What is Measured Discomfort and Why Founders Need It

What's up, everyone? Welcome back to another episode of The Crazy Ones. I am your host, Alex Lieberman, and I'm back with another journal-style episode of the show. Let me give you some context first. Last week, I put out a tweet and a LinkedIn post about my employee ID from Morgan Stanley, my very first job out of college. This post got 900,000 impressions. I feel like it struck a chord with people. And so I want to both Read the post to you. So if you didn't see it, now you will, but also give you the full story behind the post. And so this episode is all about how we should be thinking about the role of comfort in our careers and how if I had stayed comfortable at Morgan Stanley, I wouldn't have had the privilege of sharing my story with you right now. Let's hop into it. What's up, everyone? I'm Alex Lieberman. Yo, this is Jesse Pujji. And this is The Crazy Ones. So this is the tweet I put out that got 900,000 impressions that I'm going to go deeper on. Found this puppy in my closet yesterday. By the way, I was given a lot of grief for using the word puppy there. It was my employee badge from Morgan Stanley in 2015. There's no real reason to hold on to it anymore. It has no utility, but I'll never throw it out because of what it symbolizes. This badge stands for comfort. A comfortable job as a bond trader. A comfortable salary making $85,000 per year. A comfortable narrative for my family. A comfortable story to tell the world. Hey, I'm Alex. I studied finance undergrad. I'm working as a trader now, and maybe one day I'll go to a hedge fund. But there was actually nothing comfortable about this job. I didn't enjoy it. My first boss treated me like shit. I wasn't operating within my zone of genius. The job required deep mathematical and analytical skills. My zone centers around creativity, storytelling, and relationships. I felt lost, inadequate professionally, and knew deep down this story of comfort was a delusion, a delusion created by the comfort of stagnancy and the comfort of doing what was expected. So, yes, this badge stands for comfort. But what it really stands for are the perils of comfort, the mirage that comfort creates, and that to be truly comfortable long term, you must accept discomfort today. Because if I subscribe to comfort, then I'd still be in that job or one like it, feeling inadequate, out of place, short of my potential, and ironically, incredibly uncomfortable. End tweet. If you actually— we can link to it in the show notes. But if you go to the actual tweet, there's a picture of my Morgan Stanley ID from 2015. I was at Morgan Stanley from 2015 to 2016. I look very young there, so you can check out the post. As I reflect on this story and I reflect on my first job, as I'm talking about it out loud, I think the most interesting thing about this post is that being comfortable actually becomes incredibly uncomfortable over time. And I think that's because there is this difference between external comfort and internal comfort that we don't talk about. We are given a definition of comfort by the world that we are taught to believe in, that a corporate job is less risky than a non-corporate job, that strong work-life balance is important, that getting paid more is better than getting paid less. But internally, I think we as people have a way more nuanced view of comfort internally. Some of us feel most comfortable when we're growing and acquiring skills quickly. Some of us feel most comfortable when we're obsessed with something and actually don't have perfect work-life balance at points at all. Some of us feel most comfortable when we feel true ownership over the work we're doing. And so my view is that when our external comfort and our internal comfort are out of whack, we ironically feel very uncomfortable in life. Now, I'm not suggesting that having a steady job and making money to provide for your family is bad. It's not bad, and it should be the top priority, in my opinion. But I do think once you climb above the point of financial survival, comfort becomes a really complicated topic that so many of us wrestle with on a daily basis. And all I can share is my own experience with comfort and the benefits of putting myself in places of discomfort. I feel most uncomfortable when I am in a state of comfort for too long because I feel fear that I am not growing or gaining new skills or maximizing my potential. And so the rule that I've created for myself has always been to force myself into a state of measured discomfort versus having discomfort forced onto me because of my own prolonged comfortability. And let me explain what that means. I did it with Morgan Stanley and making the jump to Morning Brew full time. That was uncomfortable. I did it with building the Brew and putting myself out there to sell advertisements, manage employees, raise money, having never done it before. I forced uncomfortability when I stepped down as CEO 2 years ago and confronted this really weighty question of who is Alex Lieberman outside of Morning Brew? But let me go a little bit deeper with this because I used the phrase before of measured discomfort and measured discomfort in my mind is different than just simply being uncomfortable. I think this idea of forcing yourself to be uncomfortable and avoid comfort in your life is a kind of tired cliché that has merit, but it needs to be qualified. Like everyone says, right? I'm not the first person who said, you know, in order to be comfortable in your life, you have to accept discomfort. But there's not nearly enough nuance there. First off, being comfortable at times in your life isn't necessarily a bad thing at all. If you've just had a family and you're in the process of moving into a new house and your only sense of stability is your comfortable job, I think that is totally fine. And forcing discomfort in your career at that moment in time isn't necessarily the best move. Second point here is all discomfort isn't created equal. Just as we make educated bets in our lives on the partners we want to be with long term, or we make educated bets as entrepreneurs, on new products we want to launch or new initiatives we want to start. The way that you introduce discomfort into your life should be equally as educated and measured. And so for me, whenever I am forcing discomfort into my life, I'm always trying to put myself in situations where some high percentage of the uncomfortable situation leans into these foundational skills that I am already great at. Things like creating content, storytelling, building relationships. And then there's another percentage of the new uncomfortable situation that I've put myself in that does require me to build up new skills to be successful. So just take the example of me starting this new ghostwriting agency. It is what I would define as measured discomfort. I am starting an agency business which I've never done. I'm charging clients directly for something which I've never done. I'm looking for a CEO from day one, which I've never done, but I've completely stacked the deck in my favor with this opportunity because it leverages my brand, it leverages my skills, and it leverages the stuff that I love doing. And so with that, I'm going to continue to try and seek measured discomfort in my life. And I suggest you do the same. Now, if you got to this point in the episode, it means you're one hell of a listener or a viewer, and I would love to hear from you. So shoot me an email at thecrazyones@morningbrew.com. Introduce yourself and feel free to share a topic for an episode that you want me to cover in the future. It could be a problem you're experiencing with your business, an idea for a business that you have that you want to get someone else's thoughts on, or anything else that you feel like you go to sleep thinking about or wake up thinking about as it relates to entrepreneurship, your business, or your career. With that, thank you so much for listening and I'll catch you next episode.