Should I Quit My Job? How to Decide

There was no singular moment when I knew I should quit my job.

But just how I made that decision might surprise you.

Should I Quit My Job?

Today is the first Monday in a long time that I didn’t wake up with an alarm clock.

Instead, I woke up naturally at my body’s preferred wake-up time (around 9 AM). I didn’t have to rush my zombified self out of bed an hour-and-a-half earlier to make it into the office. I didn’t have to battle caffeine-addled commuters on the highway to get into work on time.

I actually ate breakfast.

Don’t get me wrong, the odds that I’ll go hang out by a pool somewhere all day are slim. I have a mountain of things I want to get through today. But they’re my projects. I chose them.

Words don’t do justice to how liberating it feels.

And it’s all because I quit my job on Friday.

How I Knew I Should Quit My Job

December 20, 2013 was my last day at work.

For the last 30 months or so, I’ve been an in-house attorney for a technology/entertainment company. For those of you who don’t know what an in-house attorney is, think of it as being a lawyer who only has one client.

The fact that you have a single client lets you become more embedded in the business you represent. You’re typically co-located with the businesspeople you work with, instead of sitting in a different building or a different state with only other attorneys.

On the plus side, this means your business people can drop by your office at any time with a question.

On the minus side, this means your business people can drop by your office at any time with a question.

Lawyers work long hours. I probably don’t need to tell you this. In-house attorneys don’t work quite as long as our law firm counterparts, but I was still supporting 9 PM calls to Indonesia and taking breaks from Chicago Bears games on Sundays to revise a contract.

Long hours aren’t horrible for a single twentysomething with no children. But what they don’t tell you about the legal profession is that your main job is to say no.

No to the business people who are nominally your clients. No to anything new, interesting, or innovative. It’s a risk-averse profession. The message I received from my supervising attorney was simple: the less deals we do, the less downside risk there is.

(Never mind that if you don’t do any new deals, the company doesn’t make any money.)

The drive to take action instead of constantly acting as a roadblock eventually made this work situation untenable.

You Don’t Have to Belong to a Tribe You Don’t Like

Life often involves dealing with people and situations you don’t enjoy.

But one mistake people make over and over is belonging to a group—a profession, a company, or a social circle—that by its very nature makes you uncomfortable, unfulfilled, or unhappy.

There are singular moments of discomfort in every kind of group, but these Negative Tribes we belong to do things that go against our values. Negative Tribes de-motivate instead of motivate. Negative Tribes enervate instead of energize.

One reason I had to leave the lawyer tribe was that I simply disliked the people who were in the tribe. I disagreed with their values, and I’m sure they disagreed with mine. Law as a profession attracts people who are risk averse, materialistic and unwilling or unable to understand opposing sides (that last point is surprising, since we’re taught in law school to consider multiple viewpoints).

Yes, there are exceptions to the stereotype. But if you hang around lawyers long enough you can’t help noticing the vacuous, status-based sense of self-worth and overriding fear of uncertainty and the unknown.

I could not remain a part of this Negative Tribe, committed as they were to rigid formality, hierarchies, and processes.

So I quit.

The conventional calculation says I spent three years and six figures going to law school. Another brutal summer studying for and taking the bar. And thousands over the years in bar dues and fees to become a part of the profession.

The Herd would shriek at my turning my back on these “investments” and the supposedly secure paycheck it promises. But this is the sunk cost fallacy at work. I won’t ever get the energy, time, and money I’ve already spent on this profession back. But that doesn’t mean I should keep going at it in some fruitless attempt to “get so good that I can’t be ignored.”

It’s one thing to have to deal with close-minded and fearful minds on a one-of basis. You can’t avoid it completely in life. But it’s another thing entirely to be a member of a Negative Tribe that you have to deal with day-in, day-out.

No corner office, no perk, no parking spot is worth that sacrifice.

Life is too f—king short.

What Quitting Was Actually Like

I’d like to tell you that my quitting was a triumphant moment of ass-kicking and f-bomb-dropping. That bridges were burned and names were taken. That two-and-a-half years of indignities and abuse were dealt back out in a brilliant, blistering, expletive-filled rant.

The reality is that it was bittersweet. Despite how wrong the job was for me and despite how wrong the organization was in general, I couldn’t help feeling some attachment to the people I spent two-and-a-half years working beside.

You get to know them as people. You see that it’s really the processes, the profession, and the culture that turn them into bad colleagues. You learn that bad corporations really do warp the brains of the individuals within them.

It still hasn’t totally hit me that I won’t be seeing them again.

When I turned in my notice a month ago, I was calm. I kept the anger and resentment at bay. I focused on the good times and the learning experiences along the way. I needed to say goodbye. But I didn’t want to say “good riddance.”

Are You Earning or Learning?

