Quit Your Job, Love Your Life

It’s been about five months since I left my job.  In that time I’ve experienced just about every emotion possible, and over the last few weeks I’ve come to one very important realization.

I love my life.

Had you asked me that six months ago, I may have lied and said the same thing, but deep down I’d know it wasn’t true (and if you read older posts, you would know it wasn’t either).  I was on the same path as so many others for a long time, and even though I knew there was another way to do things, I could never imagine what it would be like to actually pursue something out of the ordinary.

I couldn’t imagine working whenever I wanted on my own schedule.  I couldn’t imagine staying up all night to work on projects that I was passionate about.  I couldn’t fathom having the ability to head down to paradise for a week, while still being able to be productive in the process.

Now its the norm and I can’t imagine going back.

Why Settle for this?

Why Settle for this?

Last week Matt Cheuvront wrote a post entitled “Breaking Away From Generation Now”.  It was an excellent piece about about how people from our younger generation expect things to happen quickly.  We have been bred to believe that if we aren’t living our dream right now we are settling in life.

In many ways I completely agree what he is saying.  We can’t continue to beat ourselves up over changes we have yet to make, and we need to be appreciative of everything that we have accomplished.

With that said, I’m going to play devils advocate for a minute.

We may be movers and shakers – we are no doubt the future of society and the world in general, but we’re also incredibly impatient – we’re inundated with stories of entrepreneurship, location independence, and “living the dream”…

  • You have to quit your job…now
  • You have to move across the world…now
  • You have to start your own business…now

I admire the heck out what many of my fellow Gen-Yers have accomplished, but this “now, now, now” attitude is brainwashing us to think that if you’re doing ANYTHING less than your most idealistic dream, you’re “settling”.

There is a lot of truth in Matt’s statement.  The now, now, now attitude can be a little much, and people may harp on it a little too much (like myself for instance).

When You Can Have This?

When You Can Have This?

However, the bottom line is, life is too short to keep doing shit you don’t love.

I’ve heard that said over and over by the likes of Gary Vaynerchuk and Adam Baker; and they are absolutely right.  We have no idea what tomorrow holds.  So to spend years in jobs we don’t like waiting for the perfect time is a waste, because there is no perfect time.

Iv’e mentioned before that it took me about a year and a half to finally work up the nerve to leave my job.  Had I known what was waiting for me, I would have done it a year and a half ago.

While I agree that for many people taking a leap without planning is not possible, and frankly, foolish.  But if you are unhappy and you aren’t actively preparing to make changes in your life I view that as settling, a word Matt argues should be stricken from our vocabulary.

Don’t settle.

The easiest thing in the world to do is fall into a comfortable routine that you can repeat over and over again until your death.  For awhile I thought that was what I wanted.  I thought I wanted to settle down, get married, and buy a house as soon as possible.  And for many people they are perfectly happy doing that, and that’s fantastic. Just don’t do it because its the easy path.

Have a plan.  If you are unhappy, take the time to figure out what changes you need to make and prepare to make them, don’t settle because you are scared of what might happen.

The fear of uncertainty is easier to overcome than a lifetime of taking the easy way out.

Since I’ve been in Thailand, I’ve been working with a wide variety of people who are achieving this lifestyle in radical ways.  Over the coming weeks and months I plan on sharing what I’ve learned.  If you want to make a change, see the world, or just have the freedom of time back, there ARE ways to do it.

I’ve written half a manifesto about how to overcome the fear of uncertainty, because after all that is what we are all afraid of isn’t it?  Tell me one other thing in the world people are afraid of.  Bet you can’t do it.

Think about the uncertainties in your life that are keeping you from doing the things you really want to do, and lets start solving the problem.  Once that is done, the rest will fall into place. I promise.

Thanks to Matt for the inspiration to write this. Take his advice, don’t beat yourself up about the things you haven’t done…just don’t settle in the process.


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Financial Samurai March 16, 2010 at 5:15 am

Congrats Sean! I loved being a study abroad student for one year as well when I was younger. It was the most fun I’ve ever had! It’s different now b/c I want to save money and try and retire early. If I didn’t study abroad and live all around the world growing up, I might have been more itchy to travel.

As of now, going abroad once or twice a year for a couple weeks is good enough.

Enjoy your journey as much as you can, and don’t forget to save while you’re there too!



Sean March 16, 2010 at 5:19 am

Thanks Sam!

One thing I also should make clear that doesn’t come through very well in this post, is that for many people they love their jobs and don’t need to travel. I think that is awesome, and have a ton of respect for it. This is written for those who are unhappy, but are afraid to make the change.

