09/01/25 - Wakie Wakie 4:44

Welcome to Your 444 Newsletter!

Where generosity, boundaries, and real leadership collide.

Today’s topic?

Are you helping people… or handicapping them?

I was talking with a couple business owners the other day about this exact thing.

They’d been helping out friends.
Paying rent.
Covering bills.
Even fronting money for “business ideas.”

But instead of being grateful, those friends got more entitled. 
Like it was expected.

That got me thinking.

When we step in and do it all for someone, are we really helping them… or setting them up to fail?

4 Thoughts to Reflect On

1. Support can quickly turn into dependency.
   What starts as a hand up can easily slide into a handout.

2. Entitlement grows when accountability shrinks.
   If someone expects your help without owning their results, it is a red flag.

3. Good intentions can create bad outcomes.
   Rescuing people from every setback means they never build resilience.

4. True help empowers, not enables.
   The goal is independence, not lifelong babysitting.

4 Lessons I’ve Learned

1. The best “help” is teaching someone to solve their own problem.
   If they cannot repeat the solution without you, it was not help.

2. People value what they invest in.
   If they put in nothing, they will likely value nothing.

3. Money without guidance rarely fixes the root issue.
   Habits, mindset, and discipline matter more than a quick cash infusion.

4. Boundaries protect both sides.
   Without clear limits, help will eventually create tension or resentment.

4 Challenges for You This Week

1. Write down one place where you might be over-helping.
   Ask yourself: Am I empowering, or enabling?

2. Have a direct conversation with someone you are helping.
   Set clear expectations about what is yours to give and what is theirs to own.

3. Stop rescuing someone from the same mistake twice.
   Let them own the lesson.

4. Hit reply and tell me your honest thoughts on this.
   Have you been through it? Did helping backfire? I want to hear it.

So let me ask you… have you been truly helping people grow, or just carrying them?

Hit reply and tell me your take.

Mark Evans DM