Someone reached out to me on LinkedIn recently with a question she’d been sitting with for a while. She wanted to teach at a business school and believed she needed a PhD to even be considered. We talked through what a PhD actually involves — the workload, the timeline, the commitments — and at some point I asked her:

“Why do you believe you need a PhD to teach?”

She paused for a long moment.
Then said quietly:
“I’m not sure. I guess I’ve just always assumed that’s the rule.”

And that pause stayed with me.

Because once we looked at the facts, the belief didn’t hold:

• Business schools regularly bring in professors of practice

• Many programs intentionally hire industry experts as guest lecturers

• Credibility comes just as much from experience as from credentials

The belief felt true.
The actual landscape was different.

Once she saw that, something opened up.
She remembered she already knew someone who led a program.
She reached out.
A short time later, she was invited to guest lecture.

No additional degree.
No multi-year detour.
Just one assumption replaced with reality.

We all carry unwritten rules into mid-career.

Rules we never agreed to.
Rules we rarely examine.
Rules that quietly limit what we believe is possible.

Things like:

• “Before I can do X, I need another degree.”

• “If I make a change now, I need to settle for a lower position.”

• “I don’t have the skills I need.”

• “There’s one right next move… and I have to figure it out perfectly.”

These beliefs often form early in our careers when we have less experience, less perspective, and far fewer examples of nonlinear paths.

But by mid-career, our reality has changed.

We’ve grown, our values have shifted, our priorities have evolved.
Yet the old beliefs stay embedded, shaping decisions long after they’ve stopped being useful.

In many conversations I have, this is where people get stuck — not because they don’t know enough, or aren’t capable enough, but because the mental model they’re using is outdated.

Mid-career isn’t the end of the story. It’s the moment you finally have context.

• You know what energizes you.

• You know what drains you.

• You’ve lived through restructurings, promotions, failures, successes, and everything in between.

• You have a sense of how you want to contribute — and what you want to move away from.

This stage isn’t about starting over.
It’s about becoming more accurate about what actually works for you.

But accuracy requires something most people don’t make space for:

Questioning the beliefs that quietly shape your choices.

When you examine them, one of two things happens:

1. You confirm the belief is true and act with more clarity.

2. You discover the belief is outdated, incomplete, or simply false — and new paths open.

Either way, you move forward.

This is why micro-experiments are so powerful.

They test beliefs in the real world.
They replace assumptions with data.
They reveal what’s actually possible.

Inside my workshops, the most transformative moments often happen at the end and within two hours — when someone tries the smallest version of an idea they’ve been carrying for years.

Not a full pivot.
Not a full commitment.
Just enough of an experiment to challenge the story they’ve been living inside.

And almost always, the outcome surprises them.

Sometimes the idea loses its appeal.
More often, the experiment expands their sense of possibility.

Either way, they now have evidence, not assumptions.

A gentle question for you:

What belief about your next chapter have you been treating as a fact… without ever checking if it’s true?

You don’t need to overhaul your career to explore this.
You don’t need a grand plan.
You don’t need to be “ready.”

You just need a small experiment — something you can test in the real world — to see what the belief is actually made of.

If you want help identifying that experiment or untangling the belief behind it, feel free to reply or reach out.

This stage of your career doesn’t have to be navigated alone — and sometimes one conversation is enough to help you see a path that was there all along.

Subscribe now

Two weeks ago, I lost my job.

After going through a period of grief and disorientation, I decided to embrace the unexpected event as an initiation to explore the “Room with a Hundred Doors” — an exercise where you imagine stepping into a room filled with possible futures and notice which ones pull you in. The result:

One door pulled me in. It seemed like journey leading to a brighter future.
A future I’ve quietly wanted… but feared for years.

So I used a tool I normally save for clients:
The “Yeah, but… what if?” exercise.

And it forced me to finally look at what was actually stopping me.

The Exercise That Won’t Let You Hide

Here’s how the basic version of the “Yeah, but … what if?” exercise works:

1. Name what you want.
   Example: I want to become an author and speaker.

2. Notice the fear that answers (“Yeah, but…”).
   Example: … you don’t have the writing skills.

3. Counter with: “What if …”
   Example: … you would take a writing class .

4. Notice the next fear the shows up in response to “Yeah, but …”
   Example: … my ideas might bot be good enough.

5. Continue with a “What if …” and keep on going back and forth until something real surfaces.

In most cases, one of three fears shows up underneath everything:

1. Fear of failure

2. Fear of the unknown

3. Fear of judgment

The ones that came up for me?
Fear of judgment.

