"And if it seems evil to you to serve the LORD, choose for yourselves this day whom you will serve... But as for me and my house, we will serve the LORD." - Joshua 24:15
There's a meeting you've been avoiding for months.
Maybe it's with the investor who could fund your business. The client who could 10x your revenue. The mentor who could unlock your next level. The partner who could change your trajectory.
You know exactly who I'm talking about. Their name just flashed in your mind.
You've rehearsed the conversation a hundred times. You've written and deleted seventeen different emails. You've found forty-three reasons why "now isn't the right time."
The Anatomy of Avoidance
Let's diagnose what's really happening when you avoid that crucial conversation:
You tell yourself: "I need to be more prepared" Translation: I'm afraid they'll say no
You tell yourself: "The timing isn't right" Translation: I'm afraid I'm not enough
You tell yourself: "I don't want to seem pushy" Translation: I'm afraid of rejection
You tell yourself: "I'll reach out next week" Translation: I'm afraid of success
That last one catches people off guard. But sometimes we're more afraid of success than failure. Because success requires us to become someone new, and change even positive change is terrifying.
Why Discomfort Is Data
Your nervous system is giving you information. The fact that this meeting makes you uncomfortable means one of two things:
It's dangerous (unlikely most business meetings won't kill you)
It's important (very likely your subconscious knows this could change everything)
Discomfort is your internal GPS telling you that something significant is on the other side of this conversation.
The bigger the discomfort, the bigger the potential impact.
The Three Types of Conversations You're Avoiding
Type 1: The Money Conversation
This is with someone who could significantly change your financial situation:
The investor who could fund your vision
The client who could become your biggest account
The employer who could double your salary
The partner who could scale your business
Why you're avoiding it: Money conversations feel transactional and you don't want to seem greedy.
Reality check: Business is about value exchange. If you solve their problem, they should pay you well for it.
Type 2: The Opportunity Conversation
This is with someone who could open doors you can't open yourself:
The industry leader who could endorse you
The connector who knows everyone you need to meet
The mentor who's achieved what you want to achieve
The collaborator who complements your skills
Why you're avoiding it: You feel like you're asking for a favour.
Reality check: Successful people got successful by helping other successful people succeed. You're offering them a chance to invest in potential.
Type 3: The Truth Conversation
This is with someone who needs to hear something difficult:
The business partner who isn't pulling their weight
The client who's scope-creeping and not paying fairly
The team member who's toxic but talented
The mentor who's giving you bad advice
Why you're avoiding it: Confrontation feels uncomfortable and risky.
Reality check: Avoiding difficult conversations doesn't make problems disappear. It makes them worse.
The Five Stages of Meeting Avoidance
Stage 1: Denial
"I don't really need this meeting. I can figure it out on my own."
Stage 2: Rationalization
"I need to be better prepared. Let me spend another month getting ready."
Stage 3: Procrastination
"I'll definitely reach out next week. This week is just too crazy."
Stage 4: Self-Sabotage
"Actually, maybe they're not the right person for this. Let me find someone else."
Stage 5: Regret
"I should have reached out months ago. Now it's probably too late."
The cure for all five stages: Make the call. Send the email. Book the meeting. Today.
The Discomfort Decoder
When you think about that meeting you're avoiding, what specifically makes you uncomfortable?
If it's fear of rejection: Remember that "no" is data, not judgment. Every rejection teaches you something and gets you closer to the right yes.
If it's fear of inadequacy: You're not trying to impress them with who you are today. You're asking them to invest in who you're becoming.
If it's fear of seeming desperate: Desperation is about your energy, not your ask. Confident people make big asks calmly.
If it's fear of success: Ask yourself what you're afraid will change if this goes well. Usually it's identity, you'll have to see yourself differently.
The Meeting Request Framework
Here's how to request the meeting you've been avoiding:
Subject Line: Be direct and specific "Partnership opportunity - [specific benefit to them]"
Opening: Acknowledge their time is valuable "I know your time is precious, so I'll be direct."
Value Proposition: Lead with what's in it for them "I've identified an opportunity that could [specific benefit]"
Specific Ask: Don't be vague "I'd like 20 minutes to discuss this. Are you free Tuesday at 2 PM or Thursday at 10 AM?"
Confidence Close: Assume they'll want to hear more "Looking forward to sharing the details."
Example: "Hi Sarah, I know your time is precious, so I'll be direct. I've identified a partnership opportunity that could add £500K to your annual revenue with minimal additional overhead. I'd like 20 minutes to walk you through the framework. Are you free Tuesday at 2 PM or Thursday at 10 AM? Looking forward to sharing the details. - David"
This Week's Assignment: The Uncomfortable Meeting Challenge
Day 1: Identify the one meeting you've been avoiding that could most change your trajectory.
Day 2: Write down specifically what you're afraid will happen. Then write what could happen if it goes well.
Day 3: Draft the meeting request email using the framework above.
Day 4: Send the email. Don't edit it seventeen times. Good enough is good enough.
Day 5: If they don't respond in 48 hours, follow up. Once.
Day 6: Prepare for the meeting as if it's already confirmed.
Day 7: Email me what happened. Subject line: "I had the uncomfortable meeting"
The Biblical Truth About Difficult Conversations
"The heart of man plans his way, but the LORD establishes his steps." - Proverbs 16:9
You can plan forever, but God establishes steps through action. That uncomfortable meeting might be the step He's trying to establish for you.
"You do not have because you do not ask." - James 4:2
Maybe your breakthrough is waiting on the other side of a conversation you haven't had the courage to start.
The Three Outcomes (All of Them Good)
Outcome 1: They say yes Your life changes. The opportunity you imagined becomes reality.
Outcome 2: They say no You get clarity, stop wondering "what if," and can move on to other opportunities.
Outcome 3: They say "not now" You plant a seed for future opportunity and practice having difficult conversations.
All three outcomes are better than continuing to avoid the meeting entirely.
The Meeting Avoidance Tax
Every day you don't have that conversation, you're paying a tax:
Opportunity Cost: The deals you're not closing
Mental Energy: The headspace consumed by avoidance
Confidence Erosion: Each day of delay makes it harder to reach out
Timing Risk: Windows of opportunity close while you're preparing
The longer you wait, the more expensive your hesitation becomes.
Tomorrow You Stop Avoiding and Start Approaching
You can keep finding reasons to delay that crucial conversation. You can keep telling yourself you need more preparation, better timing, or increased credibility.
Or you can accept that your discomfort is data telling you this matters.
The meeting you're avoiding could change everything. But only if you actually have it.
Stop interpreting discomfort as a stop sign. Start treating it as a green light. The conversation you're avoiding is the gateway to your next level.
David
P.S. "Be strong and courageous! Do not be afraid or discouraged. For the LORD your God is with you wherever you go." - Joshua 1:9. If God is with you in that meeting, what exactly are you afraid of?
P.P.S. The meeting you're avoiding isn't just about business. It's about becoming the kind of person who has difficult conversations, makes big asks, and doesn't let fear determine their ceiling. That person is worth more than whatever deal might come from the meeting.
