Day 1
Both emails arrived before noon on a Monday. One confirmed interest in a story I'd write about a trip to North Dakota. The other offered an unsolicited assignment on the bonds formed after a retired soldier with PTSD mailed his Purple Heart to a NASCAR driver.
These two deals sold out in 2 hours and 14 minutes, exceeding half my typical monthly freelance salary. After texting my editor SUCCESS about the big morning, he asked about my best month ever and challenged me to beat it, documenting the journey.
My peak as a solopreneur was September 2015 at $14,772. I haven't topped it since. Scanning my story ideas list yields tumbleweeds—no clear path to $14,772.01.
I accept the challenge anyway.
"To achieve my best month ever, I must see myself not as a helpless man on a wire, but as the pilot."
Day 2
It's 4:40 a.m., and I can't sleep. Failure looms, but what bothers me more is avoiding something I dread. Writing stories? I love it. Selling them? That's the dentist appointment I hate.
Wait—scratch that. I love selling. I hate trying to sell.
I vow no 80-hour weeks or 600 pitches. Success must be sustainable and true to me, just better. Hitting $14,772.01 demands intention, swallowing doubts, taking risks, and breaking my usual rules.
I dive into my story ideas and brainstorm.
Day 3
I call Pat, my salesman mentor. He urges filling my pipeline—advice he's given me countless times.
"Pipeline" evokes Air Force One, where Harrison Ford dangles helplessly behind the jet. That's often me as a solopreneur: connected yet at the mercy of external forces.
For my best month, I shift to pilot mode.
Like a pilot scanning ahead, I eye my empty pipeline from mid-December to mid-January. Solution: a baseball season preview for a magazine I've contributed to. I had the idea last year but procrastinated past deadline.
No repeats. I pitch it. The sale matters less than the intentionality. Thunderclap #1: Intentional selling puts me in control.
Day 8
Progress: No baseball response yet, but four assignments accepted. Two sold out, and I proactively pitched a low-hanging apple. Direct, targeted emails sealed them. At $11,500, this feels achievable—maybe surpassable.
Day 17
Unbelievable streak: Three $2,000 stories sold in three days, including baseball. Each broke my rules.
Standout: A Green Beret shot four times in Afghanistan, who recovered over three years and found racing his Porsche eased PTSD. Violations:
Except in rare cases, new clients rarely justify effort. A solid idea for an established client beats a great one for unknowns.
Don't pitch multiple stories to one client simultaneously—save the second for later, especially newbies.
Don't shop the same idea widely at once. One acknowledged but ghosted; I sold elsewhere. Then they circled back post-sale, eager to collaborate.
The Green Beret sale hits $17,800—past target. Recalculating (adding the three easiest to my prior peak): New goal, $20,272.01. Eighteen days ago? Laughable. Now? Why not?
JONATHAN SCHOEPS / SHUTTERSTOCK.COM
Day 24
House money means experimenting—even tackling sales fears like seeming pushy or desperate.
Lunch with salesman Matt reveals his tactics, like a photo of someone pounding a door: "I know you're there." Too bold for me.
Where's the persistence line? "Professional perseverance," he says.
Thunderclap #2: I'm aggressive as a journalist; be so in sales. Merge storytelling and selling.
Idea: Clients commit to X stories yearly at X rate. No takers before—fear of no stifled it. Now? Excitement for yes.
Pitch Southwest Airlines Employee Magazine, nodding to their bold culture. Result: No from them, but another client commits blindly unprompted.
Day 25
4:22 a.m., insomnia from excitement. Reviewing techniques tried and untried—it's fun. Six years viewing sales as YouEconomy drudgery? Shifted to mastery mindset.
At $20,100. One more seals it.
Day 30
The finale I hesitated to share.
"Avoid distractions"? Nah—ideas spark amid them. Surfing for Rush band news (they disbanded), I find Rush Camp: a Pennsylvania resort weekend for fans dissecting Geddy Lee, Alex Lifeson, and Neil Peart.
Bear-to-honey vibes. Subculture gold for an editor seeking them. But I'm a fan—pitching as participant risks foolery. Rule #1: Don't pitch what makes me look dumb.
Falconry pitch last year? Hesitated on foolishness, sold elsewhere anyway.
Coach Michael advised weaponizing doubt. Rule: "Don't hand editors no-reasons."
Quest demands difference. Casual email teases corny pitch. Response: "Ha! Love corny. Send it."
Thunderclap #3: No longer fear 'no.'
Days pass. Assume rejection. Then: Buy! Hints at double fee. We placeholder $500 above expected.
Day 30, two hours early: $22,600 total. Even stripping starters, new record. Friends will chuckle at Rush Camp clincher.
Started skeptical; ended transformed. Rules? Obsolete. Liberating.
Weirdly: I'll never break them again.
They're not mine anymore.
