Eccentric People and Luck

When times are good, people call us lucky. When times are bad, people call us lucky. It’s not an accident that luck stays on our side. And luck if often the side of the eccentric.

Ever feel like some people just seem to keep winning while others can’t seem to catch a lucky break? I spend a few hours every day studying successful people AND unsuccessful people and it’s made me view “luck” differently. 

Dan Nicholson, in his forthcoming book Rigging The Game has entire chapter dedicated to the concept of eccentric people finding more efficient paths forward. I can’t share that with you yet, as the book hasn’t been published but…

Take this bit from James Clear:

“In ancient Rome, soldiers used leather messenger bags and satchels to carry food while riding across the countryside. At the same time, the Romans had many vehicles with wheels like chariots, carriages, and wagons. And yet, for thousands of years, nobody thought to combine the bag and the wheel. The first rolling suitcase wasn’t invented until 1970 when Bernard Sadow was hauling his luggage through an airport and saw a worker rolling a heavy machine on a wheeled skid.

Throughout the 1800s and 1900s, leather bags were specialized for particular uses—backpacks for school, rucksacks for hiking, suitcases for travel. Zippers were added to bags in 1938. Nylon backpacks were first sold in 1967. Despite these improvements, the form of the bag remained largely the same. Innovators spent all of their time making slight iterations on the same theme.

What looks like innovation is often an iteration of previous forms rather than an improvement of the core function. While everyone else was focused on how to build a better bag (form), Sadow considered how to store and move things more efficiently (function).”

Sadow was eccentric and was asking a different question than everyone else. In order to truly adopt the form over function orientation, one has to learn how to think for themselves. Easier said than done. In order to learn to think for ourselves, we must train ourselves to bias function over form; to focus on solving the problem instead of improving the tools. 

What does that look like in reality?

Things that an “unlucky” person might focus on:

“I need to grow my business bigger”

“I need to grow my revenues”

“We need to hire more people”

“We need to increase adspend and find another channel that converts!”

Here’s a recent example”

“I need to make enough to pay someone else to do XYZ so I can get ten hours a week back to think and spend with my family.”

Nic: “How much do you need?”

“$10,000 a month extra would cover the salary with some wiggle room. But there are so many options, Dan Henry’s program, Some YouTube Course, Sam Ovens… I’m trying to decide what to invest in – I was told maybe your Network would be a good fit”

Nic: [Asks a bunch of questions and finds out that this person is driving 55 minutes each way, 6 days a week to the office every day]…

“K. Well an office space 5 min from your house is $2,500 a month. So there’s 11 hours of your time back in just drive time.

So now you have your time back and $2,500 to cover.

Go through your bank statements – business and personal – and cancel every single recurring payment you think you can live without. Add them back in later if you need them. (This is Dan Nicholson’s two oreo principles)”


  • 11 hours a week back 
  • $3,200+ in recurring expenses and subscriptions eliminated. 
  • Got the time back without having to do more work or invest more time. Makes sense, no?

The difference between focusing on the tools and the outcome, or the function over the form.

Eccentric people, and people that always seem to win have a different set of values, they are looking for the most efficient way to achieve and outcome instead of trying to improve the tools all the time.

There is always a more efficient path forward. If you want help finding it let me know.

If you want to find it yourself, keep on the Daily Email List and I’ll keep feeding you the tools. Promise. 


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