The 100 No’s Challenge: Stop Being Afraid and Ask for More
When I started my Fractional CMO business, I played it safe.
I set my prices based on what I thought clients would say yes to, not what I was actually worth. I hesitated to reach out to bigger clients because I assumed they wouldn’t be interested.
I avoided asking for collaborations with people I admired because, deep down, I was afraid of hearing “no.”
Then, one day, I had a conversation with a mentor that changed everything.
He told me: “If you’re not getting rejected, you’re not asking for enough.”
That hit me hard.
I realized I was spending all my energy protecting myself from rejection instead of pushing myself toward real opportunities.
So, I decided to change my mindset. Instead of avoiding “no,” I started chasing it.
I made a goal to collect 100 rejections as fast as possible. 100 No’s.
✅ I raised my prices and quoted higher numbers.
✅ I pitched myself to big-name podcasts and live events.
✅ I cold-messaged decision-makers who I assumed would ignore me.
And guess what? I didn’t get 100 rejections.
I got way more YES’s than I expected.
The lesson? The biggest opportunities in your business are sitting on the other side of an uncomfortable ask.
That’s what this week’s GRIT Challenge is about.
Step 1: Understand the Rejection Mindset Shift
Most of us avoid rejection because it feels personal—like it’s a reflection of our worth. But rejection isn’t about you—it’s about the other person’s timing, needs, and priorities.
Instead of fearing rejection, reframe it as progress. Every "no" gets you closer to a bigger, better yes.
🔹 Think about it: How many potential clients, collaborations, or opportunities have you already lost because you were too afraid to ask?
This week, let’s change that.
Step 2: The 10 Asks Challenge
Your challenge is simple: Make 10 uncomfortable asks this week.
These asks should push you outside your comfort zone—whether it’s pricing, outreach, or collaborations.
Examples of Asks You Can Make:
✅ Raise your prices – Quote a higher price than usual and see what happens.
✅ Cold outreach – Message a dream client, investor, or collaborator.
✅ Ask for referrals – Reach out to your existing clients and ask them to introduce you to one person.
✅ Pitch yourself for a speaking event, podcast, or media feature.
✅ Follow up with a past lead who ghosted you.
✅ Negotiate better terms on a deal.
The goal isn’t to get 10 YES’s. The goal is to get comfortable with hearing NO.
Step 3: Track & Celebrate Your No’s
Every time you get a no, log it. Keep a simple Rejection Tracker.
Why track your rejections?
Because data kills fear. Once you start seeing patterns, you’ll realize that rejection isn’t as scary as you thought.
Rejection Tracker Example
📥 Download: Rejection Tracker Excel File
Step 4: Flip Rejections Into Opportunities
Here’s a secret: Most No’s aren’t final.
💡 How to Turn a No into a Future Yes:
- Ask for feedback – I understand now isn’t the right time, but could I ask what would make this a yes in the future?”
- Follow up later – Timing is everything. Many no’s turn into yes’s if you check in a few months later.
- Keep the relationship open – If someone says no, don’t disappear. Engage with their content, send value, and stay in their orbit.
🫵 Weekly Challenge
👉 Make 10 uncomfortable asks.
- Write down 10 bold asks you’re going to make.
- Start today—send your first uncomfortable ask NOW.
- Track your rejections and celebrate them!
💡 Remember: Every No gets you closer to a game-changing Yes.
📌 Community Bonus
- If you’re part of the SoloGrit community, post in the SoloGrit community about the event you’re joining or what you learned from it.
- Engage with peers by providing encouragement or feedback on their updates.
- Midweek, post an update on your progress to celebrate small wins and inspire others.
Together, we grow with G.R.I.T.
Cosmin Gabriel
I'm on a journey to connect Leadership Solopreneurs to succeed together through a SoloGrit mindset.
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