What a Connect-the-Dots Puzzle Can Teach Us About Wealth Planning

Minnesota artist Phil Hansen holds the Guinness World Record for biggest connect-the-dots puzzle, a stunning image of a Native American elder referred to as Big Head by early 20th century photographer, Edward Curtis, created using almost 53,000 dots.

The challenge was more than it seemed. Most of the numbers to complete the puzzle were five digits long, each dot taking more and more space. To solve that problem, Mr. Hansen had to create a coded system and a key to follow it. It took him and his numbering team more than 300 hours to finish the piece.

Guiness officials asked for documentation of everything ─ the column system, the numbering key, and images of the completed piece. Before approving the record, they demanded someone solve the puzzle, which they did in 19 hours split over several days. But the puzzle worked and was beautiful in its clarity and story.

Is this a metaphor for managing wealth?

Embracing the Shake

The Artist described the challenge in his TED Talk, “Embrace the Shake.” Thousands of dots. Huge physical constraints. Tight spatial math. A precise process that had to work from start to finish.

Here’s the part that matters: Hansen’s hands shake. Permanently. A neurological condition ended his early dreams of traditional drawing. For a while, he told himself a familiar story: I can’t do this anymore. Not how do I do this—but I can’t.

The breakthrough didn’t come from learning better technique. It came when he stopped fighting the limitation and started building around it with a process. The shake became part of the process, with a team to help him.

Why This Sounds Familiar

Attempting to solve practical, often complicated problems involving money is emotionally fraught. Stories we tell ourselves become our beliefs. Feelings manage our lives instead of actions.

People rarely get stuck because they don’t have ideas or opinions about what to do. Save more. Spend with intention. Plan. Manage risks. We grapple with these questions in private. Friction shows up in the emotional stories we tell ourselves:

This is going to feel restrictive.

I’ve already waited too long.

An index fund is all I need.

I don’t trust the advisor.

If I look closely, I might not like what I see.

Those stories feel factual—but they’re usually just familiar. And familiarity is comfortable, even when it’s costly.

Connecting the Dots

A good financial plan isn’t about adding complexity or finding a secret strategy. It’s about sequencing the dots in a way that respects who you are—your habits, your fears, your priorities, your energy. The math matters, but it only works if the person does.

Breakthroughs—financial or otherwise—rarely come from sudden genius. They come from giving ourselves permission to engage differently. To stop treating discomfort as a warning sign and start treating it as information.

And yes, sometimes that means embracing a little shake.

If you’re feeling stuck, overwhelmed (overconfident), or quietly avoiding decisions you know you’re capable of making, the next step might be a new story that helps you move from one dot to the next.

The roadblocks we face are usually the ones we place in front of ourselves.

Remove them, and a picture of your confident financial life will appear. A reminder that any big problem is a series of small ones. What matters is progress.