Quit Your Job Without Quitting (To See If It’s What You Really Want)

A note from Jonathan: Every day I get emails from people asking if they should quit their job right now to do what they “really want to do,” or if they should wait and follow a plan.

In nearly every case, my answer is “Yes, you should absolutely have a plan. Why would you want to come crawling back to your employer because you didn’t think things through?”

That’s why I love this essay from Ben. His story and what he’s learned will help you to be able to “quit without quitting” to see if it’s even something you want, before you take the plunge.

Take it away, Ben!

It was finally time for my exodus from Corporate.

  • I built savings to cover a year of expenses to support myself and my family
  • I established a second stream of income from a side business that I was really passionate about
  • I laid out an exciting plan to build up my side business into a full-time gig
  • I grew a supportive network of friends and family
  • I highlighted a specific quit date in red on my calendar
  • I even gave myself extra incentive to quit in the form of a check for $500 written to the campaign of my most hated politician that would be sent directly to him if I didn’t quit by my “quit date”

So my quit date came and went. My friend that held my check sent it off to the worst politician in the world.

I set another quit date; wrote another $500 check. My quit date came and went. He mailed the check again.

I was out $1000, the worst politician in the world was re-elected, and I stayed in Corporate… totally confused about why I’d stalled after building so much momentum to quit.

Quitting is a Roller Coaster Ride

It’s scary and at the same time exhilarating.

When you quit, your Corporate identity and career path are washed away and you’re left with unknown possibilities.

For some, unknown possibilities can be really exciting. But when your life in corporate is built on controlling outcomes, the unknown is incredibly uncomfortable. Even though it can be scary, there’s an intriguing magnetic attraction to it.

There’s a surge of adrenaline. You’re afraid, but you feel more alive than ever. Part of you would rather be back at the mothership, but the new experience awakens something within you. It’s the intense exhilaration of freedom, and as soon as you experience it, you crave more.

You discover your surroundings in an entirely new way resulting in a flood of mentors, books, and experiences to help you find your own path to the freedom promised land. New doors begin to open and opportunities abound from controlling your own schedule, making your own rules, and creating a business on your own terms.

While quitting may sound like the best path for everyone, please recognize that it’s not.

The biggest problem with quitting has been that you really can’t know if it’s right for you until you actually do it — which makes quitting a heck of gamble, and often results in the worst kind of buyer’s remorse you could imagine. It also makes quitting an incredibly risky move (and maybe even a little moronic).

But what if you could experience quitting to see if it’s right for you before you actually do it?

Marrying Someone You’ve Never Met

Quitting your job is a huge decision that can have catastrophic consequences like going broke, losing your friends and family, and destroying that Corporate identity that’s been years in the making.

Quitting a job without tasting freedom first is like:

  • Marrying someone you’ve never met
  • Buying a car without test driving it
  • Purchasing a house without going inside first

When I stared into the quitting abyss for the first time, I felt alone and unprepared. All my friends and family were from a structured, corporate environment.

I’d known plenty of people who talked about quitting, but no one who had actually done it.

In fact, I actually didn’t know anyone personally who was really making it outside the prison walls, so why did I think I’d be any different? I’d been groomed to function at a high level inside the Matrix of Corporate.

Quitting was the equivalent of putting all my chips on a bet where I didn’t know the odds. How could I know if quitting would be worth it?

Eat the Quitting Appetizer

To answer whether quitting would be worth it, I recognized I had to try it first.

To help illustrate this point, consider one of the problems of going to a new, expensive restaurant.

As you sit down at your table, you’re all in for whole she-bang. You’ll order off the menu, you’ll dine, and it all ends with a massive check regardless if you enjoyed your meal or not. Your dinner becomes a sunk cost.

When you quit your job you’re all in too. There’s no turning back and changing your mind. You’re just hoping quitting is worth it, and hope is not a strategy.

Instead of buying the entire quitting meal, first, try the appetizer.

Taste quitting without quitting to see if it’s for you.

How to Simulate the Freedom of Quitting

To taste quitting and determine if it’s right for you, you can create your own quitting simulation.

There are 5 areas where you can experience the freedom of quitting, and explore (and even build) your tolerance for uncertainty, risk, and vulnerability.

By taking bolder actions in your simulation, you’ll get a bigger taste of freedom as well as a more realistic experience of quitting.


