How I Feel.

When I tell people I sold my business, they always ask me the same question.

How does it feel?

Here's the honest answer.

I sold my business 3 years ago and I'm 2.5 years out of leaving the CEO role.

I’m generally feel happy, I'm definitely a little bit lost, and I'm 100% not fulfilled. 

When I share this with people they’re a little bit taken aback. 

They think to themselves how is that possible? 

Alex is 30 years old, sold a business by 28, made life-changing money, has a big audience online and has been wildly successful by every objective measure. 

How isn’t he fulfilled & how is he lost? 

It's a very fair question and honestly one I feel nervous to talk about publicly out of fear about complaining about a highly privileged problem.

But it's a problem nonetheless and one that I know a lot of high achievers experience in their lifetime.

So what's my answer to their question?

It's simple.

Identity is a prerequisite for happiness. 

Personal accomplishment does not equate to fulfillment. 

And you can’t truly feel settled in your direction unless you understand your purpose. 

I’m going to spend the rest of the episode talking about how I came to these realizations. 

Let’s start with why I’m generally happy. 

I’m generally happy because I have immense gratitude for the position that I’m in. 

Financial freedom has given me freedom for how I want to spend my time and because of that I feel incredibly fortunate to be able to avoid a lot of the typical stressors in life. 

I’m not worrying about money on a monthly basis. 

I’m not worrying about work-life balance or if I’ll be able to spend enough time with my family or friends. 

I’m not worrying about if I have the time or money to care for my physical or mental health. 

And the gratitude I have for not having these worries gives me a high level of base happiness. 

So why am I not fully content? I think it’s because I don’t have clear direction or purpose. 

After leaving the CEO seat for Morning Brew, I didn’t just give up my job. I gave up my identity. 

Because from 2015 to 2020, I was Alex Lieberman CEO & face of Morning Brew. 

That’s how I perceived myself and that’s how I believed the world perceived me. 

And because that’s how I thought about things, I perceived my value as a person to be a reflection of that identity. 

Not the identity of Alex Lieberman the boyfriend. 

Not the identity of Alex Lieberman the son or brother. 

Not the identity of Alex Lieberman the member of his community. 

My entire self-worth was defined by my work. 

And so when I left the CEO role two things happened. 

First, I didn’t know who I was. 

Second, I had 40 hours per week to ruminate about how I didn’t know who I was. 

And that was a realization for me. 

I always thought financial freedom leading to time freedom was a good thing. 

And it is, but there’s a very important nuance. 

The beauty of not having to worry about money is about being able to choose how you spend your time rather than just having a ton of free time. 

Which is why, candidly, the first 6 months after selling Morning Brew was brutal for me. 

It was the most directionless I’ve ever felt.

Since I was a little kid I wanted to be like my parents and work on Wall Street, so every moment leading up to me getting that job on Wall Street was in service of that goal. And then once I decided to make the leap to morning brew, every moment was spent in service of making morning brew a successful company. So April 2021 was truly the first time in my life that I didn’t have that next thing. 

Now I’ve definitely made progress over the last few years in emerging from what I dramatically call the valley of despair to being in a better place. 

How have I done that? 

Well, I spent time identifying the things that made me feel most alive during my time building morning brew. 

And that was actually pretty easy for me to figure out. 

I loved being creative. 

I loved being scrappy. 

I loved problem solving with smart people. 

I loved bringing a product into existence. 

I loved selling/storytelling. 

And I loved meeting other founders. 

So what I’ve done is between my work with Morning Brew as well as having a hand in other endeavors like storyarb , coaching founders, and creating content online, I’ve kept myself busy scratching the itch of those professional things that I’ve loved most.

On top of that, I have tried to better prioritize all of the things in life that were put by the wayside during the most intense building years of Morning Brew. 

I got married to my amazing wife who I feel so lucky to have as my partner and honestly best teacher. 

We got a dog, which is literally the single highest ROI purchase of my life. Our dog brings me an irrational amount of joy. 

I’ve tried to prioritize more things that feel like play, whether it’s building lego sets or going to an immersive theater show with my wife or taking Spanish classes. 

And I’ve spent money on things dedicated to my health like a therapist, nutritionist, and personal trainer, all of which I would have been way too frugal to pay for prior to exiting the brew. 

