3 Lucky Breaks That Led Me to a Freelance Writing Career

TypewriterA lot of people want to know how to become a freelance writer. “How do you get paid for writing?” is what they often ask. When I think about what got me here, three lucky things needed to happen in order for this to occur.

  1. I met the “right” people. When I first decided to switch gears from therapist to writer and as a new freelance writer in Hawaii, I got lucky only because I met the right people. For example, I connected with a newspaper writer from San Jose Mercury who connected me with another writer. This writer ended up being friends with a business owner who just so happened to need a copywriter. Knowing someone in the industry, upped my reputation and helped me to land my first gig.
  2. I asked the “right” questions. A lot of times we don’t succeed not because we ask the wrong questions, but simply because we don’t ask. When an opportunity comes up, take the risk. If this comes to you in the form of a new acquaintance who is living your dream job, ask him or her how they got there. If you meet an editor, ask them if they’re looking for writers. It’s not asking that will prevent you from getting that freelance writing gig.
  3. I got the “right” gigs. I did my hard work. At the beginning, I didn’t always get paid to write. I didn’t always get paid well to write. But I did it. Over time, my portfolio grew and I could be more choosy. To become a freelance writer, you have to work hard like every one else. Sometimes this means rolling up your sleeves and writing about things you don’t really care about. Over time, you’ll get to choose.

I hope you catch what I’m saying here. To be honest, while there may be some luck involved, a lot rests in your hands. Instead of waiting for opportunity to come your way, make your own. Go to networking events (I only went to one before I scored my first paid magazine writing opportunity in Hawaii). Contact people in the area you’re interested and ask if you can do an informational interview (Talking with an expert in the field landed me my first copywriting job). And tell everyone you know you’re looking for writing opportunities. But most importantly, write whenever you can and about anything, just write! Every single thing that you write matters, because it’ll make you that much better of a writer.

The Secret Sauce to Freelance Writing Success

{Secret Sauce by trixieandmilo}
{Secret Sauce by trixieandmilo}

I’m pretty sure you’re going to be disappointed when you read this.


Because the title made you think you’re getting the answer to quick, fast, and easy success.

I’m going to be honest with you.

Although books and blogs like to sell you sexy solutions, the truth is it’s all a marketing ploy to nab your cash.

I know because I fell for it too.

Truthfully, just like there’s no secret to holiday weight loss, there’s no secret to doing well in freelance writing.

Here’s the bottom line:

You want to do well?

You need to leave an imprint on your seat to do it.

Hard work. Time. Energy. That’s the difficult truth.

Just like there’s no real pill to lose weight, (there’s only that hard pill to swallow that it takes exercise and good diet), the only way to a bustling freelance writing business is to work hard.

You need to confront those demons, face those fears, write, write and write again.

That’s it people.

You don’t need to subscribe to a program, add a certain type of text, update your social media sites at certain times of day or buy a book to know that. Those things help. They are the go-to resources to get you started. But rely solely on those things and you will have a lot of good resources collecting dust on your shelf.

Do the work. Get the jobs!

That’s it.

That’s the secret.

 Psssttt…Here’s another: You have until the end of this week to win my biggest giveaway yet. Alls you got to do is comment, share or like this post.

Be the Writer Every Editor Wants to Work With

Talent can take you far in life. But hard work will push you further than talent alone.

{Etsy photo by TheLovelyGreenWall }
{Etsy photo by TheLovelyGreenWall }

What I’ve learned in the last 6 years I’ve been freelance writing is there are other skills besides writing that can benefit the successful freelance writer. And that’s a good thing! This means that I don’t need to be as creative as Young House Lovers John and Sherry, funny as Martha Beck or as pushy as some go-getter writers to be successful.

Talk about a load off of my back. If I had to be naturally talented like the authors I drool over, I would have given up on this business several lousy paychecks ago.

What I’ve learned has been key to finding more jobs irrespective of where I live, how much experience I have or what I’ve done in the past. It’s helped me overcome and even make use of a degree and work experience that have no relationship to my career as a writer. It’s also given me confidence to pursue different directions in my writing. So here it is. It’s all the work that I’ve compiled from making tons of mistakes and learning in the process. It’s how you will become the writer editors seek out.

