”Every man must know when it’s time to move on.”
-Unknown
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.
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
I'm an entrepreneur, coach and author of Live Off Your Passion, here to help you build a career around work you Love. I'm also a tad obsessed with life experiments, adventure & learning. 
Awesome article, Scott. “Do you want to be your boss?” is a great question to ask yourself when considering leaving Corp. This is a great measure to see if it’s time to hit the road.
I would add that another option instead of quitting is to stay and make a bigger impact in the Corporate game you are playing. After all, someone has to stay and make a difference.
I like that, when I don’t tend to like my boss, I still want their job and prove it can be done differently.
Don’t run away from the stuff that’s wrong, take it head on and make a change. Or leave anyway.
Whatever makes you happy, but glad to see the 2nd option being pointed out here as well.
Thanks ExcutiveX
Agreed Kurt. It’s a very important part of the equation!
Really well put! Think of how much bigger time your effect on the world would be if instead of just leaving, you found a way to modify the environment for everyone else, in all of the employees’ favor. That would be epic!
I too agree that the system needs people like you, creating the change, and not just folks hitting the road. The tough thing is that hitting the road is usually the fastest way to improve your own situation (when in a toxic environment). The incentives to stay often aren’t that great!
Hi Scott,
Great article. If I may add, asking the best questions often gets you the best answers. And this is certainly a great question to ask yourself.
It sure is making me think hard right now!
Cheers,
Jeremy
Let me know what you come up with after all that thinking Jeremy!
“Happiness not spent today, does not equal more happiness tomorrow.”
This is such a great and wise observation. I know that I did that for a time in a job, I kept telling myself “it’s going to get better”. . and of course it didn’t! I’m not sure who said it first but this reminds me of “If you always do what you’ve always done, you will always be who you’ve always been” Looking around at the people we surround ourselves with is a great way to evaluate where we are headed. . .
Great food for thought! Thanks! (And congrats to your wife!)
Environment is huge. Simple as that. Glad you found your way out when you realized things we’re going to change…
Thanks for sharing in our excitement too Amy. Chelsea deserves it!
Just one person? Dang.
The person who has been the most inspirational to me lately is Ash Ambirge (http://www.themiddlefingerproject.org/). After losing everything, she launched an eBook from her car, and now she takes names and kicks ass while travelling to romantic locales.
Wow Bethany! I just spent ten minutes on Ash’s site. I freakin love it! Thanks for turning me onto her. A Living Legend indeed!
Hi Scott,
Great article!
My sister asked me that same question 3yrs ago and it helped me decide to quit my job.
Unfortunately I fell off the wagon and while on a working holiday am back working in the same job. It was just too easy and the excuse that I get paid more doing this, therefore I will have more time to travel/figure out what I really want to do was easy to believe.
I am finally coming back around (I have to say in part thanks to your website).
Keep the inspirational words coming .. they are finally sinking in and I am determined to find my why and start living my legend.
Thanks,
Jessica
That’s what I’m talking about Jessica!!! Love hearing that you’re seeing the light. Not always an easy thing to do but so worth it. Come back and tell me what you start building and we’ll have to write you up as a Living Legend!
Hey Scott, another thought inspiring post and the new brand works well – congrats.
This post resonates with me. I’m totally behind your sentiment and I can’t agree more with it. Yet I’m still thinking ‘I really wish I could…’. It’s a mix of fear of maintining an income as the main bread winner, plus the practicality of switching to a different well paid job if you want to do something else entirely.
My chosen route was to set-up an on-line business in parallel to working full time. That started a year ago and it’s taking longer than I had hoped. I find the venture and work both tend to suffer unless I only spend my time working. So I’d love to see a post (or some thoughts from readers) on a set of transitionary options to get where you need to be, when jumping ship isn’t practical.
For those that are doing it – the very best of luck! Kudos for having the courage!
