How to Quit Your Day Job

How to Quit Your Day Job

The purpose of this article is to guide you through the steps necessary to go from: a) working at a job that turns you into a zombie you’re not happy with to b) beginning self-employment.

What this guide is not: The following is not meant to teach you how to create a successful business. That is beyond the scope of this article.

So, if this isn’t meant to teach you how to create a business, how can it help you to quit your job? Well, it turns out there is a lot more that goes into quitting your job than just creating a self sustaining income. You’ll have to figure out how to talk to your family and partner about it, set and stick to a firm date, and create a savings fund to cushion your transition (unless you prefer no safety net when you jump). This guide intends to address these often un-talked about concerns.

Being dissatisfied isn’t enough

A lot of people know that they would rather not be stuck in their current work situation. But knowing what you don’t want and being dissatisfied isn’t enough. And while dreaming about what you’d rather do is great (it keeps your hope alive), it’s not enough either.

At some point you’re going to have to address the gritty, practical and tactical side of how you’re actually going to change your situation. 

Below, I’ll address each of these topics related to taking the plunge (actually quitting your job and doing what you want):

  1. Is self employment right for me? Or am I just jumping on a bandwagon?
  2. Finding your niche and hanging up your shingle.
  3. Setting your date for your final day of work.
  4. Approaching the topic of quitting with your partner and loved ones.
  5. Safety nets, savings accounts, and preparing for the transition.
  6. Saying “I quit” and reclaiming your time.
  7. Acclimating to freedom and the schedule-free life.

Let’s get started, shall we?

Is self employment right for me? Or am I just jumping on a bandwagon?

There are a lot of blogs out there (this one included) that tout the benefits of self employment: more freedom, greater control of your work, and choosing the people you want to work with, to name a few. All of this is awesome, trust me, but are you also willing to accept the responsibility?

When you’re self employed you are the one responsible for making sure enough money comes in each month to pay the bills. When you work for someone else, you don’t have to think about that. You just wake up and do your job.

Are you also okay with running the details of overseeing administrative work, scheduling, taxes and operations in your business? Most people talk about the rosy and alluring side of working for yourself, but they don’t mention some of the very real changes you have to make that you might not have known about.

I’m not saying that it’s not worth it, it is. But it’s not right for everyone.

So, the first step is to ask yourself… Do I really want this? If the answer is yes, then proceed. And if it’s not, that’s okay too. You’re not any less cool than the “lifestyle design digital nomads.”

Finding your niche and hanging up your shingle

I mentioned earlier that this article isn’t intended to teach you how to start or run a business. But we should at least cover the two most important steps: selecting a market and opening for business.

A lot of people email me telling me how they’d like to start a business. But they’re paralyzed. They’re unable to make a decision about the market they’ll get into and continually second guess themselves. There’s a place for exploration and discovery, but at some point you have to saddle up.

If you don’t firmly choose a market you’re not even in the game yet. You’re just sitting on the sidelines. And it’s hard to build a business that way (obviously).

Once you select a niche, it’s time to hang up your shingle. And by that I mean actually putting up a website and making an offer.

If you have a “blog” that you want to eventually “monetize,” then you don’t have a business. You don’t have a business until you actually have something for sale. Until you then, you only have a hobby. That’s fine if that’s what you want. But then why are you reading this article?

Obviously you don’t just want a blog, you want a business. So don’t put off creating an offer until you have X amount of subscribers or “1,000 true fans” or whatever you think you need to start. If you wait to put out an offer, you have no idea if people are willing to buy something from you. And that really sucks. You might spend a lot of time building an audience that is just there to hang out. Great if you want a hobby or community, bad if you want a business.

Setting the date (or tying the knot)

People that are engaged know this. If you haven’t set a date, then you getting married may or may not happen. Who knows, right?

Same thing goes with quitting your job. Without an actual date it’s just a nice idea.

So if you haven’t already, what I want you to do right now is set an actual date. Write it down. Put it in your calendar. And if you’d like type it out in big 48pt. type, print it, frame it, and put it on your nightstand.

Now it’s going to happen. Why? Because now your mind has shifted from “Nice idea” to “Damn, I’ve gotta figure out how to do this by this actual date.” It makes a huge difference. I’ve created a template you can download here and fill out: Quitting Date Template

Talking about quitting with your partner and loved ones

If you want to quit your job, at some point you’re going to have to tell your partner (or whomever is close to you) about it. When I first mentioned that I wanted to quit my job to my wife, I wasn’t very smart about it. I just said, “Hey honey, I’m going to be a professional blogger and quit my job. Just thought I’d let you know.” And she said, “Oh, yeah. Right. That’s nice babe.” Needless to say, because I didn’t really explain my plans, it was seen as a fleeting fantasy and I didn’t get much support. So, don’t do what I did.

