15 Apr 2019

How to Win Your First Freelance Client

The most agonizing part of being a freelancer is managing deal flow. Most of the time, you’ll have your head down doing your work until you complete a particular project. When the dust settles and you’ve collected the cash from your final invoice, you look up with abject terror to realize there’s nothing on the horizon.Or maybe you’ve taken a hacksaw to the chain that’s been binding you to your 9 to 5, only to realize you’re a newbie, fresh product — no one knows that you’ve quit your job and are now in the freelance game

How do you score those first few important clients when you’re new to the hustle or you’ve found yourself in a financial Sahara?

First, let’s talk about gig sites. Repeat after me: Just say no to Upwork.

Competing on price is a zero-sum game. You will always be the loser.


There’s nothing more demeaning than a financial race to the bottom. Sites like Upwork and Fiverr benefit those who are hiring because they force freelancers to compete on price. And let me be crystal clear about this: Competing on price is a zero-sum game. You will always be the loser. There will always be someone who will offer to do the work for half your rate in half the time, regardless of whether the product is garbage.

Upwork is the biggest con going. Trust me, you can build a legitimate freelance career without having to devalue your work or deal with a middleman taking a princely cut.

Okay, whew. Digression over. Let’s get back to business.

Decide What You Want to Do

Don’t freak out. This isn’t a lifelong commitment. For my first two years of freelancing, I only did social media projects until I woke up one day wanting to tear my hair out. I was good at social media strategy, but I hated social media strategy. That’s when I realized that just because I’m good at something doesn’t mean I need to do it for a living.

But don’t feel bad if you have to take gigs you don’t want at the beginning or during droughts. Sometimes you don’t have the luxury of being picky. I’ve taken on projects because, at the end of the day, I had bills to pay.

Now, get clear and specific about your goals by asking yourself the following questions.

What do you want to do?

Decide on the products/services you want to offer. Let me share three magical words with you: multiple revenue streams. Generating income from various sources not only minimizes the risk of not getting work, it also diversifies your work. Your ideas are fresh and you rarely get sick of what you do. I have five streams going right now: strategy work, 1:1 coaching, writing, performing audits (i.e. I tell you what’s wrong with your business), and products/courses (coming in 2019). All of my work comes from my experience in storytelling and marketing, but I’ve chosen different ways to use my skills to make money.

Who do you want to do it for?

Visualize your dream client. And no, your dream client isn’t just someone who pays you on time, although that is certainly dreamy. What kind of business are they in? How large is the company? What are the company’s values, and do they align with yours? How does your client value you? For example, I’ve shifted my model this year to use my 20+ years of experience to help women-owned businesses and POC/marginalized business owners. The majority of my clients are small to mid-sized companies, and they view me more as an integral partner than as a vendor. These businesses aim to create products and services that truly meet the needs of their customers. They operate from a place of honesty and integrity, which aligns with how I want to live my life.

Why do you want to do it?

Yes, we all want to make money, but that goal isn’t self-sustaining. After a while, you’ll realize money is a thing, but not the only thing, and then you’ll risk being resentful of the work you do. Do you have big dreams of leaving the world in better shape? Do you have a skill that would truly help and transform other people or make their lives easier? A sense of purpose can be a constant motivator.

Where do you want to do it?

Does your work have a geographic component? Where are most of your ideal clients located? Do you want to work virtually or one-on-one with people, in person?

2. Validate Your Idea

Do the research. Is there a demand for your work? What are people paying for it? Make sure you price yourself wisely — there are scores of online calculators that can help you figure out your rate. Determine if you want to be paid by the hour or by the project. I could write a whole piece on

hourly vs. project, but for now, I’ll just say that at this point in my career I only do project rates.

3. Shout It From the Rafters

Tell everyone you know that you’re freelancing: your mom, your best friend, your dog, the barista at Starbucks… you get what I mean. Work can come from anywhere, but no one will offer you work unless you announce that you’re looking for it. I routinely send brief emails to my network outlining the kinds of projects I’m taking on and asking if they or someone they know is looking for a bomb-ass consultant. Email everyone in the free world: Do you need help? Do you know anyone who needs help?

