Doubt was doing my financial planning.

Before you read any further, write down one number:

“How much is enough?”

Don’t calculate it. Write the first number that comes to mind. Then write the year you first decided on it. Come back to both at the end.

I was making Google money and still afraid it wasn’t enough.

I was on the 10th floor of the Google Chicago office with an older colleague. We had started on kids, college and savings. His kids were already through college.

I was the breadwinner with multiple dependents, and I walked him through every what if I was carrying. Each one came with a dollar amount.

He listened to all of it. Then he said three things I still hear.

“After a certain point, you just won’t need all the stuff you have now. You are optimizing for a future that is just as bloated as your current situation. Give it time. It’s going to thin out.”

“Your parents didn’t have a master plan for you, and you turned out great.”

“Stop catastrophizing your future. Doubt is the source of all failure.”

I agreed with every word. Then I went back to my desk and kept planning exactly the same way.

Here is what took me years to admit.

My number for “enough” was never math. It was a False Number.

I built it on the most expensive years of my life and copied those years forward forever. Then I let every what if add to it. A number that kept moving was a number I never reached. A number I never reached meant I never had to decide anything.

I was attached to being the producer. The earner. The one carrying everyone. As long as the number stayed out of reach, that identity was safe.

A False Number looks like responsibility. It works like permission to never choose.

This fall, three clients brought me a number.

One had carried a target for years from a rough calculation she never revisited. When we priced her actual life, her real number was less than half.

One could have stopped working and was interviewing for a role he didn’t want, because it felt safe.

One had set her number by a cousin she had compared herself to and competed with her whole life. Every time she got close, the cousin’s life moved the goal again.

Three different numbers. The same fear underneath. The money question turned out to be the easy part. The hard part was finding a reason that was their own.

Planning and catastrophizing look the same from the outside. Both happen late at night. Both involve spreadsheets. Both feel responsible.

The difference is where they end.

Catastrophizing ends with another what if.

Planning ends with an answer.

So when a what if shows up, I ask one question:

“And then what would I do?”

Then I answer it, in writing, all the way to the end.

I know this works because one of my what ifs came true. Google laid me off in May 2024. The thing I had feared for years happened, and I had to answer “then what” in real time. I did. The answer was better than anything my fear had predicted.

A fear you answer becomes a plan. A fear you refuse to answer keeps growing, and it will keep setting your number for you.

Try this, this weekend:

Even with the answers on paper, this is hard.

You chose the life you’re living. You chose it because it was familiar, and you built your expectations and your habits around it. Admitting that means admitting you could choose differently.

And accepting that all of it is temporary, the job, the expensive years, the version of you who carries everyone, is plain scary.

It’s also the good news. Seasons end, including the expensive ones.

Keep the job. Keep the ambition. Quit the fear.

When the reason is yours, you move faster and the work costs you less.

Reply with the what if you keep answering with another what if.

One line is enough. I read every one, and I’ll write you back with the question I’d ask next.

With clarity,

The Activated Leader Program
1:1 for senior leaders navigating transition, identity, and what's next.
➜ Explore coaching

For conferences, leadership summits, and corporate off-sites
➜ Book Lilah

Half-day and full-day sessions for leadership teams navigating transition together.
➜ Book Lilah