Take yourself seriously no matter what stage you’re at.

When I first decided to quit job hopping to finally pursue a freelance writing career, I was scared silly. I didn’t know what I was doing and was sure I would mess up. And I did. But I’m glad I did. It forced me to work hard. I threw myself in my work. I signed up for classes. I called people and asked them for advice, suggestions, help. I bought books, dogearing and highlighting as I went along. I joined and then started my own writing group. I did everything I could to learn as much as I could because if I was going to do this, I was going to give it my all. That’s what I also found inspiring when watching Jiro Dreams of Sushi, a 2011 documentary about a Japanese man who makes sushi making an art. Here’s what he says about success and hard work:

“Once you decide on your occupation… you must immerse yourself in your work. You have to fall in love with your work. Never complain about your job. You must dedicate your life to mastering your skill. That’s the secret of success… and is the key to being regarded honorably.”

Be honest.

There have been many times at the start of my career where I felt like a fraud. I was amazed people gave me jobs and believed that they would eventually see how inexperienced I was and fire me. So I hid my insecurities and pretended I knew what I was doing when I didn’t. This backfired on me big time and I learned it’s much better to be honest about what was expected of me. In two words, be transparent. It’s how you build trust with any potential editors and how you work with integrity. If you can’t finish an article on time, let an editor know right away. If you’re not clear about the assignment, ask. It’s simple things like these that make you much easier to work with and be the type of writer editors will contact again and again.

Be flexible.

I’m no writer diva. My belief is that every writing gig that comes my way is an opportunity and I like to bend in the wind of all opportunities. This means that for the most part, I’m going to get up real early, drive far, or write fast if it will make my client happy. I will deliver quality content and I will change pieces, organize them differently and do so happily. As long as I am treated well, my aim is to be a client-pleaser.

These are just a few tips I’ve learned that can make working with editors and clients easy-peasy. It not only makes the relationship work better for the current assignment, but it makes me more likely to gain future ones too. Basically to stand out from the millions of other writers out there (some who have more impressive portfolios than you), you need to treat your clients as people, think about what would make them happy, work hard and deliver quality content. Those are the things that have and continue to help me. What’s helped you?

Get Off Your Writing Couch and Do Something!

Thank you Stephanie and Jan for reminding me about 2 things: 1) To keep up this blog! 2) To be more compassionate. 

Their comment comes on the heels of a short answer I compiled for O magazine. If you want to read my little published shpeal on compassion, it’s right here.

{Etsy art by wordwillow}
{Etsy art by wordwillow}

But the main reason I’m writing this is that I think too many of us get comfy in our writing couches and stop taking chances. Maybe we had HUGE dreams about what it would mean to be a freelance writer and since we didn’t achieve them, we kind of just gave up.

I had big dreams too. I wanted to be a self-help writer who writes about mental health issues, the environment and writes copy for cute whimsical companies on the side. On days when I have too much time to think I get down about that. Until my logical side slaps my creative side and says the following: “Doh dude, you already did that! Get back to work!”

It’s so easy to get lost in the once-in-the-lifetime dreams like writing for O magazine when your dream life is right in front of you. We think that to be successful means we need to be published in a huge publication, be known in the writing industry or be a published author. But for many of us it means making our clients happy, getting new gigs, challenging our creative muscle. Just because you’re in the latter category, doesn’t mean you’re a loser or you’re never going to get there. What it means it that you’re right now on the writing road to success. You’re just in the early stages and the only way you won’t get there is if you give up.

This quote by author Christina Katz came to me in the form of a Writer’s Digest newsletter and I’m so grateful for it. For any of you out there who feels bummed out that you haven’t “made it yet,” read this:

“Stop waiting for big success and aim for a series of small successes instead. Many writers are waiting to hit the mother lode, so to speak, of writing success. But success lies in taking aim at targets you are likely to actually hit and then hitting them one after the other. That’s how experience is gained in an otherwise complex and mysterious profession.”
~ Christina Katz

The Truth About Being a Writer

{photo by Brandi-Ann Uyemura taken on site in Serenbe, Georgia at a home designed by Ballard Designs.}

There are a lot of people who want to be writers. Some of them are friends and acquaintances I’ve met along my path. They envy me in a shameless way. My life seems as close to Carrie Bradshaw as possible without the single life and the large shoe closet. Many, I believe, think that I spend all day shopping and galavanting.

