First I quit my job. I was fed up and feeling stuck. Stagnant. Downright pickled. I posted my declaration of independence on my birthday when I knew everyone would already be checking my Facebook. Catching the gravity-slingshot of another year turning.

And then I had to set some goals and do some research and build some backbone. I noticed that all the greats on Medium are telling startup success stories…well this here’s a prospector’s journal. Success may be in the offing but this is no cozy retrospective: this is a living, breathing, all-singing-all-dancing blind sprint through morning fog full of rocks.

Expect sweatstains, burnmarks, ominous smears of unknown origin. Cuts and bruises and twisted ankles. Expect backtracking, introspective doubt, gainsaying self-aggrandizement. But also expect to learn something from my mistakes. I certainly do.

It’s a Matter of Quillpower

The mantra is this: I am an entrepreneur. I am an entrepreneur. I am an entrepreneur. I am an entrepreneur. I am an entrepreneur. I can’t tell you what a difference this simple thoughtcrime makes. Say it again for posterity. And again for luck. I’m done counting someone else’s money. I’m done scrubbing someone else’s floor.

Does this sound like a manifesto? Well that’s because it is. I’m writing this for me — you, Dear Reader, are my accountabilibuddy. And the stakes are thus:

If I don’t succeed at this my dream, I’m doomed to return to bartending or teaching; grow a soft belly and a long greasy beard, wallow in morosity for the rest of my life until I drive my puttering motorcycle off a cliff in a “tragic” accident.

1. Read. Everything. Often.

You’re already on the right track. Medium is a welcoming place abuzz with great ideas. I’ve been inspired by almost every article I’ve read. Take nothing as gospel but gobble greedily. And expand your reading. Novels, trade publications, blogs, newsletters, highschool essays…be a glutton for words of all kinds.

Sample expert copywriters and feast upon their websites. And browse the shitty ones too so you know what NOT to do. You should be slavering with appetite and restless when you’re doing anything else. That’s the entrepreneurial spirit.

If you paint, you study brushstrokes. If you sing, you listen to music. If you write…you read. But you already know that.

2. Get Organized

You know the drill: the start of any creative project is a deluge of ideas and a disaster of order. You can’t jot notes fast enough. They appear scattered across eighteen notebooks and five different apps and if only you could just find the one you wrote about that thing you were thinking of…

Write down your goals
Write down your business plan
Build a spreadsheet to keep track of client pitches.
Start a financial statement (Googlesheets has a great template)
Set aside 25–30% of every dollar you rake in for taxes

If you build it, they will come. Infrastructure means traffic. Traffic means clicks. Clicks mean conversions. Conversions make happy clients. If you’re a freelance copywriter YOU are your first client.

Three Main Branches of My Freelance Writing Business Model

Business and Marketing (my own)
Pitch Hopper
Work Progress Administration (yeah I’m a punny nerd)

I’m a visual learner, I think. Or maybe I just like to have something to stare at while I think about other things to preserve the appearance of productivity. In any case, this is my Pitch Hopper:

“Pitch Hopper” ©2019. Sharpie on 3x5 on corkboard with pins. Image by Paul Blumer.

3. Write Out Your Goals and STRATEGIZE

Goals are incredibly useful tools — but they’re only effective if they’re SMART (Specific, Measurable, Achievable, Realistic, and Timely).

My business goals and strategies are still a bit clunky because I’ve never started a freelance writing business before. I’ve done freelance, but I’ve never entrepreneured about it. As I understand it though, business goals are always a work in progress as things change and business grows. Revisit and revise them often.

