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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When instructed by parents to apologise, the child says, “I’m sorry”. The right words, said without intention.

As we grow into adulthood, habits can persist, expecting instant forgiveness (assuming that the words have not been overuse).

When that doesn’t work, in a rush to minimise the uncomfortable situation, we offer up explanations for our mistakes. While this might ease our discomfort, we dismiss the feelings of others.

An apology, done well, is a chance to show that you care. An opportunity, to take responsibility, recognise the hurt that was caused, and offer up the willingness to repair.

It’s not about the words but making the space for reconnection.

Consider, “Hey, I agree to a call at noon. I couldn’t make it and had to reschedule. I want to take responsibility for that. Is there anything I can do to clean that up with you?”

If I could sink my teeth into the whole earth
And actually taste it,
I’d be happier for a moment…
But I don’t always want to be happy.
To be unhappy now and then
Is part of being natural.
Not all days are sunny,
And when rain is scarce, we pray for it.
And so I take unhappiness with happiness
Naturally, just as I don’t marvel
That there are mountains and plains
And that there are rocks and grass…
What matters is to be natural and calm

In happiness and in unhappiness,
To feel as if feeling were seeing,
To think as if thinking were walking,
And to remember, when death comes, that each day dies,
And the sunset is beautiful, and so is the night that remains…
That’s how it is and how I want it to be…

Fernando Pessoa

I was stuck in the dark for months. Fatigue, depressed with no agency.

The problem is then, I have too much free time and a restless mind.

I wanted to find work that excited me, but nothing sparked my curiosity. I spent hours in bed wondering if I should rest more or get out. I wanted to enjoy my free time but I didn’t.

I swap thoughts like what if I’m not going get better, to I’m okay right now. Many people are relaxing like me, I don’t need to produce to enjoy my day.

It took away my guilt, but I still don’t know what to do with my free time.

This is till The Enjoyment Experiment, and something shifted.

The basic setup is to do what feels good, and stop doing what feels bad. For 5 days, enjoyment is the only metric.

It eliminated second-guessing, and conserved my mental energy. It unlocks more curiosity, generosity, and enjoyment of life.

It gave me permission to nap as long as I wanted and remove the guilt. As soon as the thought came up, it was gone.

It’s not an instant fix. I was tired, and I didn’t feel like doing anything. So removing the self-blame, giving myself more time to rest, hence more energy for the times I’m awake. Then when I woke up, instead of a frantic mess, I asked what would be most enjoyable to do right now?

As I looked for and felt enjoyment, I found more enjoyment. I stopped comparing myself to what I should do instead.

At first, it was scary to allow myself to rest as much as I wanted. But I figured it was a 5 day experiment so the downside was going to be limited. I extended the experiment.

I used to make decisions on energy and engagement. Now, I believe that enjoyment might be an even better metric. Or at least a worthwhile experiment.

If you have enough resources, and life feels like an uphill climb, why not do the opposite for 5 days?

It may not be purposeful or productive. A life enjoyed is a meaningful life too.

P.s. Hat tip to Joe Hudson and the Art of Accomplishment course

The past six months have been the scariest experience of my life.

After enduring months of constant fatigue and confusion, I hope that sharing my experience will provide insight if you or a friend are facing similar situations.

My daily routine was: to wake up at 9am, gym, and email for 2 hours. Then I would tire and go back to sleep till 4pm. Some days, I never leave the house for the rest of the day.

One month in, with no increase in my energy levels, I decided to cut back on all my projects – coaching, volunteering with AWARE, and podcasting. I only kept working on my animation studio projects.

I tried various things to improve my symptoms – coaches, somatic therapy, nature walks, volunteering to deliver meals, renting my own place, meditation class and even praying through different religions. There are slight improvements, but it did not sustain. My symptoms did not improve and time is passing like sand.

I’m confused if it’s burnout, grief and midlife crisis. I explored it all. The trouble is psychological “problems” are not definite.

I was running out of ideas.

I never anticipated that my emotions would be affected. I couldn’t feel. I had no feelings, no anger, no sadness, no joy. Making decisions became ten times harder. Sometimes, it would take me days to reply messages.