Yes it is partially that I suppose.

But the truth is, I spend more days sitting on my butt, pulling out my hair, trying to find the best words to squeeze into my prose. It’s not fun nor glamorous. Yet, it feels to me like freedom-the freedom to express myself and communicate in a way I couldn’t do verbally.

For all of you who want to be a writer, know this truth.

Writing for a living is not easy. It’s not an outpouring of soul divulging like it is in a diary. It is not about seeing your name in print (although it is fun to see it). It is not about being called an author or a writer (that you can get from simply printing out a business card).

The truth about writing is that it is hard work. My brain hurts afterwards. That’s the only excuse I have for emails I send to you with misspellings and grammatical errors or Facebook updates that sort of doesn’t make sense. It’s why I fumble over words when I talk. The process of writing words that seem effortless takes a surprising amount of effort. And that’s just the writing part.

You also have to factor in interviewing skills, transcribing, editing, and of course marketing. It’s a party hat few TV writers show you. Mostly because it’s not all fun or glamorous to do so. It’s simply work.

While the outcome, the finished product could look pretty, to me the process can be ugly and quite messy. I guess it’s like anything worth doing. Please remind me of this the next time I’m in the throes of my work.

I Really Want to Be a Writer But…

{iPhone photo by Brandi-Ann Uyemura.}

There’s always a reason to give up.

Let me count the ways. Your mounting bills, the bad economy, the competition, your lack of time, fear of rejection, there’s already enough books out there, your stuff’s no good, no one will read it, you hate feeling vulnerable, etc.

And it doesn’t get easier. They ebb and flow, rising as your confidence rises. They strengthen as your courage deepens. In fact, the more you grow, the greater the challenges become.

Over time you either grow accustomed to them or you begin to listen. If you choose the latter, you may lose your inner voice. You may think that no one is rooting for you, that you are alone on the journey, that there are people who expect you to fail. This type of thinking not only hurts your chances of writing success, it hurts your spirit.

There have been many times on this path that I’ve doubted my course. And I still do. I know I probably will always feel uncertain about my choices just as I have days where I’m completely sure. But one thing I’ve learned to do is separate myself from the negative voice. I’ve also learned to reach out right when I feel like closing in. I’ve learned that there are people who I have never met who are cheering for me (like these people here.) And I learned that No ONE knows the purpose of my life, only I do.

A lot of people tell me that they want or wish they could be a writer. I understand the longing. It’s been my secret desire since I was a kid. It only took me a few decades to gain the confidence to pursue what I thought I didn’t have the skills to do.

But here’s what I’ve learned.

If you really, really want to be a writer, then do it. Don’t wait until you’ve got enough experience, you have more time, you feel less insecure, the perfect writing job comes along. Do it now!

This lady taught me a few years ago something that I only got now. She told me that if I wanted to be a writer to do it. She said, “I believe you can.” I took her words as generous and kind as gifts from a sweet person. I only realized now that anyone can do it. The key is you’ve got to have the passion and the belief that you can.

It doesn’t matter how much experience you got or how much talent you have. We all need to start somewhere. If you read my writing when I first started, you’d realize how far we all have go to get good at something. It’s the process by which all people rise to the top.

So stop whatever moaning and groaning and procrastinating that you’re doing and do what you say you’ll do. Don’t wait until tomorrow because tomorrow offers another excuse to put it off.

You say you want to be a writer? Well go ahead and write right now!

How Bad Do You Want to Be a Writer?


{via Real Simple}

That’s the questions I have been asking myself these last 6 weeks since I officially and finally moved back to Hawaii.


I know that’s the question most of the world would be asking. Why would a writer have a difficult time writing amongst turquoise hued skies, pearly white sand and a “you could get lost in it” ocean.

Lots of room for inspiration right?

Yes. It’s true. I’ve been writing more for my fiction piece than I did when I lived in California. But on the other hand, finding new writing gigs have turned out to be pretty dismal.

