It All Began One Day at My “Good Job”

It All Began One Day at My “Good Job”

Despite the fluorescent lighting, cheerless gray cubicles and confining schedule, I had a good job.

Or so I was told.

The truth is that I actually enjoyed the work that I did. It was purposeful and felt good to do.

I was paid well, enough to live comfortably and buy the things I wanted. And most days, I didn’t get too annoyed with the coworkers I never had a say in choosing to work with.

I was managing an employee recognition program for the largest non-profit healthcare company in the world. Such a place with over 200,000 employees is bound to get political and overly bureaucratic.

Most days, I didn’t let it get to me, though.

It was my job to read the submissions or nominations that came in from one coworker to another, nominating them as an “everyday hero.” Often they were notes of appreciation for the great work they did on a daily basis, but sometimes the stories were feats of truly heroic proportions. Life-risking, miracle-making, story-book stuff.

It was great to be surrounded by that energy regularly. It warmed my heart.

But something still wasn’t quite right. I felt stifled, confined. While I was helping to do good for an organization I believed had good intentions, something kept gnawing at me that I couldn’t ignore.

Why was I so dissatisfied? Why did I feel so guilty for the way I felt?

After all, if I was going to listen to my friends and parents, I should have been thrilled for having such a good, secure job. I should feel lucky that I’m not unem- ployed or struggling to make ends meet.

I should have been grateful, and I was. . . but something was missing.

It wasn’t that I didn’t have clarity on what I didn’t want. I knew that this job, this path that I was on to become a “lifer,” wasn’t for me. I knew that if I stayed there I wouldn’t be able to live with myself.

The only problem was, I didn’t know what to do instead.

Then one day, as I was browsing the web at my assigned work station, trying to distract myself from some of the less-than-awesome tasks I had to complete, I found an article that caused me to rethink everything.

It was Steve Pavlina’s “10 Reasons You Should Never Get a Job,” and it confirmed to me that having a job was not the path for me.

I realized that day that I was meant to work for myself, giving my gifts freely to the world in the way that I designed. I realized that a prefabricated, templated career path wasn’t for me, and it was killing my soul. I wanted to create a fiefdom instead.

More importantly, I realized that I wanted to transform my experience of work from one of drudgery, rigidity and following the rules, to one of freedom, a deep calling and a sense of total control over the direction. I wanted to stop building someone else’s vision, and start building my own.

I knew that it was time for me to become the master of my own time, direction and life.

It was then that I wrote down on a slip of scrap paper that I would quit my job and work for myself full time on June 1st in the year 2009.

A year later, I handed in my resignation letter on May 29th, 2009. I’ve never looked back since.

In the next post, I’ll share with you the fundamental shift I made to make quitting and reclaiming my freedom possible.

Making this shift allowed me to…

  • Replace my day job income, before I quit.
  • Build a healthy savings to cover expenses as a safety net.
  • Quit with confidence and calm.

Until then, I’d like to know from you:

What’s the biggest roadblock for you to reclaiming your freedom? Time, money, stress? Let me know in the comments below.

One person that comments I’ll hook up with an advanced copy of my newest course on the money freedom roadmap.

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54 Comments on "It All Began One Day at My “Good Job”"

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Tom Sharp

Money is certainly a consideration, although I don’t earn a massive salary anyway, so to some extent it’s not like I’d miss all the money I never really earned, but the biggest roadblock for me would have to be ideas. What else would I do if I worked for myself? Working out what to do next is the issue, not how to do it…

Vincent Nguyen

Here’s the link to Steve’s article that Jon mentioned:

The biggest roadblock for me, back when I was still in college, was to overcome my family’s objections. Turns out, when it was time to leave the script, I got just a bit more support than I was expecting. Dived in with both feet and haven’t looked back.

Angie Mroczka

I’ve already taken the “freedom” plunge, but still encounter a mountain of issues with time, money, and stress in trying to keep it. Each bill sitting unpaid on my desk is a kick in the gut.

James Pelosi

For me, it’s the cost of health and dental insurance for my family of four. I’d have left my “job” long ago if I could find a solution.

James Pelosi

Health insurance & dental insurance for a family of four.


The biggest road block for me is money right now. I’m a little bit away from having a 6 month safety net, but we just found out we need to buy a new car. We will be able to make a 50% down payment on the car that we want (something certified) but we’ll need to make payments while I work on that 6 month safety net, too. So it’s a bit of a setback.

