Steve Schlafman (@schlaf) is a professional transition coach who helps high performers navigate complex work-life transitions and discover their next calling.

Previously, he was a Partner at several of the top venture capital firms in New York City.

Steve has received certifications and training from coaching and therapeutic schools including (but not limited to) The 15 Commitments of Conscious Leadership, Aletheia, Internal Family Systems (IFS), Nonviolent Communication (NVC), Men’s Emotional Leadership (MELT), Enneagram and more.

He graduated from Northeastern University and has lived a life of sobriety for the past 10 years (and counting).

Listen to the podcast on Apple Podcasts, SpotifyOvercast, or your favorite podcast platform. You can watch the interview on YouTube here.

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”It’s just the way I am. I’m not a consistent person.”

It’s entirely possible that there are things you do consistently that you didn’t do when you’re a child.

And so perhaps a more honest answer is “It’s really hard to change my habits, and it is not important enough right now, to put in the work.”

Do you brush your teeth every day?

Stockholm syndrome is when a kidnap hostage develops trust and affection with their kidnappers.

The opposite of a healthy connection.

So when we say connection or community…

What we don’t want is… to be held captive, obligations or stuck relationships.

And what we DO want is to feel cared for, to feel someone has our back, to be able to be ourselves.

But what are you willing to offer?

It’s simple, but it might be scary.

It’s to go without guarantees.

To have someone’s back, to care for someone and allow others to be themselves.

But if you do it enough, on a long enough timescale, care will come back to you.

Someone is waiting for you to show up.

There is a certain kind of truth that is hard to come by.

The ones we rather not tell our friends. The ones that we don’t often get.

The ones we think about on the therapist’s chair “Why are we so unable to think of ourselves as damaged and crazy? Self-righteousness.”

Of course, there are people who have told us before.

There are our friends. But they don’t want to risk an unpleasant evening triggering us. And then run the risk of getting back an unequal amount of harsh truth.

There are our parents. They are very kind and maybe also blinded by their own affection for us.

So it leaves another category, our exes. You could expect that they have probably told us. But after all, there is a reason why they are our exes.

So we can go through life, with an average person who met us for 20 minutes could end up with deeper insights into many of our flaws.

How about a pact?

A pact for our friend to tell us the truth. Where part of the friendship is actually to go deeper, to hold each other’s secrets, to be honest with each other. A pact where self-disclosures will not be used against us.

“Hey JAKE, I’ve been thinking about a way to increase my self-awareness. How about a pact? You to tell me inconvenient truths. And I trust that it is for my best interest in mind”.

Poverty, debt, global warming, over-productivity, anxiety and burnout.

It pushes us and pushes us, to work not caring about our happiness.

Conglomerates who own many brands, create monopolies and increase prices.

Robbers in the system who take more than what they give.

It sucks.

And before capitalism? It was kings, and empire and slaves. If you’re born into the whole family, you’re stuck. I’m not sure if we want that either.

On the other end, in the same capitalist system.

Patagonia gave $3 billions for the climate with the system of capitalism.

People built libraries, museums, and Wikipedia.

Capitalism gave us more choices. To be born as we are, and through a series of choices create our life. We benefit from the positive choice and learn from negative consequences.

Capitalism gave us (almost) equal opportunity, but not equal outcomes.

Almost equal opportunity because we are humans. And humans have bias.

Unequal outcomes because people make different choices. And different choices create different outcomes.

We have choices to change our jobs, to support local with spending habits. And make things better.

There are people who work hard, and give back.

And many others who improve on capitalism, install guardrails and policies to make the system better.

As GK Chesterton says, “Capitalism is the worst form of economic arrangement, except for all the other ones that we’ve tried.”

Instead of blaming, I wonder what’s a better system? And more importantly, how will you choose to spend that choice today?

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