Each area represents an aspect of work that’s important in the quitting process. Here they are in ascending levels of action and freedom:

  • Relationships – Creating your community of mentors, teachers, and supporters outside of corporate life.
  • Flow – Controlling your own workflow, and your own to-do list.
  • Space – Designing your own workspace outside of corporate walls.
  • Hours – Developing your own work schedule.
  • Identity – Trying on the identity of an entrepreneur.

7 Strategies to Try Quitting without Quitting

Now, to help you develop your own plan to experience quitting without quitting, I’m sharing my own 7 strategies.

I’ve tried them all, and I can personally vouch for their effectiveness. I’ve ordered them in terms of how much freedom you’ll experience from each (smallest freedom pop to greatest freedom rush).

The closer the action is to unscripted doing, risk taking, and putting yourself out there the more it is like quitting and the bigger the freedom pop.

Check these out, and then apply the appetizer scale below to determine your best next step.

  • Marinate Yourself – When I started down my road to freedom, my problem was that I didn’t know anyone personally who had lived life outside the Corporate confines. It felt like I was pioneering something on my own, and I felt alone and lost. Turns out there are lots of people out there who can be great role models. I marinated myself in freedom by reading about and hanging out with entrepreneurs, freedom teachers, and movement makers and that eventually made me hungry for more. I started by following a few bloggers like Jonathan Mead and the Trailblazer community; then I started identifying people in my local community.
  • Create a Freedom Account – This is a huge deal. When you’ve got a few months of expenses stashed away in the bank, you feel freer at work. If they fired you tomorrow, you know you could survive and bridge yourself to the next gig. You can be bolder with your decision making, take more risks, and say more about what you really think. It makes work much more satisfying when you know your freedom is in the bank.
  • Color Outside the Lines (Without Asking Permission) – You experience freedom by deciding what you want to address at the office and then getting others to join you in making an impact. Start a grass roots movement at the office to inspire. Do this by listening to the griping or by bringing up the elephant in the room that’s plaguing the office. Then offer an idea to solve it and ask others to join you.
  • Take on a Secret Identity – By taking on a secret identity you will see what it’s like outside the confines of Corporate life while still getting your steady paycheck. For me, I took on a secret identity and blogged for a year without anyone knowing who I was. It allowed me to experience running a business and expressing my personal views freely before taking the next step.
  • Work Free (But Not For Free) – It can be a challenge to experience real freedom sitting in your office chair or within a cubicle where everyone can hear your every move. Freedom means you get to work where you want and when you want. Try working from home a few times and see how you like it. I’ve personally amped this up by working from a local coffee shop, the park, and even a bar!
  • Start Your Contingency Plan – Your contingency plan is a business that you start outside of your day job, so you can get hands-on experience in doing what you love and making money doing it. Your contingency is ultimately more valuable than any retirement plan. Your contingency is tied to what you love doing in your spare time and that you’d do for free (although you won’t be). Often times a steady corporate paycheck can help give you funds to start establishing this by hiring a coach or investing in some online learning tools.
  • Get Your First Paying Client – When I landed my first paying client I experienced freedom like I never understood before — I even actually cried. It’s like getting your parking ticket validated on a grand, personal scale. You don’t have to leave Corporate to get your client. You just have to be willing to help someone and negotiate a fair rate and value.

The Quitting Appetizer Scale

Here’s what to do next:
Pick two strategies above and schedule them on your calendar. After you’ve tried them, use this Quitting Appetizer Scale to decide on your next move:

Food Poisoning
Tasting quitting made you sick to your stomach. You actually wanted to vomit. Go back to the mothership. They miss you.

Quitting didn’t taste that good but you recognize that it’s actually good for you (like eating your vegetables). You recognize it’s an acquired taste. Select 2 more strategies from above and see how they sit with your stomach on the next go around. Your system may need some time to acclimate.

Yummy Satisfaction
You enjoyed the appetizer and are intrigued. Schedule and implement all 7 strategies above and see how it impacts your work day. By experiencing more freedom in your work day, you may find yourself getting promoted or experiencing the confidence to transform your current role.

You’ve tasted the appetizer, and now you want the main course and the dessert. You’ve even been back several times and they call your name like Norm from Cheers every time you walk in the door. Time to start putting together your exit strategy. To sustain yourself as you prepare, implement all 7 strategies.

To help in applying these strategies to quit without quitting, here are 2 case studies from some of my clients.

Case Study #1 “Andy” – 15 Minutes to Freedom

My client, Andy, worked for one the top consulting firms in the world.