Actually come up with a plan that details at the very least:

  1. How you’re going to become self employed
  2. How much money you’ll need in savings
  3. How much you expect to be making at the time you quit

He or she may not believe you at first. My wife was skeptical even when I broke down the numbers.

But when the money started to come in, she started to believe that this might actually be possible. And guess what? It was. Some people will respond and be more supportive when you show them results. But either way, talking to your loved ones about it and showing them you consider them in your decision (because it most likely affects them, too) goes a long way.

It’s scary to know that you may be met with skepticism and disbelief, but the more you show them with your actions the more they will begin to take you seriously.

It should also be noted here that if you want the best support on your path to work freedom, it’s best to look for that from people that are already self employed or currently on the same path as you. They will be the most sympathetic and are more likely to cheer you on. It’s not fair to ask the same of people living in a completely different reality.

Safety nets, savings accounts, and preparing for your transition

Should you have a cushion when you jump or are you confident that you’ll land on your feet? This is something you’ll really need to consider. When I quit my job to work on Paid to Exist full time, I had about three months worth of savings. It wasn’t a ton, but it was enough to make me feel a little better about it (I was also making a job-replacement income from Paid to Exist at that point for several consecutive months).

For some people, only three months of savings would scare the shit out of them. For others, it’s more than enough to give them that kick in the ass to make the leap.

So, you’ll need to ask yourself a few questions:

  1. How much money do I need in savings to feel comfortable quitting my day job?
  2. When do I need to save this money by? (Hint: it should be your quit date that you defined a few minutes ago. You did do that, right?)
  3. Do I expect to be making the same amount of money from my business (job replacement income) as I’m currently making from my job when I quit? Or am I okay with quitting without making any money (or only some) from another source?

I know a lot of people that are okay with only having a giant savings and no money coming in yet from alternative means. I wasn’t one of those people.

I wanted proof that I could consistently make the same amount of money I was making at my job before I felt safe quitting. So did my wife. You’ll need to decide what you’re most comfortable with and plan accordingly.

Saying “I quit” and reclaiming your time

When it finally comes time for you to give notice to your employer, you must follow through.

You will likely second-guess your decision at this point. This is perfectly natural. But now is not the time to back out.

You’ve been working diligently for months (or perhaps years), and you’ve done all you can. Nothing else at this point will prepare you anymore. You have to get in the water to learn how to swim.

A month or so before your quitting date, it’s a good idea to take some time to think about what you’ll say to your employer. Writing it out helps. You can have fun with this too.

In my resignation letter I told my boss “I will no longer be requiring your employment services.” Obviously you don’t want to burn any bridges (or do you?), but feel free to be creative. This is something you’ll remember for the rest of your life; why not make it fun?

You may even want to write your resignation letter now. Doing this helps make it more real and in turn will help you follow through.

Acclimating to freedom and the schedule-free life

It would be a bit dramatic to say that reclaiming your time is the same as being released from a long sentence in the state penitentiary. But it does have a parallel in that you will need to take some time to adjust. Things will feel funny at first. You’ll feel weird not having to ask for permission to take a long lunch or go for a hike in the middle of the day.

One day you might wake up late and start automatically thinking about the excuse you’ll tell your boss. Rest easy, you’re the only one you need to answer to now. But the schedule-free life also comes with its own set of challenges. Now that you have the reigns on your time, you’ll need to develop your own methods to ensure things get done.

You could have worse problems, right?

The last thing to do once you’ve finally quit is celebrate. Do something special for yourself and savor the rite of passage you’ve just undergone. When I quit, a friend gave me a clock to symbolize that I’d been “given back my time.”

You might consider doing something like that for yourself. Just like writing your resignation letter in advance helps to make things more real, so does deciding what you’ll do to celebrate on the final day.

Freedom is created

You have to create your own freedom. If you don’t, no one else will do it for you. If you don’t have a plan for yourself, it’s likely that someone else does. Or you’ll just end up living by default, by a template you certainly didn’t design.

If you want to be your own master, you’ll have to reclaim ownership of your mind.

So… over to you. What do you find to be the most challenging or daunting thing when it comes to quitting your job? Or if you are already self employed, what was it when you were preparing to quit?

photo courtesy of Paparatti

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85 Comments on "How to Quit Your Day Job"

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Laneth Sffarlenn

Wow. Thanks for writing this. Bookmarked, shared, saved and read – I am going to have this post memorised as the most sensible, easy-to-understand and invaluable post on preparing for the transition I’ve read.

These are things that I have thought about but not seriously given complete focus to – I now have a template for a game plan, and for that I thank you.

Now to get to work :)


Thank you thank you thank you! Step by step process is what I need. Bless you…

I love that you provide templates to keep us motivated and moving forward.

