Before you begin

How to use these

Most of the people I work with aren't short of motivation, talent or opportunity. What they're short of is a clear sense of what they actually want, as distinct from what they've absorbed from family, peers and the idea of success around them.

These five questions are how I start to find it with them. They're simple to read and harder to answer. A few suggestions:

Don't answer all five at once.

Read them through once and notice the one you'd rather skip. Start there.

Write by hand if you can,

and write more than feels necessary. The first answer is usually the one you've rehearsed. The second or third is usually closer to the truth.

Don't edit while you write.

No one needs to read this but you.

Come back in a week.

Answers change when you've lived with a question for a few days.

The Five Questions

Start with the one you'd rather skip

01

What would you do if the outcome were guaranteed?

Most decisions are shaped less by what we want than by what we're afraid of losing. Take the risk away for a moment and look at what's left. What remains is usually closer to what you actually want.

Try this

Write your first answer. Then ask yourself, "And if that were guaranteed too, then what?" Keep going until an answer surprises you.

02

Whose approval are you still working for?

Many accomplished people are still answering to someone: a parent, a first boss, a group of peers, who may not even be watching any more. Naming them doesn't make them disappear, but it lets you decide whether they still get a vote.

Try this

List the people whose opinion you weigh before a big decision. Next to each name, write whether you would give them that role if you were choosing today.

03

What did you want before you learned what was realistic?

Somewhere along the way, most of us adjusted what we wanted to fit what seemed possible. Some of those adjustments were wise. Others were made early, in a hurry, and never looked at again.

Try this

Go back to a time before your career took shape. What did you want then? Write it down without judging it, then underline the part that still feels true.

04

What are you calling a constraint that is actually a choice?

"I can't" often means "I won't, because of what it would cost." That cost may well be worth avoiding. But calling it a choice puts the decision back in your hands, which is where it already was.

Try this

Write down three things you've told yourself you can't change. Rewrite each as "I'm choosing not to ___ because ___." Notice which of the sentences still sound right to you.

05

If nothing changed for five years, what would you regret most?

When every week is full, it's easy to postpone what matters. Picturing five more years of exactly this makes the cost of waiting visible, and usually points straight at what you've been postponing.

Try this

Describe an ordinary Tuesday five years from now, with nothing changed. Then write one thing you'd want to be different about it, and one small step you could take this month.

The Five Questions workbook cover
Free workbook

Answer them on paper

Download the printable workbook: all five questions, each on its own page with room to write, plus the notes above. Tell us where to send it and the download starts straight away.

“If one of these stayed with you, that's worth paying attention to. You don't need to act on it today. Just don't lose it.”
Sumit Arora

I'd like to hear which one it was. Reply to the email the workbook came with and tell me. I read every reply myself.

After the questions

Two ways to do this work with us

Clarity Weekends
Two days · small group

Clarity Weekends

A weekend away with fourteen to sixteen people, working through questions like these properly, with time and space to answer them.

Learn More
The Self Clarity Accelerator
Four months · January 2027 · Sintra, Portugal

The Self Clarity Accelerator

For managers, founders and business owners in a period of growth. Online sessions, a retreat in Sintra and one-to-one coaching, with sixteen to twenty people. Applications close on 30 October.

Learn More