End of Month Zero

Goal: Make $1000 freelance writing

Strategy: Contract 4 clients

Tactic 1: Pitch everyone I know (at least 20)
Tactic 2: Study cold emailing
Tactic 3: Build a professional website
Tactic 4: Keep writing

By Month 3

Goal: Make $2000 per month

Strategy 1: Build a client list of 10

Tactic 1: Pitch 5 interesting clients per day
Tactic 2: Send my own weekly newsletter full of anecdotes and hilarity
Tactic 3: Get on LinkedIn and spit-polish my profile
Tactic 4: Gobble up articles on SEO and performance monitoring
Tactic 5: Post daily on social media

Strategy 2: Build readership on Medium and earn royalties

Tactic 1: Write a killer article every week
Tactic 2: Network by clapping and linking and following the phenomenal writers I enjoy
Tactic 3: Link all my articles to each other and elsewhere (stay evergreen!)

By Month 5

Goal: Make $4000 per month

Strategy: Maintain a client list 20 strong

Tactic: Pitch and/or upsell 5 clients per week

End of 2020

Goal: Make $9000 per month

Strategy: Build baby build!

Goal: Publish Stirred and Shaken, a bawdy novel about the cocktail world

Strategy 1: Build my audience

Tactic: Publish 2 articles per week about relevant topics

Strategy 2: Write a cocktail column for the food desk of Richmond Magazine

Tactic 1: Nail my assigned eggnog article (link forthcoming)
Tactic 2: Network with bartenders via visits and USBG events

Strategy 3: Get a literary agent

Tactic: Pitch and keep on pitching!

4. Build a Stunning Website

This is your calling card. Your brand is your voice. If you don’t showcase compelling copy on your own website how can you expect anyone to believe you can do it for theirs? Look up dozens of examples and create your own style in your own voice. Clients want authenticity. You be you, as the kids say.

I use Wix. It provides a bit more freedom than SquareSpace and a much easier interface than WordPress. I’m more of a drag-and-drop designer than a learn-some-code designer. My time is more effectively spent writing and pitching and daydreaming.

5. Pitch Everyone You Know

It’s a numbers game. Plain and simple. Success is a percentage. Increase the whole and you increase the slice. And just like selling girlscout cookies or Cutco knives that one awful summer, the first thing to do is pitch all your family and friends.

This has the dual benefit of helping you practice your pitch while also giving some confidence-building early hits. I’m fortunate enough to know several people who own cool businesses so I perused their websites and jotted notes about what I thought was missing. Then I sent emails explaining what I was doing and how I thought I could help.

Cold emailing sucks — until it doesn’t. Think of it as another wordcraft. A brief space to demo your narrative knack, your persuasive prowess, your vibrant voice.

Use empathy to figure out your pitchee’s pain points and solve them. Don’t point out what’s missing. Don’t point out the lifelessness of unstoried images nor tell an executive their website looks like somebody’s webdesign assignment. I did that. It didn’t work. (link forthcoming)

My first pitches:

My father-in-law
His close friend
His other close friend
My dad’s best friend growing up
Marketing Director of my climbing gym
Richmond Magazine’s food editor who’s enjoyed many a cocktail of mine
All of Indeed.com

Of those seven, two are in contract and two are prospects. One is scheduled for followup. And one requires a thoughtful and empathetic re-pitch.

6. Clean Up Your Calendar

I suddenly realized I had about six derelict old calendars and some inexplicable entries I must have written long ago. I jettisoned everything except my shared calendar with my wife and created a new one called Quillpower and scheduled my first client phonecall.

You’re about to have meetings and followup reminders and deadlines. Start organizing now so when the waterfall hits you you’re ready to channel the flow and irrigate your brand. I’ve never missed a writing deadline in my life and I’m not about to start now.

7. Launch before you’re ready

No one runs harder than someone chased by a bear. I’m not ready for this. I’m terrified. So I picked my birthday as an arbitrary launch date and quit my job.

Now I have to start making $2000 per month by the time my emergency savings run out. Else I can’t pay my mortgage or my student loans or my electric bill or my verizon or my…I have two months. Tick tock mothafu*ka!

And all I have to do next (besides the infinite work of building) is decide: To niche or not too niche.