Accelerate Your Career #1: How to Get Unstuck In 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 career. This week on Founder's Journal, we're doing things a little differently. We are dropping our first mini series all about how to accelerate your career. And instead of just one episode Monday, Wednesday, and Friday, this week, we're giving you two: a new show you don't want to miss, plus a classic episode you maybe haven't heard before. Put it all together, and you're getting a mini curriculum on taking your career to the next level. So make sure you listen to all six episodes, and we can't wait to find out what you think. Today, I'm talking about How to Get Unstuck In Your Career. Let's hop into it. 

There is nothing more common than feeling mediocre about our careers. It's really unfortunate, but it's really common. In fact, last week, I took that to Twitter to find out just how common it is for all of us to feel not so great about the jobs that we're in. What I did was, I asked people to DM me who felt stuck in their careers and for them to walk me through what's making them feel stuck and how they're working through it. This is not an exaggeration. I ended up receiving more than a hundred personal stories about career stuckness and how people are navigating, what is honestly, an unfortunate time in their professional lives that ends up having an impact on their personal lives. 

So, what I wanna do is, I wanna share the story of one listener who wrote in and in sharing their story, I want to also provide you with a playbook for getting unstuck in your career and recreating professional momentum if you're experiencing anything like the feelings that this person was feeling. So let me give some background on the listener first. This listener is in their late twenties, they've worked in marketing and partnerships/business development since graduating from college, they started at a Fortune 500 brand and then switched a few years ago to an earlier stage startup.

Step 1: Identify That You’re Stuck

In recent months, they started feeling just not good and de-motivated in their current role. And it was affecting everything, not just their nine to five, it was affecting their life because they're really career competitive, and so when they don't feel good about their job, they just don't feel good about their life in general. This is the first step of getting unstuck from a job. It's realizing that you are stuck. It may sound obvious to you, but for a lot of us, we don't have the awareness to understand what we're feeling and that our jobs can be the cause of feeling not so great. The thing about this person is, they knew they didn't feel good, but they weren't sure why they were feeling de-motivated.

And that's totally normal. I have found personally that oftentimes my body and our bodies lead our brains and it takes a lot of introspection and self-work to be able to get the brain to catch up to the body. And in the case of career, it's like a puzzle to figure out why you don't feel happy in a job once you know that you don't feel happy.

Step 2: Figure Out Why You’re Stuck

 And that is the second step in getting unstuck in your career, which is knowing why you are feeling stuck in a job once you know you feel the feeling. For this person, it was because they didn't feel like they were learning or growing anymore. They felt guilt about getting paid and feeling unhappy, and they felt like they worked their way up the steepest part of the learning curve, they had plateaued, and they were just kind of coasting on autopilot.

For them, it was a learning and growth thing, but in having these a hundred plus conversations with other listeners on Twitter, the most common reasons for feeling stuck, I found include: one, not escalating as fast as possible in your company, whether that's in terms of salary or title; two, you are not actually enjoying the work that you're doing, it doesn't feel fulfilling or purposeful; three, the feeling of not aligning with your company's culture; four, the feeling of knowing you want to leave, but feeling like you've pigeonholed yourself in your career so you don't have a lot of options; five, wanting to leave, but you're stuck on a work visa, which limits your options; six, your company feels slow and lacks innovation, and you just feel like you move at a faster pace than everyone else; seven, you feel burnt out and overworked because your hours are long or you aren't taking enough vacation; and finally, eight, you have a bad manager, and you're not sure what to do about it. 

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Step 3: Find the Source of Stuckness

So once this person that I was just describing knew that they were stuck because they felt de-motivated, because they feel like they weren't growing and learning, and they felt bad making a good salary despite this, they wanted to more clearly understand what was it that felt like it was stifling their growth, right? Like, they knew they weren't learning, but why weren't they learning? They knew they weren't growing, but what was causing the stifling of their growth? So what this person ended up realizing after lots of conversations and lots of introspection was they had a feeling of not having ownership over the strategy of their business and not feeling like they were sitting at a steep enough part of the learning curve because they didn't own the strategy.

You see, when they had moved from that Fortune 500 brand to the smaller company a few years prior, they were early enough in the company's life cycle that they were actually the one building playbooks, versus executing on someone else's playbook. But that was no longer the case.

This person's startup had been acquired in the last year or so, and that accelerated this feeling of having plateaued. They went from the feeling of being in a small place where there were one, a few business or partnership hires, they were creating the playbook, to being in a larger, slower moving business where they were answering to the playbooks of people above them. And so that is the third step of getting on stuck in your career: once you know how you feel, and once you know why you feel stuck, it is about figuring out what about your situation is causing you to feel that feeling of stuckness.

