How To Quit Your Job Like A Boss (And Be Your Own)

Hacks to quit your job like a boss and become your own.

Always wanted to quit your job in a BIG way?  Ever think of becoming your own boss?  Here's the key to success.


I'm sitting in Starbucks enjoying some coffee last week and trying to get a few reports done...and there are two guys in their mid-20's having a conversation next to me.

I'm not sure if the bourbon I'm smelling was snuck into their coffee or seeping from their pores.

"Dude - I quit my job like a BOSS yesterday," said one of them.  

"How did you do it?"

"Bro - I walked in and said 'I want a raise'.  And he said 'no'.  And I said 'the hell with you - I QUIT!' and I knocked over his bookshelf and I LEFT."

"No you DIDN'T!"

"Yeah, man.  I quit like a BOSS.

No, You Didn't

Let's examine this little exchange between two friends.  I kept my mouth shut, but I'm going to weigh in here from a professional perspective.  This guy didn't quit his job like a "boss".  He quit his job like an idiot.  This, my friends, is how you quit your job like a boss.

Have a Plan

Successful business owners started somewhere.  And if you've got that entrepreneurial mindset, you need to start with a plan.  You need to know exactly what you're going to do after you leave and exactly how you're going to pay for it.  This means having a rainy day fund.  I'd recommend at least eight months of expenses covered, plus pad and whatever money you're going to need to launch your next endeavor.  

Start networking and talking to people.  Write down your plan.  Make sure that your new business plan includes the financials, the marketing, the resources and the contacts you'll need.  Be realistic.  Chances are good that you're not going to quit tomorrow and own a yacht the next day.  You're not the Wolf of Wall Street.

Have a timeline.  Know when you are going to give your notice - and yes, you need to give proper notice.  Two weeks minimum.  No, I don't care that you don't like your boss.  If you want someone to give YOU the respect of notice one day, you need to do the same now.

Make sure you square away the important elements that you may not have thought of.  Health insurance, for example.  Retirement plans.  Dental.  Vision.  It's all fun and games until that root canal takes two months out of your emergency savings.

Make a plan and stick to the timeline. 

Plan To Fail

You will fail.  I'm not talking crash and burn style.  But you WILL make mistakes.  Anyone who tells you otherwise is full of it.  I've said it before and I'll say it again - as a business owner, you want to fail...because it means that you're innovating.  

The question isn't whether you'll see failures.  It's what you learn from them.  It's how you grow stronger.  It's whether you're able to get up, shake off the dirt and eat a slice of humble pie.  This is what separates the successful business owners from the guys that sit at Starbucks smelling like bourbon and talking about how they quit like a boss.

Talk about your failures.  Ask people to analyze them for you.  Embrace them.  Be proud of them.  You earned those stripes.

Don't Burn Bridges

There's a pretty good chance that you like at least SOME of the people you work with now.  So why would you burn them?  And keep in mind that even if you do NOT like them, karma sucks.  

I've got a good friend who owns a number of extremely successful businesses.  He once shared with me a story about how an employee quit...then went to his competitor and asked for a job and an advance, saying that my friend hadn't paid him what was owed to him.  Turns out it was all BS.  The potential new boss saw right through it...and went back to the potential hire's former boss.  Why?  Because sometimes, as business owners, our biggest competitors are our best friends.  Whoops. 

Remember Your Priorities

If you're single, your priority may be YOU.  But if you have a family, they are your priority.  When you are a mother or a father, sometimes you need to bite the bullet and suck it up at a lousy job for longer than you want...because you have a family to provide for.  There's nothing wrong with this.  You should be commended for this.  Selflessly putting others first makes you a better person, not a person who missed an opportunity.  Sure, you want to live on the sunny coast and drink mojitos after work.  But when you have kids - it's no longer about you.  Nothing chaps my ass more than someone who puts their own desires before the needs of their kids.  A person like that will NEVER have a place in our companies.

Don't Steal

At the end of the day, what is your integrity worth?  A couple of notepads?  A few boxes of pens?  What is the value of some office supplies when it means you have to sacrifice your credibility and your integrity?

If you have to steal something, steal memories of moments when you could sit around for five minutes at lunch and know that you'd get paid at the end of the week no matter what.  Because when you work for yourself, you're ALWAYS hustling.

Finish the Job and Fill Your Own Position

When at all possible, don't leave a job unfinished.  There are always going to be elements of the project you were working on that nobody else knew about.  Don't leave people scrambling to figure out where you left off.  It says something about the character of a person when they will see something through.

If it's possible, find someone else in the company with potential and train them on some of the vital details of your position.  Help make the transition for the company as seamless as possible.  And when you finally put in your notice, offer to help them transition between employees.  It will go a long way - whether the boss takes you up on it or not. 

Cement Your Legacy

Go out on a high note.  Always.  Just finished a big project that went well?  Just achieved an award, exposure or an honor for you or the company?  You want people to remember you for the good you did - not for knocking over the shelf on the way out.  Cement your legacy in a positive way.  


I couldn't run my business without a little help from the Big Guy In The Clouds (I figure that's as politically balanced as I need to get).  A little God in your life goes a long way - regardless of what you call Him.  At the very least, recognizing that we can't do it all ourselves helps to ground us and teaches us when to ask for help - whether that help is in faith or in friends and family.

Freak Out For Five Seconds

You just finished your last day.  You've walked out the door and you have the entire world in front of you.  It's ok to be terrified.  But you only get five seconds.  Freak out for five seconds and wonder what the hell you just did.  Then get over it.  There's a reason why you quit - and if you followed my guidance above, you'll realize you quit because you have a plan and a purpose.

Remember that five seconds of freaking out.

Because one day, you'll be sitting in a Starbucks - because you can sneak over there in the afternoon when you're the boss - and you'll hear some kid who smells like bourbon talking about how he quit like a boss.  You'll smile, you'll laugh to yourself and appreciate that you did things the way that you did.