How To Quit Your Job (And Still Win)

geoffblades's picture
Rank: Neanderthal | 2,054

You're going to quit at least one job in your life, probably several. In fact, 2.8 million Americans quit their jobs every month. You know what's heartbreaking about that statistic?

Virtually none of those 2.8 million people know how to quit their job and still win.

You need to approach quitting strategically. You must recognize early when it's time to leave, and set a plan in action to do so in a way that most benefits you.

People who ignore their unhappiness--who wait until their situation is so desperate that they're forced to quit--they're the ones who leave with too little to show for it.

To avoid that happening to you, and to help you get what you want from quitting your job, here's a step-by-step guide to quitting your job and still winning.

First, you must recognize when it's time to quit.

How To Tell It's Time For You To Quit

Knowing when to quit your job requires being brutally honest with yourself and asking, "Am I excited to be here?" At it's core, that's what this is all about--excitement.

Let me give you an example. When my friends or clients have decided to quit their jobs, they often come to the decision in different ways, yet they all start in the same place.

They begin with the feeling that something isn't right, that they aren't as excited about their life as they should be, that there is say, "more to life than this."

The ones who bury that feeling deep inside wind up wasting years at a job they don't want, only to, when the proverbial final straw breaks their back, exit without a strategy.

The ones who trust that feeling and investigate it are the ones who quit their jobs and win.

To start being honest with yourself, ask yourself these questions:

  • How many times did I hit snooze on my alarm clock today?
  • How many cups of coffee did it take me to get going?
  • During my day, how often did I think about doing something else?

People often assume work should be a slog. Everyone has trouble waking up. Everyone needs coffee to get going. Everyone imagines being on vacation while they work.


People who are living the life they want wake up pumped and excited to dive into their day. They don't need a liter of coffee to get going in the morning and don't spend their days fantasizing about being somewhere else.

People who are living the life they truly want tend to have one other thing in common:

They didn't magically find themselves where they are.

Instead, they've moved strategically from job to job, collecting the skills, experience, and relationships to be where they are.

In other words, they've learned how to quit their job to keep winning.

How To Quit Your Job In 3 Steps

There is a formula for quitting a job in a way that moves you closer to your dream life, and it's a simple three step process. While your specifics might differ, in general, this approach works for everyone.

1. Figure out why you want to leave

To understand what will excite you, you need to understand what doesn't excite you. Think about your day-to-day in your current job. What tasks do you put off? What kind of days leave you most exhausted?

But don't stop there. Go deeper. Why do you feel that way? Why do you put off tasks? Do you lack the skills to do them well? Are they opposed to the kind of work that excites you?

By asking yourself those questions you can understand what it is about this job that unsettles you, and begin formulating a new plan.

2. Figure out what you want

This step takes a mental flip from the last point. After listing out all the reasons why you don't want to be where you are, you need to figure out where you do want to be.

Now, truth be told, for many of us, creating a vision for our future is a daunting task, but it doesn't have to be. You've already created a list of qualities you know you don't want in your life, now focus on the positive qualities that you do like.

Maybe you hate being isolated from people in your work, and so you can begin by saying to yourself, "I'm not sure which job I want, but I know it involves lots of personal interaction."

3. Focus on the action right in front you

A mistake many people make on this topic is becoming overwhelmed. They look at what they want their life to be, and they let the weight of that massive vision crush them.

To avoid this problem, instead of constantly focusing on this "big vision" of what you want your life to be, instead every day focus on one thing: What action are you taking to keep moving in the right direction?

Don't worry about stepping straight into your dream life tomorrow, ask what action will move the needle in your life today. What skill can you start learning today that will help you get there? Who can you meet today that will bring value to your life?

You might think, "Well sure, Rome wasn't built in a day, but that's not a massive insight." But you're wrong. This is about more than incremental progress.

As you move through life, your vision will inevitably shift. What will not shift, however, are the skills and relationships you build. By focusing on adding value to your life every day, you make yourself more independent, more capable of chasing dreams even as they shift.

