- PPF Points
- 2,100
From Zero to Holy Crap, I’m Booked Solid—My Freelance Rollercoaster
Alright, let’s not sugarcoat this: when I dipped my toes into freelancing, I had jack. Zero portfolio. Nada in terms of experience. Didn’t know a soul, didn’t have a mastermind plan—just vibes and a weird amount of confidence fueled by coffee.
Fast forward 90 days and, boom, my calendar’s full, cash flow’s way better than my old office gig, and I’m actually turning down work. Yeah, that was wild.
So here’s the messy, honest play-by-play of how I hustled from straight up nothing to, well, mildly killing it. No clickbait hacks, no “manifestation” nonsense—just what I actually did, what sucked, what worked, and how you could maybe avoid my facepalm moments.
And if you’re just starting out, or you’re stuck in that classic broke-then-rich-then-broke-again loop? This rant’s for you.
Let’s get into it.
Month One: Gettin’ Real (Clients Don’t Just Magically Show Up, Sorry)
Step One: Grab a Skill That Pays The Bills
Real talk, this is where most newbies get lost in the sauce. You want to freelance, but what are you actually gonna sell? Folks keep bouncing from logo design to copywriting to selling sea monkeys—don’t.
Me? I did this:
Main lesson? Pick something. Doesn’t matter if you feel like a clueless imposter—just stick with one lane.
Step Two: Whip Up an Offer People Can’t Ignore
Forget offering “writing services.” Snooze. I went with:
”I help coaches & creators turn half-baked ideas into blog posts and newsletters that actually pull in readers and sales.”
Now I seem like a mission partner, not just another keyboard slapper for hire.
Portfolio? Hah. Built one in Notion—just a single page with:
Not pretty, but done beats perfect.
Step Three: Pitch Like a Madman (Daily)
The rule: 5 pitches a day. No whining, no “I’ll catch up on Saturday.”
Where’d I find folks?
My cold DM was basically:
“Hey [Name], huge fan of your [thing]. Random Q: need help with content? I help busy folks like you turn their ideas into posts that get traffic, not crickets. Wanna see some samples? No big deal either way. Cheers, [me].”
Short, nice, not desperate.
First Month Scoreboard
Take home: about $800. Not buying a yacht, but it made all this feel real.
Month Two: More Clients, Less Guesswork
Now things got spicy. My new motto: double down on what works, crank up the quality.
Step Four: Overdeliver Like a Showoff (Even for Small Change)
Every client from Month One? Treated them like VIPs. Early drafts, longer articles, Loom walkthroughs, free brainstorming. Because good feedback and word of mouth conquer all.
Result? Unsolicited referrals, return clients, and suddenly—I’m not scared to charge more.
Step Five: Secure the Bag (Recurring Retainers)
Someone asked, “Can you do this every month?” Uh, YES.
Set up basic packages:
In two weeks, locked in 2 recurring clients. That’s when it hit me: stable income beats relentless gig chasing, every time.
Step Six: Go Public (Kinda)
Until now, it’s been all cold outreach. Time to build an audience:
That got me noticed. And eventually, randoms started sliding into my DMs asking for quotes. Wild.
Month Two Wrap:
Month Three: Full Calendar, Higher Rates, No Burnout
Now things started to click (and get kinda stressful).
Step Seven: Don’t Catch the Burnout Plague (Systems FTW)
To avoid melting down, I set up:
Suddenly I wasn’t scrambling at midnight anymore.
And that, my friend, is basically how I stumbled my way from “who the hell are you?” to “sorry, I’m booked for this month.” No magic. Just picking one thing, pitching consistently, not being a douche—and learning fast.
Go get ‘em. Don’t overthink it.
Alright, let’s not sugarcoat this: when I dipped my toes into freelancing, I had jack. Zero portfolio. Nada in terms of experience. Didn’t know a soul, didn’t have a mastermind plan—just vibes and a weird amount of confidence fueled by coffee.
Fast forward 90 days and, boom, my calendar’s full, cash flow’s way better than my old office gig, and I’m actually turning down work. Yeah, that was wild.
So here’s the messy, honest play-by-play of how I hustled from straight up nothing to, well, mildly killing it. No clickbait hacks, no “manifestation” nonsense—just what I actually did, what sucked, what worked, and how you could maybe avoid my facepalm moments.
