The Limiting Belief That Prevented Me From Hitting a $10K Month

And how it might be manifesting in your freelance business, too.

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When I was 22, I was a bartender in Washington, DC. One night, a pot-bellied man strutted in and ordered the Capitol’s finest beverage: a Grey Goose and Red Bull. 

At the end of the night, I gave him his $50 tab. While he was small in stature, his generosity wasn’t: He left a $250 tip.

When I entered his tip into the POS, the software short-circuited (the machine wouldn’t accept tips over 300%). I called my manager, Stephen. 

“Damn. I’ll have to call the POS manufacturer,” he sighed. 

“I mean, it’s fine,” I blurted. “Just put in $200 or something.” 

Stephen’s head whipped around. “What? Are you crazy?” he laughed. “The guy paid you $250. Get your money.” 

That night more or less summed up one of my attitudes toward money: Guilt.

Guilt for accepting the man’s money for such little effort. Guilt for bothering my manager to do his, you know, job. 

And this guilt has been costing me ever since. 

What needs to happen to earn $10,000 a month? 

Fast-forward to today. I’m 28 and have traded in serving Long Island Iced Teas for running my freelance writing business. 

Despite my four years of experience, wonderful clients, and a steady stream of inbound leads, I’ve yet to hit that coveted $10,000 milestone (my best month was $9,165 [so close, yet so far]).

I’m well aware this is a vanity metric—there are so many ways to measure business success–but who isn’t captivated by that elusive number?

We could always use more. Hell, in this day and age, we need more (my local Food Town is selling blueberries for $10.99. Send help). 

If your business is in this position, you’re probably wondering: 

What needs to happen to hit that number? A new service offering? A séance in the scented chambers of a reiki money practitioner? 

I couldn’t figure this out on my own. So I hired business coach Nick Bennett—and one conversation with him totally transformed the way I see money. 

Things are not always as they appear

“You don’t seem motivated.”  

In October, I went on a call with a potential ghostwriting client. I told Nick I’d send her a proposal later that week. Here’s our transcript (reduced for length): 

Nick: “You should be able to send a proposal in 20 minutes. It’s funny–you don’t seem motivated by money.” 

Me: 

Nick: “What’s preventing you from sending that proposal ASAP?”  

Me: “I’m buying myself time. I’m afraid I won’t be able to juggle them. 

I see freelancers handle 8-10 clients at a time and that’s terrifying. What if everyone needs something all at once? Then I’m up until 2 AM on the verge of tears because I’m about to let everybody down?” 

Nick: “Is this a real problem or a story you told yourself about something that could happen?” 

Me: “It’s a combination of both. 

Of course, we have limits on how many projects we can handle. But I tell myself that if I didn’t struggle, the work isn’t worth paying for.

So I’ll often self-sabotage and complicate things so the writing feels ‘worthy.’

My worst fear is letting a paying client down. They’ll feel ripped off and I’ve basically stolen from them.”

Nick: “Three things:

1. Fear comes not from a lack of skill or ability but from a lack of preparation.

2. There is immense value in executing things repeatedly and efficiently. 

3. It’s your business and you can move deadlines if you need to. 

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Getting out of your own way

Nick’s comment was a punch to the spleen. I’d always prided myself in being Type A, (where my Virgos at?) the kid in elementary school with color-coded planners and straight A’s. “Unmotivated” was not in my vocabulary.

But Nick was both wrong and right. 

I was unmotivated in the sense that nothing was stopping me from sending the proposal aside from fear. 

But that fear? It came from the polar opposite of “unmotivated.” It stemmed from being so driven that I believed every project needed to cost me blood, sweat, and tears to be worthwhile. 

The result: 

• I’d underestimate my bandwidth and efficiency…and let thousand-dollar clients slip through my fingers. All. The. Time. 

How you can break the cycle

Either you’re reading this thinking I have the business acumen of an orangutan or you can relate. If it’s the latter? This is what we should internalize from Nick’s advice: 

1. Fear comes not from a lack of skill or ability but from a lack of preparation.

Imagine a potential ghostwriting client comes to you. How can you prepare so you’re confident in your execution? This could be: 

• A Templatized Proposal. A simple template in BoldSign that lets you send contracts in minutes. 

• Pre-Written Interview Questions: A list of 10-15 questions for your client that you’ll base your content on. 

• Notion Systems: A Notion home base you can copy-paste for different clients that include a content calendar, recorded calls, and proven LinkedIn templates (Ryan Law’s course on Writing Thought Leadership is great for this).

So instead of going, “Shit I don’t have the capacity for this I’m going to burn out but agh the money” you go, “I have everything in place so this is seamless.” * 

* There will be a learning curve with your first few clients. But once you get the process down this should go much faster. 

2. There is immense value in executing things repeatedly and efficiently.

Say you want to buy a pair of sneakers. Do you care that Converse put in blood, sweat, and tears to craft your shoes?

No—you care that it was created ethically and sustainably and at a reasonable price point. If that means it was put together in an assembly line in just 30 minutes, cool. 

In other words: The only thing that matters is value. 

The same goes for your services. All your client wants is results. If you feel guilty charging high rates because your process is ‘easy’ and ‘systemized’ you’re missing the point. 

3. It’s your business and you can move deadlines if you need to. 

Of course, there are times when life gets bananas and you can’t meet deadlines. Instead of descending into agony, guilt, and heart-thumping anxiety, remember: 

• You are the boss. If you need to move a deadline, do so. 

• This is marketing, not medicine. Nobody will die if you don’t submit a LinkedIn post on time. (Although a marketer, somewhere, might get an inexplicable chill down their spine). 

How your fear might be self-sabotaging you

All of us have big goals. But none of us realize how often our fear subconsciously sabotages us from reaching them. 

A simple mental exercise for you to try: 

“If I accomplish [insert goal here] I’m afraid that…” 

I know you’re probably like, “Alice, I’m not afraid of hitting $10,000 are you insane” but do me a solid and pause. Think. Take a moment.

Maybe you’re afraid that it’ll mean burnout and disappointment because you equate money to struggle. (Like yours truly). 

Maybe you’re afraid that it’ll change how people see you because you associate money with greed.

Whatever comes up, don’t dismiss it. The first step to hitting your goals is recognizing how you’re standing in your own way. ♥️

P.S. If this newsletter helped you–and only if it helped you–I’d love it if you subscribed. I mean, you made it to the bottom of this page.

That’s a good sign, amiright?

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*This post is sponsored by Novo. All opinions are my own. Novo Platform Inc. (“Novo”) is a fintech, not a bank. Banking services provided by Middlesex Federal Savings, FA. Member FDIC.