How I Became a Freelance Writer

Why I Left my $50k Job and Went on Becoming a Freelance Writer

Just about two years ago, I was working as a chief strategist with a top-notch content marketing firm in California. I was doing well and earning a decent living.

But one day I quit my job. I abandoned my $50k salary + other corporate benefits to work as a full-time freelance writer.

You might be wondering why did I leave the stability of a steady job to freelance. Well, there are obvious reasons.

Why did I do it?

I had decent, friendly, and cooperative colleagues; a manageable boss; achievable targets; and a comfortable working environment. Still I had to pray each morning for the strength required to get through the day.

My work had become very much mechanical. My job was to assess the company’s different projects and products down to the daily administrative activities to make sure they’re aligned with the company’s goals. I had no way doing the thing I was most capable of and loved – writing.

As I was preparing for another job switch, my grandfather passed away all of a sudden. It was a tough time for my granny, and it was only me who she could look to for help and support.

I was born and brought up in Amity, Oregon. Soon after my birth, my parents died in a car crash, and it was my grandparents who raised me up. I was the only child of my parents. So there was no one else to take care of my granny, and I couldn’t leave her alone.

I was thinking of a way out to handle this crisis. I had to find out something so that I could maintain my steady cash flow and at the same time, take care of my granny.

This was the time when the idea of working as a freelance writer popped up in my mind. I thought being self-employed would give me the flexibility and freedom to take care of her and at the same time, work on my own schedules.

But I was afraid to leave my steady job all at one. I had no idea about the freelancing world and the future it held.

I knew I needed detailed planning.

How did I make the switch?

I talked to many people, combed the internet so many times for answers. But more than anything, it was strength and belief that I was searching for – something that would make this patchy transition somewhat less painful.

After reading stories of survivors who had already trodden the path I was going to take (namely Laura Pennington and Melyssa Griffin), I decided to save up 12 months’ worth of living expenses before leaving my job altogether. My goal was to live for an entire year comfortably if there was no income from my freelance ventures.

It was during the mid of 2014 when I started working on my freelance writing business. After Googling “how to become a freelance writer”, I came across many freelance job boards like Upwork and Elance. Though I bid for each and every job on the board, I was offered none. Perhaps, the reason behind my repetitive failures was my lack of experience as a freelancer.

Whatever, I didn’t give up. I took another path. I went on approaching small to medium-sized businesses that required writers on board and had a decent marketing budget. After a few pitches, I started getting offers.

Initially, the jobs included blogging for attorneys and writing articles for some financial firms. I made about $1,000 in my first month apart from my regular paycheck. This, albeit small, was incredibly exciting as my efforts had finally started paying off.

In the next few months, I had around $10,000 in savings from my freelance work and another $15,000 contract in my bag to do some editing work. But I had miles to go, and there was something lacking, which was making me doubtful about the switch. So I pushed the accelerator further.

I started working every night for 5-6 hours after my day job, and also during the weekends. I had to carefully analyze my income patterns to determine if freelancing was a viable option for me, and also build a 12 months’ living fund.

It was December 2014 when I sold my 2008 Chevrolet to add another $10,900 in my savings. Selling it wasn’t a big decision as I had my grandfather’s 1984 Chevy Cavalier to drive to and from Amity.

It was during February 2015 when I got an assignment worth $40,000 and recognized the serious potential of taking this full time.

In August 2015, I bade goodbye to my day job. This time I had no worries, I had no more fears.

How did I manage stuff like 401(k) and health insurance?

As I left my job, I rolled over my 401(k) money into an individual retirement account (IRA). Previously, I thought of cashing out the funds as I needed money. But later dropped the idea as this way I’d lose about 50% of the account balance in early withdrawal penalties and taxes.

I had lost access to my employer’s group health policy too as I resigned. Hence, I purchased a separate policy from Kaiser through Now I pay about $200 every month for my health insurance – though somewhat in excess of what I used to pay, but completely manageable.

Now, after freelancing for about a year, I can say without any hesitation that it’s been one of the best decisions that I’ve ever made. Apart from the steady income flow that I had never imagined possible, I’ve also cultivated a sense of fulfillment, independence, and inner-happiness that are very much important to me.

So this was my journey. Do you have any further questions for me? Please don’t hesitate to ask. I’ll be happy to answer them in the comments below.

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