Not fear of doing the thing.
Fear of being seen doing the thing.
Fear of what people might think when I finally step toward that future bing judged for it.

Naming that hit like a truth I’d been avoiding. It made me want to confront the fiction I carry with the gathering of facts through conversations and prototyping – more about that in the next email.

One Last Thing

If you’re wrestling with a future you secretly want, don’t be surprised if the fear isn’t about the work at all.

For many of us, especially mid-career, the real fears are:
Being seen and judged for wanting something different.
Fearing to fail at something that is significant but uncertain.

And while the fear might feel real, naming and recognizing it for what it is can be a significant step towards the futures we secretly want.

Till next week,

Ingo

Hi,

Last week my role was eliminated.

It was one of those moments that hits your system in layers.
First the shock… then the adrenaline… then the wide-open “okay, now what?” feeling that is equal parts thrilling and disorienting.

Suddenly my future felt like a map with a giant white spot in the middle.
Part of me was excited — maybe this is the moment to build something new.
Another part of me was overwhelmed — what if I choose wrong?
And a smaller, quieter part felt strangely hopeful — like a door I couldn’t yet see had just cracked open.

Whenever I’m overwhelmed by choice, I pull out an exercise I’ve used for years.
It’s simple, visual, and grounding.

I call it: “The Room With Many Doors.”

The Room With The 100 Doors

1. Draw Your Doors.

Take a sheet of paper and draw one door (rectangle) for each future you consider.
Label each door with a future you’re considering (e.g. Ranger).

Then — this part matters — draw each door open, closed, or partially open. Representing how accessible that future seems to you. Don’t overthink this, just trust your gut. Your pencil usually knows the truth before your mind does.

2. Visualize what’s behind each door.

Let whatever image comes up, come up:
sunny field, fog, forest trail, chaotic city, warm light, a blank nothingness.

These metaphors reveal how your body feels about each option — long before your brain starts negotiating with itself.

3. Note the answer to three questions per door:

• What makes me hesitate?
And is that hesitation fact (real constraints) or fiction (assumptions, fear, unknowns)?

• What makes me want to walk through that door?
Meaning? Growth? Freedom? Stability? Creativity? Impact?

3. Check for patterns or what is missing?

Reviewing what you created, reflect on the patterns that show up and what seems to be missing. I was surprised to see no computer in any of my futures although that has been 90% of my work.

Subscribe now

Why This Works

This exercise taps into what psychologists call “construal level theory” — the idea that we think about the future on two levels:

• abstract meaning (the big picture) and

• concrete detail (the actual steps).

Drawing the doors pulls both levels into the same frame.
It helps your brain hold excitement and reality at once — turning vague possibilities into choices you can actually compare.

In other words: it makes the abstract future tactile enough to work with.

What It Revealed for Me

As soon as I drew the doors and what’s behind them, patterns showed up:

• Several futures would give me the same core things I care about — creativity, meaningful contribution, working deeply with people, space to explore.

• One door was almost closed because of real constraints. Others were partly closed for no practical reason, just fears (fiction) of an uncertain future or inability or limitations.

• And one door — the “Author + Speaker”-door — had this bright yellow sun and a journey hidden behind it. The image surprised me as I realized how it made me want to start walking on that path, but I also felt hesitation and fear.

Regardless of the future, reflecting on the doors showed me that I need:
companionship, path clarity, the excitement of growth and exploration, and a mentor who can help me on my way.

That alone shifted me from “I’m overwhelmed” to “Okay, I know where to begin.” Next step, finding and connecting with the right people to get clarity.

Wondering about Your Future?

Try the exercise.
Give yourself 20–30 minutes.

You’ll likely discover:

• which futures energize you

• which fears are real vs imagined

• what themes your options share

• what each path offers you emotionally

• and what you need to move forward (not in theory, but in practice)

Most important: it gives you the smallest next step toward the door that’s calling your name.

And in moments like this, clarity rarely arrives all at once —
it usually comes one doorway at a time.

If you do the exercise and want to share what you learned, hit reply.
I’m in the room with you.

Ingo

When I rewatched Jia Jiang’s TED Talk — the one where he set out to get rejected for 100 days — I expected to be inspired to write about trying things out or prototyping.
What I didn’t expect was how familiar his fear sounded.

On his very first day, he walked up to a stranger to ask if he could borrow $100.
By the time the surprised stranger responded “Why?,” Jia had already uttered a “sorry,”spun around and fled the scene.

Later, reflecting on that moment, he admitted:
The fear didn’t come from the “no,” the stranger even asked him “Why?” It came from the version of himself he had to step into just to make the ask.

And that’s when I realized:
This is exactly what so many professionals experience when they consider their next chapter.

