Smart entrepreneurs and intrapreneurs get stuck in the “thinking loop,” and the cost is slow progress and shrinking courage. In this article, Jef Menguin shows how mentorship breaks the loop by giving you guided perspective, better questions, and one clear next move. Read it and share it with your team so you stop circling, decide faster, and build real momentum.
You’re building something.
Maybe it’s a small business you’ve been dreaming about for years. Maybe it’s a project inside your company that you believe could make things better—faster service, a new product, a smarter process. Either way, you’re not playing. You’re trying. You’re putting real effort into something that might actually change your life.
And yet, you feel it.
The strange kind of stuck that doesn’t look like failure.
On paper, you’re doing fine. You read. You watch videos. You take notes. You make plans. You improve your deck. You revise your proposal. You “prepare.” But your progress feels slow, and your confidence feels thin. When it’s time to decide, you hesitate. When it’s time to pitch, you stall. When it’s time to ask for support, you tell yourself, “Later, when it’s clearer.”
If you’ve been there, you’re not alone. You’re not lazy. You’re not unqualified. You’re just looping.
I’ve seen this pattern in aspiring entrepreneurs and intrapreneurs—the builders who create from scratch, and the builders who create inside systems. They’re smart. They have potential. They care. But the work doesn’t move the way it should. Not because they lack talent, but because they keep carrying the thinking alone.
So pause for a second and be honest: what decision have you been holding by yourself for too long?
You’re not failing. You’re just looping.
Let me describe a familiar scene.
A would-be founder is still polishing the pitch deck at midnight. He tells himself he’s being responsible. He’s just “making it better.” He wants to look credible when the time comes. But the truth is, he’s scared to talk to customers because customers can say no. A deck can’t reject you. A spreadsheet can’t laugh. A logo can’t tell you your idea is confusing.
Then there’s the intrapreneur. She has a good proposal—something that could improve a workflow, reduce costs, maybe even raise revenue. She keeps adding more details, more charts, more backup slides. She wants the plan to be bulletproof before she shares it. Deep down, she knows the real risk isn’t the idea. It’s the meeting. It’s the questions. It’s the moment someone senior says, “Why should we do this?” and everyone looks at her.
Both people are doing “smart” work. But they’re also avoiding the work that moves things forward.
That’s why this kind of stuck feels confusing. It doesn’t look like procrastination. It looks like preparation. It looks like diligence. It looks like being a responsible adult.
But it’s still stuck.
When you’re smart, you can justify almost anything.
Smart people are good at building explanations. That’s not an insult. It’s a skill. You can take a delay and turn it into a story that sounds noble.
“I’m just gathering more information.”
“I want to make sure this is right.”
“I need to be more confident before I pitch.”
“I’m waiting for the perfect time.”
“I just need to learn a bit more.”
These lines feel responsible because they carry a hidden promise: Once I know enough, I’ll finally move.
The problem is that “enough” keeps moving, too.
So you read another article. You watch another video. You attend another webinar. You rewrite the proposal again. You polish the deck again. You add more features to the product. You keep thinking, tweaking, refining—while the real world stays untouched.
And here’s the cost that doesn’t show up on your calendar: you start losing trust in yourself. Not all at once. Slowly. Quietly. Every time you delay, your brain learns a lesson: “We don’t act.” Every time you postpone a decision, you train yourself to doubt your own judgment.
That’s why smart people don’t just lose time. They lose courage.
The loop looks productive. That’s why it’s dangerous.
This is what I call the Thinking Loop.
You think.
Then you doubt.
Then you gather more information to reduce the doubt.
Then you delay, because the information didn’t really remove the fear.
Then you repeat the cycle, now with more knowledge—and the same hesitation.
If you’re an entrepreneur, the Thinking Loop shows up as endless planning instead of customer conversations. You stay in “research mode” because research feels safe. You keep rebuilding the product instead of selling it because building feels controllable.
If you’re an intrapreneur, the Thinking Loop shows up as endless refining instead of proposing. You keep waiting for alignment before you even start the alignment conversation. You keep treating leadership like a final exam instead of a discussion you can lead.
