5 Questions to Ask If You Don't Love Your Job

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 am giving you five questions you must ask yourself if you do not love your job. Let's hop into it. 

5 Questions to ask if you don’t love your job

It really, really sucks to feel stuck in a job that you don't love. It is something that you spend most of your waking hours on for literally half of your life. So being in a spot you feel good about is super important. Now, whether you're a C-suite executive at a startup or a big company or an entry-level employee just out of college, it all sucks the same to feel stuck and I have five questions that you should ask yourself to get unstuck. Let me walk you through them. 

#1: Do you have the need or the luxury to love your job? 

The first question, do you have the need or the luxury to love your job? So I think about jobs kind of like I think about humans and life, meaning, you know, you have Maslow's hierarchy of needs where at the bottom is survival and at the top is things like self-actualization. And I think it's a similar thing with jobs where survival and care for your family is at the very bottom of the pyramid. And it comes before everything else, like loving your job. So when I say, do you have the need or luxury to love your job? I'm speaking here about specifically the luxury. Are you in a place where you can even think about loving your job, because you may just be trying to make ends meet for yourself and for your family. That's the first thing. The second thing is, is loving your job important to you? It is not a requirement for you to love your job. Many people just think about their job as a job, things that they do to make money, to then love other aspects of their life. And that is totally fine. For some people, t isn’t important to love their job because they also just don't want to trade the time, constantly searching for a new job that they would love at the expense of time spent on other things like family, vacation, hobbies, etcetera. So that's the first question. 

#2: What don’t you love about your job? 

Second question: What don't you love about your job? So I've talked about this in a previous Founder’s Journal, but typically the most common reason people do not love their jobs, it doesn't have to do with the company. It doesn't have to do with the culture. It doesn't have to do with not growing. It has to do with their manager. Not loving your manager is oftentimes the number one reason that people don't love their job. You spend so much time with your manager. It is your most important relationship. So feeling good about that relationship really shapes your whole experience. And I'm going to talk about in a minute how my first job, my first manager, I really didn't like, and it totally ruined my experience. Now, outside of hating your manager, there are other common things that make people unhappy in their job. So just some of them include feeling like you're no longer growing, not jibing with the culture of the company, not aligning with the mission, not agreeing with the direction of the business anymore, not feeling like you're valued, feeling like there's a lack of work-life harmony, feeling like upper management is not transparent with you, not knowing the direction of the business, or not feeling like you're being paid appropriately. Understanding what you don't love about your job allows you to figure out two things. First, what you need to change. And second, if that change that you need to make happen to love your job is possible within your company. So these 10 things I broke down are common reasons that people don't love their jobs. It is so important for you to know which of these are the cause of you feeling stuck or not loving. So then you understand what you need to do about it. 

#3: What are my options?

The third question you need to ask yourself, what are my options? And there are a lot of options. There are a lot of options within your company, and there are a lot of options outside of your company. So you have moving within your company. So that could look like changing parts of the business. We've had people in Morning Brew moved from being content writers on our newsletter to copy writers in our advertising business. Moving to different divisions of the company can absolutely help with things like not loving your boss or not loving the work that you're specifically working on, or not feeling like you're growing enough anymore and needing to re-steep in the learning curve. Another option could just be changing bosses. And this is something that I did when I was at Morgan Stanley. I absolutely hated my first boss and I don't use the word hate lightly. I really don't hate anyone in life. I hated my first boss. She did not care about me at all. She was verbally abusive and the story that I've continued to tell myself, and I say the story, because it isn't necessarily fact it's my opinion, was that all she cared about was her own career and anyone who got in the way was dead to her. And because I was a entry-level analyst and because I had to learn and make mistakes, I was dead to her from the first week I was under her. I was not loving my job, not because of the work at Morgan Stanley or the culture of the company, but singularly because of this person. And so I ended up having a conversation with my boss's boss about this situation. And I ended up being able to move roles because if they weren't amenable to this, I would have quit. And my second boss was absolutely amazing. It was a total 180, and it totally changed my experience at Morgan Stanley. The third option you can think about is: Can you shift what you're working on? Meaning stuff you're spending time on, do you not enjoy it? And is there an opportunity to delegate it or get rid of it? And this is a great place to use something like the Eisenhower Matrix that I've talked about in the past and we can link to it in the show notes, which basically allows you to think clearly about what you both want to work on and what you have to work on and how you can delegate or delete work that is both not mission critical to the business or to yourself and that you don't love doing and it doesn't bring you energy. Now, a final option, not inside your company is, is it worth exploring things outside of your company? And the way I think about literally changing jobs and moving outside of your company is I think of this as a last resort. And I think of it as a last resort, not because you necessarily owe something to your company, but simply as a function of opportunity costs. There is a ton of cost in the form of time and energy it takes to look elsewhere. And so I would think about looking outside of your company, when you feel like you've exhausted all of your options internally, and you think that there is no way to take the thing you don't love about your company and change it internally. So you must look outside for finding that thing you love. Now, one other caveat I'll add here is in terms of these options, one other thing to think about it almost goes back to the first of like, do you need to love your job? Or do you have the luxury to love your job? Is similarly, do you have the luxury of looking outside of your company? Meaning are there things tying you to your company that make it hard to leave? So there are just situations where you're tied to your company for one reason or another. For example, there are candidates that I've talked to in the past for Morning Brew, who loved the idea of working at Morning Brew, but they could not do it because they were on a company-sponsored visa and it was not practical for them to change jobs, even though they didn't love their role. So that's just something else to keep in mind. 

