Your Best Self #5: Feeling Lost & Achieving Your Next Big Win (Classic)

What's up, everyone. Welcome back to Founder’s Journal, my personal audio diary, where I give you, the business builder, the tools you need to think better in order to build better, whether that's building a business, a team, or a new product. This week on Founder's Journal, we're doing things a little but differently. We're dropping a mini-series focused on being your best self. I'm giving you mental models, strategies, and tips to get you in the right mindset before the new year. That means instead of just one episode Monday, Wednesday, and Friday, this week we're giving you two: a new show that you won't want to miss, plus a classic episode you maybe haven't heard before. In this classic episode originally published on October 13, 2021, I talk about feeling lost and share how I'm working to find direction as I step into a new role at Morning Brew. Let's hop into it. 

Figuring out where to invest time

I would be lying if I said the months since selling Morning Brew as well as moving into my new role from CEO to executive chairman have been easy and pure euphoria.

I've spent weeks worrying, wondering, and thinking. I've worried if I'm a one trick pony, I've wondered what's next in my life. I've thought about what gives me energy and fulfillment. And much of this time has felt, to be totally honest, directionless. I know what I'm doing within Morning Brew and that direction is clear. But outside of the day to day, I don't know what I'm working towards. And with this move from the CEO to the executive chairman role, I've been given time, a fair bit of it. I went from working, you know, 70 hours a week on Morning Brew to let's call it 30 to 35 hours a week.

And I see many different directions with what I can do with that new found time. I could spend time working on myself, going all in on therapy, executive coaching, and studying ways of thinking like Buddhism or Stoicism. I could get operational experience to strengthen a muscle that candidly, I don't feel like I've adequately built up and I could do that through something like buying small businesses, like mini golf courses. That is actually something that I have looked into doing. I could go back to the zero to one part of business building that I love and start a little side business for fun, which would also provide some great content for Founder’s Journal, because it'd take me back to the early stages of building. Recent idea that I had was building a direct-to-consumer mindfulness business that started with meditation cushions as the first product. I could go really deep into NFTs and Web 3.0 and just explore a corner of the internet that's new and uncharted with a lot of smart people that are pouring into it. I can do so many different things with the time I now have, but that's part of the problem. And right now I feel like I'm dabbling with eight different things, but not doing any one thing super well. And I'm not sure if that's a good or a bad thing. Is it bad that I'm kind of exploring and dipping my toes in a lot? But the analogy that I think of for what I'm doing right now is, I'm thirsty and I take a full pitcher of water and I pour that pitcher into eight different glasses. But since I'm spreading that water across so many glasses, I'm not being fully satisfied by any glass.

And then part of me is like, why am I trying to effort so much and put so much pressure on myself right now? Why don't I just use this time to recharge and have no expectation of what's to come and just enjoy each day and what that day presents, which then brings me to thinking about why is it that I'm thinking about going deep in NFTs or getting more operational experience or starting a little side business? Why can't I just be still for a second? And I have two answers to that question. The first is that I'm a striver. I'm competitive with myself and I'm always looking to grow and improve. If I don't feel like I'm growing, I feel like I'm not living.

What motivates me: growth and external validation

And right now I don't feel like I'm growing enough. I feel like I'm being creative, which is great. I feel like I'm consuming a lot of content and learning that way, which is great. I feel like I'm helping to grow the Morning Brew brand, which is great, but I don't feel like I'm building towards something and learning by doing. The second answer to the question about why can't I just be still is that I like external validation. I care what other people think. I'm worried that I'll become irrelevant and that there has to be something after Morning Brew that makes me interesting to people because I feed off of validation from others.

On the first point, there's both beauty and struggle in the fact that I'm a striver. It has served me well in my professional career, but it also causes suffering. It causes me to feel unsuccessful if I'm not great at everything. It causes me to never feel satisfied even after building and selling a business. And it blinds me from just appreciating what I've accomplished and enjoying, just being and living in the present. Here's a perfect example. My girlfriend asked me yesterday, if I never do another thing other than Morning Brew professionally will I feel successful? And my answer to her was a resounding no, I wouldn't.

She asked why and I said, because I'd feel like a one trick pony and I'd feel like I peaked too early in my life, and I didn't realize my potential, whatever that means. But see the ironic part of this whole thing is that I believe no matter how many businesses I build, I'll never feel like I reached my potential because the ceiling will just keep moving as I do more. So the question is how can I harness my desire to grow, but do so in a way that's chasing a never attainable target? On the second point, this is what scares me most. 