Uncertainty is a scary thing, and most people will let it get the best of them, when they don’t need to let it.

Eugene March 16, 2010 at 5:38 am

You nailed it Sean. When they say people have a fear of change, its the uncertainty behind it that drives the fear.

The big problem is being in a job that you don’t like, but is JUST comfortable enough. Because when facing the uncertainty of leaving you’ll always say “Well, its not THAT bad. What if things get worse?”.

Great post!

Jenny March 16, 2010 at 5:43 am

You nail it here. It’s not “settling” if you are actively making plans and making daily progress toward making those plans a reality. The “now” mindset may work for some, but if you’re working toward your end goal, it’s okay to finance it with a little extra time in the cube. On a side note, my eyes are watering from two nights in a row of <5 hours of sleep, haha.

Legal Nomads March 16, 2010 at 5:51 am

There’s a lot to be said for the taking that first leap of faith – and infinite rewards at your disposal once you do. Of course, there is a difference between being rash (leaving with no savings at all) and deciding to do somethiing different than the status quo with your life. Unfortunately, people often conflate the two; it’s easier to make excuses than to actually pack up and leave.

Nice post.

Matt March 16, 2010 at 6:20 am

Great post Sean. I love the line “Life is too short to keep doing shit you don’t love”. I’ve been thinking a lot about that. I hate life between fabric covered walls and am making an effort to finally break free from that. I don’t want to settle when there are so many better things I want to do.

The fear of uncertainty is indeed a strong one. I think your point about planning is important. At some point I need to make the leap of faith but to do so without some kind of plan in place is reckless. Of course you cannot plan for every little thing that may come up so at some point I just have to say this is it…i’ve planned the best I can…and then just go for it.

I want to be able to look back on my life and say “I’m glad I did those things” rather than “I wish I had done those things.”

Jane Rochelle March 16, 2010 at 7:15 am

Hi Sean,
I love your latest post! My husband and I always….always come back to the same question. What about health insurance? It’s the one obstacle that we can’t get past when we’re ready to throw away the lines and sail into the life we’ve imagined!! Any resources/suggestions?
Thanks! (great blog!!)
Jane teenytinypieces@gmail.com

Dena March 16, 2010 at 9:39 am

Thanks for the dose of inspiration/motivation, Sean. I can never say enough how happy I am for you. I’m not exactly where I want to be (YET!) but I sure as hell am on the path to getting there.

😉 Keep up the great posts. I can’t wait to read about what you’ve learned so far.

David Walsh March 16, 2010 at 9:57 am

Synchronicity is a hell of a thing Ogle. We’re both here in Bangkok, and you were publishing this post an hour ago as I was walking into the place we both call our “office” here. Before I left my place tonight, I threw on a t-shirt that I’ve had for years. Caught myself in the mirror on the way out, stopped, and actually looked at it for once. Distinctly remember thinking Damn. If this isn’t a metaphor for my worldview, I don’t know what is.

If you can’t read it, it says.. “NOW NOW NOW NOW NOW”

There’s a huge difference between patience and hesitation. I agree with Matt that there’s a lack of patience and loose grasp that things take time – but will never agree that we should be more hesitant in executing the things we do have the freedom to control. Patience means you’re waiting on something outside your control. Hesitation is just fear of uncertainty, like you said.

All we have is now. You get that, and you live that. It’s why we get along. The future is not guaranteed, and impulsive now-seekers won’t wait around as if it is. You could call it a Bangkok state of mind.

Sharp post.

Sid Savara March 16, 2010 at 10:23 am

Hey Sean,

“The fear of uncertainty is easier to overcome than a lifetime of taking the easy way out.”

Reminds me of something I read in the four hour work week:

“Most people will choose unhappiness over uncertainty.”


DantePasquale March 16, 2010 at 10:52 am

Hi Sean,

I really like the way you presented your article. Life IS too short and if you’re not doing what you like/love, then definitely try something else!

I’d like to offer a slightly different perspective as a non-gen-y’er…I’m a member of the apply titled F U Generation. The generation that immediately followed the boomers.

We’ve been by necessity dealing with the ‘now’, not because we were raised that way, but because the boomers sucked up everything and left nothing behind! No jobs, no environment, no housing, etc. We’ve moved from career to career as they’ve been decimated by globalization and boomers entering, then leaving both physically and financially.

This has been our “now” as in, my job is gone, now I have to find another, or my house is gone, now I have to find another. We’ve been doing this for 30 years and it’s getting a bit tiring! You push to find a career that you enjoy only to find out that its gone!

