Free · Nine questions · Two minutes · Your level, and what comes next
Free quiz · Haven Smith & Company
How organized is your digital life, really?
Nine questions, three each on organizing, protecting and preparing. Two minutes, and you will know where you stand and what the next thing to do is.
Two minutes · Nine questions · No account needed
61%
of US consumers reuse passwords across their accounts
48%
have no instructions for their digital accounts and files
23%
have a will, and still have no digital instructions
Password reuse: GoDaddy Consumer Pulse, 2025. Digital instructions: Trust & Will 2026 Estate Planning Report, a survey of 5,000 US adults conducted by Talker Research, January 2026. That last number is the one worth sitting with. Having a will is not the same as having a plan.
What it actually measures
Three pillars, three questions each.
This is not a security quiz. Only one of the nine questions is about keeping people out, because most of what disrupts a person’s digital life is not an attacker. It is a lost phone, a dead laptop, a changed number, a forgotten password.
The nine come straight out of the three guides we publish, so what you are being scored against is a method rather than a vibe.
Pillar 1
Organize
Know what you have, and whether it has a home you could find in the dark.
Pillar 2
Protect
Not just locking the door. Knowing your way back in when the key is gone.
Pillar 3
Prepare
Whether any of it is reachable by anybody other than you. Most people score worst here.
The five levels
Five levels, from Shoebox to Sorted.
A score on its own tells you where you are. The ladder tells you what comes next, which is the part you can act on.
0–3
The Shoebox
4–7
The Sticky Note System
8–11
The Single Point of Failure
12–16
Good Bones
17–18
Sorted
Who wrote the questions
Twenty years inside the systems that bill you.
In October 2008, our founder started her first week of training as a financial planner at the Raymond James headquarters in Tampa, Florida. She was sitting in the company theater when the market crashed. Reading the room, she decided to pivot, and earned a master of science in human factors and systems engineering.
She built her career in financial technology instead. In the decades since, she has been part of building the digital systems we use to run and maintain many aspects of our lives, working in product research and design, fraud prevention, cybersecurity, compliance and privacy at organizations including JPMorgan Chase, Apple, Oracle, and T-Mobile.
Which is why the nine questions are not the ones a security quiz would ask. They are the ones that decide whether a bad week is an inconvenience or a catastrophe.