Questions That Kill Comfort

Weekly Leadership Insights with Jake Luehrs

ONE THING TO PONDER

The more effortless something looks, the more effort was put into it to make it look effortless. 

Questions That Will Create Perspective

This edition isn’t going to be some long dissertation. I’ll get straight to the point.

These are some questions from 2025 that have caused me to pause, gain clarity, and move purposefully in the right direction. 

Some of them stung. Some of them shifter perspective. All of them are worth sitting with as the year winds down.

1. What is my definition of success if money or titles weren’t part of the equation?

Strip away the external markers. The salary. The corner office. The impressive bio. What's left? That's what you're actually chasing. 

2. Am I being authentic to my ego or my soul?

This one exposed me. I realized how much I was doing for approval, for applause, for the validation of people whose opinions shouldn't have mattered.

Your ego wants to be impressive. Your soul wants to be real. Which one are you feeding?

3. If all external validation disappeared, what parts of my life would still feel meaningful and worthwhile?

Imagine no one's watching. No likes. No recognition. No pats on the back. What would you still do?

4. Am I acting like a victim to the very problems I’m creating or perpetuating?

Ouch. We've gotten really good at complaining about circumstances we're actively choosing. The job we won't leave. The relationship we won't address. The habits we won't break.

You're not trapped—you're just comfortable blaming something else.

5. Are you more interested in being ‘special’ or happy?

This is a slippery slope. It's easy to chase attention, to perform, to build a version of yourself that gets noticed—while being miserable inside. Special gets applause. Happiness brings peace.

6. If I disappeared tomorrow, would the world see what I contributed or just what I accumulated?

What's the legacy? The stuff you own or the lives you touched? The status you achieved or the people you helped become more themselves? This question cuts through the noise.

7. Who are you blaming your life on today?

Your parents? Your boss? The economy? Your ex? As long as you're blaming someone else, they have the power

8. Is the life I’m living right now a result of my choices or fears? Which one is driving?

Be honest. How many decisions are you making because you're scared? Scared of failure. Scared of judgment. Scared of being alone. A life built on fear is a life full of regret. 

9. Is it a blessing or a curse to feel so deeply?

I've wrestled with this one all year. Feeling deeply means you hurt more, but it also means you live more. I'd rather feel everything than live muted and safe. 

10. What blessings have my challenges given me? 

If you look back at the challenges you’ve faced this year, there are likely significant upsides that have come from the. A new relationship, a shift in priorities, a sense of confidence…if you look, you’ll find it. 

Bonus question:

What is my reputation with myself?

Forget what others think. How do you talk to yourself when no one's listening? Are you kind? Critical? Encouraging? Brutal? That voice—the one only you hear—matters more than any external opinion ever will.

As the year ends, here's my challenge:

Pick one of these questions. Just one. Sit with it. Journal on it. Let it make you uncomfortable.

Because discomfort is where clarity lives.

And clarity is what you need to step into next year as someone new.

I'll see you on the other side.

Onward and upward!

PS - Share this with anyone you can think of that has done great things but may be struggling!

LEAD & LEARN : WEEKLY PICK

PODCAST

Let’s Make The World Wildly Better: Rutger Bregman On Moral Ambition

The Rich Roll Podcast

This won’t be for everyone, only for those that are truly striving towards meaning and authenticity. It’s a very interesting listen. Moral ambition has become something more challenging to wrap our heads around it seems. And this conversation explores the depths of humans, how we operate, and why we may feel a bit lost. 

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