My Top 4 Biggest Career Mistakes

What's up, everyone. This is Alex Lieberman, co-founder and Executive Chairman of Morning Brew. 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. Today, I talk about the biggest mistakes I have ever made in my career. Let's hop into it.

The 4 biggest mistakes I’ve made in my career

So from the outside, it may look like I have all my shit together. I've built a company, I've sold a company. I built a following on social. I have a podcast. But I can assure you that most of the time, I do not feel like I have it all together. Not at all. And I have made more mistakes than I can count at various points of my very short career. So in the interest of time, I'm going to tell you about my top four, the four biggest mistakes I have made over the course of my career and what I have learned from them.

#1: Consensus thinking rather than critical thinking

Time for mistake number one: Consensus thinking rather than critical thinking. For some background, if you don't know, I was born into a Wall Street Family, grew up in a suburb in northern New Jersey. And I grew up with my number one value being family. My parents and my grandparents were role models. And I wanted to be just like them. I dreamed of being a world-class trader because that's what my dad did. That's what my mom did. That's what my grandpa did. And I literally had it on my whiteboard in my room growing up. And I never questioned if being a trader was right for me. I just assumed that it was. You see, I created this story that success was synonymous with Wall Street. And since I want it to be successful, this is what I had to do. And that very story literally dictated my behavior for the first half of my life. I went into my dad's office monthly growing up, I went to the business school at Michigan. I had four finance internships, and I ultimately took a job in sales and trading, all because I had created this story that I had to be on Wall Street. But just imagine for a second, if I had stopped myself and asked, “What am I good at and what type of work do I enjoy doing?” things probably would have looked very different. Because the answer to that question of what am I good at includes things like thinking creatively, building relationships, storytelling. And if you were to compare those skills to the skills needed to be a world-class trader on Wall Street, these lists would look like polar opposites, which is why my choice to recruit for sales and trading and ultimately join a big bank out of college can only be described as consensus thinking, and in this case the consensus was my family, without any critical thinking. 

#2: Hiring the wrong people 

That leads me to mistake number two: hiring the wrong people. The biggest mistakes that I made as a CEO were always tied to hiring. And when I reflect on why I mishired at many points in time, it usually boiled down to one of three buckets: wrong experience, wrong role, or a rushed decision. So with the first, basically every role in every job has one or two “musts,” things that an employee must do in order to be great at their job. And it is so easy to hire someone because you think that their background or their experience or their resume mitigate certain risks, but far more important than mitigating risks is hiring someone whose superpowers satisfy a must. Now with the second around the wrong role, one of the most painful things is when you hire someone who is talented, but you put them in a role that didn't need to exist. And I've had this happen to me in the past. In the past, I've taken a bunch of individual needs in the business, needs that weren't getting done, and then I lumped all of those needs together into a single job. I ended up hiring a senior person to do the job only to realize a few months later that the job didn't need to exist. There was a reason that these tasks weren't being done before, and it was because none of them were priorities. Bundling them together didn't make them any more of a priority. It just put together a bunch of non-priorities for someone too senior to do things that weren't a priority. That was a brutal experience.

With the third around rushing decisions, this is the most ironic hiring mistake. In an effort to fill a role quickly, I've ignored red flags, I've bypassed standard parts of the hiring process, all to bring a person in the door because I felt rushed. And typically this has happened when we're running a hiring process, we’re two months into the process, we had a few great candidates and for one reason or another, none of those candidates worked out. And so we felt like w’ere really far into this thing and we just needed to bring someone in the door. And the irony of the situation is that not only does rushing the hiring process not work, it ends up slowing everything down. What you end up doing is you hire someone, then you fire them a few months later because they weren't the right fit and you end up in the same exact spot you were before, but now you're several months behind schedule. Next up: mistake number three. 

#3: Resisting my superpowers

And for me, mistake number three was resisting my superpowers. As I mentioned a minute ago, we are all story-making machines. And the stories we create, if not closely examined, can dictate our behaviors for literally decades. And I mentioned that story about needing to be a trader on Wall Street. Well, I had another story of my own that I created as soon as I got into the startup game. And the story was simple: A startup CEO is like the captain of the ship. You lead from day one and you continue to lead until the ship goes down. I told myself to be successful, I had to be like Musk, Bezos, or Blakely, running my business for decades until it sells or went public. But here lies the mistake in that way of thinking: A CEO's role is not static. It is actually highly variable, especially in high-growth startups like Morning Brew. You see, the first job of the CEO is to find product-market fit. The second job of the CEO is to build the machine and build it so that you can scale. In each of these stages, the leader is still the CEO, but the CEO's job changes dramatically. Initially in stage one, it's about vision, storytelling, and building. In stage two, it's about strategy, operations, and management. And I watched the needs of the CEO role change before my eyes, but for a long time, I didn't question if these new responsibilities allowed me to grow in the way that I wanted to. My story blinded me from doing what I love, honestly, not that differently from going into finance at the start of my career. 

#4: Spending too much time in the weeds

Mistake number four, the last large mistake that I've made in my career: I spent too much time in the weeds. School did not teach us to prioritize. It taught us how to complete assignments, take tests, and busy ourselves. We were trained to seek instant gratification and productivity for productivity’s sake, but that's not how running a company works. To lead effectively, you need to do this careful dance between knowing what's going on in the weeds while rising up to the clouds to assess your strategy and make sure you're headed in the right direction. A number of times on the entrepreneurial journey, I did work that felt good because it kept me busy and I got to check off boxes, but it wasn't necessarily the most important thing to do. And what I found as a leader is once I started managing people, the most important work was oftentimes not the thing that felt busy or gave me instant gratification, but it was the thing that felt like if I focused on it for a long time, it would push the whole company forward.

I want to hear from you

And so those are the four biggest mistakes I've made in my career. Not thinking critically, not hiring well, not doubling down on my superpowers, and not getting out of the weeds. With that, I would love to hear from you. What is the biggest mistake that you have made in your career, and what lesson did you learn from it? Shoot me an email to alex@morningbrew.com and while you're doing that, please, please, please subscribe to Founder’s Journal and leave a review on the podcast player of your choice, whether it's Apple, Spotify, or another one. It is the number one way we grow this show and get to the top of the charts. As always, thank you so much for listening, and I'll catch you next episode.