Reflections at Forty One

At about 6:15 this morning, I completed another rotation around the sun and turned forty-one. Even though I'm relatively young and healthy, typing this number makes me more reflective because I've officially landed in midlife.

Despite COVID and the state of the world, the past year has been the most fulfilling, productive and expansive of my life. I transitioned from being an institutional VC to a coach. I moved from NYC to the Catskills. These were just two of the many events that shaped my life.

In the days leading up to my birthday, I carve out a few hours to contemplate the past twelve months. This session provides the time and space to reflect on wins, milestones, peak experiences, people who helped, and lessons learned. The process is not only cathartic but also illuminating.

I'm extremely grateful to be in good health. I'm extremely grateful for my family, friends, and the founders I serve. I'm extremely grateful that I'm able to work for myself and support my family through my work. There's just so much to be thankful for in 2020. I feel so lucky.

Without further ado, here's my recap of the past year. I hope the next trip around the sun is filled with just as much growth, fulfillment, and good health!

Personal Evolution

How are you different?

• I'm a coach, solopreneur and angel investor

• I'm more attentive and involved with my daughter

• I'm in tune with my physical and mental wellbeing

• I'm focused and inspired creatively

• I'm more introspective

• I'm preferring the woods over the city life

• I'm less interested in sports

Highlights

What were the notable wins, milestones, and experiences?

• Watched my daughter take her first steps and say her first word

• Quit my job as an institutional VC to pursue coaching professionally

• Moved from NYC to the Catskills

• Launched High Output, my boutique leadership development company

• Closed a $5M angel fund

• Published an Entrepreneur's Guide to Finding a Coach

• Shipped the first version of the Founder Library

• Relaunched my personal site schlaf.me

• Deepened my spiritual and meditation practice alongside my teacher Ryushin

• Celebrated five years of sobriety

• Read 'The Mind Illuminated' which elevated my mediation practice

• Returned to my bike after a serious cycling accident in 2019

• Started a virtual AA group with an incredible community of men

• Saw the Preservation Jazz Band in New Orleans (pre-COVID)

• Cooked my first Thanksgiving meal for my family and in-laws

• Began intermittent fasting and lost 10 pounds

• Experienced several nine-figure exits in my RRE portfolio

• Attended EVRYMAN's Men's Emotional Leadership Training in the Berkshires

Lessons

What were your key learnings?

• It's ok to make a change and move on if your head and heart aren't in the game

• Progress on creative projects happens will small steps rather than giant leaps

• When you're feeling burnt out, make time to slow down, rest and recharge

• If you don't ask for help, no one will come to your side

• Sharing progress and updates publicly builds momentum and accountability

• One of the most effective ways to help another person is to just listen

• Seek collaborations with only people you respect and want to learn from

• What you spend your time on reflects what you value

• Health matters far more than wealth and status

• Having a platform and audience is a privilege - use it to inspire and help others

• If you don't prioritize time for deep work, you'll never get much accomplished

• What you say no to is just as important as what you say yes to

• You can transform yourself and your career at any age

• Being a solopreneur is hard, really fucking hard

• Time spent in email takes you away from creative and important work

• Deciding to take the leap is harder than actually taking the leap

• All relationships, even the most healthy, are challenging and demanding

• There's power when we tap into our bodies, feel our emotions, and express ourselves

• A purpose of life is to be fully present and aware as much as possible

• Shut it down after 9:30pm, there's always tomorrow

Expressions of Gratitude

Who helped along the way?

• Eliza for supporting me through a career transition and putting up with me in quarantine

• Faye for teaching me that love, curiosity, and patience is boundless

• Lhaden for showering Faye with love, support and attention

• My coaching partners for trusting me to serve you on your journeys

• Ryushin for teaching me the dharma and being an invaluable mentor

• My portfolio founders for giving an opportunity to invest in and support you

• Sunil Arora for being a friend, mentor and collaborator

• Andrew Taggart for helping me manage the transition from VC to coaching

• Elizabeth Woodbridge for mentoring and coaching me in the early months

• Chris Sparks for providing tough love and getting me to focus, focus, focus

• Julia Austin for challenging me to be more intentional about diversity

• Semil Shah for being a sounding board and resource as I was getting started

• Holly Whitaker for being a good neighbor and always believing in me

• Edith Cooper for giving me the confidence to quit my job and start High Output

• My COVID-19 AA Group for providing the community I needed in quarantine

• My Coaching Mastermind for helping each other evolve as coaches and humans

• Rishi Tripathy for allowing me to guide and mentor him this summer

Intentions

How do you want to show up next year?

• Spend more quality time with my wife

• Cultivate deeper curiosity and wonder about people

• Serve my clients and founders with an open heart and mind

• Devote significant time to creative endeavors

• Find comfort and serenity in saying no and setting boundaries

• Aspire to improve as a coach every single day