The 11 PM Text Message Problem: Why You Can't Sleep and How to Fix It
It's 11 PM. You should be winding down. Instead, you're reaching for your phone.
There's that issue you need to tell your business partner about. That problem with the property you need to flag. That concern about a team member you need to raise.
If you don't send the message now, you won't be able to sleep. Your mind will keep churning on it.
So you send the text. Maybe you get a response. Maybe you don't. Either way, the issue doesn't get resolved—it just gets transferred from your head to someone else's phone at an inappropriate hour.
Sound familiar?
Jason Jannati, EOS implementer and business coach, sees this pattern constantly. And he has a solution that addresses not just the symptom (the late-night messages) but the root cause (you have no system for capturing and resolving issues).
The Real Problem: No Container for Issues
The 11 PM text message is a symptom of a deeper dysfunction:
You don't have a trusted system for handling issues.
Without a system, issues float around in your head. They nag at you. They create anxiety. They demand attention at inappropriate times because there's no other place for them to go.
Jason describes it this way:
"Let's get it all out of that 11:00 at night text message you gotta send or else you're not gonna be able to stay up at night."
Notice the phrasing: "you gotta send or else you're not gonna be able to stay up at night."
The issue isn't just inconvenient—it's holding you hostage. It's disrupting your peace, your rest, your ability to be present with your family.
All because you have nowhere to put it that you trust will actually get addressed.
Beat the Bushes: Get Everything in One Place
The first step in the solution is deceptively simple:
"We want to beat the bushes, get all the issues onto one place, into one place."
Not scattered across:
- 11 PM text messages
- mental notes you hope you'll remember
- sticky notes on your desk
- random emails marked for follow-up
- things you mentioned in passing conversations
- concerns you've been meaning to bring up
One place. One issues list.
This is the container your anxiety has been searching for. A single repository where issues go to be tracked, prioritized, and systematically resolved.
The psychological relief of this is profound. When you know there's a place where issues get captured and a process that ensures they get addressed, your brain can let go.
You don't need to send the 11 PM text because you trust the system. The issue goes on the list. It will be addressed at the appropriate time with the appropriate people.
Enter IDS: Identify, Discuss, Solve
But having an issues list isn't enough. Plenty of organizations have lists of issues that never get resolved. The list just becomes a graveyard where problems go to be documented but not solved.
That's where IDS comes in.
"Then we wanna work on this concept called IDS. This is a really good one. This is again one you guys can take here: Identify, Discuss, Solve."
Three steps that transform an issues list from a passive document into an active problem-solving engine.
Let's break down each step, starting with the most critical and most commonly mishandled: Identify.
Identify: The Root Issue, Not the Comfortable Issue
Jason provides what he calls "the best example I have" of why the Identify step is so crucial:
The Process Problem That Wasn't
"We were in a session working with the leadership team, working through stuff, and they kept coming up with 'We have this process issue, we have this process issue.'"
Surface level, this seems productive. The team is identifying problems. They're engaged in problem-solving. They're focused on improving processes.
But Jason saw something deeper:
"And I looked at them and I said, 'Is it a process issue? I feel like everything you're doing is really just to avoid this person right now. It doesn't seem like process. It seems like this person.'"
Read that again. Everything they were doing—all the process discussion, all the "we need better systems" talk—was really just avoidance.
"So is it a process issue or is it a people issue?"
Why We Avoid the Real Issue
Jason explains exactly why the team was talking around the real problem:
"The people issue was harder to talk about. It was harder to face. It was a more complicated to face."
Three reasons right there:
1. Harder to talk about Process problems are neutral. "Our system needs improvement" doesn't implicate anyone. It doesn't make anyone uncomfortable. It doesn't require difficult conversations.
People problems are personal. "This specific person is underperforming" or "This individual's behavior is toxic" points the finger. It creates discomfort. It feels confrontational.
2. Harder to face Process problems feel solvable. Create a new workflow, implement a better system, done.
People problems are messy. They involve emotions, relationships, livelihoods, difficult conversations, potential conflict. They require courage to address.
3. More complicated to face Process improvements have clear paths: document the new process, train the team, implement it.
People issues have uncertain outcomes: the conversation might go badly, the person might get defensive, you might have to make hard decisions about employment, relationships might be damaged.
No wonder we avoid them.
The Cost of Avoiding the Real Issue
But here's what happens when you identify the wrong issue:
You solve the wrong problem.
The team could spend weeks or months improving processes. They could document workflows, create new systems, implement technology solutions.
And the underlying people problem would persist. Because it was never a process issue to begin with.
Jason states it clearly:
"But the root issue was a people issue. It wasn't a process thing."
All that time, energy, and potentially money spent on process improvements would be wasted. The real issue—the problematic team member—would continue creating problems.
Meanwhile, everyone on the leadership team knows what the real issue is. They're just all conspiring together to avoid naming it.
The Discipline of Root Cause Identification
This is why the Identify step in IDS is so critical:
"We want to clearly identify what is the root issue."
Not the surface issue. Not the comfortable issue. Not the issue that's easiest to talk about.
The root issue. The real issue.
This requires:
Courage to name uncomfortable truths
Insight to see past surface symptoms to underlying causes
Honesty to stop playing games and address what everyone actually knows
Facilitation from someone (often an outside perspective) who can call out the avoidance
In the example Jason gives, he was that outside facilitator. As the EOS implementer working with the leadership team, he could see the pattern they were stuck in and call it out:
"I feel like everything you're doing is really just to avoid this person right now."
That single observation cut through weeks or months of dancing around the real issue.