So, for your generation, its even more important to be proactive in career and life choices because, man is life short. There’s so many things you want to do, want to try, want to excel in and there’s just not enough time or money! So, START YOUNG!!!

ciao, keep up the excellent writing,

Elisa March 16, 2010 at 12:16 pm

Sean – I agree very much that you have to love your life. Really, you have to live it day in and day out, it is your closest companion. So if you don’t love it (and thus yourself) nothing else ever seems to really fall into place.

I think what stood out for me, and stands out for me more and more as I read different articles of location independence and entrepreneurship and “breaking free” is that these are things that make SOME people happy. Not everyone will be happy as a business owner. Not everyone will love living out of a backpack and seeing the world while owning less than 100 items.

We fault prior generations and people for choosing the “safe and stable” route to secure their happiness, but aren’t some of us just instead substituting start-ups and hostels for pensions and white picket fences?

Sarah March 17, 2010 at 12:59 am

Uncertainty was something I dealt with for nearly three months leading up to my departure. Unlike you, I didn’t have to work up the courage to quit the job I loathed (getting laid off took care of that quite nicely in the end), but the uncertainty that followed it — where my life was going, what I would do next, how I would do it — definitely was one of the more trying emotions I’ve ever felt.

Since leaving home, a lot of people ask me how I worked up the courage to do what I want and love, saying they could never do the same, despite their unhappiness. You hit it right on though: it just needs to be done.

As for uncertainty, the only thing I’m unsure of now, is if/when I’ll ever go back home.

Looking forward to seeing you in Bangkok again in a few weeks!

Josh Sager March 17, 2010 at 6:49 am

Sean, how are you picking up on the language? Have you been working at it at all, or just going with the flow?

Caroline W March 17, 2010 at 3:11 pm

Hey Sean, another great post! Sometimes I think it can be hard to distinguish whether you are being “settling” or “being patient.”

I made the ambitious goal to quit my job last December, but kept getting into that mental battle of “can I really do this? now? It would be better if I waited x more months” and “I want to just walk out today and never come back! I’m ready to get on with my plans and life!”

I did quit like I promised myself I would. I’m still not entirely where I’d like to be in life, but I’m working on it and working hard.

One of the key things about the “generation now” is that while we may want things *now* we’re also equally committed to working hard to get it – or I like to think we are! And, we want to live life without regrets.

Walter March 17, 2010 at 11:11 pm

It is unfortunate that we have the propensity to avoid facing uncertainties. Perhaps we want to take control of all the circumstances in our lives and so we don’t take much risk. Life is full of possibilities, we can achieve everything we want, the only catch is that we have to step above our fears and face uncertainty. 🙂

Mike March 18, 2010 at 12:05 pm

i have been following your blog for a few months and i find many of your articles very interesting. However, i am not clear on how you are earning an income (aside from this website). You have mentioned working with Tropical MBA, is there a post i have missed that discusses this at all?

Wilson Usman March 18, 2010 at 3:34 pm

I could not agree with you any more. I was once that person, I was so afraid of what would happen if I quit my door to door sales job. Mostly because I they brainwashed us so bad, telling us that there wasn’t anything out there and that we were losers if we quit. Well I quit and here I disastrous happened I am alive. I didn’t settle and now even though I might not be where I want to be yet I know I am getting closer than I was before, to what I’ve always wanted my life to be.

Kevin March 19, 2010 at 6:42 am

It’s pretty easy to say that when you’re young, single, healthy, and child-free. I’m curious if you’ll still feel the same way once you find yourself needing healthcare, or a college fund for your kids, or a retirement fund for yourself.

If it really were that simple, don’t you think we’d all be doing it? Can you see why your attitude might be perceived as a little arrogant by those of us a little further along in life?

Here’s a great idea for a blog post, Sean: What do your 5, 10, 20, and 30 year plans look like? You could do a separate post on each one.

David Walsh March 19, 2010 at 4:31 pm

At any age, I’d argue it’s arrogant to presume we have the luxury and privilege to create 5, 10, 20, 30 year plans. It seems to be a fallacy that arriving at knowledge later than another has any bearing on the validity of it. Circumstances are circumstances, and we filter what we learn through them. If I smoke for 20 years and realize it’s given me lung cancer, it doesn’t mean the 14-year-old that knows better than to smoke isn’t right. We are who we are when we learn what we learn – and we adapt accordingly. It’s irrational to fault someone for exploring a path that our own decisions have made more difficult. I’m not terminally ill, but I come from a long, unwavering line of healthy, vibrant men that drop dead of heart attacks at around 50. What most call middle-age, I’ve always assumed would be a privilege. No opinions injected here – just genetics. My timelines have always been relative to that. To shape a retirement plan for 65+ would feel naively presumptuous. I’m not reckless (ok, yes I am) but I live accordingly. It doesn’t make someone else wrong for planning a retirement, but it makes me question the assumption that we have that type of control over something as fragile as our own lives.