He had Ivy League credentials and had worked his way up in his firm into a high paying position with huge golden handcuffs.

When we first started working together he wanted to “run from his company like he was running from a fire.” But his fear of what was on the other side of quitting kept him from making any big changes. So we designed a few steps he could take to try quitting without actually quitting.

First he started taking a 15-minute lunch break away from his desk down in the park outside his office. Although he wasn’t ready to give up eating lunch at his desk, he’d set the alarm on his phone to time his moment of freedom, then when the alarm went off he’d go back to work.

These 15 minutes were just the appetizer he needed to get curious about the whole meal. The 15 minutes evolved into an hour and then into working from home one day a week.

His momentum built and he negotiated temporarily going part-time with part-time pay on a project which cut his hours dramatically for 3 months.

These 3 months gave him the biggest dose of freedom in his career. He poured his heart and soul into discovering the best way to kick-start his own business and he knew he was onto something. He negotiated his way onto another part-time project where he was paid less, but had insurance and the possibility of ramping back up to full-time if he needed to.

This entire process lasted just over a year and by the end he was hooked on freedom and knew it was for him. He quit his job and launched his own company with 2 friends.

Case Study #2 ”Kay” – Thumping the Butt

Kay was an HR Director within a large organization.

She was good at her job, but had outgrown her responsibilities. She had always yearned to know what it would be like on the “outside” –but hadn’t been willing to find out. She wanted to get the experience of quitting without quitting because she wasn’t ready to give up her steady paycheck, insurance, and HR career path that she’d developed over the last 2 decades.

Kay hired me to help her explore life on the outside. We worked together to clarify her strengths, values, and passion and then created a plan.

She learned about becoming an entrepreneur, got to know business owners outside of the Corporate world, and began to dream about her own possibilities. But after tasting quitting, she discovered that she wasn’t ready for the emotional roller coaster ride of doing her own thing.

Although she’d decided that the timing on quitting just wasn’t right for her, the experience awakened an entrepreneurial spirit she never knew she had.

By quitting without quitting she got incredible results. She:

  • Found her job satisfying again, like “thumping the butt of a cigarette.”
  • Developed an entrepreneurial spirit within her work day
  • Ultimately got promoted to COO

Turns out quitting without quitting has benefits even if you don’t quit!

My Special Gift to Paid to Exist Readers

I’ve put together a special package of resources for Paid to Exist Readers.

Check them out by clicking here.

Include your email address, and I’ll send you a copy of The Burnout Manifesto as well as my best time-saving strategies.

Here’s what you’ll get:

  • The Burnout Manifesto – A list of 7 keys to rediscovering your passion for the job, and reigniting your career. In this manifesto I give you the EXACT keys that I used to reignite my own career.
  • The Time Savings Report – Time is one of the most precious resources, so I put this together to help. It’s my personal list of tips for freeing up an extra hour of time per day without hardly trying.

Ben Fanning is the Burnout Specialist who helps frustrated professionals rekindle their passion for the job. You can click here to get his no-cost resources to energize your work day.

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kiran shauBenChris WoodhamAlisonDakim Recent comment authors
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SJ Scott


This is a great point, and one I think most people that are contemplating quitting a job should read.

Diving in blind feels great, but it is much better to plan, prepare and make sure that it is something you want.

When I quit my job (quite a few years ago) I did something similar. I STILL probably didn’t plan and try it on for size enough, but at least I accumulated some knowledge, experience and had a plan for success.



Thanks, Scott. Congrats on your move and having a plan before you made the leap!


Ben – great post my man! Really cool to see how far you’ve come and excited to see where it goes! Great analysis too :)


Thanks, Tom! Really appreciate that!


I lost my house (a good thing). My savings. My 401k. A girlfriend. A shit load of possessions I sold off to support myself. And any illusions I held about how great it is to be free of corporate suffocation. Bottom line, it fucking rocks not having a boss. But it also stinks if all you know to do is flail at the blank canvas. Still, it doesn’t stink as bad as trudging into monotony every day. In the end, I took a year “off.” Learned a lot of shit I never would’ve learned had I not just quit. Failed… Read more »


Admire your tenacity, A-ron. Sounds like you sat down for the proverbial 7-Course Quitting Meal right out of the gate. Thanks for sharing your learning with us here!