Even though my friends took time out of their schedules to meet me, I couldn’t feel grateful. I understood that I should be, but the feeling just wasn’t there. I ended up feeling bad about myself instead.

On top of emotion, I couldn’t access my intuition either. It just seemed like it was an endless series of wrong decisions.

As I came to terms with the new reality, I contemplated the idea of “What if things don’t get better?”

It terrified me. I started to grieve all the future I had dreamed of and began asking. “How should I begin to chart my life?”

When I’m at home, I was often torn between resting and going out.

Maybe that’s what depression or uncertainty feels like. I hope now that I’ve experienced this, I can be there for my friends when they ever find themselves in this situation. I’ll also practice more of this letting go exercise.


I remembered my grandma during her last few years, she never gave up gardening. Now I understand that it was her way to feel a sense of contribution.

I yearned for someone to help brainstorm ideas about possible causes and solutions.

Looking back, I appreciate the people who checked in on me, traveled to visit me, brought me food and spent time with me, sharing similar experiences in the past. Some invited me to their religious prayers. Others shared possible diagnoses, explored ideas, and provided loving support.

To those of you, I want to thank you from the bottom of my heart. You made this journey less lonely.

In the face of uncertainty, sometimes that is all I can hope for.



After a battery of tests with a functional doctor, I found out that I’m low on vitamin D and H Ployri stomach bacteria infection and a small intestine bacteria overgrowth (SIBO). I started an antibiotic treatment last week. And, I’m feeling better now. Hopefully, it last.

It’s been 5 months that I felt low energy, low mood and unproductive.

A question I’m wondering is: “Do I need rest or I am being lazy?”

I want to start writing again to make sense and look back at this period

Here are a few random thoughts and happenings:

  • Not getting things done, sucks. Not contributing to my friends, sucks. Not knowing what to do, sucks. Having ample time, no energy, a wanting to contribute but not being able to, sucks.
    • I remember my coach declined work because she wanted to focus on healing her cancer. She put on her oxygen mask first.
  • I visited a Somatic therapist, D. I asked D if “I needed more rest or am I being lazy?” She says: “She doesn’t like to diagnose people. She likes the body to realize what it needs.” We did several exercises. I could feel that my stomach was tight and something was stuck.
  • During a meditation class, T, instructs us to imagine like we are a fly on the wall. I felt vastness, then as I looked at myself from the outside, I felt my body becoming heavy like thick mud. In the next prompt, my body goes back to normal.
  • My friend, Abby, says she had a similar experience. For her, It’s the “body” beneath the body.
  • A journal prompt, “How can you make a task I don’t like, 10% more enjoyable”. I journaled about wanting to find my purpose, then I got confused and tired.
  • In an article from an ex-founder, after stabilizing from long COVID-19 illness, she felt anxiety when planning for intense physical exercises. She decided to find a therapist or coach.
  • After being a volunteer photographer for a half day, I felt physically tired and went back home to sleep.
  • I’m scared that my low engagement, and napping, will become the reason why I’m tired. Like a muscle getting atrophy because of low usage.
  • When watching YouTube videos, skip to get to the point, then immediately forget the point. I am multi-tasking, skipping, and switching. I’m distracted and not enjoying the videos.
  • Weird sense of optimism in the night, around 9 pm. 2 nights straight.
  • I gave care to my clients, Rebekah and Regina.
  • Maybe I ought to do more meditation?
  • I went to a Secret Moonrise dance night event, the weather was perfect. It felt like a good workout. I didn’t feel as amazing as I thought I would.
  • After a morning doctor consult and x-ray, I felt tired. I brought a bag of chips, canceled appt, slept from 1pm – 4pm, did a client call then went back to rest again.
    • It felt like I couldn’t predict my energy level. E.g. Room rental, appt to yoga, appt with friends.
  • I went an integral coach, T, for a consultation. He shares that it could be that my new way of being has emerged from previous coaching with Christina. It has been beaten down because of the sale of the childhood home, and disappointment to find a new home. With the passing of the previous coach, I’ve lost the guide back to the new way of being. Without a guide, I have to rely on myself. But as the endeavor might be too huge, I get scared and go into hiding.
  • I asked if I had a billion dollars tomorrow, what would I do? I would hire all the best coaches and teachers to learn about spirituality and orient to the new way of being.

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