My biggest roadblock, my internal negative self talk. I’m phenomenal at what I do, not to toot my own horn, but I’m one of the best in my little corner of the world. But, This is my fourth or fifth time doing the exact same thing for a different company in less than 10 years. I know that what I do in the corporate world is easily translatable to individuals. Creating an efficient, productive life by ensuring they become highly accountable for their results based on their commitments and individual missions in life. That is my biggest roadblock – how… Read more »

My biggest roadblock is money. Like you said – replacing my normal income and having a buffer.

It wears on me and saddens me every time I think about it!

Ross Bartleman
It’s hard to pinpoint a single obstacle that stands in the way of me reclaiming my freedom. The roadblocks at the top of the list are fear, depression, the paralysis I feel when I think of my outstanding debt, unresolved grief and an all-pervading sense of unworthiness. I’d say the most damaging of these is the last one, which stems from a belief I don’t deserve to have a free life in view of my past failings or that I should pay for my perceived “wrongs” by serving time in a prison of my own making. Hence, the notion of… Read more »

Roadblocks for reclaiming my freedom, in order:

1. Stress

2. Money

3. Time


The biggest roadblock is that I am too comfortable. I’ve been in my career for almost 15 years now and the idea of letting go of it terrifies me to my core. It’s all I’ve known and what’s more, it’s become a part of my identity.

Shaun Daws

I’m in a really good job right now, but would love to one day strike out on my own. As a parent, the main roadblocks are the combination of time poverty and the expectation of maintaining our current standard of living.

Really looking forward to the rest of this series!

Right now money isn’t a big deal, because I save a lot from my day job and I can use it to live for at least six months (if not a year) away from home and launch something during that time. Stress is fearing whether it will result, and having to job hunt to prevent my savings from depleting if not. And time because my day job plus commute keeps me from fully concentrate on something that matters… The biggest setback of all, however, is the “what will they say” thing. My boss just took her maternity leave, and before… Read more »

The biggest roadblock to reclaiming my freedom is knowing where to start. I have a ton of wonderful ideas to start a company, an abundance of invaluable business experience (small business, corporate and nonprofit) and a true desire to help others. I’m a born problem solver who loves to help people figure things out. I’m just not sure how to leverage my skills into a way to earn a living on my own terms while assisting others to reach their best too.

Craig P

The lack of clarity of knowing what it is I want to do and the fear of failure. I imagine every worst case scenario. With a wife and children, I worry about keeping a roof over our heads , health insurance,etc. I can’t even imagine how great it would be to be the one controlling my destiny, I revel in the false sense of security a “real job” brings.

My biggest block is time management and making my products fast enough. I am a type A in that I want my products to be top notch. I work full time and think everyday, gee if I could work full time on this I would be so much happier and well off emotionally, finically and spiritually if I can spend my days doing what I love most, creating educational lessons and activities for experiential education and environmental education using the most current methods called Universal Design Learning and differentiated learning. This elementary level content totally changes the academic environment of… Read more »

You inspired me to document my story. In fact your site planted a seed that could not stop growing once I let it see the light – I quit my job with nothing in place, and good things happened. I would appreciate if you could read my post
“Quitting a “good” job for a better career”

I hope you will forgive me for using your terminology of “good job” – it just resonated with me so closely.

Thanks for this post Jonathan. I used to think it was time, stress and money but I’ve come to realize that those are all excuses. When there’s something I really want to do, like hang out with my family, I make the time for it. When there’s something I really want to have, I hustle or negotiate to get it. I have a two year old and a two month (both boys) so I am quite familiar with stress. But I don’t regret any of my stressful experiences with my babies. The truth is I’m afraid. Afraid that I’m not… Read more »

I love how you describe it as ‘reclaiming your freedom’- because I feel like that exactly what I lost when I got a ‘real job’. Even when I used to really enjoy my job, there was still something about me that wasn’t settled.
Personally, I’m tied into a job contract until next March. From there on, though, I plan on working only for myself. It’s a terrifying prospect, but I can’t wait for the challenge.
I look forward to your next post!


Hey Jonathan,
thanks for all the wisdom you share. I just read the 4 agreements blog post – read the book years ago. Have you read Ruiz’ 5th Agreement? Its awesome too.
Its taken me a while to get this limiting belief, but its what stresses me out the most:
People don’t want what I have, (and that offering is all I’ve got, so if it doesn’t work out, I’m in deep shit).
So there you go.