It’s not our dream future that unnerves us.
It’s not knowing if they have what it takes to make that positive future a reality.

Why a Positive Future Still Feels Threatening

Research from Stanford and Harvard [1-3] has a simple explanation:

When your future self isn’t clear, your brain reacts as if you’re imagining another person. And we don’t easily invest in strangers.

This neural “distance” leads to hesitation, avoidance, and the quiet pressure to stay the same—even when the future you want is meaningful, exciting, and aligned.

But here’s the important part:

You don’t eliminate this fear by thinking harder about the future.
You eliminate it by reducing the distance between you and the person you’re becoming.

And the fastest way to do that is the same way designers test ideas:

You prototype.

10-Minutes: Prototype for Your Future Self

This is the approach I use in my own life and with mid-career professionals I coach.
It works because it gives your brain a safe first experience of becoming the next version of you—without the pressure of commitment.

1. Write a quick snapshot (3 minutes)
Complete:
“If things unfolded well over the next 6 months, here’s who I’m becoming…”
One messy unpolished paragraph.

2. Pick one behavior to prototype (3 minutes)
Circle a single element of that future self:

• more honest in meetings

• more spacious in thinking

• more grounded under pressure

• more expressive

• more curious

Choose the one that feels energizing.

3. Run a micro-experiment (4 minutes)
Shrink it to the smallest possible version:

• Ask one honest question in the next meeting

• Protect one 30-minute thinking slot this week

• Share one idea you usually keep to yourself

• Take one step toward a project you care about

Small is the point.
Prototyping isn’t about success. It’s about experience through exposure.

Every tiny action makes your future self feel a little less like a stranger.
And the moment that happens, fear loosens its grip.

A Closing Thought

Jia Jiang didn’t become more confident because he received fewer rejections.
He became more confident because he practiced being the person he wanted to become—one tiny experiment at a time.

That’s the real path to any meaningful future.

Not clarity.
Not certainty.
Not readiness.

Just one small prototype that rewires your relationship to who you’re becoming.

Subscribe now

References:

1. Ersner-Hershfield, H., Wimmer, G. E., & Knutson, B. (2009).
   Saving for the future self: Neural measures of future self‐continuity predict temporal discounting.

2. Hershfield, H. E. (2011). Future self-continuity: How conceptions of the future self transform intertemporal choice. Journal of Personality and Social Psychology, 101(2), 366–379.

3. Bartels, D. M., & Rips, L. J. (2010). Psychological connectedness and intertemporal choice. Journal of Experimental Psychology: General, 139(1), 49–69.

For the longest time, I’ve wanted to start a YouTube channel.
I can picture it clearly — sharing reflections on purpose, work, and what it means to live a life aligned with what matters.

And every time I think about it, two feelings arrive almost together: excitement and fear.

Excitement about the dream, the creative freedom, and the chance to connect with people who care about the same questions.
Fear that I won’t keep it up, Fear that I’ll run out of things to say. Fear that it and thus I won’t be good enough.

That inner tension — wanting to start yet holding back — isn’t just procrastination.
It’s the natural push and pull of a meaningful goal.

Why The Push And Pull Is Holding You Back

Psychologists call this an approach–avoidance conflict.
It happens when the same goal triggers two competing systems in the brain — one that pulls you forward, and one that quietly holds you back.

A 2016 review in Neuroscience & Biobehavioral Reviews (Coombes, Cauraugh & Janelle) showed that when we imagine pursuing a meaningful goal, the brain lights up both the reward system (which motivates us to act) and the threat system (which protects us from failure).

That’s why big ambitions feel both energizing and paralyzing.
The same research found that when people shift focus from the large outcome to a small, process-level action, the threat response eases and they’re far more likely to take the first step.

So instead of thinking “launch a channel,” think “record one short reflection.”
The excitement stays; the fear quiets.

How To Get Started …

If there’s something you’ve been wanting to begin — something that lights you up but also stirs hesitation — try this short reflection:

1. Name the goal.
   Write down one thing you’ve been wanting to start or explore.
   Example: “Start a YouTube channel about meaningful work.”

2. Map the light and shadow.

   • Under Light, list what excites you. Example: “I’d love to share ideas that might help others think differently.”

   • Under Shadow, note what detracts or scares you. Example: “I’m afraid I won’t stay consistent or that no one will watch.”

3. Choose a thread of light.
   Pick a single element from your Light list that genuinely excites you.
   Example: “I’m most excited about learning in public — just exploring ideas out loud.”

4. Take one small step.
   Make it approachable by asking yourself: “What’s the smallest thing I could do to begin?”
   Example: “Record a one-minute voice note sharing a thought from this week.”

