10 Questions If You’re Not Making Enough — or If You Know You’re Meant for More
A Self-Assessment for Entrepreneurs Ready to Lead with Clarity, Not Compromise.
Whether your income feels stalled—or you’re simply ready to stretch into your next level—this assessment was designed to help you identify what’s really at play beneath the surface of your business.
These are the questions I return to most often with private clients. They reveal where tension lives, where your message may be misaligned, and what kind of structural or internal recalibration could shift everything.
This isn’t about diagnosis. It’s about discernment—with yourself, your business, and your voice.
✍️ How to Use This Self-Assessment
Read each question. Choose the answer that feels most true for where you are right now.
Resist the urge to answer from your ideals. This is a no-performance zone.
When finished, scan for patterns: Are you mostly A’s? B’s? Do C’s or D’s dominate? Are any E’s creeping in?
Then scroll down to decode what your patterns reveal—and what to do next.
The Questions
1. How do you feel about charging for your work?
A) Confident. I know my value.
B) I charge, but sometimes worry it’s too much.
C) It feels uncomfortable.
D) I avoid the conversation.
E) I adjust based on what people say they can afford.
2. What’s your first thought when someone doesn’t buy?
A) Not everyone is a fit—and that’s okay.
B) Maybe I should offer a discount.
C) I feel rejected.
D) I assume I did something wrong.
E) I question the whole offer.
3. How often do you share your offers?
A) Consistently—it’s part of how I lead.
B) A few times a week, when I remember or feel confident.
C) Rarely—I don’t want to seem pushy.
D) I assume people already know.
E) Only when I need cash flow.
4. Is your offer clear, simple, and ready to buy today?
A) Yes, and I know exactly how to talk about it.
B) Mostly, but I tend to over-explain.
C) It’s still taking shape.
D) I keep tweaking or hiding it.
E) I’m waiting until it’s “perfect.”
5. How often do you directly invite someone to buy?
A) Frequently—it’s how people transform.
B) Sometimes—I still hesitate.
C) Rarely—I feel nervous.
D) I wait for them to initiate.
E) I hope they’ll just decide on their own.
6. What happens when someone shows interest?
A) I guide them clearly into next steps.
B) I share more, but worry I overshare.
C) I second-guess myself.
D) I avoid responding.
E) I downplay what I offer.
7. How do you feel saying your price out loud?
A) Calm and grounded.
B) A little shaky, but I manage.
C) Awkward—I rush through it.
D) I avoid saying it at all.
E) I offer a discount before they ask.
8. Do you follow up with people who didn’t buy?
A) Yes—it’s part of my process.
B) Occasionally—it feels uncomfortable.
C) Rarely—I feel awkward.
D) I assume they weren’t interested.
E) I tell myself they couldn’t afford it.
9. What’s your biggest hesitation around making more money?
A) None. I’m ready.
B) Fear of outgrowing people.
C) Concern about working harder.
D) I don’t trust myself to hold it.
E) Deep down, I question if I deserve it.
10. How do you feel about the future of your business?
A) Energized. It’s only going up from here.
B) Curious—I want clarity.
C) A bit uncertain.
D) Anxious.
E) I’m questioning whether I can really do this.
What Your Answers Reveal
✨ Mostly A’s — You’re Structurally Ready for More
You’ve built a strong foundation, and now it’s time to expand—cleanly, boldly, and without burnout. You don’t need more hustle. You need refinement. Strategic calibration, higher-level partnerships, and a stronger container for growth.
✨ Mostly B’s — You’re at the Edge of a Clean Breakthrough
You know your stuff. You’ve done the work. But doubt still lingers. With the right support to help you reframe how you hold your voice, your pricing, and your presence—your income could shift far more quickly than you realize.
✨ C’s and D’s — You’re in a Cycle of Hesitation
The expertise is there, but second-guessing is slowing you down. You may be waiting for some elusive permission or “readiness” that never quite comes. You don’t need another course. You need momentum, strategy, and a coach who sees where you’re already strong—and helps you lead from there.
✨ Too Many D’s or E’s — You’re Doing This the Hard Way
If business feels heavy, unclear, or discouraging—it doesn’t mean you’re failing. It means you’ve been trying to build alone. With the right structure, support, and strategy, everything can shift. Ease is not a fantasy. It’s a function of clarity.
🧭 Ready to Lead with Clarity—and Earn Accordingly?
If this self-assessment surfaced more than a few “I’ve been there” moments, you’re not alone. The truth is, most entrepreneurs aren’t missing talent or desire—they’re missing structure that fits who they actually are.
If you’d like my help, here are two distinct ways to work with me, depending on what kind of momentum you’re ready for:
🌿 Grow Your Money Voice
90 days to recalibrate your pricing, your messaging, and your income behavior—without the emotional noise.
This program is designed for entrepreneurs who are ready to stop second-guessing what to charge, how to talk about what they do, or when to make the offer.
If you’ve been stuck in hesitation, overexplaining, or inconsistent earning—this is your reset.
It’s not fluff. It’s not mindset only. It’s structure, clarity, and aligned action—built around your real voice.
Next cohort begins May 22. Click below to learn more.
💎 Lucrative Elite 1:1 - A high-level private mentorship for entrepreneurs ready to lead and earn at their true capacity—without apology, performance, or compromise.
This is a 9-month partnership for those who’ve already built something—and are ready to scale, refine, or restructure it with clarity and integrity.
Whether you’re evolving your business model, expanding your income, or reclaiming your leadership with cleaner lines—this is where it happens.
Private application only. Very limited availability.
No pressure.
Just options.
I’ll have more offers in the near future.
If you’re here, you already sense what’s possible.
And if you’re ready, I’m here to help you build what holds.
—Brian