The obstacle is how to replace my day job income with passive income from what i love to do before quiting my unspiring day job. I must thank you for the impact your articles and your ebookd have made on me. I am a big fan of your philosophy. Thank you

Richard Thayer

I left my work over a year ago to build my private practice. My vision is to change the stigma of addiction, introduce new therapies to promote healing and help is many people as possible with our program. The problem is I have no resources, using pennies, barbed wire and hope.

Tommie Slade
My biggest roadblock actually started back when I was a kid. I was conditioned by my parents first,,they didn’t know any better, to accept the way things were, to accept that hated job just because, at least there was money coming in, to not question anything and above all, settle for a sure thing vs an uncertain dream… As I grew up, it was much the same thing, had dreams but because it was uncertain in an uncertain world and times, it seemed safe even though no total happiness. Now, I am 51, afraid to branch out on dreams it… Read more »
Jane Manthorpe
Hi Jonathan, love your post as I resonate with it totally. I always new being in the corporate world was not for me as events gave me the nudge that I was here to do something else. Sorry for this long post, but to explain the biggest roadblocks has to come with some story: I had been lost for many years, 27 years in fact and trapped in a career just for the money which was a very highly paid but very stressful career. I was having real peer pressure from my dear father to be self-efficient and successful no… Read more »
Jane Manthorpe
I always new being in the corporate world was not for me as events gave me the nudge that I was here to do something else. Sorry for this long post, but to explain the biggest roadblocks has to come with some story: I had been lost for many years, 27 years in fact and trapped in a career just for the money which was a very highly paid but very stressful career. I was having real peer pressure from my dear father to be self-efficient and successful no matter what career, so to have a good pension; i.e. work… Read more »
Christine Cox

Excellent article… Just what I needed this morning. I say that because this week we received word that the hospital I work at was to be closed “stat”-yesterday was my last day. So after hours of hearing ” when one door closes… (Fill in the rest)… today I may be able to think about this, “Freedom” you speak of :)


The obstacle is how to replace my day job income with passive income from doing what I love to do-paid-to-exist as you will say. I wish to thank you for the impact your books and article is having on me. I am a big fan and believer of your philosophy. thank you

Denise Wally
My biggest roadblock to freedom has been fear (false evidence appearing real) of lack of security….health insurance, steady paycheck, ya da yada… Fortunately, my boss did me a huge favor yesterday, he essentially unconstructively criticized a project I’d been working on and blamed me for his shortcomings in communication. This irrational behavior has given me the impetus to finally quit a job with no other job in the wings. In fact I don’t even want another job for at least a month or two. My lifestyle will be slim for those two months but somehow I know it’ll be okay.… Read more »
This is almost exactly the kind of post I was struggling to write today! Feeling discontent with my job doesn’t quite describe it. The best alternative I could come up with was “an itch under the skin, that wouldn’t go away even if I scratched it”. But your post describes it so much more succinctly, Jonathan. My biggest roadblock is time. I have more time than I care to have. I signed a contract with my company that doesn’t let me quit before 1 December, 2015. Even though I desperately wanted to quit at the beginning of this month. I… Read more »
J .

Question: What’s the biggest roadblock for you to reclaiming your freedom?
Answer: Not enough income. And not coming in fast enough.

Erik Carter
Wow. This is exactly what I was thinking and how I felt before I left my job last week and opened my own law office. The “what else will I do” was holding me back. But when I too realized the items you listed in the “More importantly” paragraph – and did a budget of what my own office would look like – it was literally a no-brainer. It’s the difference between “I love my job” and “I love what I do” I have always loved what I do. So now i am doing it on my own terms. I… Read more »
I’d like to say that money is my greatest roadblock to living my life the way I would really like, but at the moment I feel money issues are really more of a symptom of other things I need to overcome. A while back I felt as I am sure so many others have and decided I needed to quit my job that paid well, but was tearing me apart emotionally and physically. I had a decent savings and a plan to create something great for myself. Unfortunately I hadn’t replaced my income before I made the leap. I got… Read more »
Elizabeth Elliott

My biggest roadblock is all the “good” distractions; social invitations, volunteering too often to help, a good novel, or, to be honest, Netflix.

Tonje Garberg
Hi Jonathan! Thank you for this wonderfull site and concept. I just recieved your course waking up getting shitt done, and it was so great for me! I have set a date for quiting my job, and it will be the 31.12.14. I started building my own company In august and its going quit well. But i also just came In the situation that my husband wants to leave me and i am worried, because i do not know If i will manage to keep my house. I have a big Dream inside of me that wants to succeed with… Read more »

Believing that what I want to do is actually going to make me enough money to leave my primary job.

