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Why asking for money feels like physical pain (it literally is)


Issue #154 | August 5th, 2025

Hey there,

In last week's email about making your first sale, I challenged you to make one simple ask: Reach out to someone in your network and offer to solve a problem for them.

Based on the responses I received, I can tell exactly where most of you got stuck.

It wasn't identifying the problem.

It wasn't creating the solution.

It wasn't even knowing who to contact.

It was the ask itself.

"I know exactly who I should reach out to," one reader wrote, "but every time I start typing the message, I delete it. What if they think I'm being pushy? What if they say no? What if this ruins our relationship?"

Sound familiar?

Let's get unstuck.

Quote of the Week

“You have not because you ask not."

—James 4:2

Story of the Week

Why Your Brain Treats Sales Like a Physical Threat

Here's what's actually happening when you're about to ask someone to buy from you: UCLA neuroscientist Matthew Lieberman discovered that social rejection activates the same neural pathways as physical pain.

Your brain literally can't tell the difference between someone saying no to your offer and being physically hurt.

This explains why asking for money feels so visceral and why advice like "just get over it" doesn't work. You're not being dramatic — you're experiencing a genuine neurological response designed to keep you safe.

But here's the thing: Your brain is overreacting. It’s treating a sales conversation like a life-or-death situation.

The Three Big Lies Your Brain Tells You About Selling

Lie #1: "I'm being pushy and annoying."

This comes from what psychologists call the spotlight effect — our tendency to dramatically overestimate how much others judge our actions. The truth? When you offer a genuine solution to someone's problem, you're being helpful, not pushy.

Lie #2: "They'll definitely say no."

Stanford researcher Frank Flynn (no relation to me) found that we consistently underestimate people's willingness to say yes by 50-100%. We assume rejection is the default when, in reality, people buy things they need from people they trust.

Lie #3: "This will ruin our relationship."

Actually, successful transactions often strengthen relationships. When someone pays you for value and sees a great result, they feel good about the exchange. You've solved their problem and they've supported your business — it's a win-win.

The Sales Reframe

Understanding this science allows us to flip the script entirely:

  • Instead of thinking, "I'm bothering them with a sales pitch," try, "I'm offering a solution to their problem."
  • Instead of, "They'll think I'm just trying to make money," remember, "They want their problem solved more than they want to keep their money."
  • Instead of, "This will make things weird between us," consider, "This could be the start of a valuable business relationship."

The Simple Sales Formula That Works

Here's how to make asking for money easier:

  • Lead with their problem: Start the conversation by focusing on their challenge, not your solution.
  • Be specific about the outcome: Saying, "I can help you get more organized," is too vague. Try, "I can help you create a system to manage your emails in just 30 minutes a day." It’s clear and actionable.
  • Make it easy to say no: Phrases like, "If this isn't a fit, no worries at all," remove pressure and paradoxically make people more comfortable saying yes.
  • Price it fairly: Charge enough that you're motivated to deliver great results, but not so much that it feels risky for them.

Your Sales Challenge

This week, practice asking for money with the science on your side:

  1. Choose someone who has a problem you can genuinely solve.
  2. Remind yourself that your fear is real but not rational — a "no" won't actually hurt you.
  3. Remember that people buy solutions to problems they care about.
  4. Focus on their outcome, not your income.
  5. Make the offer and notice that your relationship survives, regardless of their response.

The more you practice selling, the more you'll prove to your brain that it's safe. Each conversation — whether it results in a sale or not — builds confidence for the next one.

Remember: People want their problems solved more than you think. Rejection hurts less than you fear. And successful transactions strengthen relationships more often than they damage them.

Here's to asking with confidence!

Our Next Course Accelerator Starts in 2 Days!

Our Heroic Online Courses Accelerator kicks off this Thursday, August 7th, inside the Accelerate tier of the SPI Community!

What's an accelerator?

A structured, facilitator-led program where a small group of members complete a course together on a set schedule.

Why join?

Because completing an entire course alone is tough. Accelerators bring people together to stay on track and accountable, so you can keep making progress.

Over 7 weeks, you’ll:

Define and design your course: Nail your niche, outline your content, and build a course that delivers real results.

Market and launch: Create a sales page, choose your launch strategy, and prepare for a successful debut.

Create high-quality content: Learn tools and mindset strategies to film, produce, and confidently deliver your course.

This is your chance to stop planning and start building — with the guidance and support to follow through.

Still on the fence? Keep scrolling for a special opportunity that will help you decide.

Join Our Upcoming Live Q&A!

Still unsure about joining our upcoming Heroic Online Courses Accelerator?

We’re hosting a live Q&A tomorrow, August 6th at 9:00 AM PT / 12:00 PM ET, led by Ashley Gore, our Education and Programming Specialist at SPI and the facilitator of this accelerator.

This is your chance to get clarity on how an accelerator works, why it’s one of the most loved things we offer, and what it’s really like being a member of the SPI Community.

Ashley holds a Master’s in Curriculum and Instruction, has over 10 years of experience designing powerful, inclusive learning environments, and has built two businesses of her own.

She’s been in your shoes — and more importantly, she knows exactly how to help you get that online course off the ground.

Cheers,

Pat Flynn

Founder, SPI

Dad Joke of the Week

What do you call a chicken that is afraid of the dark?

A chicken.

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