I know it’s only been a month since I started looking, but I learned fast that my usual writing gigs finding route (searching the web) just wasn’t going to cut it this time. In fact, what made it harder was that in the time that I’ve been here, I’ve been getting call after call from recruiters trying to fill writing jobs up there. {*Sigh.}

What I learned is that every state may have a different protocol for finding writers. While I was lucky to have been a freelance writer for the last 5-years in Silicon Valley, where everything is basically online, I now knew that if I wanted to avoid being a starving writer, I needed to put myself out there. Hence my recent transition from shy, introverted work-at-home writer, to pretend extrovert. I’ve been attending networking events like nobody’s business. Not an easy feat for someone who’d rather stay at home with a good book than talk shop and hand out business cards.

But it’s been worth it.

I’ve had one job offer, and a handful of leads since I started networking. It’s not easy, but I think the more you practice your elevator speech, the more comfortable you’ll feel connecting with others. And not in a car salesman sort of way, but in a way that genuinely depicts who you are, what you’re passionate about and what you want to do.

If you do that, you’ll find just what you’re looking for in no time.

The Freelancing Lessons You Don’t Want to Learn the Hard Way

{flickr photo}

If life is one big class, then I got a lot of my lessons solely from being a freelance writer. As I reflect on these last 5-years, I’d have to say while it hasn’t been an easy road, it was a necessary one. Hopefully, you won’t have to stumble in the dark as I have. Read up on what things I wish I didn’t have to learn the hard way.

Get clear about whether you’re getting paid or not.

Money is an uncomfortable issue. And when you’re first starting out, you just feel grateful for getting any writing job. But being clear about whether you’re an intern or a paid client is vital. Don’t be like me and find out after the fact. If you think bringing up payment is uncomfortable, try doing it after you find out they were never expecting to pay you in the first place!

Don’t believe that any class, course, webinar, books etc. will have THE answer to helping you succeed as a freelance writer.

Not that they aren’t helpful. But realize you’re going to have to do the work yourself. Don’t expect miracles just because a writer, blogger or business person says they have the key to making you a millionaire. Otherwise you’ll be like me, a little more broke and not that much wiser.

Have some type of written contract.

I’ll admit it took me a few times to really understand the importance of getting things down on paper. For the sake of saving yourself and your client from future conflict, make sure you specify exactly what is expected of you, what you’re willing to do for them, by when and for how much. This will prevent you from angry clients who may be surprised by the final bill.

Never overestimate what you can deliver.

It’s much better to underplay what you can do, then to oversell. If you tell them that you can complete a project within a few days, just to get the job but realistically you can only do it in a week’s time, you’ll eventually lose their faith in you and inevitably lose this client. Always over deliver. I know that getting projects done way before it’s due or submitting more than what’s expected of me has had positive results. And the opposite? It’ll leave you with an unhappy, dissatisfied client.

Be pleasant and easy to work with.

They may hire you because of you’re experience and talent. They’ll keep you because you’re a pleasure to work with. In the past, I worked with a few difficult writers, writers who were disagreeable, unhelpful and not very dependable. They make work so much harder. Know that you’re not just delivering good writing to your client, but good customer service. That’s how you get continuous business. That’s how you succeed as a freelance writer. Make sure you pack up your ego and remember being nice and helpful goes a long way when it comes to your business.

What about you? Any lessons you had to learn the hard way?


Being a Shark Can Help Your Writing Business

{photo by bryan scott photography}

Don’t judge me, but I’m a big fan of reality TV. Just like I love a good memoir and an autobiography, I get a high from watching real life people do crazy ass things. To me, it’s just inspires me to do something crazy myself.

One of my favorite shows is, “Shark Tank.” It seems antithetical to my very nature to be a shark when it comes to making money. But maybe that’s why watching it thrills me so. It’s also observing the inventors, creators and designers who work up the courage to give their 5-minute shpeal on what makes their product so shark worthy that a panel of millionaires would invest in it. It’s scintillating stuff for me. Better than a high from a horror flick or a roller coaster ride. Two things this scaredy-cat introvert would never do.

Anyway, I got to thinking that the things that make a few of these business people successful on the show can also be applied to what makes us freelance writers successful too. Qualities like consistency, determination, integrity, honesty, humility and a crazy perseverance to keep going despite flat out rejection and brutality honest responses (non-responses count too).