Most importantly, this makes you less fragile. The more capable you make yourself, the less vulnerable you are to the whims of the job market. As James Altucher says, "The best entrepreneurs are not risk-takers. They spend every day reducing risk."

You're adding something permanent to your life: Potential.

A Good Exit Plan Means You Leave Without Burning Bridges

If you follow the process above and remain focused on taking actions that benefit you, it is easy to quit your job without ruining relationships.

A lot of people fantasize about giving their boss "a piece of my mind," on their way out the door, or making some dramatic exit--like this woman who literally made a video announcing her resignation:

Not taking anything away from the hilarity of the video, or the benefits of her newfound fame, but that is the worst way to quit your job.

When I quit Goldman Sachs, I sat down with my bosses and told them I had to leave. I was open, positive, and respectful, and they responded in kind.

Professionals understand that sometimes a job is a bad fit. It's nothing personal. If you quit in this way, as a termination of a contract but not a relationship, then you can leave without burning your bridges.

Often, this means being patient.

Take Your Time To Quit

From the day I began my work exploring leaving Goldman Sachs, it took me another six years to actually leave the firm. Six years!

I know that sounds ludicrously long, but that is how long it took me to make two more career moves inside the firm, stash away some savings, and, most importantly, do the work to convince myself that I was making the right decision.

This did a number of things for me:
- I got clear on why I was leaving and what I wanted to achieve first
- It gave me the space to build a strategy for what came next.
- It demonstrated to my bosses that it wasn't about them or the firm, but the result of many years of reflection.

I built this system by actually living it, and so I've made my fair share of mistakes along the way. I could have planned a little better, I could have been more focused on the next small steps, but the one thing I nailed was the timing of when I quit.

When you quit, don't just rush to your boss and tell him/her it's over. Take your time to decide what the next step is for you, begin building the skills and relationships you'll need, and only quit when you know you can hit the ground running.

Why Quitting Your Job Is The Key To A Great Career

There's an anxiety many of us feel when we tell our colleagues and our friends that we're quitting. We're afraid of the financial and professional repercussions, sure, but on an even deeper level we're afraid that we are being ungrateful.

A lot of people reading this article are probably in this place right now. Even equipped with the system I've laid out, they feel held back by this sense that what they have right now is all they deserve.

Fuck that.

A company will fail if they pay employees more than they contribute to the company, it's math. If you think that by pursuing the life you want you are screwing someone over, you're making your job too personal.

Jobs are an economic contract. You are selling your employer the precious hours of your life in exchange for getting what you want.. If your job isn't getting you that, then what choice do you have?

Never let fear force you to settle. You can have--and deserve--nothing less than exactly what you want in life, and oftentimes that means quitting a job or two.


Comments (39)

Oct 11, 2016

Does anyone want to move to Thailand with me and start a blog?

In all seriousness good post.


Oct 12, 2016

Does anyone want to move to Thailand with me and start a blog?

In all seriousness good post.

Only if we go to Bangkok and I get to have a shark in my apartment.

Oct 17, 2016

With the caveat that they must have friggin' laser beams attached to their friggin' heads.

Oct 11, 2016

Excellent post! Super relevant.

Oct 12, 2016

Six years? What privilege - I find that for a significant share of people, their desire to quit results in a weakening job performance, and they get let go anyway.

How to fight this?

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Oct 17, 2016

You're right. That's a big part of the reason I do what I do.

If you hate your job, quitting isn't the solution.

The fact that you're in the job already tells you that you have made one "wrong" career decision, so why do people think that pulling the ripcord will somehow solve it for them?

Instead, I looked out at the world and said, how do you create the life you truly want? In looking at it this way, I saw, clearly, that wherever you are headed, you will get there from where you are now.

so, even if you hate your job, you want to ask yourself: How do I best "use" this job to get where I want to go? Then you want to chart the course and keep delivering the performance that creates options for you.

Former banker and investor, advisor to senior Wall Street pros. Learn more at

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Oct 12, 2016

Thanks for writing this -- super helpful and lots of insight. I'd love to see a follow-up in how you assess new opportunities and how you went about looking for a new position. Thanks!

