Becoming a Freelance Writer: My Road to Success

By Jon Sofen

My Pre-Professional Writing Life in Under 400 Words

A little over a year ago I found myself at a crossroads in life.  I was approaching 30 years old and had come to the realization that I was a big-time underachiever.  I had opportunities in life that many never have.  But, to be quite honest, I constantly failed at taking advantage of them.  Part of it was laziness, and part of it was just plain being clueless.  You could have stapled a piece of paper onto my chest that said “this is an opportunity, moron, take advantage of it” and I would have ignored it.

Okay, enough negative talk.  I was a knucklehead in my 20’s at times, but who wasn’t?  I did some good things too.  I held a decent job at a reputable company between 2002 and 2007 before taking my shot at starting a business.  I was pretty excited about that.  Became fascinated with the insurance industry and knew I was good at sales, so I started my own independent health insurance agency.  Risky to go out on your own in a field like that, but I was determined to make it work.

I didn’t do too bad selling insurance for the first 6 months.  In fact, I bet I sold far more than your average new agent.  My dad had run a successful insurance agency when I was a kid for about 15 years before moving onto something else.  That was my reasoning for getting into the business.  Like father like son, I guess.

However, after about 6 months of selling insurance, I realized it just wasn’t for me.  Not that I wasn’t good at it, because I was decent, but because I didn’t enjoy it.  Dealing with insurance companies on a daily basis was a nightmare.  Even worse were my customers.  No offense to them, but a majority of them probably couldn’t even read this story.  Too many words in it.

So I got out of the business and decided it was time to find something else.  I still wanted to run my own business because I just am not cut out to work for “The Man”.

How I Became a Writer

At this point I believe I was 28 years old (fast approaching 29).  Basically, it was time to get my act together and figure out what I’m going to do with the rest of my life.  I started playing poker for a while because I’m really good at it.  Made a few bucks, but got bored of it quickly.  It was no longer just a game, so it had lost its appeal to me.

Then I started doing research on different business opportunities, but didn’t find anything I could realistically do that was of much interest to me.  Then, one day I accidentally stumbled upon a Craigslist job board for writers.  Clicked on a few of the ads and thought they might be fun projects to do.  I had always enjoyed writing but I just assumed you couldn’t make much money in the field unless you were some sort of famous writer.

Just for the heck of it, I actually responded to a few of those ads expressing interest.  I didn’t expect anyone to contact me back.  But two of them did, and they both wanted me to write articles for their websites.  I was to be paid approximately $400 total for these two gigs.

At this point, I still wasn’t even thinking about becoming a freelance writer.  I just wanted to make a few bucks.  But I did give effort on these projects even though they were kind of boring subjects.  One was writing articles on funeral proceedings and the other was for a Yellow Pages-type website.

After I completed the projects, the reviews from my clients came in.  Both were very positive and complimentary of my work.  They both paid me the money right away.  I was ecstatic.  I had never written professionally before, but always enjoyed English classes back in school.  So I had no idea of what to expect.  After receiving the compliments, it truly did make me feel good.  I thought “I haven’t received compliments on my writing since High School!”

That was when I realized I should look more into freelance writing.  I didn’t want to stick to topics that bored me, however.  So I searched internet forums to see what was out there.  What I found was it isn’t very difficult to become a freelance writer.  And there are tons of different types of freelance writers.  If you enjoy journalistic writing, you could do that.  If you like writing novels, you could do that.  If you enjoy writing content for websites and Blogs, you could do that.  Or if you enjoy copywriting, you can freelance that way as well.

I love to write, I am good at writing, and I also enjoy building websites.  So it was pretty much a natural fit for me.  And there you have it – I was about to become a Freelance Web Content Writer.

Section 2:  It’s All About the Strategy

How I Found Clients

As you know, I had some early success with Craigslist, but I knew that couldn’t be my only outlet for finding clients.  I spent a few days devising a strategy for getting business.  After taking advice from other freelance writers I befriended online, I decided to use the following strategy:

  • Build a website displaying what services I would offer and why I was a worthy writer.
  • Bid on jobs on sites such as Elance and oDesk.
  • Continue using Craigslist to find work.
  • Post on business related internet forums while showcasing my writing talents and expertise in certain fields.
  • Write as many articles on, while targeting specific keywords that potential clients would be searching for on Google (and other Search Engines).
  • Start a writers Blog to use as a means for building my portfolio and proving my writing skills.

My plan was to devote a portion of my day, each day, to all of those tasks.  If I couldn’t get enough business within a couple of months by doing that, there was no way I would ever succeed in this field.  I always keep a positive attitude, so I was confident this plan would work.