This is why smart people get stuck in the most painful way. They don’t stop moving. They just keep moving in circles.
Here’s a question worth sitting with: where are you “preparing” when you should be “testing”?
And another: what are you avoiding that no amount of thinking will solve?
Same brain. Different result.
I want you to picture two people with the same level of talent.
Both are capable. Both work hard. Both want to build something meaningful.
The first person tries to do everything alone. When they hit a wall, they push harder. They search for answers. They collect frameworks. They keep improving the plan. They tell themselves they’re being disciplined. But what’s really happening is they’re trapped inside their own assumptions. They can’t see what they can’t see, so they keep repeating the same kind of thinking—just with more effort.
The second person still works hard, but they stop doing the hardest part alone. When they hit a wall, they bring one real problem to someone who has already faced a similar wall. Not to get rescued. Not to get a shortcut. Just to get perspective.
And something changes—not because the mentor gives a magic answer, but because the question changes.
Instead of “How do I make this perfect?” the question becomes, “What’s the next real move?”
Instead of “What if this fails?” the question becomes, “What would success look like in the next two weeks?”
Instead of “What should I do?” the question becomes, “What am I avoiding?”
That’s when the loop starts to break.
Because some problems don’t need more intelligence.
They need a different vantage point.
From figuring it out alone to thinking with someone who’s been there
Here’s the shift most smart builders miss.
They assume mentorship is about answers. About being told what to do. About someone older, wiser, more successful handing them a clean solution.
That’s not what actually happens.
Mentorship works because it changes how you think, not just what you know. When you talk to someone who has already walked a similar path, you borrow their perspective. You get to stand where they’re standing, even for a moment. And that moment is often enough to see that the problem you’ve been wrestling with isn’t as complex as you thought—or that you’ve been solving the wrong problem entirely.
So the real shift isn’t from ignorance to knowledge.
It’s from solo thinking to guided perspective.
From trying to be strong alone to being smart enough to think with someone else.
That shift doesn’t make you dependent. It makes your judgment better.
What mentors actually do (and what they don’t)
Let’s remove the romance around mentorship, because the myths get in the way.
A mentor doesn’t save you. A mentor doesn’t carry you. A mentor doesn’t remove risk.
What they do is far more practical—and far more powerful.
A good mentor spots patterns you can’t see yet, because you’re too close to the problem. You’re inside it. They’ve already lived through similar moments, so they recognize the signals faster. When you say, “I think I need to add more features,” they might hear, “I’m afraid to charge.” When you say, “I just need more data,” they might hear, “I’m avoiding a conversation.”
That’s not magic. That’s experience.
Mentors also help you avoid expensive mistakes—not by making you cautious, but by helping you choose better. They know which mistakes are useful and which ones are just painful. They help you skip the kind of trial-and-error that only burns time and confidence.
And perhaps most importantly, mentors help you decide. They don’t decide for you. They help you see that a decision is already waiting—and that delaying it is also a decision.
This is why mentorship doesn’t remove the work.
It removes the wrong work.
Why smart people resist mentorship
If mentorship is so useful, why do smart people avoid it?
The reasons are rarely logical. They’re emotional.
Some people don’t want to look needy. They’ve built an identity around competence. Asking for guidance feels like admitting a gap they believe they should have already closed.
Others assume mentors are too busy. They don’t want to be a burden. They imagine rejection before it even happens, so they reject themselves first.
And some people quietly believe this: If I were really good, I wouldn’t need help.
That belief sounds strong. But it’s also heavy.
Because it turns every challenge into a personal test of worth. And when things get hard—as they always do when you’re building—you don’t just question the problem. You question yourself.
Refusing mentorship isn’t independence. It’s unnecessary friction.
The strongest builders aren’t the ones who carry everything alone. They’re the ones who know when to borrow perspective.
So ask yourself this, and don’t rush the answer: where has pride been slowing you down?
How to find mentors without making it awkward
Most people get stuck here because they think mentorship has to be formal. It doesn’t.
