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How to Escape the 9 to 5: A Practical Plan for Cautious People

November 4, 2010

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For some people, the decision to quit their job and embark on a new life of adventure comes easy.  The blogosphere is awash with stories of individuals who decided to jump ship, jump on a plane and start a new life in an instant – I’ve even featured some of those stories on this blog in interviews with people like Rob Wringham and Everett Bogue.

However, for some people – in fact I’d argue for the majority – the decision to make big changes is a little more complex. Some folk just don’t feel comfortable with the idea of packing up all their belongings and jumping ship at the drop of a hat, maybe they’ve got family or financial committments or maybe they’re just more cautious by nature.

Whatever the reason, this six step escape plan is aimed at all you people out there filled with a slow-burning desire to escape the 9 to 5 but who would just like go about it gradually and with some sort of a safety net.

Step 1 – Get out of debt

If you’re serious about quitting your job, the first step you need to take is to reduce your ‘life overhead.’  As fellow escapee Everett Bogue said in his recent interview for Rainy Day Wonder, “The easiest way to be simultaneously starving and still be making tons of income is to have a lot of life-overhead.  If you need $5,000 to survive every month, then you need to be making $5,000 every month.  When you’re trying to make that much money, you only have a few employment options — most of them involve sitting at a desk all day being told what to do.

In his excellent book Unautomate Your Finances, Adam Baker advises us to set up a ‘debt snowball,’ a neat psychological approach where we throw all our resources at clearing one debt at a time as a means of building up momentum and maintaining enthusiasm.

Step 2 – Streamline your finances

One of the best ways to start driving down your debt is to completely reassess every item of your regular monthly expenditure – from utility bills and nights out, to grocery shopping and mortgage payments.  An easy strategy is to simply make a note in a book every time you spend money – this way, you get to see quite quickly where most of your money is going and can identify swift ways to slash outgoings.

The next step is to work out ways to drive down costs on each area of your monthly spend.  For those of you living in the US or the UK, two really useful sites are GetRichSlowly (US) and MoneySavingExpert (UK).  The ultimate aim is to drastically reduce your cost of living.

Another useful tip is to stop buying so much crap.  Web guru Leo Babauta recommends minimalism and simple living as a great means of establishing  your independence and tells us how to do it in his brilliant book The Simple Guide to a Minimalist Life.

Step 3 – Build up an escape fund

After following the first two steps, you should now find yourself in a situation where your income is greater than your outgoings (if it isn’t, go back to step one and start the process again).

Now is the time to start building up an escape fund.  This fund will be one of your main safety nets once you finally quit your job. Only you will know how much money will be enough but, as a guideline, if you’ve saved enough to cover your cost of living for around six months you’re pretty much there.

A quick way to reach your target is to get rid of all the stuff lying around your house that you never use and raise some useful funds in the process – I heartily recommend another of Adam Baker’s books, Sell Your Crap, for sound advice and effective strategies to maximize the money you make by doing this.

Step 4 – Go part-time

Now that all of your finances are lithe and limber, you will find that you have more freedom and flexibility to take some time out to work out to do what you want to do.

The financial security provided by your escape fund means that there is now nothing to stop you from going part-time.  More and more workplaces offer flexible working hours so you’d be well advised to take advantage of everything your employer has to offer.

A three day weekend will enable you to spend more time figuring out the details of your new dream life. Even better, drop down to a three day work week and you will already have achieved the moral victory of spending less days at work than on your own projects.

Another strategy is to work from home.  The key here is to prove to your boss that you can be much more productive when you’re free from all the distractions of the ‘office environment.’  If you go down this road, try out my tips for achieving a two hour workday so that you can easily get the office work done leaving you free to spend the rest of the time on your own stuff – at the firm’s expense!

Step 5 – Develop your own projects

Once you’ve got over the initial excitement of all that free time – it’s time to work out what you’d really like to do with your life and to develop concrete strategies for achieving your goals.

Take some time out to explore what really drives you.  One useful technique is to literally do nothing for a few days – let your mind wander and get those neurons firing!  The main thing is to be creative and consider all possibilities.

