When the Future You’re Most Excited About Is Also the One That Scares You Most

And how a simple “Yeah, but… what if?” cracked something open for me.

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