Oct 14, 2016

1) How did you balance building skills for your next job/your post-quitting phase while also handling all your work in IB so that you could maintain your relationships with your bosses?

2) How do you manage to keep in touch with prior bosses? How often do you reach out to them, what do you say, do you meet up, etc.?

Oct 17, 2016

honestly, man, by working all the time.

and by getting so clear on what truly matters to winning in banking, so i could get as effective as possible, and buy more time to focus on these topics.

keeping in touch: it's so easy. one coffee every year is staying in touch for a lot of very busy people.

Former banker and investor, advisor to senior Wall Street pros. Learn more at

Oct 16, 2016


Great post, +2SB.

Would like to get your thoughts on a couple of related topics.

I have been noticing with some of the recent graduates (2-4 years on the job) a number of folks have short tenures at their first few jobs. For instance not uncommon to see someone in an analyst job for 6-8 months at a firm they didn't like, then work somewhere else for 10 - 14 months and move again. Some of these moves make sense in regards not being able to do what you wanted to do at full time recruiting and continuing to network shortly after being hired and making the move to your target industry.

How forgiving do you think hiring managers are in these instances? I've mainly seen 2 short stints at a year or less on a persons resume but don't think I have seen three yet.

Also what's your take if a person has a few of these shorter stints. Say 2 years in first job, then mad a bad move and quit in under a year but job they move into to escape the "bad" job isn't a good fit and want to make another move - should these kids simply wait for say 2 years in a job they don't like just to rack up some time in seat and make their resume look nicer? I think internal moves within same company are viewed differently (I.e. Join IBD but move to a Markets role a year later).

There is an analyst I know that worked at an IB sweatshop out of undergrad and didn't want to put up with that 6 months in and moved to a boutique (still IB) and is now quitting 10 months into job 2. Heard some people comment around the office "they've had 3 jobs in 3 years." - even though this person has worked <2 yrs.

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Oct 17, 2016

you're right, for all the obvious reasons job hopping is harder to sell through.

my view is, however, the right candidate, positioned the right way, with the right skills of influence / selling can sell through any objection.

it's all about preparation: i was off Wall Street for 18 months when I applied to the jobs at Carlyle and Oaktree. 500-1,000 hours of interview prep enabled me to leap to the buyside at a senior level.

you must be wary of what your resume says about you, but even more wary about wasting your life in a job you know is wrong for you.

that's no validation of a kid who thinks the working world is too tough and wants to quit every job, but for people who are serious about driving towards what they want.

Former banker and investor, advisor to senior Wall Street pros. Learn more at

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Oct 17, 2016

Nice read. Watched Altuchers Ted talk on Youtube in work the other day. Hes something else. +sb

Oct 17, 2016

Nice read. Watched Altuchers Ted talk on Youtube in work the other day. Hes something else. +sb

I never really liked him but lately have been enjoying more of his stuff. I think he makes a lot of good points and whether you like him or not, you have to admit he is a really good writer.

Oct 17, 2016


Oct 17, 2016

Love his stuff, I quoted a part of this story on how to quit your job on my blog/site, this article was the reason for me to quit my job from the financial industry in 2016, to go into affiliate marketing.

I agree with him and want to add that most of us should start looking for an alternative way of income. With the ever changing economy you should invest in yourself; your own brand, since there is no competition in your own brand.
Just like I did this year. I took the plunge, got unsafe/uncomfortable and started a new career, I'm not financially self-sufficient yet, but well on my way and I don't regret any second of it.
The last few months everything changed for me. I would just suggest to read my about on my blog/site and see if you can relate to it.

Philippe H.

Oct 17, 2016

Love his stuff, I quoted a part of this story on how to quit your job on my blog/site, this article was the reason for me to quit my job from the financial industry in 2016, to go into affiliate marketing.

I agree with him and want to add that most of us should start looking for an alternative way of income. With the ever changing economy you should invest in yourself; your own brand, since there is no competition in your own brand.Just like I did this year. I took the plunge, got unsafe/uncomfortable and started a new career, I'm not financially self-sufficient yet, but well on my way and I don't regret any second of it.The last few months everything changed for me. I would just suggest to read my about on my blog/site and see if you can relate to it.