You don’t need to ask someone, “Will you be my mentor?” That question puts pressure on the relationship before it even exists. It turns learning into a label.
Instead, start smaller. Start human.
Ask for perspective, not mentorship.
If you’re an entrepreneur, look for someone who has recently built what you’re trying to build—someone who remembers the uncertainty, not just the success. If you’re an intrapreneur, look for someone who has navigated decision-making, influence, or innovation inside an organization similar to yours.
Then make the ask specific and light.
Not, “Can you guide my career?” But, “Can I ask how you approached this kind of decision?”
Not, “I need advice on everything.” But, “I’m stuck on one choice and I’d value your perspective.”
When the conversation happens, your job isn’t to impress. It’s to listen, apply, and follow through. Nothing builds trust faster than action. Nothing kills a potential mentor relationship faster than doing nothing with what you were given.
Here’s a simple rule that works in both business and careers: advice turns into mentorship when effort is visible.
And often, one good conversation is enough to break a loop you’ve been stuck in for months.
What changes when the loop finally breaks
When mentorship enters the picture, life doesn’t suddenly become easy. You still work hard. You still face uncertainty. You still make mistakes.
But something important shifts.
Decisions stop feeling so heavy. You no longer feel like every choice is a referendum on your intelligence or worth. You make a call, knowing it’s not perfect, but clear enough to move. And when you move, you learn faster.
Your confidence also changes shape. It becomes quieter. Less performative. You’re no longer trying to look smart all the time, because you’re more focused on doing what works. You start separating your ego from your experiments. If something fails, it doesn’t crush you. It just informs the next move.
For entrepreneurs, this often shows up as faster feedback. You stop hiding behind planning and start engaging the market earlier. You test ideas instead of protecting them. You sell sooner, adjust sooner, and recover sooner.
For intrapreneurs, it shows up as clearer influence. You stop waiting for permission that never comes. You frame ideas better. You anticipate objections instead of fearing them. You walk into meetings calmer, because you’ve already pressure-tested your thinking with someone you trust.
Nothing dramatic. Just momentum.
And momentum, over time, changes everything.
A small win you can experience this week
You don’t need a long-term mentorship agreement to feel the difference. You just need one honest conversation.
Here’s a simple test you can try this week.
First, write down one decision you’ve been delaying. Not five. Just one. Something real. Something that has been sitting with you longer than it should.
Second, write down the cost of delaying it. Lost time. Missed opportunity. Quiet stress. Be specific. Seeing the cost makes the delay harder to justify.
Third, think of one person who has faced a similar decision before. Not someone perfect. Someone real. Someone reachable.
Then send a short message. Keep it human.
Tell them what you’re building. Name the decision you’re stuck on. Ask for fifteen minutes to get their perspective.
One conversation. One question.
That’s all.
Most people are surprised by how willing others are to help—especially when the ask is clear and respectful. And even if the answer you hear isn’t what you hoped for, you’ll walk away lighter, clearer, and more grounded than before.
That’s the win.
A simple tool to come back to when you’re stuck again
Because you will get stuck again. That’s part of building.
When you do, come back to this.
Before you spiral into more thinking, answer these questions on one page:
What decision am I avoiding right now? What am I afraid might happen if I choose? What’s the smallest next move I could make this week? Who has already faced a version of this before me? What’s the one question I need to ask them?
You don’t need perfect answers. You just need honest ones.
Use this as a pause. A reset. A reminder that you don’t have to carry everything alone.
Stop trying to be strong alone
Smart people don’t fail because they lack ability. They fail—or stall—because they carry too much by themselves for too long.
Mentorship doesn’t make you weak. It doesn’t make you dependent. And it certainly doesn’t make you less capable.
It makes your thinking better.
If you’ve been stuck on the same decision for weeks, don’t try to think your way out of it again. That’s the loop talking.
Borrow perspective. Ask the question. Have the conversation.
One honest exchange can save you months of circling.
And sometimes, that’s all it takes to finally move forward.
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