#4: What do you need in order to love your job?

Now, the fourth question to ask yourself, when you feel stuck and don't love your job is, what do you need in order to love your job? What does loving your job look like for you? And so I'm going to end up doing a future episode on this concept, which is called Ikigai, but just the TLDR on it is it's an amazing framework to figure out how do you want to spend your time? Ikigai translates to reason for being, and I think it's an especially helpful tool for when you're trying to figure shit out in your career. And what Ikigai, is you can just envision it visually as this really complicated looking Venn diagram. So it's basically four circles that intersect with each other and those four circles in the Venn diagram that is Ikigai includes what you love, what you're good at, what you can be paid for, and what the world needs, and specifically looking at what you love, because that's the topic of conversation, there are a few questions you can ask yourself to better understand what is the type of work that you love doing. The first question is, are you absorbed in your work, or said differently, the thing that Gary Vee says is procrastination is actually a great signal of work that you don't truly love because you procrastinate when you don't want to work on something. If you love something you're going to want to work on it. The second question you can ask yourself to figure out what you love is, are you more excited about going to work than you are about leaving work? That's generally a good proxy for, do you love the work that you're doing? And the third question is, do you have an emotional connection to your work results? Meaning do you love your work enough that you take pride in it enough such that you care about the output of your work? And so this is how you think about what you love doing, which helps you think about the change you need to make in your company, or to leave your company to find work that you love when you don't love the work that you're currently doing. 

#5: What are the risks of pursuing something different than the status quo?

And then finally, the fifth question to ask yourself, when you feel stuck or you don't love your job is, what are the risks of pursuing something different than the status quo. Now there aren't right or wrong answers to these decisions that you make. There are just trade-offs. There are trade-offs to doing nothing and allowing the status quo to happen, which is just doing the same job you're doing and feeling stuck. There are trade-offs to changing your boss or your role or changing the content of the work you're working on within your company. And there are trade-offs to looking elsewhere and changing jobs. You just need to understand those trade-offs. So using me as the example, when I decided to leave Morgan Stanley and start Morning Brew, I spent the majority of my time thinking about trade-offs and understanding what trade-offs I was willing to live with versus not willing to live with. In this example, I was willing to live with the risk of my business failing. I was not willing to live with the regret of someone else building what I wanted to build. And that is why I ended up leaving Morgan Stanley and a stable job for at first zero salary to do Morning Brew, because the trade-off of regret of seeing someone else build Morning Brew, because I stayed at Morgan Stanley, I could not stomach that. And so these are the five questions you need to ask yourself when you're in a job that you don't love, or you feel stuck in and you are trying to figure out what the fuck to do. If you enjoyed this episode, please share it with co-workers or friends that would benefit from my thoughts on how to get unstuck from your job. Just copy the link and share it in iMessage or share it in SM if you're one of those green bubble people or share it in your company's Slack or Teams channels, just do it discreetly, so your boss doesn't see it. Thanks again for listening, and I will catch you all next episode.