[AUDIO CUT IN] Brian Henry: Brian Henry, producer of Founder’s Journal here. I just want to pause you right there. That question, “How do you harness growth while chasing an unattainable target?” Do you actually have an answer to that? 

Alex Lieberman: Yeah. First of all, shout out to Brian producer of the show, makes this whole thing possible. Ha I, yeah, it's a really hard question to answer because like I said, there's stuff that I love about myself in terms of being a striver and being competitive. It serves me well in certain parts of life, but like if my goal is to be happy and fulfilled and I never feel like I'm hitting the mark or the expectation of myself, how can I do that? That's always really hard for me. And I think one of my answers is not to focus on the output, but to focus on the input, focusing on putting my best foot forward on the things that I'm working on. And so I think if my, if my target becomes, oh, now I've, you know, I've built one company that sold for a lot of money. The next company I built has to sell for 10 X more, while I think that creates the wrong anchor from day one. I think instead, how can I frame it on things that I can control? Right. I can't control the outcome of the business, but I can control, you know, using my time purposefully and working as hard as I can on something that gives me energy. So I would say it's focusing more on the inputs than the outputs, which is easier said than done, and also figuring out how do I worry less about the future, and if I'm going to reach my target, and more about just like today, how do I spend my time as wisely today as possible? Again, in theory, I think it's, it makes sense. For me it's like, how do I match my emotions and my body to kind of like the rationale? So, no,  it's a really good question and something I'm always thinking about. Appreciated the question, Brian and excited to do more of these. 

So on the second point about why I can't be still, and I talked about liking external validation and I care about what others think, this is the one that scares me the most. I hate that I feed off of the attention of people who follow me on social media or people that stop me at the dog park and say, “Hey, you're that Morning Brew guy, right?”

Why external validation is dangerous

I hate it because that's not happiness that I can control. I also hate it because at the end of the day, if I truly want to care what people think about me, all I should want to care about are my few people, the people who are going to stay with me for much of my life, my family, my girlfriend, my friends, and at the end of the day, I know that these people like my true people don't care what I do professionally. They just want me to be happy. They're not going to care if I do another thing after Morning Brew my life. So why do I care? And so, as I think about what I want to spend time on, how do I also know if I'm going to do it because I genuinely enjoy it or because it's what other people would want me to do, basically.

Figuring out what’s driving me

How do I know if what's driving me to do things, is the striver part of me or the part of me that requires external validation? And that's an embarrassing question for me to have to ask, but it's an honest question. And the answer isn’t obvious, because for me, at least it's so hard to identify what creates my motivation. What gets me excited to spend time on something? Is it what others think? Or is it what I feel intuitively? The only thing I can do is just continue to work on being driven by my own self-belief and my intrinsic motivation and committing to things that in the moment of doing them just feels right. And I feel a sense of flow where I'm not thinking about what others would think or what I'm going to post on social media after, but instead there's actually just no thinking whatsoever. I'm just in the act of doing. 

So why do I share all of this? And what's the lesson? Well, I share this because I really don't think I'm the only one that experiences this. Maybe this specific context is unique to me, but I think the feeling of being lost and directionless and what drives my motivation, I feel like a lot of people experience that. And as for the lesson, I'm not totally sure, but I just wanted this episode to act as an opportunity to work through my own thoughts on my career, as well as serve as a reminder for you and me that no matter our success or where we are in our careers, we're all just faking it.

I think people look at me as, you know, the successful entrepreneur at 28 years old, that built and sold a business. But I feel the same insecurities as I did before building Morning Brew. Everyone you know and look up to is constantly trying to figure shit out, find direction, know what gives them energy, be happy, and decide what to commit to next. And you're not alone. You're actually exactly where you're supposed to be at this very moment. And finally, it's just another reminder that better understanding yourself and what truly motivates you is never a waste of time because the more you gain a sense of self, the more you can be in control of your own life and also your own emotions.

 With that, I'd love to hear from you. When have you felt lost in your career? And what did you do personally, to try to work through that feeling of being directionless? Shoot me an email to alex@morningbrew.com or DM me on Twitter @businessbarista. As always, thank you so much for listening to Founder’s Journal. I have one ask of you. The number one way to grow this show is by you hitting the subscribe button. So whether you listen to the pod on Apple, Spotify, or another podcast player, pound subscribe so you can get notified when we come out with more great content on Mondays, Wednesdays, and Fridays, but also, so this show can continue to grow and inspire people to be the best version of themselves.

Thanks as always for listening and I'll catch you next episode.