Mike
You got it Mike! Just put it down on my future post list. Expect it soon. I think you’re doing just the right thing with building what excites you on the side while you continue to make some dough. The only thing to be careful of is never actually taking the side business to the next level because you’re comfortable in your main gig. As they say, necessity is the mother of invention. See how you can create the right incentive to really kick the side project up a notch.
Thanks for the great post idea!
I want to be like Esther Havens. She is a humanitarian photographer who travels the world using her skills and creativeness, and her heart, to tell stories for people who need their stories told.
Love it Steve. I will have to check her out a bit. Sounds Living her Legend in a big way!
Such an important message, Scott! I recently left my job of 18 years because I knew I could not possibly let it be the last job of my life. Mired in bureaucracy and fearful people. I jumped! I’m exploring now and rebuilding my life. An account of my progress is on: zanidyer.blogspot.com.
Your e-mails are a great source of information and support. thank you!
Congratulations on escaping Zain! What a huge victory. Hat’s off to noticing and then doing something about it!
Great to see you documenting it too.
Come back and check in with the progress!
Jeez Scott, you nearly had me packing my shit and heading for the door…
Not yet though. It will happen, and sooner rather than later. Bookmarking this for additional inspiration down the road.
Well you just had my wife and me laughing out loud
. The most important part is you have the intention to leave. If you’re anything like most folks, as soon as that starts to take over your mind, before long you won’t be able hold yourself back.
Between now and then, I’m here to get you closer to the edge. We’ll be sure that when you jump, you’ll be ready!
Producer Mark Burnett inspires me..I read his book and I someday hope to produce a reality show. Not just any reality show but a very successful reality show.
Mark does have a wild story–and great shows! Maybe start with something simple on your own youtube channel and build from there…
Scott,
This is great work!! I only wish I had had advice like this 40 years ago when I was working. I worked for 7 years before I had my children. Raising my 2 children was my passion but wonder what I could have done with those 7 years following college.
Keep up the amazing work you do! You are very inspiring!
Thank you Jan. Means a lot. I wish I would have had this advice out of college as well… Better now than later, eh?
Good to have you along for the fun!
Wow!! Amazing thought, put in a brilliant way…
I believe one should always follow where his passion lies…and your post has given me that one push which was required to take that big step I’ve been working on since last few months…
Your post has added a lot of clarity to my thought and assures me that I am on the right direction…Thanks.
Looking forward to more such thought provoking reads…
I love this idea and it’s exactly why I left a big public accounting job many years ago. I was pushing to make partner faster than anyone ever had. Then I started spending more time with the other partners and realized it was definitely not a life I wanted so I jumped ship after 7 years there. I spent the next 2 years on a “sabbatical” to find what it was that I really wanted to do. It was a couple of the best years of my life.
Due to finances, I ended up back in corporate America in a variety of jobs. I can’t stand my current boss. I took the initiative to try and change things for most my first year there and it was like beating my head against the wall. Now it’s a paycheck while I develop my own online biz (mostly on company time since I’m totally underpaid so I look at it like I’m taking back the time they’re not paying me for).
I just got a part time job with an old friend (he started one of the companies I worked for). He’s amazing and totally inspiring. He totally supports my business and other dreams I have. This time it’s something I’m excited about even though it’s a job.
So I’m learning to follow my own dream while working a job for a totally inspiring person and group of people. The best of both worlds!
Scott, I absolutely love what you’re doing here. More people really need this message. You rock!
Angela Russel has been inspiring me for a year by giving up her life in America and fighting the economic and employment systems by going where she can find valuable work. Here’s her blog! Enjoy the inspiration!
http://lovinlife1902.blogspot.com/?spref=fb
(It didn’t post before….)
Hi Scott,
I see more and more people quitting their jobs and starting their own businesses.
I worked for corporate America for 15 years until my life shifted in a way that I had to become an entrepreneur.
Working for myself is so much better than having a job.
Scott, this whole posts resonates with me. My favorite part is not to ignore the siren in our heads, but to respect it. That word respect is so key; something I’ve never thought of before, a very strong word.
