In this journal‑style episode of The Crazy Ones, Alex Lieberman challenges the widely held belief that corporate jobs offer true stability. He opens with a personal story about joining Morgan Stanley—a dream job for his family—only to experience a massive layoff in 2016 where 25% of his division was dismissed in a single afternoon. He describes the abrupt firing process and reflects on how, paradoxically, the longer employees stay at a firm and the more specialized they become, the less employable they become after a layoff. Lieberman then critiques the popular startup mantra of taking a “leap of faith,” arguing that successful founders make educated, calculated steps rather than reckless jumps. He explains that entrepreneurship decisions are driven by clear trade‑off analysis and a deep understanding of opportunity cost. The episode also examines corporate culture, noting that large firms often reward politicking and hierarchical navigation as much as, or more than, meritocratic performance, which further erodes genuine job security. While acknowledging that some corporations are merit‑based, Lieberman emphasizes that perceived safety is an illusion. He contrasts this with startup work, where most people join despite high risk because of mission, growth potential, and excitement, not because of stability. He concludes by urging listeners to apply the same clarity and realistic expectations to corporate career choices as they do to startup ventures, and invites feedback for future journal‑style topics.
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What's up, everyone? Welcome back to another episode of The Crazy Ones. This is Alex, and I am back with a journal-style episode of the show. Today, I want to talk about why the idea of stability in a corporate job is a complete lie. Let's hop into it. What's up, everyone? I'm Alex Lieberman. Yo, this is Jesse Pujji. And this is The Crazy Ones. We're going to get a little bit heady with this episode. It's a little bit less tactical than normal, but sometimes I think it's worth challenging the assumptions we have about the world, the things we've always been told to be true. And this is one of those topics. I believe the idea of stability in corporate America is a complete fallacy. And I'm going to tell you a quick story to illustrate why. Before Morning Brew, I worked for a year at Morgan Stanley. And you have to understand, this was my dream job. All of my family worked in finance. My dad did, my mom did, my grandpa did. I dreamed of working on Wall Street my entire career. The combination of that with also graduating from college and only having 10,000 email subscribers for Morning Brew and no revenue for the business yet, I felt a little bit crazy to take the leap of faith into entrepreneurship at that point, which now that I think about it, we're going to take a quick detour because I feel like this is a quick lesson in itself and we'll get back to the point about corporate stability. This idea of leap of faith, right? We talk about taking leaps of faith in our lives. I also think this is an incredibly stupid saying within the world of startups. Leap of faith encourages a certain risk-hungry, gut-driven mindset that's just not realistic for most entrepreneurs. I can speak from experience. Most of the great founders I know didn't take leaps of faith. They took Things that would more resemble educated steps in their careers. They were likely working some corporate job, and they reached a level of momentum with their side hustle where the opportunity cost of not pursuing their idea outweighed the cost of pursuing it. And all of these people, when they took these quote unquote leaps, they thought about the tradeoffs, they thought about their worst case scenario. And then after doing all of that and probably meditating on it for months, they finally pulled the trigger. I know that's what I did for my job at Morgan Stanley. And so most of the time, this is way less dramatic than a leap when people decide to start their business and go into entrepreneurship. And it's definitely not predicated on faith, right? Like, it is incredibly methodical. They're thoughtful about the decision-making process. So I think we should just take this notion of leap of faith out of the vernacular when we talk about people going and starting companies. But I digress. Let's get back on track. So I'm in this job at Morgan Stanley and I'm one month into the job. This is August of 2016 is when I started the job. So this is probably around September or October and it was the middle of the month and all of a sudden I'm in a normal workday, middle of the week, and I see people's phones start ringing like many phones ringing, not just like one person sitting next to me. And over the next 3 hours, 25% of my entire division, fixed income at Morgan Stanley, was laid off in one fell swoop. And basically the process went down like this. People anxiously sat at their desks waiting to see if they got a call from front desk. It literally— you would look at someone's— we had these phone turrets because people had multiple lines that they could talk to people on the phone. And you could also see the other people at your desk who they were on the phone with. But if you got a call from someone that said front desk, that's all it said, then you knew what that meant. You knew you were getting fired. And basically what would happen is you get the call, they'd say, come meet us, and you would leave your desk. You'd walk to the back of the trading floor. You would enter a conference room where HR and your manager would hand you a manila folder. Inside of that manila folder You would have your severance package and then you'd go collect your shit at your desk and you would leave. And literally lines wrapped around the trading floor for this unlucky, unlucky bunch of people to say their goodbyes to those who ended up staying. This is where there's the irony in this notion of stability in 9-to-5 jobs in corporate America. These people who were fired, many of them committed large chunks of their careers to a firm that they thought represented comfortability, predictability, and security. Morgan Stanley, public company, tens of thousands of employees, financial services, been around for, you know, 100 years. But the interesting thing about this is, as these people's tenure went up, as they spent more years in their career, their stability actually went down. Because as you become a corporate veteran, you naturally have to niche yourself down. You have to end up having a specialty in your career because You need to be known for being the specialist at a certain thing. You lead a division, you run product for a specific product, you're the best trader in a specific product that you trade. And so then the issue is the number of similar roles that any of these people could apply for after being laid off. You could probably count it on one hand. The irony here is that their specialized skill sets necessarily turned into a liability for them. And then there's another thing that I think is interesting about why actually working in a 9-to-5 or a corporate job is less stable than I think is the common expectation. And it's because if you subscribe to this idea that many large corporations are less so meritocracies than they are organizations defined by hierarchy and politicking and playing the political gymnastics game, Then this also suggests that people are less incentivized to actually build their skills and perform exceptionally well and grow as professionals because there's 2 games. There's the game of being great at your job, but then there's also the game of climbing the corporate ladder and knowing exactly who to build a relationship with and how to talk to them and when to talk to them, because you're rewarded for that game of politicking as well. So let me finish this whole rant on the stability of corporate America by saying this isn't me knocking the idea of going down the path, working at a big company, getting good benefits, working within a corporate bureaucracy. Because, by the way, there are many companies where it is meritocratic and there are many companies where you do have a semblance of stability. But I just want to provide an eyes-wide-open perspective on the true security that a perceived, quote unquote, safe path actually provides. And I also don't mean to suggest that working in startups is more stable than a 9 to 5. That is not the case at all. But here's where I think the difference is. I don't think the majority of people go into startups and go into entrepreneurship under this illusion that there is a ton of stability and predictability. I would argue it's the opposite. Most people go into startups in spite of the riskiness that they are aware of because they are excited by the mission or the people or the opportunity for growth. And those things are so worth it. They're willing to deal with the riskiness and deal with the possibility of being fired or the possibility of a company going out of business. All I am hoping for with this episode is that people choose corporate jobs with the same level of clarity and the same level of clear expectations as people do in the startup world. Now, I know this was less of a tactical business episode than most, but I think sometimes it's fun to just get high level and test these assumptions in business or our career that we've been made to believe that have kind of been proselytized by leaders for so long and we just accept as truth because we choose not to question it. And this is an example of an episode where I think it's worth us questioning the things that we've been told to believe. So I hope you enjoy this changeup of an episode. And if you have any topics that you want me to cover on an upcoming journal-style episode of The Crazy Ones, from getting your first customers to firing your first employee to scaling your business past $10 million in revenue or whatever other topic is present, challenging, and taking up a lot of mental real estate for you right now within your business or within your startup, just shoot me an email to thecrazyones@morningbrew.com. Thanks for listening, and I'll catch you next episode.
