How to Win Through Quitting


Afraid to take the leap and quit? Wondering if you’ll be considered a failure if you do? Don’t worry, quitting isn’t nearly as bad as it sounds and is completely necessary in life if you’d like to become a winner.

Quitting is simply admitting defeat by saying to yourself:

“I’m not good at this, it’s not going anywhere, and I can be happier doing something else.”

I’m not sure if you’ve noticed this yet, but you’re not going to be the best at everything you do in life. There are only going to be a few things in life you really excel at. Most likely these are also going to be the things you enjoy. Quitting is simply a means to recognize that you’ve failed at whatever it is you’re trying to accomplish, it doesn’t mean YOU are a failure, it just means that you’re not doing well in whatever it is you’re doing. It’s a little bit of an ego blow and has negative connotations because to society it means you’re a loser, someone who isn’t good enough, someone who is a failure.

The truth of the matter is quitting is necessary. However, quitting is a lot easier when you understand why you’re quitting. We’ll discuss that in a bit, but think of quitting as a way to remove the fat in your life that gets in the way of your super fit, super awesome life. Sound good? This may be easy for me to say, but trust me, I’ve been there too as society, relatives, friends, and family wonder what the heck you’re doing by quitting.

Here’s an example; This is what my mom said when I told her I was quitting my job and comfortable lifestyle back home to pursue my passion for diving in Hawaii:

“What am I going to tell the family at Christmas?”

This was honestly one of her first questions. Not exactly a supportive statement, right? You’ll probably get a similar reaction from people in your life when you tell them exactly what you want to do. That’s because it often requires you quitting your current life and making a significant change.

Although scary at first, quitting can be one of the best feelings in the world. Whether it’s a horrible relationship, job, or even business, quitting clears your mind and releases the sails of freedom so that you can achieve your true goals and purpose. One of my happiest moments was when I quit being a Realtor. I was done lying to myself and trying to fit a square peg in a round hole – the freedom and self actualization of quitting that job was an absolutely amazing feeling!

How do you know When you Should Quit?

Obviously quitting isn’t always a good thing. Quitting flies in the face of persistence, hard work and sticking to something for it to be successful. So what are the telling signs that it’s right for you to quit?

One of the biggest things I ask myself before quitting is “am I enjoying doing this?” If you’re not enjoying whatever it is you’re doing, you’re wasting your time. You’ve only got one life (unless you’re a cat or Buddhist) and if you’re doing things you hate, you’re wasting that life.

Also before you quit ask yourself this: “What is the worse thing that could happen if I quit, and what is the new potential for me once I’m free?” Consider asking yourself this question whenever you’re about to try something new as well. Oddly enough, it’s often hard to leap into something new even if there’s a huge upside and low downside.

When quitting we’re wiping the page clean and allowing ourselves the freedom to turn a new page and start fresh. This could be as simple as quitting a habit or as extreme as quitting your way of life. Below are some of the best areas of your life to see if you need to make some changes, and simply say… I Quit!

1. Bad Relationships – I’m sure you’ve heard of toxic people, you know, the one’s who are like a leech the suck your energy and make you feel horrible. These leeches are one of the first things you need to quit in order to be the person you want. Find people who lift you up and quit the people who let you down.

2. Your Job – This can be one of the most fun things to quit as you leave the confines of your cubicle. Jobs are simply that, jobs. They aren’t your life, they aren’t your personality, they’re simply tasks given to you to perform. If you don’t enjoy those tasks, quit, and find tasks that are more enjoyable for you.

3. Unnecessary Commitments – Many of us say yes way too often. I did this in college and signed up for what seemed like every group on campus. Spreading yourself too thin results in not giving enough time to any one particular thing, which makes you fail at everything. Quit the things in your life that matter the least so you can be successful in the ones that matter most.

4. Hurting Your Body – Quit drinking, smoking, and drugs. Quitting these bad habits give you the freedom of a clear head and allow you to be more productive and happy.

5. Your Inbox – Quit your email box. This is one I’m still working on, but your email is not your life. Check your email once or twice a day and forget it about it the rest of the day.

6. Your Fears – Quit fearing things. Fear is only a roadblock to your success and happiness. Give fear your two weeks notice and tackle it head on.

7. Your Debt – Quit buying stuff! By quitting your spending you’ll automatically begin to quit your debt since you’ll have money in your savings.

8. Being Average – Quit being average. Average in today’s world means you’re not living up to your potential. I don’t mean average in terms of money, but simply being happy, giving it your all in whatever field you choose and refusing to take no for an answer. Quit going to the 9-5 you hate, eating TV dinners, and watching sitcoms. You’re not doing the world a favor by being average.

