03/11/25 - Wakie Wakie 4:44

Welcome to Your 444 Newsletter!

Where money, relationships, and hard lessons collide.

I’ll be real with you—loaning money doesn’t just test your finances. It tests your trust.

Because when someone doesn’t pay you back?
It’s never just about the dollars.
It’s about what it reveals.
Respect. Integrity. Responsibility.

4 Thoughts to Reflect On

  1. Loaning money often costs more than the amount on the check.
    It can cost trust, peace of mind, and valuable relationships.

  2. People will show you their true colors when money is involved.
    Some rise to the occasion. Others… disappear.

  3. A broken promise over money is rarely about the money.
    It’s about character.

  4. The right people won’t ask you to risk your relationship for their financial mess.
    They’ll figure it out themselves.

4 Lessons I’ve Learned

  1. Clear boundaries protect relationships.
    When money is on the table, make your terms clear—or don’t play at all.

  2. Loaning money should never be an emotional decision.
    If you can’t afford to never see it again, don’t do it.

  3. Saying “no” doesn’t make you a bad friend—it makes you a smart one.
    Protecting your peace is part of protecting your people.

  4. Respect is earned through responsibility.
    If they don’t take responsibility for themselves, they won’t respect your help.

4 Challenges to Tackle This Week

  1. Audit your boundaries.
    Where do you need to get clearer on what you will and won’t do with your money?

  2. Revisit outstanding loans.
    Is there a conversation you need to have to bring closure?

  3. Practice saying “no” with confidence.
    Start small, but get comfortable protecting your space.

  4. Invest your time and energy in people who respect your value.
    Don’t just guard your money—guard your relationships.

"The most important thing to do if you find yourself in a hole is to stop digging."”
— Warren Buffett

People don’t just fail to repay loans—they often fail to repay trust. If you’ve ever been there, I lay out exactly how to handle it (and prevent it) in this week’s blog.

Talk soon,

See you at the top,
Mark Evans DM

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