Clarity rarely comes before action — it’s what begins to form once we start moving.

The Gentle Way Forward

You don’t have to silence the part that’s afraid.
You just have to give the part that’s excited a chance to lead.

This week, let both voices come along — fear in the passenger seat, curiosity at the wheel.

And take the smallest step that feels like truth.

Warmly,

Ingo

Chesky asked if Chip would mentor him and help the company grow up without losing its soul. By then, Chip was 52—twice the age of most Airbnb employees, from an entirely different industry, walking into a tech culture obsessed with youth. Yet he said yes.

That yes became a hinge moment. It sparked his next chapter and, eventually, the founding of the Modern Elder Academy—a place dedicated to reframing midlife as a time of renewal, not decline. Years later, when I found myself in my forties navigating my own questions about meaning and change, I spent time there as an intern and later a fellow. What I witnessed in that desert community in Baja wasn’t luck in the lottery sense—it was something quieter and more intentional.

Chip and the people around him seemed to manufacture luck through presence, generosity, and openness. They noticed opportunities others overlooked. They acted before they felt fully ready. They created space for surprise.

The Inner Science of Serendipity

Psychologist Richard Wiseman calls this luck readiness—a mindset that turns uncertainty into opportunity. His research shows that so-called “lucky” people share three habits: they’re curious about the unfamiliar, attuned to subtle cues, and quick to reframe setbacks as openings.

Luck, it turns out, is a pattern of awareness. It’s less about what happens to us and more about what we’re able to notice. When our minds are rigid or overplanned, life has no room to intervene. When we loosen our grip, our field of vision widens—and we begin to catch the threads of meaning that are already there.

That’s what I saw in Chip. He didn’t stumble into a second act; he created the conditions for it to find him. His curiosity, humility, and willingness to keep learning made him magnetic to new possibilities. He didn’t chase luck—he invited it.

A Micropractice for Everyday Serendipity

Before your next meeting or conversation, pause and ask:
“What might I learn here that I don’t yet know I need?”

Then pay attention—to what’s said and unsaid. Notice small coincidences, repeated themes, or people who seem to appear at just the right moment. Serendipity often whispers before it knocks.

Where to Practice It

• On your commute, look up instead of scrolling.

• Over coffee, talk to the person you usually pass by.

• When plans change, ask, “What is this space making room for?”

Each pause is an opening. Every moment, a potential invitation.

The Small Openings That Find Us

Luck, at its deepest level, is participation. It’s saying yes to life before knowing where it will lead.

Perhaps that’s the quiet truth Chip embodies—and what I felt during my time at the Academy: luck begins when we stop trying to control the story and start staying awake to it.

Meaning rarely arrives all at once. It grows quietly, when we begin to listen.

Subscribe now

How One Brave Message Introduced Me to My Future Self

In 2019, I was in a period of questioning—somewhere between who I had been and who I wanted to become next.

I told my friend April that I dreamed of creating a space for people in transition, a place where they could become who they wanted to be next.

She looked at me and asked, “Have you heard of Chip Conley?”

I hadn’t.

A few days later, I was listening to Chip’s interview with Tim Ferriss. Here was a hospitality veteran—the man behind one of North America’s largest boutique hotel groups—who had gone on to found the Modern Elder Academy, a school for people re-imagining the second half of life.

Listening, I felt something spark. I wanted to see it, feel it, be there. It took me two days and several drafts (and two rounds of April’s feedback) before I finally hit send on an email asking if I could apprentice or intern there.

“How about next January or February?”

— Chip Conley, two hours after I sent the email

That one connection changed everything. My time at MEA helped me clarify what I didn’t want (running a physical property) and what I did want (creating learning experiences that empower people to become who they want to be).

It expanded my network, boosted my confidence, and, most importantly, turned a vague idea into a living experience.

That’s the power of finding—and connecting with—your 2.0.

Your Brain on Possibility: Why Seeing It Makes You Believe It

Psychologists call this vicarious experience: when you witness or interact with someone who’s achieved what you aspire to, your brain encodes that success as possible for you too.

Albert Bandura—father of social learning theory—showed that observing someone slightly ahead of us increases self-efficacy, our belief that we can take effective action.

It quiets overthinking and replaces abstract motivation with real-world confidence.

In simpler terms: seeing your 2.0 builds belief.

When you reach out to someone who was once where you are, you don’t just get advice—you experience what’s next.

You feel it in conversation, see it in their eyes, and start bridging the gap between who you are and who you’re becoming.

A 3-Minute Practice to Meet the Person You Want to Become

This week, identify three people who are living a version of your 2.0—professionally or personally.