Now. It’s all we have.

Nailah March 19, 2010 at 6:00 pm

Great post! I completely agree that life is much too short to do stuff you don’t absolutely love. Taking that first plunge is terrifying and that’s where a lot of us hover, but once you’re able to live the life you truly enjoy there is no looking back. I like that you emphasize the fact that if you are planning for something different then you aren’t settling. I think we get so caught up in having the life we dream of now that we overlook that the planning stage is important and worthwhile. Thanks for the great insight!


Matthew Needham March 21, 2010 at 4:26 am

This is the first time I’ve seen your site, I read a review of this article on ameaningfulexistence

You’re so right. Life is too short for not doing the things you love and I moved to work for myself two years ago and it’s the best thing I ever did.

Glad things are going better for you!

Brian Wigginton March 25, 2010 at 4:48 pm

Working up the nerve to go out on my own after my first job was probably one of the most unnerving choices I’ve ever made. It’s also probably the best decision I’ve ever made. It’s nice to be able to take a break during the day without that little voice in the back of your mind reminding me that I’m going to have to put this on my timesheet as “Miscellaneous Overhead”. I find that I’m much happier, less stressed out, happier, excited about my work, happier and that I’m making meaningful business and client relationships, which actually has been able to make me as much or more than my previous employer! Also, I’m a lot happier now!

I can always remember hearing people say, “if I was only your age” or “that’s only something you can do when your young”. Well I want to capitalize on these moments. I want to be the one telling people when I’m older, that I did do that when I was young and it was awesome!

Great post

btw: @Jane Rochelle. I’m not quite in the same boat as you, but I got a plan with Aetna at ehealthinsurance.com

Karen March 25, 2010 at 9:09 pm

Your happiness is just so tangible in this post… so fearless. Such an inspiring journey that you are on and taking all of your readers on in the meantime. 🙂

Marina March 31, 2010 at 4:42 pm

I read your post “Am I being arrogant…” and I would not call that arrogance. What is required is plain old guts. Separating ourselves from the cocoon of comfort and facilities of our Western life is painful. You have to become responsible for yourself. Living without permanent paycheck, health insurance, pension insurance, mortgage, your hairdresser, etc. requires great deal of self-confidence and is not for everyone. I have seen it in Utila, Honduras, which is probably the capital of alternative lifestyle. People get tempted by the life without too many rules, but end up missing them and being lost without the comfort of a regular schedule and having to take care of their own needs, including finding a source of income. But, the payoff is fantastic, the sense of freedom and being truly alive cannot be explained. It starts when you quit your job, sell your possessions and realize that your entire life fits in one or two bags. The possibilities are endless. You just have to trust yourself and be totally opened to whatever comes. There is a way to test the waters, with volunteering. There are few very good volunteer organizations, like vso.org, which offer jobs to professionals who would like to take one or two years off and do something different and meaningful. It is an acceptable excuse to take a leave without pay, and the volunteer organization covers your life expenses and health insurance. Once you are living and working in a very different culture, you can quickly see if it is for you or not. By the way, the whole health insurance is a non-issue, many developing countries have excellent doctors, and the cost of a check-up or a hospital visit is really reasonable.

nokita July 8, 2010 at 4:58 pm

Hello Sean. It’s good to hear from people who have balls to quit and just travel like that, but i assume you’re traveling with the money the company paid, and if i’m wrong what do you do as a living while travel?

Sean July 9, 2010 at 1:09 am

@Nokita The company didn’t pay me any money as I left, I do variety of internet work to pay for my travels these days

nokita July 9, 2010 at 12:40 pm

Thanks for the info Sean. I’m expecting to begin a RTW trip on january but i want to know: which area do you recommend to do jobs on the internet?


Pete September 16, 2010 at 8:37 pm

Thanks for the great post. Good advice! Work day to day can be extremely difficult. Is the answer to enjoy what you do or do what you enjoy? It’s tough. Thanks for you insight though.

I stumbled upon this blog like I did yours. Though their insight on work was very meaningful: http://burisonthecouch.wordpress.com/2009/12/31/our-house/

Thanks for the post! I’d love to see more like it.

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