Alia Arlys Alford

WHOO-HOO!! Brilliantly made points with a easy-to-follow recipe to help us understand the complex dish of working-for-yourself. Try before you buy, baby….try before you buy. Great point that working for yourself is not for everyone. Some people LOVE their jobs and I say that’s excellent (quite seriously, no sarcasm to inject, here. I’ve worked one or two corporate gigs that were sweet, sweet, sweet). Everyone should love what they do and use their talents to the fullest, every single day. I just imagine what the world would be like if each human being took a really deep breath, long and… Read more »


Hey Alia, Nice recap…”Try before you buy, baby”. Wish I’d used that in the article :)

Rebecca Tracey

This is an EXCELLENT post, and also really important for anyone who WORKS with people who want to quit their jobs.It’s important to understand that the process of “I want to quit” to actually quitting is never linear.

I’m actually sending it to all the coaches I know who work in this area! Thanks for writing this!


Thanks, Rebecca! So glad to hear that this could serve as a “quit or not to quit” resource. I really appreciate you forwarding.


Ben, You have written the very words I have known for a long time. It DOES make the aspect of running the show more palatable( or perhaps less) when it is sampled in doses. It takes time to savor the perception of what your dream really entails. This is a great post with the kind of insight everyone should have as they feel that fire in their belly starting. I work with people who have burned out from the system(teachers, health care professionals etc.) and help get them fired up for a different arena in their life. I sent many… Read more »


Thanks for comment, Kathy. Health care and teaching are both really high burnout fields…my parents were/are teachers so I know. Glad to hear that starting small resonates and thanks for sharing with your clients.

Leanne Regalla

Hi Ben, Great post, and I can vouch for its effectiveness because I have used most of these strategies myself over the years. I launched a couple of side businesses (a music teaching studio and a blog). I worked from home when I could. I took advantage of flexible scheduling. I used my vacation time (which had built up due to my time on the day job) to test a new career. Every experience convinced me that the only promotion I ever wanted was to full-time self-employment, and now I’m there. I’m going to keep this article and refer my… Read more »


Hey Leanne, thanks. Awesome to hear that some of these strategies were effective for you. Congrats on your move and taking the creative world by storm!

Faith Presley

This is a very motivating article. I need to go back and make notes! Thanks for a rousing post.


HI Faith, So glad to hear that! You’re welcome!

Pathway To Personal Development

Great article!! :-)




Part of me thinks that sometimes you just need to burn the boats and get on with it. If you think about it too much, you might never do it.


Hey Josh, Good point. Burning the boats is definitely an option. At that point though you’re definitely ordering the whole quitting meal versus just trying the appetizer…so if you don’t like it you’re stuck eating it. I do think though there is a mindset that quitting is final which just isn’t true for many people I talk to. There’s often a door left open at their previous job or at a similar type organization if they find quitting isn’t for them over the long haul. So sure you can burn the boats and if even rebuild them later if need… Read more »


Great Article Ben.

It’s one of the biggest decisions you’ll ever make!

It’s the sensible thing to do to plan it all out and make the transition slowly. However, as your story said, it can be so easy to turn back when you set that date.

As tough as it is to break all connections with your old job, doing so actually gives you the energy to find a new path. Desperation demands miracles. So sometimes it’s not so bad to make the leap when you’re not 100% prepared. You’ll always learn along the way!

Who was the politician by the way?


Thanks, Joe. Definitely easy to turn back even when you set the date. Setting the date can be really helpful in just exploring if quitting is for you. Although I had a lot of incentive to do it (and I even heaped more incentive with my check(s)) , it allowed me to feel it out first before making the leap.

Financial Samurai

Never quit guys! Please get laid off instead.

I was able to negotiate a severance package worth 6 years of living expenses in San Francisco. Check out some of my posts on the subject or my book.

Do not leave thousands of dollars on the table!



Good point, Sam, to evaluate if it’s better to quit or get fired. For most folks there’s a lot more at stake than just money. While getting fired does have some financial benefits, I find that impact your confidence and even you identity on a much deeper level. Plus if you ever think you might want to get back into a “job” after going it alone for awhile you’ll likely need references or heck you might even consider going back to the gig you left in the first place. Just saying that leaving a door open could be a helpful… Read more »


Hi Jonathan,

This is a masterpiece article, I’m printing it out and also bookmarking it.

Quitting one’s job is a very tough decision to make, and from my perspective, If a man does not quit his job to start his business/venture before the age of 40, such a man may not be able to do it again for the rest of his life.