Great post Jonathan! I think you nailed it on the head that you definitely need to include your spouse/sig other in your decision. In my experience, he or she will be the biggest supporter in your new journey. In fact, I’m not sure how someone does it without the help of their loved ones? I think it’s important to also keep track of your work while still at work. Setting a date for your eventual “freedom day” is awesome and needs to happen but you need to make sure you’re still giving your employer their money’s worth. I know too… Read more »

Jonathan – this is really great stuff.

Quit your job or not, never forget that just because you sign the back of the paycheck doesn’t mean you aren’t self employed. You aren’t working for the man, you’re working for yourself and your family. You-Incorporated sells your services to an entity that pays you. If someone else offers you more or a better deal – then you are free to choose to take your business elsewhere.

As with most things in life … it’s an attitude!


Thing is, I may not have six months to work this out. I may loose my job any day now. So it comes down to this, should I look for another job that I don’t really want, or do I risk everything and try to make a go of this self-employment thing? I have about 8 months of money saved.

David Damron
Hey Jonathan— I struggle….yet I have done something similar before. Back in 2008, I posted an 8×11 note on my door that read “What are you doing today – To be in Australia tomorrow?” This note helped me focus, save, quit my 9-5 and complete that dream/journey within 10 months total. I moved to Australia and loved life. Then I moved back to the states and slowly returned back to the life I shunned before….and I hate it. I am pissed at myself. I ask myself how I let this happen daily. However, I know why. I am lazy and… Read more »
Laneth Sffarlenn
Hey David, Your comment hit me right at home. Not because I’ve been there and gone back, but because I resonate with the whole “I am lazy and unfocused” bit. I know that I could be successful if I could focus and spend the time to build it all up, but I can’t seem to break out of the outside-work habit and really knuckle down to get it done. I’ve let my current job get me into a really dark place, a desperate place, where I’m now even looking for other employment just to get out of here instead of… Read more »
Thanks for your honesty David.I’m sure there are many more people out there who share your frustration. It’s funny how perspective can change once you’ve removed yourself from the ‘reality’ of the situation for a long period of time. I did the same back in 2009 when I went on a 6 month trip from AUS to Europe. I met so many other people in all walks of life that had is ‘worse off’ than I, so I returned to my miserable job thinking that things would change – that I had changed… I hadn’t though. 6 months later I… Read more »

I echo Laneth’s comment- This is high quality and very, very inspiring. I’ve been kicking around an end date for a while, but now I’ve got one that I can commit to: My 27th Birthday: March, 28th 2012.

Andrew Toynbee
Sean – Damn right you need your spouse on board! Back in 1999 I lost my regular job and with nothing worthwhile on the horizon, I invested £50 in a franchise and went self-employed. The franchise was hard work, but very successful. However, the constant pressure and negative comments at home eventually led me to quitting and going back to the job marketplace where I am now stuck in the 8-5pm rat race. Not a day goes by that I don’t hate it. So, whilst jumping ships without okaying with your significant other might seem like a bold idea, beware… Read more »
Tom Meitner

Good work, Jonathan! That first heading is an important one: being dissatisfied isn’t enough. You need to have a place to go. Just because you’re pissed off at your job doesn’t mean you’re ready to quit. You need to sit down and figure out exactly what would make you happy, instead of focusing on what makes you unhappy.


For you people who are still doubting: Why are you holding on to something that is nothing? Don’t stick with your J-O-B if you hate it! For security? What security? For bennies? No loner necessary. Health and retirement benefits are avaialble for independent workers now. Make the leap to being independent and do what you love. You’ll be happy you did.


Wow! You’re really opening my eyes … And yes I agree with you .. Being dissatisfied isn’t enough for a reason to quit the daily job ..

Thanks mate!


Thank you SO much for your inspirational and wonderful article! I want to quit my day job but everything is vague in my mind. This will help tremendously and I especially love the idea of setting a date to make it happen. Provides clarity and motivation.

Steven | The Emotion Machine

Very down-to-earth guide about some of the things it takes to quit your day job and become self-employed. It’s always nice to hear a balanced perspective, and the fact that it’s going to take some real planning and work to make such a lifestyle a reality.

Thanks Jonathan, I’ll definitely be sharing this with some of my readers.


Awesome post, Jonathan. I’m on my way to my passion and my date has been set. Another thing I took away from this is to do/buy something symbolic when I make the transition. That is a little something extra to look forward to! Thanks for continuing to write awesome posts like this!

