purpose embodied in the realization of Self, combined with an active practice of service to others. This is a two-pronged approach to discovering what we might call “the pursuit of happiness” but probably ought to define as a state of “joy.”

Joy can be embodied. Happiness is merely felt.

Joy is a state of being that can be cultivated, whereas happiness is an emotional feeling that comes and goes.

Just as much as light is met by darkness, happiness will be met by malaise, sorrow, sadness, unhappiness. This isn’t a question, it’s the balance of life in our universe.

So, what changes if you start to seek a state of joy?

If you throw away the idea that life is meant to feel like one long stint of unbreaking happy feelings, does the idea of quitting your job change too?

What about your job or career may change if you could cultivate an embodied sense of personal purpose at the crossroads of self-activation and giving to others? Can you find that within the scope of job? Is any semblance of it absent, or impossible to find?

I quit my job because I was unhappy. That’s what I told myself. Looking back five years later, I now realize something more that I wasn’t able to express at the time: my desires for self-realization and service to others were being hampered by the world of politics.

I felt my soul regressing–my love of life devolving. The prospect of “helping people” in this public service felt more and more like a lie, the longer I went.

Quitting, by this measure, was the right decision. Is it the same for you?

2. You may know that you’re capable of more.

If you’re like me, since before you can remember you were told that you are unique, special, capable of anything and everything. This line that we were fed by parents and teachers and Sesame Street from our toddler days and until we graduated college was well-intentioned.

We might hear ourselves now telling this to kids, too–it’s so they feel empowered to pursue dreams, find their wholeness and serve the world in big ways. As adults, we feed these lines to kids because we believe it. The sight of them fills us with hope, and we know how much hope, help and inspiration this world needs.

Fast forward.

Now you’re fucking miserable–not to mention, earning $28,000/year to sit in a room and do about 1-2 total hours of typing on a computer (that an intuitive program could probably do) during a 10-hour day.

Didn’t you want to be an astronaut?

What’s wrong with this picture?

You may want to quit your job because you know you’re capable of more:

  • Maybe you’ve outgrown your role–you may crave bigger and better responsibilities in your workplace.
  • Maybe your role might not match your skills, talents or ultimate desires.
  • Your workplace culture may clash with your values and morals.
  • Maybe you do have to earn your stripes in your workplace–and maybe you’re just not gutsy enough to confidently ask for what you want.

If your heart is clamoring for more–not more stuff, more shit, more things, but more responsibility–ask for it.

If you’re like me, you’ve spent most of your young life waiting to be chosen–to be picked, honored, given an award. Somehow, we’ve never learned how to dig deep and understand what we want, and then ask for it.

Chances are good that you’re already more than capable. Take on the challenge. Ask your bosses, managers, or superiors if there’s an opportunity to take on bigger and better responsibilities. Do it before you think you’re “ready.” Dare yourself to succeed–dare to impress yourself.

Me, I asked for more responsibilities that went beyond running laundry to the dry-cleaners and driving in a car. I was given them, too. I had the honor of being asked to write a speech for my old boss to present at a memorial event commemorating Giovanni da Verrazzano in front of a few hundred people. Writing speeches was my dream, then–I wanted to become a Presidential Speechwriter.

He didn’t read it. He had it, I worked with him to write it, but he didn’t read a line from it.

He had no obligation to–no prerogative. But I know the speech that I wrote for him was good. I know it was better than the drivel he spoke at the event, which was the same old vanilla politico-talk everyone in the room had heard every politician speak dozens of times before.

I walked out of the room when I realized he wasn’t going to read what I wrote him. I walked out of the venue, outside into the cold night and stood by myself where it was quiet, and where I couldn’t hear him.

In that moment, I knew that no matter what I asked for, bigger and better responsibilities just flat out wouldn’t be honored.

Quitting, by this measure, was the right decision. Is it the same for you?

3. You may have “fallen into a career” that you never really wanted.

In my opinion this is, by far, the most common reason that I hear from people who are thinking of quitting their jobs.

It’s because this is never what they wanted to begin with.

Maybe you’ve fallen into a career that you didn’t want. Maybe it was your first job that you took out of college, and all of a sudden it’s five or ten years later and not a whole lot has changed.

But the quiet sentiment that I often hear buried in the person who’s telling me that he or she “fell into this career and never wanted it to begin with,” is one of shame.

It’s one of failure. It’s one of regret that pins self-blame on the younger versions of ourselves for not knowing what we never could have known ahead of time.

Listen. If you “fell” into a career, you’re still better for it than if you hadn’t.

One of my favorite lines from the Bhagavad Gita, an ancient Hindu text about taking up the spiritual path of yoga in one’s life, says, “On this path effort never goes to waste, and there is no failure.” 

Quitting your job will not “right the wrong” of falling into a career you never wanted. Instead, think about the career you “fell into” as a path of learning, growth and experience whereupon your efforts never went to waste.

Maybe it is right to leave the career you fell into. Just be cautious about quitting your job to attempt to “right a wrong.” Don’t keep falling back into your past.