And if you’re just starting out, or you’re stuck in that classic broke-then-rich-then-broke-again loop? This rant’s for you.
Let’s get into it.
Month One: Gettin’ Real (Clients Don’t Just Magically Show Up, Sorry)Step One: Grab a Skill That Pays The Bills
Real talk, this is where most newbies get lost in the sauce. You want to freelance, but what are you actually gonna sell? Folks keep bouncing from logo design to copywriting to selling sea monkeys—don’t.
Me? I did this:
- Jotted down stuff I sorta liked and wasn’t awful at
- Stalked Upwork, Twitter, Reddit, and a bunch of random Facebook weirdos to see what people emptied their wallets for
- Picked content writing for online peeps. Not ‘cause I’m Shakespeare—because I could learn fast, people need it, and there’s dough in it.
Main lesson? Pick something. Doesn’t matter if you feel like a clueless imposter—just stick with one lane.
Step Two: Whip Up an Offer People Can’t Ignore
Forget offering “writing services.” Snooze. I went with:
”I help coaches & creators turn half-baked ideas into blog posts and newsletters that actually pull in readers and sales.”
Now I seem like a mission partner, not just another keyboard slapper for hire.
Portfolio? Hah. Built one in Notion—just a single page with:
- Who I help
- What I do
- 2 fake-but-real-looking articles I whipped up for myself
- A ‘Book a Call’ button
Not pretty, but done beats perfect.
Step Three: Pitch Like a Madman (Daily)
The rule: 5 pitches a day. No whining, no “I’ll catch up on Saturday.”
Where’d I find folks?
- Twitter: replied to people moaning about content struggles
- Reddit: r/freelance, r/Entrepreneur, the usual hangouts
- Facebook: actually participated, didn’t just spam
- Job boards: ProBlogger, Dynamite Jobs, We Work Remotely
My cold DM was basically:
“Hey [Name], huge fan of your [thing]. Random Q: need help with content? I help busy folks like you turn their ideas into posts that get traffic, not crickets. Wanna see some samples? No big deal either way. Cheers, [me].”
Short, nice, not desperate.
First Month Scoreboard
- 100-ish pitches
- 15 replies
- 3 tiny gigs ($150–$300 range)
- One client: “If this works, I’ll need more.” Spoiler, it worked.
Take home: about $800. Not buying a yacht, but it made all this feel real.
Month Two: More Clients, Less GuessworkNow things got spicy. My new motto: double down on what works, crank up the quality.
Step Four: Overdeliver Like a Showoff (Even for Small Change)
Every client from Month One? Treated them like VIPs. Early drafts, longer articles, Loom walkthroughs, free brainstorming. Because good feedback and word of mouth conquer all.
Result? Unsolicited referrals, return clients, and suddenly—I’m not scared to charge more.
Step Five: Secure the Bag (Recurring Retainers)
Someone asked, “Can you do this every month?” Uh, YES.
Set up basic packages:
- 2 posts/month: $500
- 4 posts/month: $950
In two weeks, locked in 2 recurring clients. That’s when it hit me: stable income beats relentless gig chasing, every time.
Step Six: Go Public (Kinda)
Until now, it’s been all cold outreach. Time to build an audience:
- Shared mini-case studies on Twitter
- Dropped tips and real talk about freelancing
- Posted little wins (with clients’ permission, duh)
That got me noticed. And eventually, randoms started sliding into my DMs asking for quotes. Wild.
Month Two Wrap:
- 2 retainer clients @ $950/month
- 2 new projects ($600 total)
- Pulled in about $2,500
- Waitlist?! (I know, right.)
Month Three: Full Calendar, Higher Rates, No BurnoutNow things started to click (and get kinda stressful).
Step Seven: Don’t Catch the Burnout Plague (Systems FTW)
To avoid melting down, I set up:
- Notion onboarding page for new clients (‘cause I kept losing their info, oops)
- Super clear timelines and Google Drive folders for drafts
- Stripe invoices, Notion spreadsheet for keeping track of who actually paid
- Weekly check-ins with clients via email or Loom vid
Suddenly I wasn’t scrambling at midnight anymore.
And that, my friend, is basically how I stumbled my way from “who the hell are you?” to “sorry, I’m booked for this month.” No magic. Just picking one thing, pitching consistently, not being a douche—and learning fast.
Go get ‘em. Don’t overthink it.
