Pricing Your Services with Confidence (and Why Silence Is Your Secret Weapon)

Good morning,

One of the most common questions I hear—especially from smart, experienced professionals building portable income—is this:

“How do I price my work with confidence… without feeling awkward or apologetic?”

That’s exactly what we explored on Tuesday night’s Portable Income Call, and it’s worth revisiting—because pricing issues are rarely about math.

They’re about mindset.

Pricing Isn’t a Math Problem

It’s an emotional one.

Most pricing discomfort comes from thoughts like:

• “What if I scare them off?”

• “What if someone else is cheaper?”

• “Am I really worth that?”

If any of that sounds familiar, you’re in good company. Almost everyone feels this way at the beginning—even people with decades of experience.

A Critical Reframe

Clients are not paying for your time.

They’re paying for:

• Relief from a problem

• Fewer mistakes

• Faster clarity

• Better decisions

• Peace of mind

If you’re over 50, you’ve solved thousands of real-world problems already. You’ve seen patterns. You’ve lived through consequences. You know what doesn’t work just as clearly as what does.

That perspective has real value—whether you charge for it yet or not.

Why Marketplaces Like Upwork Feel Strange at First

Upwork is a marketplace, not a job interview.

Early work often looks like:

• Smaller projects

• Lower prices

• “Audition” assignments

That doesn’t define your worth. It creates momentum.

Think of those early projects as paid tryouts. Once trust is established, pricing almost always rises—and often faster than people expect.

Three Simple Pricing Approaches That Work

You don’t need complicated formulas.

1. Fixed-Price Projects
   Best when the outcome is clear and well-defined.
   

2. Starter Offers
   A small “yes” that lowers risk, builds trust, and opens the door to larger work.
   

3. Simple Packages (Good / Better / Best)
   Let the client choose—without you having to justify or negotiate endlessly.

The most confident pricing is often the simplest to explain.

Want the Full Pricing Framework?

If pricing still feels fuzzy or inconsistent, this is where going deeper helps.

Inside The Freedom Vault, members get the full discussion on pricing:

• How to choose between hourly, fixed, and packages

• How to state your price calmly in messages

• What to say (and not say) when a client hesitates

• How pricing naturally evolves as momentum builds

If you’re a member, this training is already waiting for you inside the Vault.

If you’d like to gain full access to the training on pricing and over 30 other topics that help you succeed with your portable income…

The Most Powerful Pricing Skill of All

This one surprises people.

When you state your price…
say it calmly—and then stop talking.

No apologizing.
No over-explaining.
No filling the silence.

That pause isn’t rejection.
It’s the client thinking.

And yes—it gets easier every time you do it.

A Final Thought

Not everyone will say yes to your price—and that’s a good thing.

If everyone says yes, you’re probably underpricing.

The right clients recognize value when they see it.
Those are the relationships that last—and pay well.

Thank you for being part of this community and for continuing to show up for your next chapter of work.

See you Tuesday.

Warmly,
Winton

Barefoot Consultants
Portable income, built with clarity and confidence

P.S. If pricing is the one thing slowing you down, The Freedom Vault was built for exactly this—clear training, examples, and practical guidance you can use immediately.