The Quest for My Best Sales Month Ever

UPDATED: August 2, 2022
PUBLISHED: August 4, 2022
The Quest for My Best Sales Month Ever

Day 1

The two emails come before noon on a Monday. One confirms interest in a story I’ll write about a trip to North Dakota. The other offers me an unsolicited assignment to write about the relationships that formed after a retired soldier suffering from post-traumatic stress disorder sent his Purple Heart to a NASCAR driver.

Sold in 2 hours, 14 minutes, those two deals represent more than half a month’s typical pay for a freelance writer like me. After I tell my editor at SUCCESS about the great morning, he wonders what my best month ever was. He asks if I want to use today as a springboard to try to beat it and write about the ups and downs along the way.

The most lucrative month of my solopreneur career was September 2015. I made $14,772. I haven’t come within sniffing distance of that since. I look at my story idea list and tumbleweeds blow by. I don’t see a path to reaching my big goal of $14,772.01.

I tell the editor I accept his challenge anyway.

Day 2

It’s 4:40 a.m., and I can’t sleep. I’m going to fail, which I don’t mind so much, but I do mind that I’ll fail doing something I hate. I feel like I agreed to go to the dentist every day for a month. I love writing stories, but I hate selling them.

“To have my best month ever, I have to see myself not as the helpless man on a wire but as the pilot.”

Wait. Scratch that. I love selling. I hate trying to sell.

I vow that I will not work 80 hours a week or pitch 600 stories. I don’t want to do those things long term, so I won’t do them short term. I want whatever success I find pursuing my goal this month to be repeatable. I want to still be me, only better. The only way to $14,772.01 is to force myself to be intentional, to swallow doubts, to take chances I don’t normally take and to break rules I normally follow.

I open my story ideas list and brainstorm.

Day 3

I call Pat, a salesman friend who has been an invaluable mentor to me. I tell him about this quest, and he tells me to use it to fill my pipeline, a variation of advice he has given me 57 billion times.

When he uses the word pipeline, I think of the movie Air Force One. At the end, Harrison Ford (playing the president) dangles from a metal cord behind a jet as it flies through the air. He has no control as wind and the speed of the plane throw him across the sky. That’s how I often feel as a solopreneur—connected, but prone to the forces around me.

To have my best month ever, I have to see myself not as the helpless man on a wire but as the pilot.

Like a pilot, I look to the distance. It’s only April, but I think about when my pipeline always runs empty—from mid-December to mid-January. What could I write then? The answer: A story for a baseball season preview magazine for which I have written occasionally. I had an idea last year, but the pitch deadline was far away, I had other stuff to do and I put it off. When I finally got around to pitching, it was too late.

I won’t repeat that mistake. I send the pitch. Whether the editor buys the story is almost beside the point. The intentionality is the point. That thought hits me like a thunderclap, the first of three I’ll have over these 30 days: Intentional selling gives me control.

Day 8

So far, so good. No answer on the baseball story yet, but I agree to terms on four others. I had two of them all but sold and a third was an apple waiting to be picked. In the spirit of intentionality, I wrote direct and purposeful emails to finalize them. At $11,500 already, I start to think this could happen easily, and I wonder how much further I can push my milestone.

Day 17

I don’t know what the heck is going on right now, but everybody is saying yes to everything. Three days in a row I sold stories worth $2,000 each, including the baseball story. To sell each, I broke or bent rules I normally follow.

A piece I sold about a Green Beret who was shot four times in Afghanistan, spent three years recovering and discovered that driving his Porsche on racetracks helps with his PTSD deserves attention. The sale violated three guidelines I typically follow:

  1. Except in rare circumstances, pitching new clients is rarely worth the effort. A decent idea with an established client is better than a great idea with an unknown client.
  2. Don’t pitch the same client more than one story at a time. Two “yes”s is unlikely, and it’s better to save the second idea for later. This is especially true for a new client.
  3. Don’t pitch more than one publication the same idea at the same time. The first publication acknowledged receipt of the pitch but never expressed interest in it. After two weeks, I sold it to someone else. An hour after I closed that deal, the first editor said he wanted to buy it. I had long worried this scenario would make me look foolish. Instead it showed my work was desired. That editor told me to keep pitching him because he wanted to work with me.

The sale of the Green Beret story pushes me to $17,800—well past my goal. I decide that counting the two stories that prompted my goal plus the one you are reading made things too easy. So I add the total from those three to my previous high-water mark and come up with a new goal: $20,272.01. Eighteen days ago, I would have laughed at this as impossible.

Today I think, why not?

Day 24

I’m playing with house money, so I will try anything, even addressing one of my biggest fears about sales: Being seen as too annoying, too aggressive or maybe even desperate.

I have lunch once a month with my friend Matt, a salesman who has been crushing it lately. He tells me about tactics he uses that I never would. He showed me a picture he sends to clients who cut off communication. It’s of a man and woman holding a giant log against a door to knock it in. The text says, “I know you’re in there.”