I also thought they should do a Shark Tank version for non-profit organizations and in googling it found this article: 7 Entrepreneurial Lessons From, “Shark Tank.” In it, they cover significant points that can help elevate individuals wanting to be a successful entrepreneur, which includes everything from being humble to being a good marketer. They comprised a great list of factors that any small business owner including writers can sink their teeth into and garner business savvy tips from.

What do you think?

Are there any lessons, tips, advice you’ve learned on the road to freelance writing that’s helped you? Do share.


Easy Ways to Increase Your Chances of Freelance Success

{found on pinterest via @Calvin Hensley}

While I’m hardly one to call myself a success (unlike this couple), I have picked up a few learn-as-you-go tips that have seriously change my career and my life. To be honest, my freelancing career started without any preparation, focus or long-term planning. I basically decided one day that it was time to stop waiting for my life to happen and start living it. Although it’s been a rocky road, I have never had trouble finding a writing gig (*knock on wood) and have succeeded in getting bigger and better jobs throughout my career. I must have done something right.

And looking back, maybe there were a few things that I did do that helped to sweeten the pot. With patience, time, hard work and a stubborn desire to make it no matter how tough it gets, you might get there too, maybe even faster than I did.

These crazy things I did may help you too:

I hoarded clips. Oh yeah I did! I wrote for free publications, local newspapers, teeny-tiny start-up blogs. I offered my writing services for free (well mostly because a lot of these places stiffed me). But in the end, building a ton of clips was a great way to start my career. When I was ready to start hitting up bigger companies, I had a melange of samples to choose from. I still do.

I acted like an extrovert. And I’m so not! But I sort-of pretended to be by searching for high profile writers that I admired and begged asked if I could interview them. Just a few minutes to “shadow” them and find out what it’s like being in their shoes. Surprisingly, I was able to meet a few newspaper reporters that way and this amazing writer. Not only did I get professional advice on how to start my career, but one of the reporters I met knew a company I was interviewing. To this day, I believe that connection helped me to land my first copywriting gig for a major retailer. I’m forever grateful for those writers who really boosted my self-confidence and encouraged me to give it a go. And I like to remind them how much that initial contact meant to me.

I pretended I knew how to blog. Basically, I knew blogging was important to my career. I was already way behind blogging although I had written in journals my entire life. So I just did it. I did it first as a way to write about my personal life and then I created a few more to take it professionally. And I did it horribly. But it was for myself on a free site and all that practice was good for my career. It was also great for networking with other creatives. I used my first inspiring blog to connect with authors, life coaches, bloggers and even an Olympic medalist. Blogging was an impressive platform and although I feared others were snickering behind my back, I believed it was worth it. I still do. Even if you and my family are the only ones reading it.

I didn’t take “no” for an answer. I’m a pretty sensitive soul. But when I wannabe, I can be pretty persistent. An old co-worker actually described me as a “bulldog.” His words. But when I really want something I’m pretty stubborn about it so I push with grace. Basically, this means that if I’m turned down for a position and I really, really want to work for a company, I keep trying. I let them know that I’d be interested in hearing about other jobs in the future. I stay in touch with new potential ideas for a publication. I’ll keep a great relationship and the lines of communication open because I know if there is a good fit, they’ll feel it too. I wait for another position to come up. And you know what? It usually does.

I knew when it’s time to let go. Sometimes I don’t act on it as quick as I should. But I’ve gotten a lot better at this. If you hold on to a job too long that’s not serving you, you’re only hurting yourself. That’s one of the reasons why I admire this writer. She knew when it was time to leave and she did. There are some writing gigs that I got that was seemingly great for my career. In fact, one led to being published on USNews.com. But after awhile, a few of these gigs didn’t work out. Maybe it was the chemistry, the finances, the work itself, but while they didn’t all end beautifully, I’m so glad I decided to end them. As they say, when you close one door, another one opens.

I learned to be picky. I think desperation makes you apply too all writing jobs just like hunger makes you eat whatever’s in front of you. The key is to keep reminding yourself that applying for the wrong jobs is a big waste of time. Nowadays, I look for red flags before I apply to weed out time wasters. Helps a lot!

These are just a few lessons learned that helped me. Garnered any great wisdom on your own crazy freelance journey? Share them please.