It did work.  In fact, it worked a bit too well, too soon.  I didn’t have a plan of action for what I would do once I got to a point where I was too busy to handle all of the work.  I planned on figuring that out as I went.  But I was lucky and landed a bunch of gigs shortly after I started.  I wish I could claim it was all skill, but my modesty will not allow me to do so.  Instead, we will just say it was luck!

However, I did find myself in a bit of a pickle.  I had too much work to complete on my own and no one to help.  You’re probably saying to yourself “how the heck is that a problem?  You sound kind of whiny!”  Well, it really is a bigger problem than you might think to have too much work.  Too much work and no help means I would be forced to turn some work in late.  And in this business, that simply is not acceptable (you better understand that).  Writers have deadlines to meet and when they do not, clients are unhappy.  I would be too if I were in their shoes.

Selecting My Clients

When I first got started freelance writing, I decided I would just take anything I could get.  I wanted to build up my portfolio and make some money early on.  But I quickly learned that taking anything isn’t always the best idea, even if it pays well.  The truth is, we can only write well on a topic that we have at least some interest in.  I took on a few early projects that I simply could not put my heart and soul into.  My work reflected that.

This business isn’t all about getting paid.  You should never become self employed without having some money in the bank and an ability to get by financially for a while in the event you don’t have income coming in early on.  Not doing so shows a complete lack of responsibility.  I had money in the bank.  I certainly was not wealthy, but I had enough in the bank to get by for a couple of months without ending up living under a bridge.

After I learned I couldn’t be a successful freelance writer by taking on any project that is offered, I became more selective.  I would only accept or bid on jobs that were of a subject matter that I had some sort of interest and knowledge in.  Sure, it limited me, but I didn’t care.  If I was going to write about topics that bored me, I would end up hating my job.  And if I wanted to work in a job I hated, I could have just gone back to working a 9-5.  No thanks!

My main interests are sports, travel, entrepreneurship, and poker.  Actually, sports is the activity I am most passionate about.  Unfortunately, there aren’t enough decent paying writing gigs within that industry.  But that’s okay because I have other interests.  I came up with a list of about 20 topics I would be willing to write about.  It included everything from marketing to travel to dating advice.

Manage Your Time Wisely or Fail Miserably

If there is one thing that can destroy your dreams of becoming a successful freelance writer, it is not being good at time management.  The whole mindset I had to change was I really don’t work for myself.  I don’t have one boss.  I have multiple bosses – all of my clients.  Many people that are self-employed do not think this way.  They think that since they’re no longer punching a clock, they can wake up whenever they want and work whenever they want.

I was determined to be on top of my game when it came to time management.  At first, I was more talk than action, and it showed up in my turnaround times.  I was of the mindset that I could do whatever I wanted, so I would put off work to go watch a ballgame.  One of two things happened – either I would turn in a project late or I would throw something together far too quickly and the quality of work was sub-par.

Fortunately, I quickly changed my ways.  I planned on sticking to a regular working schedule.  I would get up at 6:30 to go to the gym.  Then I would spend an hour returning emails, marketing, performing administrative tasks, etc.  After that, I was going to spend the rest of the day up until 5:00 (at least) doing nothing but writing.  I did a great job of sticking to this schedule and my work reflected it.

It’s All Mental

If you have any creativity whatsoever and understand how to put coherent sentences together, you can be a decent writer with practice.  But no one can write well if they aren’t in the right state of mind.  That’s the thing – writing is all mental.  So I had to figure out a way to avoid writer’s block and keep myself focused consistently.

There are a few things I do almost daily.  First off, I like to start my day off at the gym.  Staying in shape is important to your mental health, and I feel good about myself after working out.  The next thing I do is to make sure I have a light, healthy breakfast.  That usually includes a bowl of cereal and a glass of milk.  Now I’m ready to kick butt and take names!

I usually work out of the library because I find myself able to concentrate well there.  For whatever reason, I have never been great at working from home, so I try to find other places to go.  A lot of writers prefer coffee shops, but I don’t drink coffee so those types of places aren’t for me.  My dad has an office in his basement and no one is ever home during the day at my folks house, so I will occasionally go there and work.

The point I’m trying to make is you need to find your “happy place” and get into a daily routine.  This is crucial to your success as a writer.  Find a spot you can concentrate well at.  That may be your home, it may be the library, or it may be somewhere else.  Also, live a healthy lifestyle.  Don’t smoke, don’t drink too much, exercise frequently, eat healthy, and keep a positive attitude.