This article got me thinking about why I haven’t taken the leap to “freedom”. I am successful in my career field. In fact, I am a trendsetter and someone that others in this industry look to for ideas and advice. I love my work and would love to do it for myself rather than someone else. So why can’t I make the transition into being my own boss? After really thinking about it I came up with this reason; My professional life is the opposite of my personal life. I don’t have strong personal relationships with others and I don’t… Read more »

My biggest road block is FEAR. Fear of regret – leaving a good job behind (even though I do not enjoy it). Fear of making the wrong decision. Fear that my new adventure will not work out and I will need to get another job just like this, but it might not be so cushy.


I need to maintain a level of income to keep my family in this house. So my transition is slow…too slow.


The one biggest roadblock for me, would definitely have to be self doubt.
Followed closely by fear of the unknown.

It used to be money. I say ‘used to be’ because I recently had the ‘it’s time for me to leave’ conversation with a company that I consult with here in Paris, and I’ll be working with them until the end of the year. I’ve been through the calculations of how much of a financial safety net I need when I work on my business full time multiple times. It wasn’t until a month ago that I realised I had the money. And my initial reaction? ‘It isn’t enough. I need more’. I couldn’t believe what I was saying to… Read more »

I think for me it’s money (and with that my husband). He’s the more practical one and I’m the one that would take big risks and that would be one of them but he would get really caught up on the money (I would too but months after I quit and realized oh shit this is scary).


Biggest roadblock to reclaiming my freedom: the management of my time, it seems. I’ve pared down the things I do in a week to the barest essentials, like sleep, eat, exercise, and going to my job, and yet, it still seems like I don’t even have one spare hour in the day to just sit and breathe and do something I’d like to.

for me, it’s been the unknown; this path is harder when you lose years to a chronic illness and end up with tens of thousands in debt. i’m nearly out of it, which is great… but the fear of “something” happening out of my control keeps me shackled to a desk that provides health insurance and stability with the occasional round of layoffs. i want to go self employed but am scared of being alone in it, solely responsible, solely having to dig myself out of any hole that might come up. i know i’m not, but irrationally i feel… Read more »
Drew Downs

Family responsibility: namely that my wife doesn’t know what she wants to do. For me, it isn’t manly pride or ego to be the breadwinner or the demand that I sacrifice for our children, but that we are both struggling to follow our passions and I have the more visible track for mainstream, stable income that partially matches my talents.


The biggest road blocks for me are self-limiting beliefs (believing I can do it) and the lack of a clear vision. I haven’t been able to see clearly what the next step is, so I’ve allowed myself to stay stuck.

Emma Taggart

As a college student that has already worked a couple different jobs, I already know that the traditional job path is not for me. Currently I am not working at any of my normal jobs, and am trying to survive off of money I’ve made through commissioned paintings. I like hearing that you started out just like anyone else, and that it is a realistic life path! thanks x

I really enjoy reading your articles and many thoughts resonate with what I had in mind when I decided to leave my job to go on a Sabbatical. I would think the major barrier is the fear of delving into the unknown, not knowing what to expect next and forgoing the stability. If am to do it all over again, perhaps I would be more conservative with my financial planning. I am still surviving but let’s just say I am at that phase that you have mentioned in another article, where I am trying to pick up the pieces and… Read more »
William Cosentino


First time here and first article I’ve read and it describes me almost 100%! I’m still in a cubicle 3 days a week (work at home the other 2), at a great job, have a great life, but I’m determined to escape the grind and create my own grind. There’s just too much in the world to do and see besides the freedom of being on your own. Love your work and mission!!

The biggest roadblock to freedom is fear. Fear that I won’t succeed, fear that I won’t be able to support my family, fear of what others (my family) will think of me, fear of letting down my (future) customers. And all this fear comes before I’ve even tried something. I can’t imagine what kind of fear will come up when I have real-life problems to deal with. Of course, most of the time the things we fear turn out to be not as bad as we thought. I’ve found that a lot of what I’ve feared doing in the past… Read more »

Great article Jonathon. I think it sums up how a lot of people feel.
From birth, we’re prepared to ‘fit it’ to the way the world works, but I’m more excited about the possibilities of creating your own.

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