Whatever you choose to do though, make sure that it’s either fun or automated. If you’re stuck, check out John Anyasor’s awesome eBook The Power of Enjoyment and, if you’re really serious about taking this to the next stage and waking up excited about the work you do, make sure you take a look at Jonathan Mead’s inspiring course Paid to Exist.

Step 6 – Take the plunge!

After you’ve given yourself some time to work out what you really want from your new life, you’re ready to start devising some money-making strategies.  The best thing to do here is not to rule anything out.  It’s important to diversify and test out what really works for your particular situation.

Example strategies might include developing your own product (say an eBook or an album), offering consultancy services about something you’re really passionate about, or developing a whole range of passive income streams.

If you’re interested in learning more about writing a blog and building up a regular passive income check out the popular Internet Business Mastery Academy and Pat Flynn’s excellent SmartPassiveIncome blog for some great tips.  Two more great resources are Darren Rowse’s eBook 31 Days to Build a Better Blog and this ‘Make Money Writing for eHow guide.’

Build them all up and, most important of all, start having fun!  Remember, the ultimate goal is to start making money from something you love doing so much it could hardly be called work at all.

After a while, you should reach a ‘threshold moment.’  This is the crucial stage where you’re making as much money from your own schemes as from your part-time paid employment.  This is the point at which you know you’ve cracked it and should finally be able to hand in your notice and set out on a new chapter in your life – congratulations!


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Image Credit – Nina Matthews Photography

6 Comments leave one →
  1. Macs permalink
    November 5, 2010 12:57 pm


    Looked at in this way, I’m at Stage 5, but having skipped Stage 4…

    Stage 5 projects aren’t at tipping point yet, so I might well have to revisit Stage 4. But not here, something else closer to home.

    Still have loads of crap to sell off, and the living costs can be reduced more, most notably if I’m less stressed at work during the day, there’ll be less temptation to ‘de-stress’ at the pub during the evening 😉 And also I have some expenses which are a matter of ‘letting go’ of the past, or maybe re-visioning them for the future (defunct websites etc…)

    Yes, I feel the lure of daylight from beyond the dark cage I’m currently inhabiting 🙂

    • November 7, 2010 6:36 pm

      Glad to hear it Macs. Sounds like you’re almost there. Let me know if there are any themes/issues etc. that you’d like to see covered on RDW.

  2. Froztwolf permalink
    November 8, 2010 1:13 pm

    What do you suggest as an alternative in step 4 for those of us who don’t have the option of cutting down our current jobs to part-time? While I might be able to convince my boss to allow me to work remotely a day or two a week, the nature of my job makes it just about impossible to reduce to part-time.
    Getting a job outside my field could work but I’d not only have less hours worked but a much lower wage per hour too, and lose the security that I imagine step 4 here is supposed to provide.

    • Macs permalink
      November 16, 2010 12:42 am

      For my part, getting out of this job is the major motivation, so a part-time opportunity elsewhere would be great. I’m saving up my ‘notice’ at least ’til next month, when I still have two weeks holiday owing… evil, I know, I’ll never train a replacement in two weeks, but I can’t help thinking ‘Is this my problem?’ I think of all the Saturdays I’ve worked at standard rate (no time-and-a-half here, thank you very much…) and am looking forward to the look on the boss’s face…. Yes, folks “I am Jack’s bad attitude” springs to mind, I admit 😉

      If I feel a wave of unprecedented empathy wash over me, I may offer a consultancy for my higher-valued, and more stress-free, skills. But overall I’m more tempted by the ‘FU’ route… and offer those skills to competitors instead. Did I mention that I’m a bridge-burner by natural inclination?

  3. November 8, 2010 3:03 pm

    I suppose your best bet (if you stayed in the same job for now that is) would be to hold out for two days working from home. Once that’s in place, you need to be as productive as possible in completing your office work, leaving the rest of the day free for your own stuff. Check out my post on productivity here:

    If you can whittle down the office work to, say, two or three hours a day – this still leaves you the best part of two days a week to set up your own projects. It might take you a little longer than if you were fully part-time but only marginally so.


  1. Manage Your Money to Escape the 9 to 5: Part 2 – Monthly Bills « Rainy Day Wonder

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