4. Work Your Network

I’m a shy introvert. The idea of networking gives me palpitations. I used to go to networking events and just stand in a corner — the only thing that was getting worked was my cheese plate. But don’t worry: You can expand your network without being smarmy about it.

Join private Facebook and LinkedIn groups related to your industry

Connect online with people who run in similar industry circles. Why? Because who doesn’t want support — a place where you can field questions, punt ideas,and help others. Here are two more magic words: overflow referrals.

The more people you have in your corner, especially if they’re good at what they do, the better; you’ll find that work gets shared. I’ve seen countless freelance gigs posted in the Dreamers // Doers Facebook group, as well as a ton of other groups. I’ve also made a few friends online and those relationships have scored me projects.

Work your contacts

I have a philosophy that if I don’t like you, I can’t get on the phone or spend time with you. I want the time I spend with people to be gratifying. Have coffee with your peers. Schedule Skype/FaceTime dates to talk shop or buddy up with a peer for ongoing mutual support as accountability partners.

Ask your friends for specific introductions to people in their network, but don’t be vague. Don’t just say, “Can you hook me up with someone in your network?” Rather, say, “Do you know someone in nonprofits who works in social media marketing? I’d love to hook up with them for [X reason]. Could you make an intro?”

A key point: Never ask for or make blind introductions. Always ask each party if they want to be connected. It’s good professional etiquette and it ensures both parties are interested and not put in an awkward or compromising position.

Connect with past employers/former clients

You’re probably thinking, Oh, if they need work they’ll just know to contact me. Please stop thinking this. People don’t have elephantine memories and they’re not psychic. People can only see a few feet in front of them, so you have to be in front of them.

Reconnect with old clients or past employers and ask if they need help with something. Assess their business, sites, emails, and social channels and suggest ways you can help take their business to the next level. It shows you did some legwork and you have specific ideas on how to make their business better.

5. Be Open

Sometimes you need to get crafty because you have bills to pay. Work your revenue streams, but also think about smaller projects you can take on that will provide some quick cash. Recently, I created portfolios for fellow freelancers by pairing my wordsmithing and positioning abilities with designed templates on Creative Market. When you need cash, nothing is beneath you.

At the end of the day, you just need to find that person to hire you to do one thing. That’s enough to get the ball rolling.


Like what you’ve just read and want to get a 75+ page guide chockful of freelancer articles, advice, templates, and tutorials? For $49, you get a comprehensive freelancing guide that includes:

  • How to get started as a freelancer: the logistics, as well as a suite of powerful self-exploration exercises that help you solidify what you want to do. If you already have a business, learn how to shift to profit and purpose
  • My top freelancing tools–from CRM software to project management.
  • Learn everything about professional etiquette–especially as you’re getting started
  • How to market your business without being shady or smarmy
  • How to network when you hate leaving the house
  • How to talk about money and knowing your worth
  • How to be assertive when negotiating–advice from two c-suite executives
  • How to build portfolios that win business (+ a free tutorial template)
  • How to deal with clients who make you doubt your sanity, intelligence, etc.
  • How to deal with imposter syndrome
  • What your worst clients can teach you
  • How to manage tough clients and know when to fire a bad client (+link to an interview I did on the topic)
  • New Business Kit, which includes: cold pitch letter template, new business checklist, a proposal tutorial, and template + how-to, 4 contract templates, and an invoice template
  • New Client Onboarding Kit, which includes: a template for a new client magazine, onboarding checklist, and new client discovery questionnaire
  • When your business expands and you manage people–how to do it right
Social media bonuses: how to go live on Facebook and Instagram, how to create an Instagram feed that converts, and my top ten social media automation tools. And I’ve got so much more!
Posted on April 15, in Career