As I thought about where I was in my career, the words of Y Combinator partner Gary Tan came to mind:

You’re always on one side or another of the learn vs. earn [equation]. Given the nature of equity and corporations, always know that owners reap the rewards and workers are transacting their time for money. But unless where you work is a co-op where profits are evenly distributed, you’ll never extract the full amount of value that you create for the company. Always know whether at that moment you’re learning or earning. If you’re learning, then it’s worth it. If you’re not, you better be earning (e.g. being a founder, being a share holder). Otherwise you’re just wasting time.

Emphasis is mine. You can read his entire post on what he wishes he knew at 16 here.

The “learn vs. earn” problem was on my mind. I knew I had hit a learning plateau months, maybe even years, before. I could see my future. All I had to do was look at my boss, who was doing the same things I was doing, but with a different title and marginally better pay.

I was neither earning nor learning. So what the hell was I still doing there?

How a Bi-Weekly Paycheck Tricks You Into Obedience

The biweekly paycheck is one of the most ingenious inventions of the corporate wage-earner system.

Instead of paying you for completing projects and reaching milestones which, when you think about it, is the logical way of doing things in a knowledge-work economy, corporations release a steady drip of paychecks every two weeks like clockwork.

Why do they do this? Corporations are taking advantage of human psychology.

Just as you reach your low point after fourteen days of humiliating, degrading work and you start to think, “Hey would life really be all that bad if I just quit?” they give you another ultra-addictive endorphin hit of cash to keep you coming back for more salary slavery.

Getting that paycheck gives you that momentary rush. That rush is enough to keep you going for another two weeks. Then the cycle repeats.

That is not a formula for human dignity or fulfillment. It is a formula for addiction.

And that’s why it’s so hard to wean off the corporate teat. I knew that the longer I stayed, the more comfortable I’d get with mindless drudgery. Comfort is the enemy of creation.

So while smart individuals like Hugh Macleod and Austin Kleon advocate that you keep your day job, I decided that it wouldn’t work for me. How can you create when you come home every night a husk, unable to process or relax, let alone create?

Watching the TV until you fall asleep in exhaustion is much more inviting when you’re in that state.

I should note that I began Agile Lifestyle while I had this job. And as great as the journey has been since we started back in April of 2012, I knew there was an upper limit to how high it could get without more attention being paid to it.

So I decided to take the plunge. See how far this online business thing can take me. Fully walk the walk.

Should I Quit My Job? Here Are The Considerations

Signs You Should Seriously Consider Quitting Your Job

1. You complain about your job constantly. To friends, family, your significant other. To anyone who will listen. And not just about the usual office dramas or inefficiencies. But big things. Like the meaninglessness of what you work on or the utter dysfunction of the department you work in or the disrespect of the people you work with.

2. You’ve already begun looking for a way out. Your resume might be on Monster already. You’ve already put feelers out to see if any of your Facebook contacts know of any openings. You’re willing to become a Starbucks barista for the insurance.

3. You feel betrayed. By your boss. By the role you were promised that didn’t come through. By your organization’s leave policy. By the relocation package that was yanked last minute. The resentment has been festering for months now.

4. Your organization is engaged in some ethically dubious shit. Funny accounting, illegal importing, insider trading. These are all things you don’t want on your resume. Document everything. Get in touch with an attorney. Be prepared to say nothing at your exit interview.

Prep Your Escape

Fit the signs? I still don’t recommend you quit out of nowhere. Even in the worst working situations, you should be able to prepare for life without a W-2 beforehand.

1. Get your financial house in order. Sell or cancel the things you can live without. Implement some basic strategies to manage your cash. Start living on a budget if you haven’t already. Track your expenses for 6 months. You’ll need it for step 3.

2. Simplify, simplify, simplify. Think minimum viable lifestyle (MVL). Your MVL is the minimal expenses you need to fund the lifestyle you can live with. Reduce your household expenses until you’re lean, nimble, and agile. The lower your MVL, the longer your runway to income replacement.

3. Build a long Personal Runway. Create as long a runway as you can manage before quitting. That requires you (a) know how much you spend each month for your MVL and (b) save 50% or more of your income. I built up 24 months of Personal Runway before quitting, meaning that if I don’t make a dime between now and January 2016, I’ll still be able to pay all of my expenses. It’s been a long time coming for me though. If you can manage 12 months, you should be fine.

4. Have a vision for what you’re going to do. Dissatisfaction with your career is not enough. You have to have a vision of what you’re building towards. A number of entrepreneurial ideas don’t take much money at all. Now’s the time to get serious about finding your Personal Hedgehog.

There’s a time when quitting your job is the right move. I believe it was the right one for me. But even if you decide to pull the trigger, know that the transition won’t be an easy one. You’ll be anxious. You’ll be second-guessed.

Know that the “safe path” no longer exists. Every career path has its set of risks.

But the biggest risk is not taking a chance.

Photo Credit: Kevin Krebs via Compfight cc

Opt In Image
How Much Time Would You Save With the Right Tools?
Get the 'App Guide' for Download NOW

In this free guide, I reveal the top 7 apps that make my career and personal life run smoothly. Hint: 5 of the apps I use every day are totally free! Sign up to receive blog updates, exclusive content, and the resource guide FREE!