What I Do When I’m Feeling Lost

What's up, everyone? Welcome back to another episode of Founders Journal. I'm your host, Alex Lieberman, co-founder and executive chairman of Morning Brew. Before we hop into the show, I have a 10-second favor to ask of you. We have tons of new listeners to the podcast, and my goal is to get to know as many of you as humanly possible. Either before you start the episode or right after you finish it, shoot me an email to alex@morningbrew.com. If you want the easiest option, like the 2-second option, just say hi in the subject line and I will respond, getting the conversation going. If you're a little bit more ambitious and maybe you have 30 seconds of time, shoot me an email telling me a little bit more about yourself and why it is that you listen to Founders Journal. I can't wait to get to know many of you over the coming days. And now for today's episode, I'm going to talk about feeling a little bit lost in my life right now. Let's hop into it. When I tell people I sold my business, they always ask me the same question, how does it feel? And here's the honest answer. I sold my business 3 years ago, and I'm 2 and a half years out of leaving the CEO role. I 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 and 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 candidly very privileged problem, but it is a problem and a challenge 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 an immense sense of 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 then? I think it's because I don't have clear direction or purpose. You see, 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 and face of Morning Brew. That is 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, member of his community. My entire self-worth was defined by my work. And so when I left the CEO role, 2 things happened. First, I didn't know who I was. Second, I had 40 hours a 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. 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 and stepping out of the CEO role was absolutely brutal for me. It was the most directionless that I have ever felt in my life. 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 very dramatically call the Valley of Despair to being in a better place. How have I done that? Well, I spent a lot of time identifying the things that made me feel most alive during my time building Morning Brew. And this list of things was actually pretty easy for me to figure out. The things that gave me energy. 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 and storytelling, and I loved meeting other founders. So what I've done is between my work with Morning Brew currently, 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 selling the Brew. But despite doing all of this reflection and better focusing my time and spending time on things that hopefully will push the ball forward, I still don't feel full. I don't feel like I have a clear direction, and I don't feel like I'm fully living my purpose. And herein lies the problem. I have a few potential paths to choose from, but none of them feel like great options. One path is finding a new problem and a new idea that I'm excited enough about, and I go all in on it to build a business that maybe could be even bigger than 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 a 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. Building a business is actually a great way to scratch our extrinsic itch for power, pleasure, greed, and wealth. But if I've learned anything from my experience with Morning Brew, none of these 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 exact spot that I'm in in this very moment? From my perspective, the only reason I'd want to fully and entirely 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 committing myself 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 and chairman for StoryYard. I'm spending time with advising and coaching founders. I'm playing a little bit of golf. I'm spending time with my wife and our dog. I am finding opportunities to satiate my need for learning and play like Legos, art, and Spanish. Yet I still don't feel full. So here I am in this very moment, just thinking about what do I do next? And the honest answer to that question is I have no idea what my next move is. And I also don't think that there is a right answer. But here's my thought process and here's my game plan. 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 that I need 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 and fulfillment at 30 years old. These are questions that can take a lifetime to answer, and it truly feels like a gift to have an early start within this journey. But finding something that you want to truly commit to, like actually go all in, it's a lofty goal and it will likely take a ton of trial and error. I need to have self-compassion along this journey. Which leads to the second rule: try a lot of shit and be in tune with my body. I believe the only way to find your purpose is to actually go out and look for your purpose, not think about your purpose and over-intellectualize it. 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 that I do 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. At all. Volunteering with causes that I'm passionate about, like mental health nonprofits or nonprofits that support bullying or children who lost parents, for example. Spending time being creative, whether it's learning how to do woodwork or refine my photography skills. Spending time being a present parent if and when we 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 am 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 and 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 directionlessness and 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 feel like I have a deep sense of purpose. I don't know exactly how I'm going to get there, but I know I will eventually. I have a plan and I'm gonna keep you in the loop along the way. Thank you so much for listening to Founders Journal, and I'll catch you next episode. Thank you.