Agreed. I think we tend to look at the singular income model as the most safe, when its actually paradoxically the least.

There is this overwhelming notion that in order to be an entrepreneur you have to be building an app / raising VC $$ / living in SF. None of those things are true. The whole "quit your job and fail spectacuraly" mantra that has emerged from silicon valley is absolute bullshit. Failing is embarassing. Anybody can be an entrepreneur. All you have to do is find a customer and sell them something. There are some fantastic success stories about average folks making a very nice income on the side or quitting their jobs and they are in far greater order than those that exit for $50m+

Oct 17, 2016

Here are some good tips when you're quitting your job.


Oct 17, 2016

You hate your job and you pretty much have no choice but to resign, correct? And you submitting your 2 weeks or resigning on a particular day is no concern to your new employer. As long as you show up to the new job per the agreed start date, they don't care. Resign as agreed and whether you want to start the job right away or take a few days off, you negotiate the start date with them.

Oct 17, 2016

Would it be possible to tell HR of the new company (if it even comes up) that you mentioned you were going to resign and due to the competitive nature of your role, you were asked to leave immediately?

I know that in sales, and several other positions where a conflict may exist, there really is not such a thing as a two weeks notice. You are escorted out immediately after giving two weeks. I am not sure what kind of paper trail this will leave with your existing company when the new company checks but it could be worth a shot.

Oct 17, 2016

Resign as soon as you get the offer. The new company won't care when you resigned. They'll only care that you show up for work.

Oct 17, 2016

Resign as agreed, and say nothing to your new employer unless questioned by HR during their background check. I would be surprised if that happens, but if it does just go with your story that you wanted a break before starting the new job. Say nothing more, nothing less - bases covered.


Best Response
Oct 17, 2016

This annoys me. Honestly, and I'm not trying to be mean, your lack of willingness and ability to just reason through these potential outcomes is probably why you're getting fired. I doubt you're someone who, when tasked with something, takes it upon themselves to solve a problem or go to Google to figure something out, instead resorting to asking your boss every single question that comes up.

Look - just be honest and accept the resignation. If someone asks, don't lie. Just say you left the company. This in all honesty is not hard. You are in a tough spot, yes, but there's little you can do. Shape up and deal.

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Oct 17, 2016

As someone mentioned above, a person's indecisiveness reeks and it leaves a terrible impression.

Oct 17, 2016

Hi all,

Thanks for your feedback. Your insight is very much appreciated.
Since this is unprecedented to myself, i'd like to take opinion from others to ensure nothing i missed. It is quite a risky game with very limited margin of error here, so ideally i'd like to know my options and the associated pros/cons before making my call. This could be one of the reasons why i am not quite there yet. The good thing is i know my limits now, so what i need now is to secure the role which is more aligned with my background and grow from there.

My gut instinct aligns with the posters above that it shouldn't bother the prospective employer at all. whether i resign as long as i can commit to the start date.

Thanks guys.

Oct 17, 2016

Hey rahulekbote, I'm here because nobody responded to this thread after a few days...maybe one of these resources will help you:

  • Shall I Resign or not? part 2- how to resign? manager who has confirmed their decision and agreed with me that i can resign to avoid having to dismiss ... their HR today who asked me about my current package and said she will get back to me by this week with ... resignation by employee and i am free to say why i didnt like my job. So this is covered. Now the issue is the
  • I hate the living sh*t out of my job as a current salesman. I hate sales with a burning passion. I need out. Please help. before taxes with commission. I'm 26 years old, and have been working in sales for 1.5 years. My job ... the smart kid in class that others trusted to get the job done, but didn't necessarily want ... a beer with. I'm fine with being that guy, I don't want to be a party animal. I don't want ...
  • Best time to resign (starting new job) Basically I am working switching jobs (to banking from other sector) and start with new job from ... around 23 Aug. My current job requires a 4 week notice period. THe banking guys are going to send the ... might be the best time to resign? After they've completed the check? After I've signed the ..
  • From BO to FO and back again, or, how I learned to stop worrying and love technology in investment banking. I went from never having heard of investment banking as a profession, to ... banking as a profession. Warning: this is a bit long (will sum up with tl;dr). Unlike what seem to be most ... Office Certainly a difficult jump to make--back office to front office, with a part-time MBA no less, but ...
  • How to Renege (Gracefully) I have an offer from an IB, but I already accepted from a Big 4. Any further steps? There were ... more along the lines of a better and unexpected opportunity? 2) Also, should I call the bank to inform ... class="h4 m-t-none">Job Search Advice Forum Resources</p><ul class="career-resources ...
  • Was just asked to resign...what should I say on interviews? Current 2nd yr analyst who did something stupid which led to being asked to resign. Unsure of how ... If so, thinking about what to actually say to help me land another job ASAP. Thanks resign laid off ... did you leave your old job". Unsure how much info HR gives out surrounding ...
  • Shall I Resign or not? a Treasury Manager in a large corporate. At the beginning of this year, i have started a new job with a nice ... big promotion jumping two grades to the management level at a new company. It came along with a huge ... rise in my pay cheque along with added responsibility. But the learning curve proved to be steep for me ...
  • More suggestions...

If we're lucky, maybe these professional users will respond: @Financier37" @Gilbert-Tu" @Olivier-Travers"

You're welcome.

Oct 17, 2016

Are you moving to IBD? Is this firm in IBD or something else?

The reaction will be nothing- literally. As soon as you say no, the recruiting team will cross your name off and move to the other analysts they've been pulling the same tactics on. I don't mean to sound rude, but you're not so special that seniors will waste energy by reacting negatively- if at all. They've got other potentials to recruit and a business to run.

Oct 17, 2016

I read the title and was prepared to answer the question as asked, since I have done his better than most. I will do that after responding to your situation.

You were an intern: Nobody will really care, at all. Generally, I would say that you can maintain good relations with people by treating them honestly and not using them. Clearly, you have failed on those fronts, so I would generally write off those relationships going forward.

As a full-time employee, it is actually remarkably easy to maintain good relationships with former bosses and co-workers. Everybody understands that people will put themself in the best situation for their career and if it's not with them, most people understand. If you explain why you have made the choices you've made they will usually be fine. After that, stay in contact with them: send them job opportunities, invite them for drinks/lunch/dinner, call them on occasion. Basically treat them like people you want to stay in touch with and be someone worth staying in touch with. Many of my former bosses are current clients and friends.

It's all very simple.

If you don't know who the sucker is at the table, it's you.

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Oct 17, 2016

I just reneged on a verbal commit to an ER internship in NY for a top 50 tech position in Houston. I explained my decision and they seemed very understanding; I have plans to meet with the ER VP who pushed for me when he comes down to Houston this summer. Be forthcoming and genuine, people will respect it.

Oct 17, 2016

I wouldn't worry so much about "using" these people as a stepping stone. I'm sure that while they appreciated your work and would genuinely be happy for you to work for them in the future, they also recognize that you're still young, and your career aspirations can change a number of times, and very quickly. Be honest, tell them that you want your career to take a different direction but appreciate all that they've done for you. I would do it in person, if possible, but if it's not a phone call would be fine.

Also, I wouldn't renege on your verbal offer until you have a formal one, unless you're really far from graduation. I'm sure they'll be happy for you, especially if you were a hard worker.

It's always good, imo, to have people older than you as career mentors even if they aren't in your industry. There's some advice that's universal and you never know when an unexpected connection might be able to help you out (or you could help them out!). Stay in touch through email, LinkedIn, texting, even going to informal events for your old firms.

Oct 17, 2016

Thanks for sharing. Great advice.

Oct 17, 2016

So you were still making payments on a dirt bike and you're quitting your job?

I don't know the while story here, but at face value this is a questionable move at best.

twitter: @CorpFin_Guy

Oct 17, 2016

What's your next step, GMngmt? I quit my job about 3 months ago, and I'm still trying to figure out how to make money in the next phase in my life (which will hopefully involve traveling and working from my laptop haha).

Oct 17, 2016
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