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  • We spend our time devoted to the periphery. If periphery was an altar trust that we’d all gather and worship. We cleave to the shiny objects that are social media, email, podcasting—we’re told we have to be diversified—at the expense of the one true thing you create. The thing by which you want to be known and remembered. We give equal (if not more) weight and devotion to that which surrounds our thing instead of getting laser-focused and refining our skills, being a student—all to keep getting better at the thing.
Trust me, I want to do ALL THE THINGS. Now, I ask myself what portion of my day have I committed to being a better writer, a better storyteller and brand builder? Am I learning something new, regardless of how minor that something is? Or am I zeroing in on the things that are conduits and bridges to and from the work. You’ve created all these points of entry to a thing that isn’t as good as the vehicle that got them to the thing.
Think about that. Prioritize. .
#thursdaymotivation #freelance #freelancelife #femtrepreneur #beingboss #ladyboss #protip #beastudent
  • So, I fell down in the middle of the street while walking to an important meeting. I scraped up my knee pretty bad, but kept it moving, because I have a long-term play to earn as much as I can to move somewhere super remote and quiet by the end of the year.
It’s weird to think that I’ve lived in NY for the first 39 years of my life, Los Angeles for the past four, but I’m watching old episodes of Shetland and wondering how I can get myself to a remote farmhouse, cabin, outhouse, etc. All I need is good WIFI for work.
But an island in Scotland isn’t realistic, so I’m setting my sights closer to home, California. And I’ve got time to research, thankfully. .
Until then, I’ll keep plugging, keep writing, keep up with newly-revisited healthy habits.
#freelance #freelancewriter #tuesdaymotivation #beingboss #bosslife
  • New post up on medium. Link in bio.
“If I had my way, I’d never leave my house. My home is small, and I know every inch of it. An 800-square foot box with two windows, walls, and a doorbell that plays instrumental Julio Iglesias. Half the rooms are cloaked in effulgent light and the other a cool charcoal black. I’ve become fluent at oscillating between the two. I don’t even love the space in which I live, but I’m hard-pressed to leave it.”
#authorsofig #authorsofinstagram #writing #weekendvibes #mediumstory #friyay #friyayvibes #novelplotting
  • I live in a city of four million people, which was a marked improvement from my home, New York, of eight million. I snapped this photo during my trip to Cape Town (488K people), and during that trip we traveled to towns of four thousand people and it was GLORIOUS.
It’s bizarre that I’ve always been a city girl and all I want now is small. Quiet. Remote. I feel like my dad.
I cracked my tooth on Friday (it’s all good—I got Percocet and a $3K bill), and it made me think that there’s so much I want to do, work-wise and artistically, but I’m always thinking about money. Years ago, I heard Paul Jarvis talk about reducing your expenses to feel richer. I know, captain  obvious, but it resonated with me on Friday while on Percocet.
I’m considering another move when my lease is up to a small AF town in California not too far from the Redwoods and the ocean. I LOVE California, and I can’t imagine living anywhere else in the US. And I love the idea of FEWER people. Quiet to write. Maybe I can get a dog friend for my Felix! .
So, we’ll see. Does anyone here live in a remote or super small town? If so, what do you love about it?
#sundayfunday #sundayvibes #weekendvibes #freelancing #authorsofig
  • My breaking point was over a hazelnut. A hazelnut that cracked my tooth at two-thirty this morning. Because I was stress-eating granola. But it was the three thousand dollar bill to fix said tooth that did me in. Only a few weeks before, a persistent ache in another tooth turned into a five-hour fiasco involving a dentist, an endodontist, a $5,000 bill and me texting a friend — while the fifth shot in my mouth was kicking in, and I was inhaling nitrous gas like a glass of water in the fucking Sahara — ARE YOU KIDDING ME WITH THIS BULLSHIT?
My dentist tried to reassure me, after rejecting my pleas for a fifteen-year repayment plan, that this particular tooth had already booked a one-way ticket to a root canal, so I ended up saving $2,000! Oh, cool. So, instead of dropping ten grand on two teeth, I was only paying eight. Like I have eight thousand dollars just laying around, waiting to be flushed down the dental toilet. Apparently, the hazelnut was my salvation. I started laughing and continued laughing. For a while. To the point where everyone in the waiting room was uncomfortable.
****I wrote about teeth, money, and debt in my latest medium post. Link in bio.*****
#risingtidesociety #freelancing #freelancinglife #bosslife #bossbabe #beingboss #cashmoney #fuckstudentloans #femtrepreneur #realtalk
