Are you ready to give up your day job? As appealing as a life on the backyard patio may seem, it can actually turn in to a downward spiral of depression and desperation.

Bold words. Now, I’m not trying to scaremonger the masses from wanting to quit their day jobs, but I do think you should think twice about your true motives before calling it quits. A day job, despite being the unglamorous cousin of entrepreneurism, brings security, stability and routine in to your life.

From my experience, people love to talk down the idea of routine in their lives. Many just-turned entrepreneurs will react with real spite when you ask them what they think of a Monday to Friday day job in somebody else’s company. Maybe it’s the burning need to stay consistent with their own life choices, but I believe that time will shine a light on the objectivity of those choices.

Many entrepreneurs later realise that the grass was indeed much greener on the other side. They see that being parked in an office cubicle ready to go by 9am is actually a much lighter burden than the self-inflicted misery of running an unsuccessful business and scratching around the bank to make ends meet.

It’s over 2 years since I worked my last day in Central London. I was a web developer, charged with pretty comfortable tasks and blessed with reasonably decent prospects. I was the youngest person in the agency where I worked, and probably the least likely to quit and start my own business.

I had no resentment towards that last job. Unlike many people who email me looking for answers to their own career slash mental breakdowns, I was content and had no reason to detest conventional employment.

However, I was passionate about wanting to run my own business. I developed a golden opportunity to do so in the space of six bat-shit crazy weeks, stumbling head first in to affiliate marketing and barely batting an eyelid as I wrote out my notice in a flurry of activity that still gives me a headache to look back on.

Who builds a sustainable business in six weeks? Inventors, Mark Zuckerberg and the occasional Einstein freakshow that I most certainly was not. I was in no shape or form prepared to start a business, despite harbouring some naive love affair with the idea of calling myself the boss.

Those first six months were a series of trials and tribulations of my own inflicting. I had a Plan A and a lot of newly established spare time, but little else. When my Plan A failed – within the first few days – I was faced with a sink or swim scenario where I needed to redesign a business from scratch or get back in the recession-struck waiting queue for another day job. Thankfully, keyboard sweat and tears paid off and I succeeded in reconstructing a profitable business.

What the entire experience taught me was that running a business, no matter how optimistic you may be, will always challenge you more in every way than the monotonous nature of navigating London Underground and reaching your desk before 9:01 every morning.

The nature of the challenge, or rather the acid test of how many hairs you’ll lose trying to succeed, can be boiled down in to an equation of preparation and then… lots more preparation.

You need a sensible Day Job Exit Strategy (AKA “How to escape the frying pan without burning your arse in the fire”)

You’ll have to forgive me for inflicting yet more misery-guts perspective on the proceedings, but it’s time to get real. Are you REALLY prepared for the challenges ahead? Here are some of the concerns you should be raising with your neocortex.

1. Do I have enough money to survive for 6 months if I’m not making immediate profit?

Entrepreneurs will give you varying answers for how much money is needed in the bank. I think six months of covered outgoings is a safe bet for online ventures, assuming your business plan is worth the paper it’s written on.

2. Who is going to handle my accounts?

The next logical question if, like me, you answer “Err…” to am I fully qualified to handle my accounting? My initial attitude towards taxes was one of complete disregard. I knew I would be expected to pay them, but my assumptions were about as well founded as a poor English bastard buying shorts in July. It’s not always obvious, but when you choose to become your own boss, you lose the accounting safety net of your previous employer.

3. Is my business built on moving ground?

Fads come and go. If your business idea is so niche that it isn’t capable of withstanding a small shift in the market – or the arrival and enhancements of new technologies – then you need to really think long and hard about the sustainability of it all. Don’t obsess over stealing a quick dollar in 2011. Anticipate how your business will meet a market demand for the next several years.

4. Am I mentally equipped to be my own boss?

I don’t mean this in a negative light, but some entrepreneurs are naturally better suited to the role of followers rather than leaders. It makes sense. After all, no economy can survive without willing servants to carry out orders. I think discipline and goal-setting is very important in this regard. To succeed with your own business, you have to hold yourself personally accountable.

Even when other people fuck up, it’s still your fault. Repeat the words, and learn not to take them personally.

As I personally found out, this awakening of responsibility can hit your social life with frightening force. Be prepared for the surreal shifting of priorities as “Thank God It’s Monday” becomes your new catchphrase.

5. Am I escaping a life I don’t enjoy, or creating a life I’ll enjoy more?

This is another hard-hitting question that only a very honest soul can answer. It’s a little like the analysis attached to “Is the glass half-empty or half-full?”

For many people in unhappy day jobs, starting a new business is an unfortunate learning curve that will take you to the realisation that two wrongs do not make a right.

Entrepreneurism is often a misread solution to the career crisis, when simply finding a better job would lead to greater happiness. If you’d do anything to escape your day job, there is always more than one answer to your problem. Starting an entire business is very much a niche solution, and 9 times out of 10, the wrong solution.

Your professional happiness does not hinge on running as far as possible from the office cubicle. It could be as simple as joining a different cubicle across the hall. For others, no cubicle will contain their aspirations. And for these people, starting a business is the only way to handle that burning flame of ambition.

Before you decide if you’re that person, you have to answer some basic home truths. The honest answers will lead you towards a sensible Day Job Exit Strategy. Behind all the glamour of being an entrepreneur, rest assured, it’s a living nightmare for the individual who answers those questions naively.

Recommended This Week:

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