Or Are These 3 Self-Deceptions Telling You to Quit Your Job?

By now, we’ve gone over the top three reasons that I have heard from people who are thinking about quitting their jobs.

But before we go on, I want you to ask yourself if any of these three causes might be the sneaky self-deceptions might be fueling your desire to quit:

1. You may be a dreamer throttled by circumstances–or the belief that your circumstances are holding you back.

You dream in revolutions. You’re a visionary, and so every idea you have is one of the future: the fruit of what could be. When you step out of your dreams and look at where you are, the lives that we live can sometimes look fairly unglamorous.

Being a dreamer throttled by circumstances (whether perception or reality), can feel pretty spirit-crushing.

I’ll tell you this: your life doesn’t come to fruition in sweeping revolutions. I’ve learned this the hard way.

It took me a hell of a long time–and a hell of a lot of fight and struggle–to understand that my life can deeply matter to many people in ways other than through the romantic, visionary sentiments of sweeping, grandiose “revolution.” Revolution is overrated. Tangled up in the word are romantic ideas of sweeping change, and unanimous agreement between one and all, and of unstoppable forces coming together to deliver what promises await.

But what we visionaries usually fail to remember about the love for the idea of revolution is that its allure is too quick, too easy, too frictionless and too responsibility-free.

Don’t you want to enjoy your journey, rather than skipping ahead to the final chapter?

2. You may not know what you want, so subconsciously you’re choosing to want anything but what you currently have.

This one is tough. I’ve found that this feeling of general discontent with life manifests in many ways, especially when we don’t have a solid feel or idea for what we’re doing with or lives or why we’re doing it at all. Instead, we might look around and take out our frustrations on the things around us that really aren’t so bad, but aren’t “impressive enough” for us to be wowed by them.

Just as happiness is a feeling and joy can be cultivated, purpose too is a matter of cultivation–a “feel,” yes, but a feel that can be embodied and enacted in practice, both within ourselves and in how we live our lives.

Purpose, in other words, is not a singular thing. It’s not one path that you need to walk upon or “you’re missing it.” It’s not something that can be defined in a mission statement.

If you don’t know what you want, look around and take into account all of the things–from niceties and luxuries to family and friends, opportunities and your health, clean air and clean water, even your privileges and rights–and create an inventory of your gratitude.

Through this practice of gratitude, you will start to see patterns and themes–what we might call your “values” or guiding beliefs about what the good life is for you, manifested in what you’re most grateful for.

3. You may be entrapped by the easier road of quitting to start all over again, rather than tougher one of maneuvering upon the path that you’re already on

I’ve been guilty of this self-deception–many times.

If the path that you’re on doesn’t feel 100% perfect, you might catch yourself thinking that there’s a “right” path out there that’s waiting for you–that you need to abandon the one you’re on to find the right one. Whether it’s a job or career, a relationship or the city that you’re living in, this self-deception is tempting because it means we’re probably choosing the path of least friction.

In other words, it feels a lot easier to quit and start over again.

It means we can skirt some responsibility, hard work, struggle and fight. We can dodge difficult conversations about asking for a raise or trying to mend a fractured relationship. If it feels so tough to find a perfect living space in this big city, we might pack up and head outta dodge altogether.

Sometimes we’re called to blow up our plans and start over. And sometimes, we’re called to do what’s right by fighting hard and redirecting the path that’s beneath our feet. Which is right for you?

If You’ve Read This Piece and Still Know That You Need to Quit Your Job, Do What I Didn’t Do: Start Early to Get Yourself Ahead.

You don’t need to leap too soon and set yourself back for a year or two. You can start dedicating your personal time and personal practices, habits and efforts into setting yourself up to succeed when the time is right to leap.

1. Put yourself on a tight and responsible budget.

Know how to figure out how much cash you need to survive? Budget, baby!

Start grasping an understanding of what you’re spending and where, what’s essential and what’s not. I like to spend periods of a few weeks at a time testing out different mini-budgets to gauge just how much spending is habituated and how much is a matter of necessity.

I recently spent a month simply trying to curtail my spending at the supermarket on superfluous things–not on the healthy stuff or necessities, but the stuff I really didn’t need. Cutting each visit to $40 instead of $60 – $70 can add up to hundreds of dollars per year.

2. Become the sole owner of your mental-emotional makeup.

Put yourself on a personal path of self-realization. End the blame game, don’t just “react” to your emotions, and start to accept responsibility for everything.

Take ownership of your moods, thoughts and ideas. Be accountable to yourself and keep your emotional reactions in check. No matter how much you feel like a victim or the “only one” who’s going through something, remember that there are millions of people who have it worse than you.

A simple reflection on this fact cultivates your empathy, compassion, and gratitude and builds steadfast resiliency within–which, of course, impacts how you live, work, create, interact and share with the world.

3. Assume the role of a close friend to your behaviors, habits, routines and patterns or “samskara.”

In other words, get to know yourself better–and be kind to yourself for it.

