How to Fail–Even if You Succeed at Quitting Your Job

How to Fail–Even if You Succeed at Quitting Your Job

Editor’s Note: This is a guest post from Clayton of Journey of My Own

I had just gotten out of my morning yoga class.

The rest of the day was free, and I had no idea what to do with it.

Should I try to see some tourist attractions? Should I go to the shopping mall? Should I just wander around and see what presents itself?

It wasn’t such a bad situation to be in, really. I was paying the rent. I had enough left over to have fun with.

The problems was that this was a dilemma that I had to deal with on a daily basis.

You see, I left the US over two months ago and I was living in Bangkok, Thailand.

This Was Something I Had Wanted So Badly!

How could I possibly be bored?

Sure, it was fun at first, to navigate through a confusing and new city, try to communicate in a new language, and immerse myself in an extremely different culture.

But eventually, you start to get accustomed to your new environment. Things like road-side food carts, tuk tuks, and orange-robed monks walking the street start to lose their novelty.

What was wrong with me? I felt guilty to admit it, but I was bored.

I mean, this is the kind of thing I spent over a year working toward. How could I be bored?

In 2009, I started a little online business that sold other people’s stuff. In return I got a commission.

Just over a year later, I was making enough from that to get my girlfriend to quit her job and run off to Thailand with me for three months. We were living off passive income.

I mean isn’t that the dream? How dare I feel bored?!?

Well, I really struggled with this for a while. I didn’t want to admit it to anyone. But finally my girlfriend and I had a talk. One of those talks where you just call out the big thing that no one really wants to bring up.

It turns out she felt the same way too.

After some talking we reached the root of the problem.

Sure, we “did it” and made enough money to travel through Thailand for a while…

…But We Had Absolutely Nothing to Work Toward!

Life had become nothing more than just shuffling around from one meaningless diversion to the next (and no amount of tourist attractions, shopping, or even beer seemed to help).

Isn’t that why we decided to leave the whole job thing behind in the first place? To get away from that maddening dissatisfaction and those questions that were growing ever louder, asking “Is this all there is to life?”

You see, I learned a very important lesson on that trip: Quitting your job and working for yourself doesn’t solve your problems.

There’s more to being happy than just removing the bad. Without replacing it with something positive, you only create space for self-doubt and disappointment to move in. The goal of quitting your job isn’t to be inactive or lazy. And it certainly isn’t to just be in “vacation mode” or “weekend mode” all the time.

So, there we were in the middle of Siam Square, with thousands of busy people rushing to and fro around us, with absolutely nothing to do.

That’s When We Decided to Change Direction

It was time to check in and see where we really wanted to go with our lives and with our business.

It wasn’t enough to have automated income. Life is about more than just running away from the bad, leaving your job and perpetually chilling out on the beach, margarita-in-hand. Satisfaction and growth on a personal level comes from following excitement and finding work that is fulfilling, not from escaping or running away.

To put it another way, it’s about moving toward something, not about moving away from something.

As I found out the hard way, the big prize of quitting your job isn’t to simply not do what you don’t like while just floating through life without direction. The big prize is finally doing something meaningful to you.

Suddenly when we started to focus on the impact that our business could have and all the lives that we could touch, things started to change. I actually started to feel excited. The ideas started to flow and I felt more energy than I had in long time.

We enjoyed the rest of our trip with the enthusiasm of knowing that there was something more to work toward when we returned. It’s taken a lot of work to change and re-adapt what we were doing (and in many ways we’re still doing that), but the change is for the better and it leaves me feeling more motivated and excited about life.

I’ve come to the conclusion that it isn’t enough to simply build your business or work for yourself for your own benefit. Sure the creature comforts of sleeping in, traveling, and engaging in other fun forms of mischief are nice.

But what is really going to make you stick with this in the long run, give you the drive you need to pull through the difficult times, and really succeed and thrive at working for yourself is feeling a deep and real connection with the people you help.

Although you may not even believe it yourself yet, you can offer much needed help to others. You can inspire and lead them to do things they never had the confidence to do otherwise. You can have a meaningful impact on their lives.

If you want to quit your job and strike out on your own, you can’t simply move away from a negative situation or a dissatisfying career. If that’s the only thing you do, you’ll just end up drifting or feeling directionless. Instead, create a very real vision in your mind and in your heart of something you want to work toward, something that inspires you, or something that humbles you.

What’s the thing that’s pulling you towards working for yourself?

About the Author: When he’s not having an existential crisis in Thailand, Clay Andrews writes on his relationship advice and lifestyle design blogs. Go visit one of them and say “hello” (he doesn’t bite–and he’ll probably hook you up with free stuff too!).

photo courtesy of Mark Goodwin

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22 Comments on "How to Fail–Even if You Succeed at Quitting Your Job"

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Thanks, I think I needed to hear this. I get so stuck in “I don’t want to be here, doing this, forever” that I forget to think about where I DO want to be and what I DO want to be doing. I haven’t quite internalized the idea that I really, truly can help others (though I’m trying to do it anyway), but I can recognize that I don’t get up in the morning excited to go to work. I don’t sleep poorly because I can’t get a piece of software out of my head. I DO get up excited… Read more »

@inametaphor Repetition creates more of the same. Here’s to holding what we want today.