But despite doing all of this reflection and the things that I’ve done to try and push the ball forward, I don’t feel full. 

I don’t feel like I have a clear direction & I don’t feel like I’m fully living my purpose. 

And herein lies the problem. 

I have a few potential paths, but none of them feel like great options.

One direction is finding a problem & an idea that I’m excited enough about and going all in on building that business like I did with Morning Brew. 

But then the question is for what? 

Without an idea of something to build that is in service of something bigger than myself (which David Brooks refers to as the second mountain), I’d be victim to a trap that I believe many entrepreneurs fall into. 

Business building is great for ego building. 

It offers you recognition. 

It offers you financial abundance. 

It offers you a feeling of power. 

It temporarily masks feelings of FOMO or comparison.

It’s actually a great way to scratch our extrinsic itch for power, pleasure, greed, and wealth. 

But if I learned anything from my experience with Morning Brew, none of those things have actually brought me true purpose, direction, or fulfillment. 

So why would I go through it again? Only to be 40 years old and be back in the same spot I am at this very moment. 

From my perspective, the only reason I’d want to fully commit myself to building any business (or anything for that matter) is if I feel like it allows me to live my purpose and be in service of something bigger than myself. 

But I don’t know what that is yet. 

Which brings me to the other possible path.

Doing a lot of things, but not fully commit to anything. 

And that’s kind of what I’m doing right now. 

I’m serving as Executive Chairman for Morning Brew, I’m co-founder an Chairman for storyarb, I’m spending time meeting with, advising, and coaching founders, I’m playing a little bit of golf, I’m spending time with my wife, I’m finding opportunities to satiate my need for learning & play like legos, art, and Spanish. 

Yet I still don’t feel full. 

So leaves me right here, in this very moment, thinking about what I do next. 

And the honest answer is, I have no idea what my next move is & I don’t know that there is a right answer. 

But here’s what I’m thinking. 

I need to find my second mountain. Something that I feel called to. Something that allows me to serve others rather than myself. Something that I don’t even question being fully committed to because full commitment becomes the only option. 

But as I try to climb to the peak of this second mountain, there are a few ground rules I know I have to set for myself. 

The first is that there is no timeline or time limit.

I feel so grateful that I’m able to have the privilege to tackle questions around purpose & fulfillment at 30 years old.

These are questions that can take a lifetime to answer & it feels like a true gift to have a early start in that journey. But finding something that you want to truly commit to (like actually go all-in on) is a lofty goal and it will likely take a ton of trial and error. I need to have self-compassion during this journey. 

Which leads to the second rule. Try a lot of shit & be in tune with your body. I believe the only way to find your purpose is to look for your purpose, not think about your purpose. Because it’s so easy to over intellectualize this journey rather than experience things and feel your way through them. 

And as I try shit, I shouldn’t discriminate from the stuff I try.

Building new businesses or finding a mission with a new business can be one of those things, but I also want to explore things that have no financial or social upside whatsoever.

Volunteering with causes I’m passionate about (like mental health non-profits or non-profits that support bullying or children who lost parents for example).

Spending time being creative whether it’s learning how to woodwork or refining my photography skills.

Spending time being a present parent if & when I have a child.

Maybe going back and teaching a class as an adjunct professor.

Nothing should be off the table as I try to be called to a vocation, and I should use my intuition to decide what I should test next. 

And the third rule is to acknowledge and navigate what I call ego creep.

As I’m on this journey I’m going to inevitably feel drawn to opportunities that serve my ego.

Building another business, doing another podcast, creating more audience on social media.

Those things feel familiar & comfortable and are things that 14-year-old Alex who was bullied and lonely feels so drawn to because he wants to protect 30 year old Alex. I shouldn’t judge this ego creep, it’s in all of us, and trying to push it away won’t do anything, but as I’m thinking about what I spend my time in, I just need to remind myself that I got here, to this very moment of directionless & lack of purpose, by spending my entire life chasing my ego. 

So that’s where I’m at. 

I’m very grateful. 

And I’m generally happy. 

But I do feel lost. 

And I don’t have a deep sense of purpose. 

I don’t know exactly how I’m going to get there, but I have a plan and I’ll keep you in the loop along the way.