Do You Want to Be Your Boss? (or How to Know When It’s Time to Quit…)

Do You Want to Be Your Boss? (or How to Know When It’s Time to Quit…)

 “Every man must know when it’s time to move on.”


How do you know when it’s time to quit?

More than anything, when I talk to readers, clients and friends about their careers, the biggest challenge they face is figuring out when you know it’s time to leave.

For many, it’s so hard to know when to jump or if you should at all. So much so, they get paralyzed. 

Do you ever wonder if the work you’re doing, the career you have, the way you spend 75% of every day, is worth your time? Ever curious if there’s something else that would fire you up a bit more?

Well I think I have the answer.

Let’s start with a personal story.

Four years ago my wife quit her career in corporate PR to pursue her passion for yoga, fitness and nutrition. She went off and got certified to teach yoga, do personal training and started teaching folks about what to put into their bodies through her classes and blog (for the health nuts out there, you gotta check out here vegetarian/vegan cooking and recipe blog, Food-LifeBalance. I’m her dedicated taste tester and definitely not complaining ;)).

She also recently got a sweet gig helping a fellow Living Legend and fitness fanatic manage a chain of workout studios. Last night we went out to celebrate (Congrats Chelsea!). As we drove she remembered back to her couple years in the PR industry. She vividly recalled that she always knew she never wanted to have her boss’s life. It was nothing against her superiors (who were actually great people), but for whatever reason, she just never wanted to be in those shoes.

Fast forward a couple years, and one massive career shift later, she noticed that from day one teaching at her new fitness studio, she found herself admiring her boss and the role she had – inspired by the responsibility she was given, the way she got to help people and her genuine excitement for what she was doing.

Two years later my wife has just about that same role and it’s appearing to be everything she imagined. She admired the work her boss did & the life she lived, and it inspired her to operate on an entirely new level.

I can’t say the results surprise me (of course I’m a tad biased), but this did get me thinking…

It turns out I have a sure fire way to figure out whether you should stay or go.

Before you read any further, stop for a second. Look around you. Look at the people at your office or the ones on your calendar invites. Think about the person you report to. Do they inspire you? Do you want what they have?

Do you want to be your boss?

If the answer is no, it’s time to get out. Simple as that. If you’re at your desk right now and are peering into your boss’s office in disgust, seriously grab your fish bowl and coffee mug and get the F*/# out! I mean it. Start running and don’t look back.

Ok maybe you don’t have to immediately pull the fire alarm and run out the emergency exit, but at least notice the siren that should be ringing in your head right about now. Respect it.

It’s time to do something about it.

If the people you work for do not inspire you, excite you and make you want to do epic things, you are in the wrong place. If the people who are molding and teaching you, are not people you admire, you are wasting your time.

*note: If you’re an entrepreneur then sub out “boss” for “successful folks in your space” anywhere it comes up. This stuff applies to everyone. 

when to leave your job

The longer you stay, the longer you’ll stay and the steeper the spiral becomes.

I hear from people all the time say “things will get better”, or “I’m going to stick around for the next promotion and then maybe take off”.

I have news for you. If things aren’t better now, the odds are they aren’t going to be better in a month or two. There is no saving up happiness and enjoyment.

Happiness not spent today, does not equal more happiness tomorrow. 

If you think you’ll be less stressed, less conflicted and less disenchanted at a higher level, you’re in for a nasty surprise.

And I can assure you if you’re boss isn’t someone you want to become, things are definitely not going to get any better.

A few years ago Robert Cialdini, the bestselling author of Influence: The Psychology of Persuasion, taught me that we as humans are conditioned to stay consistent to prior decisions we’ve made. It’s why we promote the products we buy, even if it turns out we don’t totally love them. It’s also why we stay in jobs that straight up suck. This trait proves incredibly powerful when building something you believe in, but turns deadly when you start to do things that aren’t congruent with who we are.

Our reasons for staying in a soul crushing career often sound something like…

  • “Well I’ve already put in 5 years”
  • “If I left now, all the work I’ve put in for that promotion will be a waste”
  • “I can’t leave my coworkers hanging”
  • “I’m only 9 months away from being Partner”

Sure, those might even sound like decent excuses in your own head. But do you even freakin’ care about that promotion? Is that really what you want? Or is it just what everyone else thinks they want so by default you’ve started to want it too?

And do you think it will be any easier to leave once you become Partner? Let’s get serious. The day you reach that next rung, you are that much less likely to take the leap to do something meaningful that you know you should have done years prior.

There is never a good time to experience massive change. I don’t care what you’re doing.

But if the person giving you the orders at work or the person you’re modeling your business off of, is not someone you want to be, NOW is the only time to do something about it.

Stop climbing the ladder to nowhere.

If you’re in a situation with people you don’t admire, doing things that don’t matter, realize that every ounce of effort you put in from this day forward is a waste. A waste of energy and a waste of potential. Every project you complete and rung you climb is going towards nothing. It’s building something you don’t care about for people you don’t look up to.

Is that any way to spend your next 30+ years? If you do, you’ll likely get to the top and want to do a swan dive right into the concrete on the bottom floor, where you could have just walked away before you got so committed in the first place.

We spend so much time climbing the ladder that we forget to ask ourselves where the top is and why would I even want to be up there. Often times it’s difficult to understand what it would mean to actually be in this high up place you dream about.

The best proxy for this is to observe the person already there – Your boss or your boss’s boss.

Notice all the folks above you who are more “successful” than you. What do they do on their days off and in the evenings? Do they have hobbies and passions or are they too busy trying to get to the next level? How’s their family? Do they even have one? What about their friends? How do they treat the people around them? Are they healthy and fit, energetic and excited?

Most of us, in racing to the top of something, only count the things that are easy to measure. In a word, money. The vision of the money shines so damn bright that we don’t even notice the carnage that those we ‘admire’ created in order to experience it. It’s time to start taking note.

Surround yourself with the people living your dreams. 

Take another look around you. Who inspires you? Who’s job do you constantly wish you had? Who lives the type of life you’ve consistently dreamed of?

Notice the folks you admire. Understand why you admire them. Surround yourself with them. If you’re an employee, find a boss who doubles as a role model. There should be no other type. If you’re an entrepreneur find the mentors and models you truly respect.

It’s time to begin working towards something that’s meaningful.

As always, it starts with the people.

If you can’t get behind the people above you, it’s time to get out.

I’ll ask one more time, do you want to be your boss?

Time to get honest.

Is your answer No? Check this out…

If you know the answer to this question is “No” for you, then it’s time to start doing something about it. I’ve created the Live Off Your Passion Career Course to help  you with that very process. It’s at least worth a look and you can always try it risk-free. Here are all the course details.

It’s time to start working around people who inspire you!

Images courtesy of Angelo González & Scott Hudson