Section 3:  Money, Reviews, and Life as a Freelance Writer

You Can Earn as Much as You Want

I never envisioned myself as a professional writer because I had always assumed it was very difficult to earn a good living.  Oh how wrong I was.  When I first got started, it amazed me at how much clients were willing to pay for me to write articles for them.  They weren’t even difficult to write because I stuck with topics I enjoyed.

So how much can you realistically make as a freelance writer?  It all depends on how much effort you are willing to put in and how good you are at managing your time.  Through the first couple of months, I was averaging approximately $1,500 per month.  As I progressed, I began to make some real money.  And it felt good!  Within a few months, I was making over $3,000 per month.  Now I’m averaging almost $4,500.  Not too shabby for a one-man operation.

As I continue to grow, I will take on a team of writers and begin to outsource more of my work.  For now, I enjoy what I do and am satisfied with the money I’m making.  But the big bucks come once you start outsourcing most of the work.

I am not a big spender, so making a ton of money has never been a big deal to me.  I spend my money on bills (of course), food, gas, sporting events, traveling and at the bars.  I rarely go out shopping because I just don’t care to.  I’m the type that doesn’t care to receive a gift.  Weird, I know.

The Reviews Make it all Worthwhile

I already mentioned how money is not my motivation.  I’m happy with making just enough to live a comfortable life.  But what makes freelance writing so gratifying is the reviews I have received.  I absolutely love it when a client thanks me for writing such a great piece.  It truly makes me feel good about myself.

Here are 3 reviews I have received over the past year from clients:

“Fast, prompt, communicated very well. Received work little less than a day, very impress with quality of work. Will work with again.”

“Jon creates some fantastic content. He will be the first person I contact for all of my future projects. I highly recommend his services.”

“To be honest, my other writer’s don’t even compare to the services you provide.  Keep it up and you will go a long way in this business.”

And here is a recent text message I received from my friend that I wrote a sales page for:

“thanks for the awesome sales page.  It is converting well.  You freakin’ rock man!”

Part of the reason I enjoy the positive feedback I receive is because of my ego.  I can openly admit to having a bit of an ego.  That’s necessary to succeed in any business, however.  If you aren’t confident in yourself it will be difficult for you to convince anyone to want to hire you.

The other reason I live for the positive feedback from my clients is that it feels really good to make someone else happy.  I know that sounds kind of cheesy, but I do have a sensitive side.  I might be a huge sports fan, a jokester, and am known to indulge in a few adult beverages, but I feel good when I get compliments.  I work hard at this job and it’s nice to have people recognize my work in a positive manner.

Living the Good Life

Being a freelance writer is an enjoyable job.  Outside of being a professional athlete, I can honestly say there is nothing else I would rather be doing.  I get to work for myself, choose who I want to work with, and do something I enjoy.  Oh, and I get paid pretty well too.  What more could you ask for?

Oh sure, I don’t live some sort of glamorous lifestyle.  You’ll never see me on “MTV Cribs”, but you can read about me all over the internet.  I mentioned my passion for sports, and this job allows me to not have to miss the games I want to watch or go to.

I can also travel whenever I want.  I just take my laptop with and I can write in the hotel.  There aren’t too many jobs out there that allow you to work from anywhere in the world.  I’m the type that will plan a road trip on the spur of the moment.  I wouldn’t put it past me to book a flight to Vegas for this weekend as soon as I’m done writing this.  I’ve been known to randomly book a vacation with very short notice.

Whether or not I ever become wealthy as a writer, I will be satisfied as long as I continue keeping my clients happy and earning more than enough to get by.  If I have money to travel, go to ballgames, pay my bills, drink some beer, take a pretty girl out on a date, and still have some left over, I’m a happy camper.  To be honest, that’s really all I need to live life the way I want to.  And because of my freelance writing career, I am able to do those things.

Section 4:  Is Freelance Writing for Me?

If you want to know whether or not becoming a freelance writer is right for you, I have compiled a checklist of necessary qualifications.  If you can honestly answer “yes” to most (if not all) of these, you will have a bright future ahead as a freelance writer.

  1. Do you have good time management skills?
  2. Do you have a firm grasp on the English language and an ability to write coherent, error-free sentences?
  3. Do you have at least enough money in the bank to get by for at least a month?
  4. Are you willing to put in up to 12 hours of work per day, especially at first?
  5. Are you confident in your writing skills?
  6. Do you have a creative side to you?
  7. Are you comfortable writing on multiple topics?
  8. Can you handle constructive criticism well?
  9. Are you able to clear your mind so that you can put all of your focus on the task at hand?
  10. Do you work well independently?

So there you have it!  My life as a freelance writer and some valuable advice for those of you that are looking to get into the business.  I hope this has inspired you in some way, and also made your decision on a career path a little bit easier.  Good luck and thanks for reading!


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