The Year After Selling Morning Brew Nearly Broke Me
The year after selling my business was one of the hardest periods of my life.
People are usually shocked to hear this and can't make it make sense.
"You accomplished what every entrepreneur dreams of." "You made life changing money, what could be so bad?" "You were given the gift of time, which is the greatest gift in the world."
What you're wondering is true and valid... and that's partially what made it so painful.
The journey of exiting Morning Brew was a paradox of the highest order.
The Outcome Was Beautiful in So Many Ways
A small idea that my cofounder and I dreamt in our dorm rooms at college blossomed into a media company that impacted millions of lives and reached a size that pushed our wildest imagination and ambition.
It was a promise fulfilled. My dad passed away when I was a junior in college. In my last conversation with him, I promised him that I'd do everything in my power to take care of the Lieberman household so no one had to worry about money.
Financial security left me and my wife with a sense of security and optionality as we looked forward to growing our family.
And it was a new home for our business that could allow us to dream bigger and take bigger swings with the opportunity for greater scale, imagination, and impact.
It Was Also Painful in Nearly as Many Ways
My company ate my identity. I spent most of my young adult years building this business and being validated as "CEO of Morning Brew" which felt good, appealed to my ego, and continued this cycle of have an idea, do good work, get celebrated for it.
My 12/10 motivation disappeared overnight. Fear-based motivators were the story of what drove me during this chapter of my life. I had a chip on my shoulder to prove those who bullied me earlier in life wrong, and I felt financial anxiety to create safety for my family after my dad's death. Once we sold, the motivators that served me in the previous 10 years would not serve me for the next 10. Looking back, I can trace how my early years shaped everything that came after.
The aftermath was lonely. My "struggles" post-exit felt like a champagne problem people would kill for. Because of that I rarely shared the journey. And because I rarely shared the journey, I bottled up many of these emotions.
Time is a gift and a curse. Once I stepped out of the CEO role, I was given the "gift" of time. But unless you know how to productively direct time, it can feel like a prison. For a year straight, I marinated in my thoughts around being lost, no longer being motivated, and needing to re-find purpose.
Getting Lost Helped Me Better Find Myself
While the 1-2 years post-exit were challenging, I now very much view it as a period of getting lost to better find myself.
I emerged from this chapter of my life with clarity around a few things.
Fear-Based Motivation Burns Fast Then Fizzles
Fear-based motivation is incredibly powerful but short-lived. Once you've nurtured your ego, materialistic needs, and childhood traumas, the fire under your ass quickly turns into fizzling coals.
Today, I try my best to listen to growth-based motivators that feed 3-year-old Alex's desires: curiosity, growth and play. This type of motivation is the energy equivalent of an ultramarathon vs. a 100-yard dash.
Freedom of Time Does Not Equal Happiness
It is true that time is finite and having the privilege of choosing how you spend your time is exactly that... a privilege. But being gifted with more time does not mean you'll automatically feel more fulfilled. Why?
Our job as humans is to create. To create families. To create communities. To create companies. When we are not in the act of creation, or at the very least have clarity around what we're working towards creating, we can feel lost.
Know Your Zone of Genius and Your Values
Deeply understanding your zone of genius and your values is the gift that keeps on giving. During my post-exit journey I got clear on two things.
First, the 1-2 superpowers I bring to the world and how they can show up in my professional and personal life. For me, those are relentless curiosity and a fervor for storytelling.
Second, how money can be translated into happiness and at what point more money doesn't convert into more happiness. Money feels most valuable to me when it's used in 3 ways: not having to worry about it, giving to my family, and spending on experiences with the people I love.
The most helpful tool that helped me get clear is something called The Best Stuff Exercise by Conscious Leadership Group, which I couldn't recommend enough.
Every Journey Has Nuance and Periods of Wandering
This was a long-winded way of saying that everyone's journey has nuance. Periods of wandering are uniquely human, profound and beautiful, but also complicated and painful.
The paradox of achieving everything you worked toward, only to feel lost on the other side, is more common than anyone talks about. But that wandering is where the real clarity lives.
Hope this helps.