@inametaphor Yeah, despite the fact that they may seem very similar, moving toward what you want and moving away from what you don’t are very different things that will take you in very different directions.

(Something some of us need to learn the hard way…)


Really does help to focus your positive energies on leaving your legacy and living from a place of abundance, rather than the negatives and scarcity. Thanks for a great guest post, Clay and Jonathan. Hope you are enjoying my motherland immensely!


@Tom Pinit Thanks Tom. You’re from Thailand? I’ve met so many amazing people from Thailand (either over there, or here in the US). Sometimes I wish everyone in the whole world was as friendly :)

Tom Pinit

@Clay_Andrews Born in the States, but my parents and all my extended family are from Thailand. So we have been going back every 3-4 years ever since we were little kids. Definitely home away from home!


@Tom Pinit I see. I’m half-Japanese. Born in the US too, but I have family back in the land of the rising sun. I haven’t ever met them though. Maybe some day :)

Tom Pinit

@Clay_Andrews Yes, I’d like to explore Japan as well. The only time I’ve spent is in Narita (airport & town), back when we had to overnight en route to BKK. Experienced my first earthquake there too!


I believe that we’re all here to help others in our own unique way. It’s up to us to find that way. Without helping and supporting others, life is pretty empty.

I’ve done a lot to help others informally and I love it. Now I’m working on turning that into my livelihood.


@PaigeBurkes _ I totally agree, and part of the fun for me is continually figuring out more and deeper and clearer the specifics of my helping others :D


@PaigeBurkes You’re an inspiration Paige.


Special thanks to Clayton for doing this guest post. He has a lot of wisdom to share and I highly encourage that you check out the important work he’s doing.


I love it all Clayton, fantastic work here. Thanks for sharing your story and wisdom.

My favourite part?

“it’s about moving toward something, not about moving away from something.” – Tweetable.

I’m focused on being a timeless, success-focused way of life, by 2042. It’s as good as done, watch for it, better yet, sign-up and get in on the ground floor at – new brand launching on new years :D

Excellent perspective Clay. I’m glad you wrote this. I’m getting closer and closer to quitting my job (or getting fired, whichever comes first.) I’ve been questioning what I’ll do. I just started a fresh new blog and my intent is to make a difference. Your post reaffirms that I’ll be just fine so long as I have a purpose to my life. I’m not just looking to quit and live happily ever after. I want to do something AWESOME…for other people! I’d like to be the one getting comments like this one, from people who have been impacted by me… Read more »
This is such a powerful and honest message. Far too often we focus on what we don’t want, and escaping what we don’t want, over nurturing and creating what we do want. And more than that, we focus on having what we want instead of wanting what we have. I see a lot of articles about quitting your job and living the life of your dreams, but the reality is many people don’t have a clear and specific goal in mind. And many others may not truly have the desire and self-motivation to be self-employed. While I am working towards… Read more »

It’s funny how realizing your dream usually means starting all over again with a new one.

Oh, and I love this… “There’s more to being happy than just removing the bad. Without replacing it with something positive, you only create space for self-doubt and disappointment to move in.”

So so true!

This is very timely for me. I’ve made lots of ‘changes’ for the purpose of following my bliss, yet still I find myself right back where I was; bored, impatient, questioning. While I feel I’m on the verge of another opportunity to ‘risk it all for truth’, I’ve been hesitating because the cycle is becoming painfully clear – jump, love / fear / excitement, settle, boredom, jump again. I’ve been really contemplating how I can possibly make the next jump towards something instead of just away from something. It is possibly more terrifying that just jumping toward an unknown. While… Read more »

No its true. I’ve worked for myself since 2003 and while there are perks to working for yourself you give up a number of things and you can quite easily find yourself not venturing out as much, which is fine as unless I have a major reason to head out.. not much point just doing things for the sake of doing them. But yeah you have to be working towards something. Without vision the people perish.

kelly park

Great post – just want I needed to hear and help me realize. I am not running away from my corporate job in Feb 2013 but running toward full time great writing.

Great behind the scenes look! I agree, quitting your job cannot be your end goal. It is not about stopping – it is about starting. It is about doing stuff that’s meaningful. At the same time, a corporate job is not likely going to give you a meaningful purpose. Sitting behind your cubicle desk, dreaming of a different life will not get you there either. You have to take action. And as you start this journey, re-examine your definition of success. It is not about successfully executing a plan. You have set out to discover what works for you –… Read more »
I recently started my business to help others, because there was only so much that I could do making money playing poker. I was rather bored with it, there is more to life the just making money. Ironic that I say that because when I started playing poker that is what allured me to it! Same with having a business online I came to it for the money. I Kow I need more then money to motivate me, more then just travel as well. I am at the point where I truly want to help others because it brings meaning… Read more »
Matthew Riley
Whenever someone asks me what I want to do with my life? I typically respond “nothing”. I want to sit all day in a chair and let the world pass me by. Up until recently I believed that to be true, that was until I finally gave myself the opportunity to do exactly that. I’m not saying I am not enjoying all the rest and relaxation I just want what I do to have some impact whether it’s just on me or on the world. We all need something to work towards something, its what keeps us sane and out… Read more »

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