Quitting isn’t a ugly word, but rather something that gives you freedom from things that are weighing you down in life. Quitting allows you to take back your life when it’s gone astray. Realize that by doing so you’re not a loser or failure, but somebody who was strong enough to realize they’re off course and change direction for the better.

If something is standing in the way of you and your happiness… quit it!

Image by fuzzcat

Investing Newbie
Not gonna lie, those are some fighting words especially given today’s economy. I agree with you 100% on quitting all of those things, except the job. I think you should consider yourself very lucky that you were able to quit your job and move to Hawaii. It wasn’t for sheer willpower but rather your finances allowed you to do so. Many people are unhappy in their jobs, but they don’t have a way out because it is their only way to quit the other toxins such as debt or even relationships (if you are dependent on a leech). However, that… Read more »

My favorite by far is #8. I’m not an average person and I’ve learned to embrace that part of myself. People who think outside the box can change the box.

Quennie Mae Lungay

Wow I am currently stuck in this horrible situation right now. This article might just be the sign I’ve been looking for..

Financial Samurai

Good post Ryan! Being average is the real bummer. We don’t have to be excellent at everything, but at least we should be excellent at something.


“Unnecessary commitments” is my problem. I’ve got too much going on. Maybe I can quit one this year. We’ll see. I love the “quit debt”..that’s a great one.

Mrs. Money

“2. Your Job – This can be one of the most fun things to quit as you leave the confines of your cubicle. Jobs are simply that, jobs. They aren’t your life, they aren’t your personality, they’re simply tasks given to you to perform. If you don’t enjoy those tasks, quit, and find tasks that are more enjoyable for you.”

Ahh I totally need to take your advice. I’m pretty much sticking with my job because I make decent money and have health insurance. :/

Quennie Mae Lungay

I made a comment on January 6th when I was still confused, but I finally did it! Thanks for sharing this insight, it helped! Here’s my post regarding the resignation –
.-= Quennie Mae Lungay´s last blog ..Do you wish to travel the world for free? =-.

Tyler J.Logan
I have been so inspired by your self-help topic about quitting. I have never seen a writer write unique self-help content. First, I agree with everything in what you have spoken because I have thought about these certian things that you have spoken about! Sometimes, we have to use discerment and use the correct wisdom when to quit at a particular thing, when it’s stress and opress a person, that’s when they need to quit! As you said, there is nothing wrong with quitting, and it’s not always bad! I agree, they look at quitting as a bad thing, and… Read more »
Tyler J.Logan
Hey Ryan! You are always welcome! I’am sorry that I have not been on your website to repond back in a while. I wanted to say thank you for writing this blog! The reason is that I lot of people need to see this different perspective on quitting. I really hope to see more self-help topics. The self-help world needs true help. However, thank you for writing this so that I could share it as my blog pick. I truly felt the readers who visit my blog needed to read this! I hope to hear from you soon. Thanks. .-=… Read more »
Guy G.
Hey Ryan, My two favorites are quit being average and quit your fears. I think simply facing fears and doing what brings us joy and fulfillment will accomplish the goal of not being average. As far as knowing when to quit a job, I have a sad personal story from before I started learning tips on budgeting and sharing them with others. Before I quit my job to go into business full time, I had some part time income from my business which I thought would cover expenses. That’s because I didn’t even know what they were. I guessed! That… Read more »
Aury (Thunderdrake)
I always found the inbox one to be a rather interesting one among bloggers. I don’t think I’ve dealt with a massive inflow of mail myself yet, or that I keep it rather organized. Though perhaps once I build my site a bit, I’ll know the feeling. Toxic relationships is an important one though.. For one is only as good as the people that surround them. As for being average.. Most people who do it, do it for the sake of conformity. Hah. I’d have to disagree.. As they’re technically doing the world a favour. Unfortunately, the average 9 to… Read more »
Matt Davis

All your posts on quitting are really lighting a spark inside me Ryan, and I’m not sure if it’s a good thing. I guess I’m worried what people will think. A lot of my friends envy my job, and envy my pay, and so to give it up in the hopes I’ll find something else is hard, but I’m going to keep pushing, and hopefully, after a month or so more of thinking it through, I’ll quit my damn job and smile the whole way out the door.
.-= Matt Davis´s last blog ..Samurai’s Yakezie Alexa Ranking Challenge =-.

Matt Davis

Posted a comment ^ about a month ago, and I’m glad I read these posts.

Turned my 40 hour a week job into an 18, and I’m extremely happy with it, and now I get to spend time working on my blog,

Thanks for the tips Ryan, I really appreciate them.
.-= Matt Davis´s last blog ..Stop Wasting Time! =-.