On another note, my wife is also a burgeoning food blogger so I empathize with your taste-testing duties. It’s a good life!
You are assuming everyone wants to move “higher” in his/her organization. My spouse was on the right job track for him. He actually enjoyed his work. He did not want to move “up” into management. His company recognized his value to the point of creating a technical track so he could move up without moving onto the management track. There’s more than one way to get the job you want.
I probably should have added that this was written in the past tense because he retired after nearly 40 years with that company.
Hi,
Dear Scott,
Thanks a million times for what you are doing. In fact, there is no word to describe what you are doing. And, you do not know how much you have changed my life. Hence, I am a big fan of your blog even though I have recently joined it. Your blog inspires me every day and I am very thankful for that!
I would like to ask a question, however, I am not so sure if I can convey it well. I hope I will.
What I would like to say is that one specific job is neither bad nor good. What we want from it makes it bad or good because there are some other people who are doing the same job with passion and enthusiasm. Those passionate people are very few. For example, there are many politicians in the world, however, one has become like Gandhi changing India very deeply. So, I think maybe my boss is not a good criteria to see if I want to go on with my job. Maybe my boss is doing the job only because of the salary or some other reasons, which I do not know. If my boss had been Gandhi or mother Theresa, I might have found politics or nursing very interesting jobs. So, I think it really depends on who is your boss and how he does his job. Some people get you interested in something that you don’t like and some make you hate what you love doing. May I ask what you think dear Scott? I greatly appreciate your kindness in advance.
Thanks for everything.
Have a nice weekend,
Nafis
Hey Scott,
I never thought of imagining having you boss’s life as the measuring stick for whether you ought to consider changing careers. Such a novel idea.
While Nafis has a point, I think we all likely have a range of jobs or careers that would more comfortably suit us.
Some people are naturally better at crunching numbers than others, for instance. Others are people who are naturally “people persons.” Work that reflects those internal inclinations are ones that can more naturally and spontaneously create more joy in our lives.
Hence, the need to change careers for some.
Thanks for the thought-provoking posts!
Love this post, and I want to emphasize a point you touched on: It may not be a black-and-white situation where either your boss is your role model or they are bitter/miserable/overworked. It may simply be that they are not who *you* want to become.
My current boss is an amazing woman whom I admire very much. She’s a terrific leader, incredibly smart and kind, passionate, educated, etc. I know her outside of work enough to know that she has a very happy, full, and rich personal life as well.
If I became like her, I would have many, many blessings in my life. A person could do a lot worse. But she’s not who I want to be. I often think about how– maybe not easy exactly, but how clear and straightforward it would be if I wanted to follow in her footsteps. My career path would be laid out in a precise, direct way and sometimes that feels very tempting, because the path I’m meant for always seems to involve a lot of hacking through underbrush and taking compass readings, you know?
But if I followed in her footsteps, I would always feel that I had lived someone else’s legend, not my own.
So yeah, it’s time to go, and it’s kind of sad because it means leaving a lot of good stuff behind. So I linger, trying to muster the faith to believe that it wouldn’t be a huge mistake to leap from a somewhat bland security into wildly exciting uncertainty.
I think about quitting my job pretty regularly. I love the work that I do and the people I work with, but it gets very stressful regularly working for a startup. However, for me, I am reminded whenever I think of jumping ship that I am not merely a rung on a ladder.
My boss was approached by P&G recently to do marketing for them for roughly 4 times his current pay. The reason he turned it down? To work with me and my team. If my boss is willing to make that sacrifice, the stress seems a lot more manageable.
Great article, Scott:)
My answer is no, I don’t want to be like my boss.
Although I have to admit that I do admire her for the passion she puts in her job daily, she really loves what she’s doing and enjoys it.
Who inspires me the most is Kim Kiyosaki.
I just commited myself to quit my job in 6 months starting from now and move to another country to begin a new life.
I really enjoy your articles.
Keep up with the good work!