Observe your gut reactions, habits and routines. Many of these happen subconsciously and automatically. When you really step outside of yourself to observe your automated patterns of thinking, speaking or acting, you continue to develop a level of self-awareness that will guide you forward when you quit your job–and perhaps, even become your own boss, accountant, marketer and customer service rep, all rolled into one.

But most importantly, be kind to yourself.

The journey you may yet embark upon is a tough one, because the path is ripe with doubt, second-guessing, insecurity and an endless sense of unknowing. You don’t know where the next pay day is coming from or when. You don’t know how people will react to your first book.

You don’t know what you don’t know. Until you know it.

So treat yourself kindly–don’t make things tougher on yourself. We’re all trying to find our own way.

4. Start to practice and develop meaningful skills.

What are those passions, pastimes, interests, hobbies and talents that you can begin to practice on a daily or near-daily level?

Most of us have heard about the concept of 10,000 hours of dedicated practice being what separates novices from those considered be be true experts. The notion, popularized by author Malcolm Gladwell but based on a the work of Swedish psychologist Anders Ericsson, means that you’d have to put in 20 hours a week of dedicated practice to a single passion, pastime or hobby for 10 years to reach 10,000 hours.

Wouldn’t you prefer to start today than tomorrow–or six months from now?

Begin. Just show up and start to put in your hours. Whether shooting free throws, writing, painting, selling or otherwise, you’d be smart to start investing your time and energy into this seemingly-monumental task of accruing thousands of hours of experience.

You will do it. Trust me.

5. Learn how to earn ten bucks before ten-thousand.

Who would you want to work with after quitting your job? What are they struggling with? What can’t they overcome on their own?

Start to talk to those people before you quit. By talking to prospective clients, you not only get to know what they’re struggling with (we could call them needs, pain points, market holes, etc.), you also begin to understand the manner in which you could best help them.

Embody a relentless desire to be your most whole self while serving others in meaningful ways.

Everyone has different wants, needs and requirements–but as you start to talk to more people about where they need help, you can turn your objective lens upon yourself and ask what you would need to do to best serve them. 

The manner in which you serve, provide, lead, give, create, share, or perform is probably even more important that what you serve them.

Because, after all, you’re just starting out on your path. You won’t create the next iPod or teach them the secrets of the Universe, but you don’t need to–you just need to start doing what you do best, and from exactly where you are.

In Conclusion, an Ode to the Inch-By-Inch Crawl

I started this blog after quitting my job five years ago today because I was desperate to believe that I was, within myself, completely capable of doing something with my life that mattered to other human beings. That’s all I’ve ever really wanted.

And it’s taken me a hell of a long time and a hell of a lot of fight to be able to say that and know it’s true–and it’s true for all of us. We’re all capable of it.

But quitting your job, escaping cubicle nation, and starting your own business don’t necessarily need to be the path that you take to serve the world, lead by example, and give from your best and most whole self.

I know a lot of people who are better suited for working within environments that give them the backing of teams, resources and write-offs. Some people are built that way–they can handle budgets and write-offs, hire interns and train managers. We need people like this to help change working cultures from the inside-out. As a collective, we all need people to work from within such environments to help direct or redirect the course of companies that many people depend on, whether a corporation or a small business.

Me, I needed out because I needed to go full-tilt. All in. Make it or break it. It’s just how I’m wired. I never would have survived otherwise.

What I do know these five years later is that love is built with time.

No matter what path you find yourself on, remember that change only lasts when it’s chosen. Committed to. Chosen again and again in hard-fought battles.

It takes time.

And whether you quit your job or stay your path or alter your course upon it, remember that this isn’t a once-off fix you’re looking for–this is an inch-by-inch crawl.

When I quit my job, as a young idealist would I dreamed that my life would change like a revolution–a single moment would spell sweeping change and and unstoppable X, Y and Z would ensue next. Win the lottery, boom, you’re set for life and all is well and happy.


Looking back at my last five years, I have come to believe that the most glorious change of all is bearing witness to the tempered, simmering evolution of your own soul.

It’s slow, but it’s honest. It’s hard fought, inch by inch, but every inch is a long-lasting victory in your own self-belief that you won’t soon forget.

Sure, I’ll admit it: I would have liked to get to this place where I am here today in only a few months’ time. But the inch-by-inch crawl is how you truly earn it. And how you learn to appreciate it. And how you learn to find your way before you know the way.

So, No, Maybe You “Shouldn’t” Quit Your Job–But Maybe You Ought to Anyways.

You’re not ready to do that–but when are we ever “ready” for the unknown, except when we finally and decisively choose it?

You don’t have enough money saved up, but that’s alright–it means you’ll need to get good at earning smart and spending smart.

“Doing what you love” is not an answer for being happy–but doing what matters most to you will always help carry you through moments of struggle and doubt.

Working for yourself is just as difficult as working a job, but perhaps there’s no more important a job than working on “you.”

Your heart.

And how it wants to become alive.