Do You Have a Board of Directors for Your Life?

Nobody claws their way out of rock bottom alone. Matt Aitchison’s version of the bottom is specific: expelled from high school, arrested in college, facing real jail time. He is quick to say your rock bottom does not have to look like his to count, and the way back was not one dramatic turnaround. It was one small decision at a time, over and over, for long enough that only looking back does it resemble a plan.

One small decision at a time

Aitchison did not talk his way out of it with a single insight or a single morning routine. He describes it as choice after choice, each one too small to feel significant while he was making it, that only added up to something big when he looked back on the whole stretch.

“It was just one small decision at a time, over and over and over, over an extended period of time, that now, looking back, added up to being something pretty significant, or big, or life-changing, a fork in the road.”

Learning to read the pitches

He reaches for a baseball metaphor for how slow and unglamorous the climb actually was. You do not hit home runs first. You strike out, a lot, until the game itself starts to slow down in front of you.

“As you step up to the plate more and more and you strike out a lot, after a while, you start to see enough pitches come across the plate that things start to slow down a little bit.”

Foul tips turn into singles. Singles turn into doubles, then triples, then a home run every once in a while. None of it was talent. It was repetitions.

The $190,000 lesson

One of Aitchison’s worst financial seasons was losing close to $190,000 on a single development project, the kind of loss that comes with a poor-me spiral built in. He does not tell that story as a warning. He tells it as the reason he can afford the hotel deal he is running today.

“Those losses and failures have really been my greatest stepping stones and teaching moments for success.”

Build a board of directors

Ask Aitchison how he keeps from sliding back and the answer is not willpower. It is who is around him. He treats his circle of mentors like an actual board, a group he is deliberately building and rotating as he grows.

“I call my board of directors. I’m always looking to fill seats in my board of directors based on where I’m at in order to get to that next level.”

Being around people further along than him has been his biggest life and business hack, he says, because they shorten his learning curve and help him avoid mistakes they already made.

It’s on you to go find it

The board does not come looking for you. Aitchison is blunt about whose job this actually is.

“It’s nobody’s job to teach you, to empower you, to put you in positions to win, but yourself.”

That is the closest thing he offers to a motto, alongside the line he says has carried him through every version of rock bottom since: “I am dumb enough to believe in myself and I am smart enough to execute every single day.”

Listen to the full conversation on the podcast: Being a Whole Life Millionaire and Living the R.I.C.H. Life with Matt Aitchison.