Most leaders don’t need more frameworks.

They just need better questions. Questions that cut through the noise. Questions that expose the truth you’ve been dodging.

Do you want to stop building yet another week of your life on top of assumptions that may not even be real?

Here are 10 questions I use with founders when they’re spinning, overwhelmed, or stuck in “figure it out” mode.

They create clarity uncomfortably fast.

If you’re brave, use them daily for a week. If you’re really brave, notice which one you avoid.

That’s the one that will change your life.

1. What am I pretending not to know?

Most indecision is just fear disguised as practicality.

You already see the move. You’re just scared of the cost.

(Use my Pick Now tool for this one—https://tinyurl.com/PickNowSprint)

2. What am I trying not to feel?

Scared? Inadequate? A lot of overachiever mode is about pushing those feelings away.

What if you were to let yourself feel whatever you need to feel, to let it pass through you without resistance?

What’s on the other side? What could you do then? Who could you be then?

3. If I wasn’t trying to impress anyone, what would I choose?

Approval is a hell of a drug.

Freedom is even better.

What do you want just because you want it? Not because it gets you something else?

4. Where am I suffering today that is entirely optional?

Shockingly often, the answer is: “Almost everywhere.”

Suffering is the tax we pay for an outdated identity. Notice where it’s happening to start to level up.

5. What’s the fear underneath the fear?

The surface fear is never the real one.

Underneath “I might fail” is usually “I won’t be enough,” or “People might laugh at me.”

If you can let yourself feel that, you can change everything.

6. What decision keeps returning to me that I still haven’t made?

The truth follows you.

It taps you on the shoulder until you pick.

If you keep seeing the same type of person or same type of situation, ask what you need to learn to get past it.

7. If this were easy, what would I do?

Ease isn’t laziness.

Ease is intelligence.

Your nervous system knows the shortcut your ego won’t take.

8. What’s the smallest action I can take that changes the trajectory?

Big moves overwhelm people into inaction.

Small moves, over time, change lives.

9. What desire have I been suppressing because it feels “unreasonable”?

The unreasonable desires are the real ones.

Everything else is conditioning.

What are you pursuing—what you want, or what you think you can have?

10. What will future me thank me for doing in the next 24 hours?

A direct line to the life you say you want.

Future you is already waiting, already watching, ready to offer advice any time you like.

And cheering for you every step of the way.

Try This Experiment

Pick one question each morning.

Write the answer without editing yourself.

Then take one tiny action based on what you discover.

This is how extraordinary futures are created — one honest question and one small step at a time.

And here’s that Pick Now tool again—use it whenever you can and watch your life change.

https://tinyurl.com/PickNowSprint

#PickNow

This week is Thanksgiving in the US. A time of reflection and gratitude.

And my good news for you this week may not feel good at first. But I assure you it’s the best news ever.

If you think you will reach a point in your life where you are finally satisfied, where you finally have and do everything you want, you are sadly mistaken.

Sixty years in, I am nowhere close to that space.

Yet I’m happier than ever. Many days, blissfully happy.

How?

Yes, I have gratitude. I take time to reflect on my relationships, my growing business, the impact that I am able to have on people’s lives, the meaning and purpose that I bring to my work.

But it is not those things that I am most grateful for. I am most grateful for the ongoing struggle. That struggle means I’m alive and growing.

Last year, I realized things were going pretty well in my business. I was working with clients I loved, I had more free time than ever, and my income was higher than it had ever been (setting aside the year my consulting firm went public and the year I got laid off and was paid out deferred benefits).

But I was listless. I was struggling to get through the day.

I was bored.

This is the other side of building a successful company, of building a successful career. It sneaks up on you and suddenly you feel depressed, because your work isn’t challenging, and guilty, because you are making way more than you ever thought you would.

So how did I get out of that?

I found a new challenge. Actually multiple challenges.

I created a group event for founders and am creating another one.

I created a tool, Pick Now, that helps everyone, not just the founders I coach one on one.

I started a podcast, The Pick Now Podcast, about the scary choices that successful entrepreneurs make over and over.

I’m speaking at events and building a keynote. I’m writing a book.

I’m simplifying my message and expanding my impact.

(And yes, I challenge myself physically and still practice tenor sax every day and love it.)

Every one of these is hard, and fun. I don’t know if they are going to work out. There is a very good chance my income will go down this year as I take these challenges on.

I would not give up those challenges for more income.

Because I am grateful for the struggle of being human. It is where I feel most alive, most “on purpose.”

And I bet the same is true for you.

Your Struggle is Built Into the System

For most of our existence, fat, happy, satisfied humans had one fate.

They were eaten.

Your ancestors were not. Your drive to continuously improve is built into your DNA. It’s what brought you here.

You think that dissatisfaction means something is wrong when actually it means the system is working perfectly.

There are two ways that you can deal with this. You can hide in the middle of the pack or you can lead it.

The Pack Is No Longer Safe

Hiding in the middle is safe but miserable. 95 percent of people get jobs, get comfortable, try their best not to take any risks, not to stand out. They strive to be useful and dependable and safe.

That worked for a long time. You could work at a factory and buy a house and get a pension. But then automation came. Then outsourcing came. Then AI came.

Hiding in the middle isn’t so safe any more.

