Jerry Colonna: How to Reboot Yourself

KEYPOINTS

• 01

  Hitting every external goal can leave you hollow if the shell was built for other people.

  By about 38 or 39, Colonna was a successful, wealthy venture capitalist who had done everything he was supposed to—and was depressed enough to want to die. He felt ‘hoodwinked,’ though no one did it on purpose. He had walked around in a shell tailored to other people’s projections. His skills, intellect and work ethic showed through, but he wasn’t doing what he was put on Earth to do. A long gap between inner and outer self, he argues, breeds depression.

• 02

  We shapeshift for love, safety and belonging, and pass it down.

  From school and family we attach identity to roles: the peacemaking youngest child, the early-parentified kid, the straight-A student, the athlete. One client said, ‘I was bred to make my family members feel better.’ Children who shapeshift to soothe a depressed father or anxious mother tend to pass the pattern to their own children, so changing it means breaking a lineage. It’s never too late. In a Buddhist teaching, waking up in the last minute of a 20-minute meditation still counts as a wonderful session.

• 03

  Ask: how am I complicit in creating the conditions I say I don’t want?

  ‘Complicit’ is deliberate: an accomplice in the bank job, not the one robbing the teller. The non-intuitive follow-up is: what’s the benefit to me? A CEO of 15 complained that nobody worked as hard as she did. Colonna asked who hired them and what she got from being in charge; she grinned: ‘I’m the boss.’ Until you’ll risk what the pattern protects, nothing changes. Being seen as a financial wizard had overcome decades of feeling poor, so he ‘had to be willing to be poor in order to be free.’

• 04

  Name what a pattern does for you before judging it—most were built to keep you safe.

  Shane said his public persona, Farnam Street, works as a protective shield. Colonna warns against the urge to self-criticize on spotting such a front: ‘I’m such a bad person’ is just another front, guarding the core issue. Curiosity, not shame, is what transforms. Tracing Shane’s fear of wasting people’s time, he noted that an embryo has no shame. It was learned somewhere along the way, and the feeling was as old as Shane could remember.

• 05

  Running on negative fuel works—until it hollows you out.

  Shane framed a commenter’s jab that he was ‘enjoying his 15 minutes of fame’ and used it as motivation, while praise slid off ‘like a fried egg’ from Teflon. Colonna sees catastrophizing as a family survival strategy common among descendants of immigrants, pogroms and famine: relax and something bad will happen. Imagine still being unable to take in the good at 84 on your deathbed. Shane’s word for it was ‘hollow.’ As Josh Wolfe says, chips on shoulders put chips in pockets. But the goal is equanimity, so mistakes bring remorse and learning without risking self-worth.

• 06

  ‘Enough’ is the antidote; reaching for the stars replaces fear.

  Colonna left venture capital while his close friends Fred Wilson and Brad Feld became two of the world’s most successful VCs. When he envies them, his journal says, ‘dude, you have enough.’ Over lunch Wilson told him he does the work he was born to do, which made him cry. He invokes the Buddhist hungry ghost, never sated, and says millions of them hold power. Breakthroughs come when brain and heart are relaxed. The healthy driver is Browning’s line: ‘a man’s reach should exceed his grasp, or what’s a heaven for?’ I am enough, but what if I wrote a book that changed the world?

• 07

  Resilience needs discernment; otherwise it becomes stubbornness.

  ‘False grit’ is persevering for a hidden reason: founders cling to businesses with no product-market fit because they fear failure. A former boxer, Colonna rejects ‘resilience is the ability to take a punch.’ The goal is to slip punches and outlast the opponent. If a son plays badly at his first hockey game, explore what’s at stake—shame, enjoyment, contributing to the team—rather than just forcing him back on the ice. The aim is knowing things can go wrong and you’re still OK.

• 08

  Teach children words for feelings; growing up is a lifelong practice.

  We tell kids to ‘use your words’ but never give them the words, especially boys, who hear ‘I’ll give you something to cry about.’ Most people learn only two modes: silent passive aggression until they explode into active aggression. That gap, Colonna says, is why toxic workplaces hand power to people who can’t speak about what they feel. At 60, after 18 years of meditation, he says he finally has ‘a little flaming butter knife’ of discernment, and that getting a bit better every day is ‘glorious.’