[...] Do You Want to Be Your Boss? (or How to Know When It’s Time to Quit…) | Live Your Legend [...]
The person whom I admire at where I work is Annie (I’m leaving out her last name for privacy purposes). The reason I strive to be like Annie is becuase she, like no one else, has a breadth and depth of health insurance knowledge that puts others to shame. And Annie is always kind and compassionate enough to share her wealth of knowledge with those who need it like me. Great post!
Thank you for all of the inspiring material. After spending too much time peering into my boss’s office in disgust, I finally took the plunge on Friday and put in my 30 day notice at my soul-crushing job! I can’t wait to start my journey of pursuing meaningful income.
Thanks for the post. It’s true about ‘The longer you stay, the longer you’ll stay and the steeper the spiral becomes’. Guilt just adds on and can make one feels bad about leaving simply because of reasons like :
- having invested the time
- being hopeful for change/things to be better
and it binds even tighter and harder to leave.
Can relate to that, and the best way is to just be honest if its making me happy or not being there.
This article was timely and packed full of info. I remember the day I realized that climbing the ladder was no longer for me. It’s kind of crazy that we so mindlessly think we have to move up and up and up when the reality is that you may just love or really like where you currently are.
Why do we do this to ourselves? I was recently in a spot where I was totally dissatisfied with the company and responsibilities. SO I GOT OUT. Now I’m doing the same job with WAY LESS responsibility but I’m 10x happier then I was. I think the key statement to this entire article is this line:
“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.”
Thanks Scott. This is great stuff.
- Greg
I’d like the post very provocative and a question I was not expecting. It can be helpful, but the single most important question? Don’t agree.
I knew when I took my latest job that I didn’t want my then boss’s job but I did see the job as a fantastic opportunity to build some experience I didn’t have with a great company where I love the products and the long term growth potential. Luckily, I have had the personal strength for 10 years not to let money or promotions drive my career decisions. Some days I hate my job and get frustrated and I know it’s time to start looking for my next position but I also have great mentors within the company that I might not have that are helping me grow towards work that I will love even more and help me reach my life’s mission.
I’d argue even if you want your boss’s job, it might not be the right job for you. Maybe you’re still driven by money and other people’s views of success and not your own happiness? What if you don’t want your boss’s job but you love your current job and just don’t want the added responsibility and stress of your boss’s job. I like the question as it does get one thinking but not necessarily an indicator of happiness.
Disenchanted… Exactly the word I used to describe my current situation. Well said. I have always used this litmus test to walk away from situations that didn’t fit my interests.
May-o!
Just proves the old adage. Its an ill wind that blows no good. – Theyve finally come up with the perfect office computer. If it makes a mistake, it blames another computer. Attributed to Milton Berle
I’m sorry to say, but I have to totally disagree with your logic.
Whether I want to be my boss has nothing to do with whether I love what I do.
I may not know my passion, but I do know one thing, I don’t wanna be my boss.
This has nothing to do with my current job! My boss has a significantly different job than I have, so your logic absolutely doesn’t make sense to me.
The thing about my job that I love is the making programs part (without coding mind you). My boss does not do that. So I don’t wanna be my boss. Doesn’t mean I have to leave the job I do have.
Links only bring you to a Bluehost “file not found” page
Great frigging advice!
I have heard this before: Ask yourself, “Do I want to have my boss’s job?” If not, you’re not in the right field.
And I can see that. The jobs I’ve liked the least were the jobs where I could’ve climbed the ladder and would’ve hated it. I’d prefer to be on the bottom, where at least I’m enjoying my position.
Hi Scott, I feel like I’m going to have a panic attack when I read your stuff. Is this also a sign that I should leave my career? I definitely want to (obviously, or I wouldn’t be here reading this in the first place) but I don’t know how to take the first step. I guess it’s fear that I am experiencing. Have other people told you that they start crying and experiencing panic when thinking about a career change?
Probably your most awesome post to date and it hit me like the proverbial ton of bricks. Thanks so much