Leadership Starts with Struggle

Your success is directly linked to how much you are willing to struggle. When I was laid off at 51, I was in the process of learning a whole new set of skills and I built a successful business from those skills. And I constantly challenge myself to do more, because I enjoy the challenge.

The times I struggle most is when I don’t have a challenge in front of me.

I hope to never be happy, because on the road to happiness is where I find the most happiness.

During this week of Thanksgiving I wish the very same for you.

This Isn’t Hustle Culture

I know this might sound like tech-bro 100 hour a week grind until you drop bullshit.

I assure you it’s not. This isn’t about grinding or productivity or inbox zero.

This is about taking on challenges that light you up.

This is about finally feeling alive again instead of constantly living in dread.

Keep Moving, Keep Growing

There is something you have been putting off. Maybe because it’s uncomfortable, maybe because you don’t know if it will succeed or if you can ever develop that skill.

In short, you keep putting it off because you’re scared.

But it keeps calling you. Not doing it is weighing you down. Avoiding it, avoiding that calling is exhausting you. And it’s time to take action.

I have a tool that can help. The Pick Now Decision Sprint can change your life in 30 days or less. And it’s totally free to my community.

Click on this link for access to the tool—

https://tinyurl.com/PickNowSprint

And let me know what you think.

Happy Thanksgiving.

#PickNow

I’ve now recorded twelve episodes of my new podcast, Pick Now.

I focus on the hard choices that founders make, over and over again, as they bring their visions into the world.

The things they struggled with, and the things they continue to struggle with, no matter their past level of success and what they are tackling next.

I’ve asked every one of my guests a version of this question—

“Do you think the entrepreneurial journey is a spiritual one?”

And every one of them has said yes.

The Questions You’re Trying to Answer

Every leader I work with has had significant success by the time they find me. But they might be exhausted. They might see that money isn’t giving them the happiness they thought it would. They might be finding they are always at work, even when they are with their spouse and kids. They might be worried about a health issue. And they wonder what all the hard work is all for.

Their questions are the same ones I continue to ask myself—

How do I stop being so hard on myself?

Why aren’t I happier?

What is my deeper purpose?

These are spiritual questions. And I find the more material success someone has, the more these questions lurk in the background.

Every leader has some version of this spiritual path, whether they call it spiritual or not.

This is mine.

Leadership is Learning to be Yourself

The first three decades of my life were largely performative. I got straight A’s in school, highest honors in college, degree from a top law school, partner track at a firm that was among the tops in the nation in my practice area.

And then in 1995, three months after my 30th birthday, I left.

At that point I would not have called my life spiritual in the least. But I was starting to see that the outer version of success didn’t feel all that fulfilling.

I was beginning to get curious. I had gone through phases, done some reading. Read the New Testament cover to cover during one semester in college, got curious about eastern philosophy during law school.

But my daytime, in the classroom and later in the office, was all about performance. About finding the next mountain to climb and then wondering why it only seemed to make my panic attacks worse.

What I Hid (Even From Myself)

I knew something was off. At the time, though, mental health was not talked about. I remember people in my family who beat their wives, who drank a six pack of beer every night and more. But it was the one who went to a “shrink” who was ridiculed.

So I told my wife when I started to meditate in 1996. But no one else.

I had buried so much. I had not let myself acknowledge all the things that I struggled with, in an attempt to “man up.” I suppose it was because any needs that I had in childhood brought up so much anxiety in my mom that it just wasn’t worth it. So I did my best, through positive thinking and self-medication, not to feel anything.

Or say anything about what I was feeling. (Not that I actually knew.)

I discovered, gradually and then suddenly, how unhappy I was in my carefully constructed life.

I left my marriage, I started going on meditation retreats, and working with spiritual teachers.

The Work at Work

And I started getting promoted at work.

I became a partner in the consulting firm I joined when I left the law firm. I managed a group of lawyers who were all at least ten years older than me. I managed large client relationships and moved from Chicago to Washington, DC. I led a team of national subject matter experts including some of the smartest lawyers, actuaries and pharmacists I had ever met.

I was showing up more. I was happier, more engaged, more calm. But I was still living two lives.

I wasn’t telling my work friends about my meditation retreats, and I wasn’t talking much about my corporate life when I was working with spiritual teachers.

Each half of me was embarrassed of the other, “weird” part. Until one day I outed myself to a spiritually curious friend. It got easier from there. But fully owning all the parts of me continues to be both difficult and incredibly fulfilling.

Finding Questions, Not Answers

We all have that work friend who has found (insert answer here) and is happy to tell you all about it.

I had a short period like that, too, where I thought I had an “answer.”

But as I studied more, as I practiced more, and as I coach more and more leaders, I have found that everyone has to find their own path. One of my early coaching mentors, Doug Silsbee, never stopped looking for ways to help people on their journeys, up until his untimely death in 2018. His “beginner’s mind” continues to inspire me.

What’s Your Path?

Most of my clients have specific “outer” goals. Revenue, profit, enterprise value. But they have seen what the traditional way takes out of them and are determined to do it differently.

Every leader I have worked with had a different version of that journey. A different version of those questions. A different way of challenging both their physiology and their psychology as they learn what works for them and what simply isn’t true.

What does that bring up for you?

For more, follow the Pick Now Podcast, subscribe to my email list, and of course follow me on LinkedIn.

And when you feel called, reach out directly.

#PickNow