  • This is our one life. We love. We lose. We overcome. We break in ways we never thought possible. We climb, ravage, and wreck. While it’s possible that every story has been told, that knowledge doesn’t stop us from reading, watching, listening, and feeling. It doesn’t disconnect us from someone’s unique experience. Instead, we live for the retelling: how individuals bear that which is familiar or common, and how their singular experience feels fresh and new.
Today, I wrote a tutorial about crafting plots. Instead of vivisecting plot arcs — because frankly, I’d rather gouge out my eyes with an acetylene torch — I invite you to consider three simple questions: what story will sustain your interest for 70,000 words? Can you commit to your story and the sequence of events that unfold for months or years of your life? Does your novel have the weight to capture and hold your reader until the end?
This year, I’m committed to sharing what I know for FREE. I’ve got no classes to sell after this (I actually hate the idea of teaching writing; I’d rather be doing it), but lots of people have asked for the goods and I believe if you’ve got the skill and privilege, you should be sharing it.
So, if you want to get your plot on (I am such a 40-something), hit up the link in my bio. If you like what you read, consider clapping (you can clap up to 50x on medium) and share it, so more people get the education love.
#authorsofig #novel #howtowrite #authorsofinstagram #freelancewriter #novelplotting #mondaymotivation #risingtidesociety #writing #writingcommunity
  • Want to write a book? I'm sharing a six-part series in how to get the job done. The first two I'm previewing on Medium. Yesterday, I wrote about writing killer dialogue. Today, I'm sharing how to craft compelling characters. If you love what you read, consider sharing and clapping (more than once!). link in bio!
Characters are delicious. When I was small, I didn’t have many friends, so I surrounded myself with books and my imagination. It’s a strange, magical thing to live your life inside your head, but this is what I did. Long, sultry summers formed a backdrop for one of the many worlds I’d created, complete with a cast of characters who felt so real you could touch them. This was more than inventing an imaginary friend or anthropomorphizing a stuffed bear; my characters were fully-formed people who had their own personalities, a particular way of talk, and facial features I’d cobbled together from television shows and magazines. They clasped pearls around their thin necks and wore sweaters and shoes made of silk and dyed blue. They were carriers of credit cards, plastic rectangular shapes I’d only seen on TV — a far cry from the crumpled bills and pennies we hoarded. My characters were breathing Frankensteins, only far less frightening. What made them real was they refused to follow a script — they rarely behaved the way I wanted them to.
#howtowrite #writing #writingtips #characterdesign #authorsofinsta #authorsofinstagram #bookstagram #howtowriteabook #weekendvibes #sundayfunday
  • Want to write a book? I got you. Below is an excerpt from my latest medium piece—the first tutorial of six I’ll be sharing on writing mechanics. You’ll get the other 5 later this month if you’re on my email list. Link in profile!
Denis Johnson once said that dialogue isn’t about what characters are saying, but what’s left unsaid. The leaner the dialogue, the bigger the bite. Darkness fell. The summer in 2005 was unseasonably chilly, and we wrapped ourselves in light jackets and thin cotton sweaters, watching the author of Jesus’ Sonchain-smoke and dole out advice with humor and humility. We were at a writer’s conference where we workshopped our stories during the day and mingled with boldfaced names in the evening. This would be the summer before I sold my first book and I was floored that my teacher at the time, Nick Flynn, found something honest and worthy in my essays that would become my memoir, The Sky Isn’t Visible From Here. Back then, I was painfully shy and prone to giving violently awkward first impressions, so instead of the cocktails and conversation, I chose to sit on the wet grass and listen to writers whom I admired. One evening, Denis Johnson gave a talk on dialogue.

Dialogue is difficult. I often think of it as the power-lifter of novel writing because it has to operate successfully on several different levels. Not only does it have to move the story forward, convey information quickly, and grant narrative breathing space (because who wants to plow through pages without an exhale), but it also has to reveal core character truths. Dialogue delivers what narrative can’t — a voyeuristic, in-depth look into the minds of characters through what they say, and more importantly, what they chose not to disclose. Characters come to life when they speak. We visualize them as living, breathing people who have a particular way of talk, a specific view of the world and their place in it. While the author has dominion over the narrative, serving as your tour guide through the story, the dialogue serves as the wild card, the wrench that could usurp everything you’ve just read and what you’re about to read.
#howtowrite #writing #writingtips #authorsofig

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