Common Issue Misidentifications
The process-versus-people confusion Jason describes is just one example of how we misidentify root issues. Here are others:
"We need more marketing" → Root issue: Our offer isn't compelling or our targeting is wrong
"We need better systems" → Root issue: We have the wrong people in key roles
"We need more capital" → Root issue: Our unit economics don't work
"We need better communication" → Root issue: Leadership doesn't have clarity on direction
"We're too busy" → Root issue: We're not saying no to wrong opportunities
"Team morale is low" → Root issue: Specific toxic individual or leadership failure
"We need more training" → Root issue: Wrong people in wrong seats
"Clients are too demanding" → Root issue: We're attracting wrong clients or setting wrong expectations
In each case, you could spend enormous time and resources addressing the surface issue while the root cause continues creating problems.
How to Identify Root Issues
So how do you actually get to root causes instead of comfortable symptoms?
Ask "Why?" five times
The classic Toyota approach: keep asking why until you get to the real cause.
- "We have a process issue." Why?
- "Because things aren't getting done consistently." Why?
- "Because different people do things different ways." Why?
- "Because Person X doesn't follow the documented process." Why?
- "Because Person X doesn't respect the leadership or believe in the approach."
Now you're at a root issue: a people problem, not a process problem.
Look for patterns
If the same type of issue keeps appearing, you're treating symptoms instead of root causes.
Ask: "What's the issue behind the issue?"
Often our first articulation of a problem is surface level. Push deeper.
Be willing to name the uncomfortable truth
The real issue usually has some discomfort attached to it. If everything feels comfortable, you probably haven't identified the root.
Get an outside perspective
Sometimes it takes someone not embedded in the situation to see clearly. This is the value Jason brought to that leadership team—he could see what they were avoiding.
From Identification to Resolution
Once you've truly identified the root issue, the Discuss and Solve steps become much more productive.
You can't effectively discuss or solve a problem you've misidentified. All your problem-solving energy goes toward the wrong target.
But when you've named the real issue—even when it's uncomfortable—now you can:
Discuss it honestly: "Okay, we've acknowledged this is a people issue with this specific individual. What do we think? What do we see?"
Solve it effectively: "What's the next best action to address this people issue?" Maybe it's a direct conversation. Maybe it's a performance plan. Maybe it's a role change. Maybe it's a separation.
Whatever the solution, it addresses the actual problem instead of dancing around it.
The Trust Required
Here's what makes the Identify step challenging in organizational settings:
It requires trust.
Trust that we can name uncomfortable truths without personal attacks.
Trust that identifying a people issue doesn't mean we don't care about people.
Trust that bringing up a difficult topic won't make us the bad guy.
Trust that the team can handle hard conversations professionally.
Without that trust, teams will continue doing what Jason's client was doing: talking endlessly about process issues to avoid the people conversation.
Building that trust is part of what the IDS framework and regular Level 10 meetings accomplish over time. When you have a consistent cadence of identifying, discussing, and solving issues—when you prove week after week that hard conversations can be productive rather than destructive—trust builds.
Eventually, you can skip the avoidance dance and go straight to the root issue.
Back to the 11 PM Text
So how does all this connect to the 11 PM text message problem?
When you have:
- An issues list that captures everything in one place
- A trusted process (IDS) for working through those issues
- A regular cadence (Level 10 meetings) where issues get addressed
- The discipline to identify root issues instead of comfortable symptoms
- The courage to discuss them honestly
- The commitment to solve them with concrete to-dos
Then:
That thing nagging at you at 11 PM? It goes on the issues list. You trust it will be addressed at the next meeting. You trust the team will identify the real issue, discuss it productively, and solve it with clear accountability.
You can let it go. You can be present with your family. You can sleep.
The issue doesn't disappear—it just has a proper container and a proper process for resolution.
The Bigger Picture
The 11 PM text message is really about something larger:
Do you have a system you trust for handling the inevitable problems that arise in business?
Without that system:
- Issues live in your head, creating anxiety
- Problems get raised at inappropriate times
- Discussions go in circles because root causes aren't identified
- Solutions address symptoms instead of real issues
- The same problems keep recurring
- You carry the mental burden 24/7
With that system:
- Issues get captured in one place
- Problems get addressed systematically
- Root causes get identified and discussed
- Real solutions get implemented
- Problems actually get resolved
- You can be present when you're not working
The Bottom Line
Most businesses don't have an issue-solving problem. They have an issue-identifying problem.
They're treating symptoms, addressing comfortable surface issues, and avoiding the real root causes that are harder to talk about, harder to face, and more complicated to address.
The IDS framework—starting with clearly identifying the root issue—changes that dynamic.
It requires courage. It requires honesty. It requires someone willing to say, "I feel like everything you're doing is really just to avoid this person right now."
But when you build that discipline:
The process "issues" get revealed as people issues.
The capital "problems" get revealed as unit economics issues.
The communication "challenges" get revealed as leadership clarity issues.
And then—finally—you can actually solve them.
So tonight, at 11 PM, when you're tempted to send that text:
Ask yourself: Do I have a system for this?
Is there an issues list where this belongs?
Is there a process I trust to address it?
Is there a regular meeting where it will actually get resolved?
If the answer is no to any of those questions, you don't have an issue-solving problem.
You have a system problem.
Time to implement IDS.
Jason Jannati is an EOS Implementer who helps leadership teams achieve the clarity and alignment needed for sustainable growth. For more great real estate content subscribe to Living Well with Rentwell on Apple, Spotify, and all other podcast apps.
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