What if the thing keeping you stuck wasn’t a lack of answers but the questions you’re asking?
And I don’t mean the surface-level stuff. I mean the questions that make you pause. The ones that cut through the noise and force you to confront what’s actually going on.
Below are the questions I hear in Mentor Pods that change the conversation fast. They’re not always fun to answer. That’s why they work.
What You’re Really Optimizing For
- What would you do if money wasn’t a factor?
This one cuts through so much noise. Because most people are optimizing for revenue when what they actually want is freedom, or impact, or time with their family. - If you hit your revenue goal but nothing else changed, would you be happy?
Sometimes the goal isn’t the problem. It’s that you’re climbing the wrong mountain. - What are you optimizing for right now: growth, profit, or freedom?
You can’t optimize for all three at once. Pick one. Build toward it. Then reassess. - What would this look like if it were easy?
We overcomplicate everything. This question forces you to find the simple path you’ve been ignoring.
Your Assumptions
- Who told you it had to be done that way?
Most of our “rules” are inherited from someone else’s playbook. Question them. - Is that actually true, or is that just what you’ve been telling yourself?
We create stories to justify our decisions. This question exposes them. - What would you tell a friend to do if they came to you with this exact problem?
It’s amazing how clear the answer becomes when you remove yourself from the equation. - What are you assuming has to be true that might not be?
Challenge the premise. Half the time, the thing you think is set in stone… isn’t.
What You’re Avoiding
- What’s the real fear here?
It’s rarely about what you say it’s about. Dig deeper. - What’s the worst that could happen if you did this? And is that actually that bad?
Most of the time, the worst-case scenario is survivable. We just don’t let ourselves think it through. - What’s the cost of not deciding?
Indecision has a price. Sometimes it’s higher than making the wrong call. - If you knew you couldn’t fail, what would you do?
Fear masquerades as analysis paralysis. This question strips that away.
Your Capacity
- If you hit this goal, what breaks?
Growth without capacity is just burnout with better numbers. - What are you doing that only you can do? And what are you doing that someone else should be doing?
Most business owners are stuck doing $20/hour work because they haven’t let go. - How many hours a week are you working to hit this revenue number?
$50K/month sounds great until you realize you’re working 80 hours a week to get there. - If you took a two-week vacation tomorrow, what would fall apart?
If the answer is “everything,” you don’t have a business. You have a very expensive job.
What You’re Leaving on the Table
- How many people asked for a proposal but didn’t buy? And do you know why?
This is money sitting on the table. Most people never ask. - How many of your clients would refer you if you asked them to?
Referrals are the highest-converting leads you’ll ever get. And most people never ask for them. - What’s your repeat customer rate?
If people aren’t coming back, you’ve got a delivery problem, not a marketing problem. - What do your best clients have in common?
Once you know this, you can stop chasing the wrong people.
What Success Actually Looks Like
- What does “winning” actually mean to you?
Define it. Because if you don’t, you’ll keep moving the goalposts and never feel like you’ve won. - If you sold the business tomorrow, what would you do next?
Sometimes the answer reveals what you actually want to be building. - What would make you proud of this business a year from now?
Revenue is one metric. But it’s not the only one that matters. - Are you building a business you’d want to buy?
If the answer is no, why are you building it?
Getting Unstuck
- What’s one thing you could do in the next 10 minutes that would move this forward?
Momentum starts with one small action. Not a plan. An action. - Who’s already solved this problem? And have you asked them how?
Stop reinventing the wheel. Someone’s already done this. Go find them. - If you’re still stuck on this in six months, how will you feel?
Sometimes the pain of staying stuck is the only thing that gets you to move.
What the Right Question Actually Does
The right one doesn’t just give you an answer, it reframes the entire problem. And most of the time, you can’t ask yourself that question. Because you’re too close to it.
You need someone else to ask it. Someone who’s not emotionally invested in your answer. Someone who’s been there before and can see the pattern you’re missing.
Sometimes, the best business decisions I’ve made have come from one conversation with the right person who asked me the question I wasn’t asking myself.
What to Do With This
Pick one question from this list. One that made you uncomfortable when you read it. That’s the one you need to answer.
And if you can’t answer it alone, find someone to talk it through with. A mentor, a peer. Someone in your network who’s a few steps ahead.
Say: “I’ve been stuck on [specific thing]. Can I get 20 minutes with you to talk it through?” Be specific. Most people will say yes. Then ask the hard questions and listen to what comes up. Be open to what you hear.
Because your next breakthrough isn’t hiding in another article. It’s one conversation, and one question away.
