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Quitting Your Job (Fleeing Comfort and Safety)

by admin on September 27, 2011

Estimated reading time: 4 minutes, 40 seconds

Back Story

I’ve had a full time job since I was 17, basically (working casual full time hours whilst in uni) and have had a comfortable, consistent paycheck for about 15 years.

This is all changed recently when my girlfriend and I recently bought a house on 10 acres up near Byron Bay. For us, it is our dream property and lifestyle.

Whilst we bought back in March 2010, and settled in June on the property, we have been waiting on my employer in Melbourne to make a final decision on whether to support a remote working arrangement (I work in a largely autonomous role in a telecommunications company). The company flip-flopped between Yes, No, Maybe but I finally got tired of waiting and pulled the plug, which meant for the first time since I graduated in 2000, I had no full time employment.

This is terrifying.

I now have a mortgage and no job.1

Again, this is terrifying.

There is a bright side, however.

There is now a deep and keen sense of urgency to get my projects VeloNomad, Wherespresso, Mayday Coffee ramped up – fast.

I can no longer be content with a monthly paycheck and hustling on the side. These babies now have to pay their way, and fast.

Change in Mind Set

I now question every spending intention: “Do I really need this?” This has the added benefit of really focusing my mind on what’s important.

As we’ve been packing up the house, we’ve been brutal with discarding things we don’t really need. As we added more and more to ebay, we’ve been absolutely shocked by how it all adds up – much of it is stuff that’s been sitting in cupboards.2

Whilst I’ve always had a bootstrap mentality, it’s now even sharper. Only activities, “stuff” and business features that we really need or that directly drive revenue get worked on and funded.


What this shows to me, is the importance of a few things:

  • Never assume you will always have access to money. Save, and save hard.
  • Question every expense – do I really need this.
  • Working for the man is not a sane and safe career path – starting your own businesses is absolutely critical.

I think the last point is the most important. Personally, I’ve never had a problem just attempting to start a business and see where it goes – I am a serial entrepreneur.

But, I can understand the apprehension others have. I want to assure you though that it is not as hard as you might think.

How Bad Can it Get?

To get over that apprehension, you need to ask yourself how bad can things really get.

Tim Ferris had a great post a while ago about Practicing Misfortune, I think influenced by Stoic thinking, about this very topic. His premise was, imagine how bad things could really get.

  • I could end up doing physical labour – not horrible, for a short period.
  • I could end up making coffees – not a bad proposition by any stretch (I’d enjoy it).
  • I might end up mowing lawns (I actually already have a domain name in case I want to start a business).
  • I won’t be able to buy everything I want (notice the difference between want and need).
  • I’ll have to live more simply and fruitfully.
  • I might be wearing older clothes.

So, when I think to what I miss most, it’ll be the high income and the comfort that affords in terms of supporting the development of my online businesses as well as never really having to worry about money.

But really, are they terrible things to miss? Is having to fend for yourself and not rely on the business decisions of others (for the company’s well being and your job) all that bad?

At the end of the day, the steady income provided by an employer is an illusion of safety. For others who feel a deep discomfit with working in a cubicle being driven mad, the safest long term path is to rely on yourself for your income.

And for that, you must strike out. It’s not easy, I promise you. I don’t want to make it sound like it’s painless and simple – it’s not. But, nothing in life worth having was ever easy (otherwise everyone would have everything they want).

How Things Panned Out

Despite the fear I felt at this move, things are panning out nicely.

We have some spare funds to tide us over, and it’s funny, the universe seems to conspire to help those that most help themselves.

Little pieces just fall into place, it’s amazing to behold.

The old adage “things always work out” is turning out to be true. I suppose once you learn to let go of the control you have, and just let things work out, they work out anyway, which frees you up to do things of actual value.

Where to Start

So, “where do I start, Tim?”

Starting out could be as simple as you starting a website aimed at deriving a small slice of income on the side. Really, there are myriad ways of doing this, and myriad ways to make money – it all depends on what your passions are, what time you have spare and so on. You could read this post by Chris Guillebeau which has some great ideas.

If you’re serious about beginning, drop me a line.

1 – whilst there are two large cities near where we’ve bought, there is limited demand for telco engineers.

2 – Thanks to Leo at Zen Habits for the constant inspiration. And Johnny Truant.

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