October 21, 2025
1
 minute read

Better Questions, Braver Advice

Boy standing alone scratching his head
Written by

Dave Trott asks a powerful question: What aren’t others doing?

Most of financial planning is built around predictable briefs. But the most valuable work often happens when we challenge the question itself.

"Can I retire at 60?"
becomes
"What kind of life do I want at 60?"

By going upstream, we find better answers.

Don’t Wait for Perfection

Trott argues that we fear embarrassment more than regret. But the greater danger is inaction. At Town Close, we know:

  • The perfect moment rarely comes.
  • The perfect answer rarely exists.

But bold, honest conversations move the needle. That’s what we’re here for.

Thinking Differently Is the Point

Everyone else may be fishing in the same pond. The real value is in the ocean of untapped insight. Clients don’t need the same advice they could get anywhere. They need advice that’s deeply theirs.