I would never send that, not even now. When I ask him where the line is between aggressive and annoying, he responds like he has been waiting for me to ask. “Don’t think of it as annoying,” he says. “We call it ‘professional persistence,’ and there’s a big difference.”

This is thunderclap No. 2. I’m aggressive as a reporter, and I should be at least as aggressive trying to sell stories as I am reporting them. For reasons I can’t explain, I have long considered selling a story and creating a story as separate. Now I’m moving toward a more holistic approach.

I concoct a way to apply Matt’s prodding. I’ve often wanted for clients to put me on contract—X amount of stories per year for X amount of dollars. Nobody has agreed to do so, so I stopped asking. Would a client meet me halfway—agree to give me another assignment without knowing what that assignment is?

Prior to this month, I would have chickened out on the idea for fear of being told no. Now I’m excited about the possibility of a yes.

The target client is Southwest Airlines’ employee magazine. Southwest became the largest carrier in America by embracing bold ideas, which I reference in my proposal. Odd outcome: Southwest said no, but another client commits to an unknown next assignment without me even asking.

Best Month Ever Side Bar

Day 25

It’s 4:22 a.m., and I can’t sleep again, albeit for a good reason: I’ve been running through the different sales techniques I’ve tried and all the others I haven’t had a chance to try yet.

I never thought I’d say this, but this is fun. Whether I will sustain that attitude beyond this month, I can’t say. For six years, I have viewed trying to sell as an unhappy consequence of being in the Gig Economy. Now I see it as a skill to be mastered.

I’m at $20,100. One more story will push me past the new goal.

Day 30

Oh, gosh. I can’t believe I’m going to tell this part.

“Avoid distractions” is not on the list of changes that occurred to me this month. It probably should be, but ideas often come to me when I’m distracting myself. Last week, I surfed around to see if there was anything new about my favorite band, Rush. It was an incredible waste of time—they broke up a year ago, so there’s still no news to be had.

I stumbled across Rush Camp, a weekend at a resort in Pennsylvania for fans to get together to talk about how much they love the great philosophers from the great white north—Geddy Lee, Alex Lifeson and Neil Peart.

I felt like a bear finding out about Honey Camp. I started daydreaming about going to Rush Camp and writing a story. I’m a sucker for a good subculture story, and I know an editor who is looking for something like this. But it’s far easier to pitch a subculture I am an observer of rather than a member, in the same way I can say whatever I want about my family but you can’t.

Before I could type the first sentence of a pitch, doubt kicked in—real, legitimate, 1,000-pound-weight-on-my-chest doubt. My No. 1 inviolate rule for pitching is “don’t pitch anything that makes me look like a fool.” And “send me to Rush Camp” sounds… well, it sounds ridiculous. I can’t pitch that can I?

Last year, I wanted to write about falconry. I crafted a pitch, worried I’d look foolish pitching it, and wavered on sending it. When I finally did, the editor said he had just commissioned someone else to write about falconry. Later, another publication I thought about pitching but didn’t ran a story about falconry, too.

“This became thunderclap No.3: I am no longer afraid of hearing the word no.”

Early in this month-long process, I called Michael Robert Moore, my coach when I first became a solopreneur, to ask for advice. He suggested the next time I had a falconry-esque idea that I use my misgivings in the pitch. I didn’t want to. “Don’t give editors a reason to say no, they’ll come up with enough on their own,” is another of my “rules.”

But this has all been about doing things differently. I sent my target editor a borderline unnecessary email so I could (casually) mention I had a nerdy pitch. Her response: “Ha! I like nerdy pitches. Bring it on.”

I ventured as far outside my comfort zone as I’ve ever been with that pitch. I was proud that I swallowed multiple reasons against sending it and embraced the singular reason in its favor—the editor might say yes. This became thunderclap No. 3: I am no longer afraid of hearing the word no.

That alone would make this whole ordeal a success.

A few days went by with no response. I assumed the editor hated Rush (concerts are 99% men) and thought the idea was so foolish she was going to revoke the other assignments I owed her.

Finally she responds. Not only does she buy the pitch, she hints it might be worth twice as much as I was hoping. We agree to revisit the fee after I attend Rush Camp and set a “placeholder” price at $500 more than what I hoped for.

The agreement comes on the last day, two hours before the deadline. It pushes my total to $22,600. Even if I take out the running start—the two stories on Day 1 that prompted the quest, plus the fee for this story—I still set a new personal record. My longtime friends will think it’s absolutely hilarious that Rush Camp pushed me over the edge.

I started the quest for my Best Month Ever with low expectations. I thought I’d have a good month and learn new tricks. I wasn’t expecting to have my entire worldview of selling blown up. I had no idea how much I held to rules that now seem contrived at best and counterproductive at worst. I had no idea how liberating ignoring those rules would be.

And here’s the weird thing: I will never break any of them again.

Because they aren’t my rules anymore.

This article originally appeared in the September/October 2019 issue of SUCCESS magazine and has been updated. Photo by mavo/Shutterstock  

Matt Crossman is a writer based in St. Louis. He writes about sports, travel, adventure and professional development. Email him at [email protected].