Dion Baker
I’ve taken the plunge from the j-o-b already (last year) and, months since making the move, it was definitely one of the best decisions of 2010. I made my exit without having income from another venture supporting me. I don’t generally recommend that move but I do recommend this… if you know its time for you to get the hell out of your job then start making your exit. It’s a shame how many of us prostitute our time for things we don’t even enjoy. One thing I’ve yet to do is a right of passage celebration for my exit.… Read more »
This post was just what I needed today! As I sit at my desk in an office building working for a corporate American company, I can feel my soul dying a little bit more every day. This post, however, reinvigorated my soul. I am now determined to make 2011 the year I get out for good! I chose my exit date: November 18, 2011. I know I won’t feel comfortable without at least 6 months worth of income saved up, so that’s what I’m working toward. Thanks for kicking my ass with this post and making me realize that I… Read more »
Laura Lee Bloor
Thanks for this, Jonathan, it’s very helpful. Money is my biggest obstacle. I’m still in step 1, which for me is: Get out of credit card debt. While my husband and I are making great progress, we still have two more years (if all goes according to plan) before we can focus on the saving portion. I also find that whenever I get dissatisfied with my blog, which is more often than I’d like to admit, I look for new, exciting projects to take on. While these other projects are wonderful, I end up regretting that they took me away… Read more »

Great tips. I do think some people get caught up in the hype of home business/self employed riches. If they took the time to think over the points you made, I think they would make better choices.

Andrew Toynbee

Quitting the day job is a definite goal for me;

Someone once said; “I’m getting paid by the hour, but I’m ageing by the minute.”

Hello Jonathan (and everybody else who commented) I am so pleased to have found your site! I’ve been looking for exactly this kind of resource online and here it is. I’ve been dissatisfied in my job for almost 10 years; I’m determined to live more independently and authentically as a self-employed person; I think I’ve found my online niche (a great idea appeared in my head just yesterday); my quitting date is 30 June 2011; and my husband and son are excited about our move from the city to the countryside. So I’m working my way through most of the… Read more »

Not many people believe that they could support themselves on their own. They opt to working for someone else and basically being a servant for little income. A good place to start becoming an entrepreneur is through online income.

Seth Czerepak

I think a lot of people are afraid cause they think starting their own business is somehow less secure. However, when you work for someone else, they can lay you off..and when they do you lose everything. When you work for yourself, you might lose one customer but you still have others to sustain your income until you find more.


Why quit working?

I do not see what is so bad about a day job. The only real problem is having a day job as your sole source of income. If you can work a full-time job and have a side income, you can live a better life than choosing one or the other.

Hey Jonathan – Love the site and find it really insightful. I haven’t had a day job for many years, but I AM trying to transition my business from being solely client-based, to creating products and passive income streams. What I find that many ‘work for yourself’ bloggers DON’T talk about is the difficulties of making the transition from an emotional point of view. I’m finding the transition quite challenging – having to deal with maintaining enough clients to bring in income, while also finding the time & energy to work on my new business model. Not to mention having… Read more »

This is my first visit to your site. I read this article and found it insightful, but I especially like the way you wrote the article. So many are boring, but this one actually speaks to your readers like they are human beings. It’s also encouraging and engaging! Right on!

I put this post on my blog. Thank you so much for caring enough to help people live the lives they are truly meant to live.


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Nice write up. I really want to quite my day job for the right reasons. I need that financial freedom. Your follow through steps are just it. Thanks


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Kimberly Sea

Very inspiring and informative post! Just what I was looking for today. I cannot wait for the day that I can quit my existence as a cubicle dweller and become self employed. One area that concerns me though is not giving up my good health care package. I guess I need to research individual health care costs and coverage and not let that factor hold me back.


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Cool… I also found some other great pointers on how to quit


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Loved it and linked to it! I guess I must be ready, because the teacher has appeared…



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Great post.
I know it’s old but it’s helped me out as I’m currently wanting to do the same. Luckily I work with my father and he already knows I’m quitting. Hopefully October.
I guess the hardest thing will be getting into the habit of thinking you work for yourself so you need to get the work done. I’m currently getting this down to a T by October.


I know it’s hard to really quit and start something new but it’s better that way  than to just stay in your work that doesn’t satisfy you at all. Thank you so much for the advises you just shared, it was of help. I came across a video that talks about the how-to transition from your day job to your dream business from Marie Forleo.


Thoroughly enjoyed the post and am trying to adjust from over 10 years of active duty military service to working full time on my blog for helping distance runners. I have already discussed this with my wife, 10 more years to ‘retirement’ sounds great for many but 10 more years of military life is easier said then done.
Thanks for the post.


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[…] hard work to prepare meals (like bobby flay) every day.It’s hard work, and scary to start your own business.There are a million different reasons not to change. To not put in the hard work. But all you […]

Jonathan,   I am cracking up right now. I downloaded the quitting date template a while back (maybe when this post first hit) and wrote down August 1st, 2012. I have had it in my wallet for ever it seems. Totally forgot about it. I just stumbled a crossed it today.   Funny thing is I just turned in my resignation at my job for….. you guessed it. August 1st, 2012. SOme of the biggest decisions I have made in my life have also fallen on this date. Took a 3 month trip around the world August 1st, 2008, Left… Read more »

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