Waking up at the crack of noon and stinking of stale beer, random memories flash through my head and I wonder how I even made it home last night. It all seemed harmless at first, leaving drinks at the local pub, but soon enough it was trays of shots, long clingy hugs goodbye and an assumed cab ride home into the night.

The end just seemed to happen; all very anti-climactic and surreal after four years working 9 to 5 with great people, great bosses (I worked in three teams during this time) and a job I really couldn’t complain about too much but still did all the time.

My name is Scott and I am a web developer / designer - that is, if you need a solid title to define what I do. Like many in our industry I am multi-disciplined and find it hard to confine my skill set to one limiting and often hierarchical definition of a role.

I am off to start a web design agency. Nothing fancy, my wife and I working from our home and trying to drum up enough business to make ends meet. Something different from what we are used to and something we are both craving for similar and sometimes different reasons.

This will be my final weekend of my final corporate week. As of Monday morning it’s no steady income, no steady clients and no real idea of what I am supposed to do next on my own time, which is kind of nice in slightly terrifying kind of way.

The Catalyst

Why would I do this to myself when all seemed to be going so well? There are a few reasons:

Groundhog Day

I was seeing the same thing over and over; often incredulous about how I could be caught in these same meetings with people saying the same things about the same problems over and over. Life in a big company can change; it just does it very slowly.

Mental Stimulation

I was not being challenged and felt I should be learning new things – the online industry is about constant growth and change and I felt like my skills were stagnating where I was.

Old Routine

Arrive at work at 8:30, coffee at 8:35am, say good morning to the same people, back at the desk for 8:55am, Google Reader until I finish my coffee now for a bit of checking emails… I began to love my creature comforts and some would say these are the enemy of innovation.

Jaded

Four years is a long time in this industry… even though I liked my job after all that time it just felt like it was time to move on. New people come in with great ideas that I had seen many times before and I ceased to be as opened minded and eager as I had been in the past. We all know what happens to these old crusty detectives when they get partnered up with the new kid on the force in the movies…

So now it’s a life of doing whatever I want, whenever I want. Everyone seems to have advice or opinions when you mention that you are going freelance and I find it encouraging seeing who would actually volunteer that advice. From the CEO of the company that “did his own thing” for over 9 years to the current freelancers in the office that were just struggling to make ends meet yet had a passion that couldn’t help but shine through.

Why did they come back? How was it when they were actually freelancing or running these businesses and was it considered a failure (or just a change) to come back to the corporate lifestyle after leaving it? I am intrigued and fascinated with this new lifestyle that many talk of, the lifestyle I am about to plunge into headfirst.

I will see firsthand and experience all of these realities and myths soon enough. The goods, the bads and the mediocre of a lifestyle I ultimately have control over.

The Good

So what are the benefits I have heard from those wishing me well?

Freedom

You can make your own hours and essentially do whatever you want. If you want to take the entire day off or knock off early to go to the beach there is nobody stopping you.

Variety

You can choose your own work. If you don’t want a job then simply turn it down and wait for the next great opportunity, there is plenty of great work out there.

Against the Grain

No commuting and fighting others for seats on buses, ferries or trains. A big plus to lower general stress levels and you gain an hour or two per day by cutting this out of the equation.

Money

Say you are off to be a freelancer to your co-workers and you get that “pursed lips drawing breath inwards” nodding from people that says you are doing the right thing. “So we will see you back in here soon eh? Making 3 times the amount”, they chuckle walking off to the vending machine.

The Bad

It can’t all be good though, so what are the drawbacks?

You Can’t Turn Off

You have to make your own hours. Is discipline a problem for you? Well say goodbye to relaxing weekends and weeknights when you can’t shut your mind (or laptop) down as you are stressing about deadlines and projects on your own time.

Cabin Fever

You will soon crave social attention (not including your cat or the local barista) which means bugging your corporate friends all of the time and asking if you can come to drinks with them on Friday without looking desperate and lonely.

Money

The big money doesn’t mean anything (is it really big though?) when it’s sitting in a client’s accounts payable inbox, waiting its turn behind many, many others invoices that need to be paid. Meanwhile, finance are throwing their quarterly pub catch-up (all free) and might get to your invoice sometime next week.

Other Stuff

Finances, invoices, customer relations and finding new work are just some of the things that will cause you to miss out on what you really want to do, and more importantly, on billable hours.

The Ugly?

The good and the bad, there you have it. Plenty to keep me awake late at night staring at the ceiling and wondering where my next pay check is going to come from or what somebody will think of my existing skill set now that I don’t have a fancy title or a talented team to back me up.

These are the things that have plagued and excited me over the last few months while I have lost sleep and pondered whether I am making the right decision or not. Whether to take that plunge and to remove myself from the comfort zone and have a go and just see what happens.

These are the diaries of a freelancer…