Reach out to one.

Say who you are, where you are, and what you hope to learn. Ask for 30 minutes of their time.

You don’t need to make it perfect; just make it honest and personal.

I had coaching clients successfully reach out to head of governmental organizations, elected European Parliament Officials, Famous Activists, and local carpenters.

Whether it’s a global CEO or the owner of your local café, the moment you connect, you step closer to the life you want.

Who’s Waiting for Your Message?

Growth isn’t built in isolation—it’s sparked in connection.

Your 2.0 is out there. Someone who once stood exactly where you stand now. Who wants you to succeed because they know how it feels like to be in your shoes.

All it takes is one brave message to begin your next chapter.

→ Enjoy this newsletter?

Subscribe to Purpose Turn Sunday for more short, research-backed stories on meaning, purpose, and the courage to grow mid-career.

Subscribe here 🕊️

On paper, he had everything — partner at McKinsey, a top executive role, the markers of success. But he felt empty, like he was “just going through the motions.”

That feeling isn’t failure. It isn’t crisis. It’s a signal that success alone is no longer enough.

So what do you do when the old sources of motivation stop working, and you can’t see the next step?

Ten Futures, No Judgment

Leadership scholar Herminia Ibarra suggests one of the most effective ways out of stuckness: exploring your Possible Selves.

Possible selves are the different versions we hope, fear, or dream of becoming — and by imagining them without judgment, we uncover hidden values, desires, and directions that reveal what truly matters.

Here’s how to try it:

1. Set a timer for 20 minutes.

2. Write down ten or more ideas of what you fear, expect or hope you become.

3. Don’t judge. Go wide. Even unrealistic ideas count!

4. Reflect on:

   1. What did I learn about myself given these futures?

   2. What do you want to do now that you know this?

👉 My challenge to you: Take 20 minutes and write down your ten selves. Push past the first obvious few — that’s when the surprises appear. Download the worksheet or just write it down.

From Special Ops to Change Leadership

I once worked with a leader in the finance industry who tried this exercise.

Among his ten selves, one stood out: a member of a special ops team. On the surface, it seemed unrelated to banking. But when we unpacked it, the insight was clear: what he really craved was solving high-stakes challenges and helping people under pressure.

Those values didn’t require a military career. He could live them out in his leadership today. That realization led him to join his bank’s change leadership team, where he channeled the same drive to tackle tough challenges and serve others — but in a way aligned with his career path.

Sometimes the most unlikely “self” is the one that points us back to what matters most.

Your Turn!

Plateaus are invitations, not dead ends. Imagining ten possible selves gives you space to play again — and to reconnect with the values that can reinvigorate your leadership right now.

If you’re curious, DM me what you’ve learned on LinkedIn, and I’ll share my results with you.

– Ingo

Subscribe now

On paper, my life looked great.

My parents were proud. I had moved from consulting, to a Ph.D., to becoming a professor. I’d built a career, taught at top business schools, and advised leaders around the world.

And yet — I found myself standing in front of a class of success-hungry MBA students asking: Is this it?

I soon realized I wasn’t alone. Many leaders who had climbed the ladder, checked every box, and earned the rewards were quietly going through the motions.

That moment — when success stops being enough — is what I call The Purpose Turn.

Why I’m starting The Purpose Turn now.

For the past decade, I’ve studied and worked with leadership and purpose. Along the way, I’ve taught at Harvard, Stanford, and IE Business School, and coached executives navigating midlife crossroads.

Here’s the simple truth I’ve learned: success can get you far, but only purpose sustains you.

And yet, we still hear more about how to be successful than how to succeed at the right thing.

Add to this a pandemic, declining trust in leaders and organizations, and what cognitive scientist John Vervaeke calls “the Meaning Crisis” — and it’s clear why so many of us are searching for more than milestones. We’re searching for meaning.

This newsletter is my way of contributing to that search. I’ll share the tools, stories, and research that have helped leaders (and myself) navigate their own Purpose Turn.

What you’ll find here each week.

• Stories from leaders (and my own journey) who’ve faced this shift.

• Evidence-based insights from psychology, leadership, and design thinking.

• Practical tools you can try in minutes to reconnect with what matters.

Think of it as a weekly reflection + action step — concise, actionable, and rooted in real experience.

Why this matters for you.

Because this isn’t just about career moves. It’s about rediscovering what makes life worth living.

If you’ve ever thought, “I should feel happier with all I’ve achieved” — this is for you.

Subscribe, share it with a friend at a similar crossroads, and let’s explore what happens when success is no longer enough.

– Ingo