I will take my time to read and meditate on your ‘7 Strategies to Try Quitting without Quitting’ and recommend it to colleagues as well.

Thanks for sharing.


Hey James,
That’s terrific!.
Thanks for sharing it!

Simon Templeton

Hi Ben, you have a great article here on how to test the water before actually going for freedom from the corporate world.

Thank you for the article. Don’t we all strive to one day be our own boss…


Thanks, Simon! Good question. I think there’s something even more fundamental at stake than being your own boss…freedom. It’s so easy to lose sight of that even if you’re working for yourself. I recommend checking out the book, “The E-Myth” by Michael Gerber.


Dear Ben, Wonderful article i should say. The strategies you suggested have tried some of them; have 10 plus years of experience, left my six year job before that tried to check some franchisee work option didn’t work due to travel issues.Did one job in the same domain for two months as i had time to join my third job and current one but didn’t like the culture. My current job is with a kind of start up ( so that i have a feel of entrepreneurship without investing) but its highly frustrating to work with people less qualified and… Read more »


[…] If you are seriously debating whether to quit your job, you should check out this site which gives some great pointers on figuring out whether changing jobs is a good move for you. […]

Steven Le

This article is so relevant! Too bad I quit my job before reading it! Although I must say I have no regrets. My job was too stressful that my health was constantly affected. Something I just could not accept!

I will be sending this page to many friends who would benefit greatly from reading it before quitting their corporate jobs.

Thank you!


Thanks, Steven. Glad you found it helpful and relevant to share :)


[…] the weekends, in addition to their training throughout the week, just like many startups begin as part-time weekend projects while the founders are still working full-time. There’s a passion burning that’s driving them […]


Excellent post Ben. I’ve tried 6 out of the 7 strategies, and I can tell you it feels lip smacking delicious. I’m ready to jump off the mothership and plunge in head first. 2014 is the year I reclaim my freedom. Thanks for the inspiration.


Hey Debashish, Congrats. Sounds like you’re taking a measured approach and testing the waters first to make sure its right for you. Good luck and let us know how it’s going.


Hi Ben,
Great article, thanks for posting. This is very timely and right on target for my situation. I’m currently working on my escape plan and look forward to making the leap out of the corporate world and into a life with purpose and passion. Thanks for the inspiration!



Peter, you’re welcome. Hope these tips help :)

Jordan Phoenix

I can’t believe I never knew about this site before. Nice read!




Thanks for this great article Jonathan! I LOVED the $500 check story! My problem is actually the opposite: quitting all the time! I’ve traveled the world, freelanced, consulted and had my own business. Pretty cool adventures but I’ve left aside my need for stability. I’m now looking for work to pay the debts and I’ll plan better to quit again but with PURPOSE this time… and a steady passive income stream also!


Yo Martin! Since you liked the $500 story maybe you can use that in reverse. Give yourself an incentive to stay at a job by using that tactic. What do you think?

Mike Goncalves

Excellent, excellent post. Such a common concern for many, including myself. Great ideas and suggestions Ben for exploring new terrain before ever leaving home, awesome! Thanks!


Glad you liked it, Mike. I agree its a common concern, and a lot of wisdom in exploring before making the leap



Great article. I wish I this a couple of years ago when I was facing a layoff. I was very happy to get laid off because I was so over corporate life but I wasn’t nearly as prepared as I should have been. I was moving from instinct and desperation to be free. I love my freedom now and my business is growing but some more formal planning on the front end would have made the transition smoother.

I’m sharing this article with all clients and social networks.

Good work


Really appreciate that, Dakim. Also thanks for sharing your personal story so we can learn from that as well.


Interesting ideas,thanks!


Thanks, Allison. You’re welcome :)

Chris Woodham
Chris Woodham

Great post! Had a lunchtime walk with a colleague. As always in my free time i find myself thinking.. that i should really be doing something I love to do. I don’t want to reach 40/50 and say ‘what if…’ simply because to me that means there is something in my life that i had not try to fulfill. After reading this post it has made me not so hot headed about the situation as i was on the verge of going f this i’m off. Now I understand that if in my free time I effectively try to get… Read more »


Wow, Chris. Well stated. I totally get the desire to do something more..especially something that you love to do. Sounds like you’re finding your motivation to explore your passion and learning you can explore it on the side first. Congrats!

kiran shau

Great article..I’m going to quit my job soon was searching to some nice tips to follow to quit my job your article helped me.
Thanks For Posting.

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