Where has the time gone? It’s already been six months since I quit my job to pursue a freelance writing career.

It’s amazing how quickly one can get used to a new routine. I love working from home and spending my days researching, writing and working on pitches. This is truly my dream job.

But the past six months have had their ups and downs. I’ve made my share of mistakes and learned a ton about running a business.

Considering making the leap from working for the man to working for yourself? Here are the six most important lessons I’ve learned in my first six months of freelancing.

Helen Anne Travis

Who’s the boss? I’m the boss! Which is awesome. And, at times, a little scary.

Lesson #1: Time Is Not On Your Side

When I was sitting in my cube, daydreaming about freelancing full time, I imagined I’d have so much free time after I quit. Not only was I giving up a full time job, I was also ditching my daily commute and reclaiming the minutes I spent each morning staring vacantly at my closet deciding what to wear.

Surely, as a freelancer, I’d not only have more time to write and work on pitches, I’d also have time for hobbies, for blogging, and maybe even to start writing a book.


If anything, I’m busier than ever. Writing pitches, answering potential clients’ emails, networking, finding and applying to gigs, following up on invoices: all that takes time. A lot of time.

On average, I have about four to six hours a day to devote to billable projects. The rest of the time is spent securing assignments, closing deals and building my brand.

Lesson #2: You Need To Know Your “Bottom”

Seeing that there are only so many hours in the week to devote to billable projects, you have to know what you need to earn each day to reach your income goals.

This is your bottom. And you have to stick to it.

Let’s say you’re able to devote 30 hours a week to billable projects. If you want to earn $40,000/year, you need to make at least $27/hour.

Here’s the math:

  • Let’s say you plan to work 48 weeks per year. This builds in time for travel, holidays, conferences, personal time and sick leave.
  • $40,000 divided by 48 = 833. That’s how much you need to make each week you work.
  • If you only have 30 hours per week to earn $833, you need to make at least $27/hour. That’s your bottom.

When I was transitioning from full time work to freelancing, I kept epic notes on my projects. I tracked the time it took to edit photos, to research topics, to write stories. I still do this.

Now I know how much time it takes to write a 1,000-word, well-researched destination guide with original photos, or a 400-word blog post, or a series of 20 branded tweets. When a client asks for a quote or tells me the budget for a project, I can refer to this guide and know what I need to make in order for it to be worthwhile.

It is tempting to work below your bottom. Trust me, I’ve been there. Making a little money sounds a heck of a lot better than making no money. But you’ll never get ahead this way.

That time could be better spent pitching higher-paying outlets, working on a personal branding project that shows off your awesomeness, or finding funny cat gifs to put in your blog posts.

Know your bottom. Don’t work for a dollar less.

Lesson #3: Freelancing Is Not The Same As Having A Full Time Writing Job

For about five years after graduating college I worked as a breaking news reporter at the Tampa Bay Times. I had a good rapport with my editors. They knew if I went to a crime scene or an interview, I would come back with a story and get it done by deadline.

But the editors at the travel magazines, newspapers and websites I’m pitching don’t know me. Not only do I have to wow them with an idea, I need to prove in a few sentences that I’m more than capable of handling the assignment and will get it done on time with minimal edits.

It ain’t easy. Pitching is probably the hardest part of freelancing.

Here are some resources that have helped me out:

  • Mediabistro’s How To Pitch guides. Access to these requires an annual subscription of about $60/year, but I made more than ten times that with the first assignment I landed using the guides.
  • The book Writer’s Market. This thick tome includes pitching guides for hundreds of consumer magazines and trade journals.
  • Networking groups. I was recently accepted into the Society of American Travel Writers. I hope by attending the group’s conferences I’ll be able to meet editors in person and not have to pitch them cold.

Lesson #4: Freelancing Has Its Ups And Downs. You’ll Be A Success When You Can Deal With The Downs

In the past six months, there have been days when I made bazillions of dollars in 20 minutes. I’ve also had days when I woke up and thought: “How am I going to pay rent this month?”

No matter how mentally and financially prepared you are for the ups and downs of freelancing, the first few dry spells are a shock.

This is why it’s so important to build time into your week for applying to gigs, writing on-point pitches, and networking like a rock star. If you do this, those dry spells will immediately be followed by deluges of work.

Seriously, it’s like all of my clients talk to each other and agree to not reply to my pitches or emails until the same day, on which they blow up my inbox with awesome assignments.

I still get pretty nervous during the down times, but I’m betting established freelancers are grateful for the lulls. They know these are great opportunities to work on pitches, start that novel, or pick up the phone to interview someone interesting.

Lesson #5: It’s Not Really That Lonely

Tell anyone you work from home and eventually they’ll ask: oh my goodness, do you go stir crazy during the day?

Not really. I like being able to focus on my work with minimal distractions. And if I do get cabin fever, there are plenty of opportunities to get out of the house during the day. There are networking lunches and interviews, or I can take my computer to the library or coffee shop.

Now don’t get me wrong. When Greg comes home from work each day I practically run to the door to greet him. And I find I’m waaaaaay more social than I was before I started freelancing. An excuse to get out of the house and interact with real people? YAY!!!!!!!

Lesson #6: You Don’t Have To Travel Far To Find A Great Story

A few months ago I attended a weeklong networking event in London called World Travel Market. Every destination in the world was there: Lebanon, Kenya, Utah, you name it.

I had awesome meetings with representatives from Croatia, Malta and Italy, to name a few. But you know who I hit it off with the most? The folks at the Tampa stand (where I live now) and the Visit Citrus County booth (where I used to go on field trips in elementary school). Maybe I had to travel across the world to meet them. But it was worth it.

This travel-writing gig has me looking at Central Florida in a whole new light. There are so many awesome stories here.

Of course I want to keep traveling and writing about new places, but I also want to write more about where I live and where I grew up. Maybe that’s what makes one a successful travel writer: the ability to see stories wherever you go, even your own backyard.

Go Tampa!

Travel writing has me looking at my hometown in a whole new way.

Bonus Lesson: Having A Support System Is Awesome

I couldn’t do this without Greg. Don’t worry, I won’t get all mushy on you. But man, having someone who believes in you, who acts as your cheerleader during the down times, who asks about your projects and helps you flush out your ideas – that’s just priceless.


Running your own business is hard work. Be grateful for the friends, family and loved ones who cheer you on.

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