Step 4: Determine if Stuckness is Fixable Internally

Now, the reason it's important to understand what's causing you to feel the way you are and not just why you feel stuck is because by knowing the 'what' you will then get clues to figure out how you actually go about fixing it. And more specifically, you basically want to answer for yourself a very simple question. Is the problem of feeling stuck fixable within your company, or do you have to start looking elsewhere?

A good shortcut that I use for answering this question is one of how much control do you have over what's causing your stuckness? If it's something like culture or your passion for the mission of the company or poor leadership, these can be extremely difficult to change, which means getting unstuck will be very difficult. If it's something like your learning process has slowed or you're having issues with your boss, or you haven't gotten the promotion or the raise you wanted, these tend to be far more in your control.

So the more in your control the stuckness is, the more possible it is for you to fix it within your company and stay where you are. The less in your control it is, the more that you should probably start thinking about looking outside of the walls of your company.

So bringing it back to this person's story, they felt like their stuckness could be fixed internally because it was a problem with growth and learning, not something like culture or poor leadership. So what this person did was for the first several months after the acquisition happened of their startup, they made the most of the situation. When they first had these feelings have stagnancy, they over communicated those feelings to their boss, which is what led them to having an opportunity to move from a pure partnerships role, to owning an entire line of business, more similar to, like, a GM.

But despite their best efforts to make it work internally and the belief that a role shift could put them on a steeper part of the learning curve again, they realized things just still weren't working. They gave it a shot, but they didn't feel fulfilled by it since it was very much executional still versus, like I said earlier, actually owning the strategy and creating a playbook from scratch rather than following someone else's playbook.

So bringing it back to step four, this person thought that the solve for their problem of being stuck could be done internally, they thought it was a fixable problem, but once they gave it a chance and they knew that it wasn't the case, they ended up building up the courage to start looking externally. And one big reason that they got this courage was because one, they had a very close relationship with their boss and they were willing to be vulnerable and share exactly how they felt, and they have tons of conversations with family members, with close friends, with other people in the industry that gave them the validation to start looking elsewhere.

Step 5: Make a Game Plan For Solving

And so this leads to the final step of the unstuck process, which is if you're going to look externally because you've realized it's too hard to get unstuck within the walls of your current company, you need to have a game plan for doing so, and you need to narrow your search, otherwise it just becomes overwhelming.

There are so many companies out there and in a world of remote work, geography can't be the filter now. You literally can be an employee anywhere in the world, in a remote world. And so to have a game plan, you need to have some filter. It can be a filter by stage of company, it can be by job function, industry or seniority. So for this specific Founder's Journal listener, they filtered by two things.

The first was life of the business. They wanted to be in an early stage startup. They had a network through their boss who could introduce them to venture capital firms that had portfolio companies that were early stage; this person also had a hypothesis that they would enjoy being the first business hire at an early stage company, because they could be the one to create the playbook versus follow someone else's, which is something that they knew was important to them; and they thought that this would allow them to be both a senior person in a company, but also be a generalist, because most of the time, as you grow in your career and you become more senior, it becomes very difficult to be kind of an athlete or a generalist. You have to start specializing in a specific function of the business, like marketing or data growth. 

The other thing that they filtered by was the industry. This person has a 50/50 rule where you bring 50% expertise and knowledge to your new job, which will make you good in your role, and then 50% will be a totally new experience, which will allow for the learning curve to be steeped. So this person narrowed down to early stage companies, generally seed stage to series B, less than one hundred employees usually, and they stayed within the industry that they're currently in. And what they did for themselves, was they had a process for organizing their entire search process. 

Sample Job Filter Template

So they basically made a personal CRM for themselves, customer relationship management, which is like something like a Salesforce, they basically made their own personal Salesforce in a Google sheet. And that Google sheet included the following fields: it listed 15 companies that they were getting intro to through their boss's network, it listed the number of employees at each company, how much funding they've raised, what the company does, when it was founded, and who founded it. And then there was a column for their own vibe check, meaning when they ended up speaking to someone at the company, how did they feel generally about their vibe and the energy they felt after having that conversation? And so for anyone that wants it, I actually created a quick template that just mirrored what this person did so that you can track your job search if you got to this step in the unstuck process.

TL;DR

And so through this listener story, I hope you have gotten not just one real life experience, have someone working out, being stuck, but also a step-by-step plan for recreating momentum in your career. Just to sum it up. Step one was identifying that you're actually feeling stuck; step two is figuring out why you're feeling stuck; step three is figuring out what's causing you to feel stuck; step four is figuring out if it's a solvable problem within your company; and step five is having a game plan for resolving it, whether it's an internal solve or an external solve. I hope you've enjoyed this first episode of our first Founder's Journal binge on accelerating your career.

I Want to Hear From You

Stay tuned for five more episodes this week, all around things you can do to level up as a professional. Now I'd love to hear from you all. We have a ton of new listeners. This month is the biggest month of Founder's Journal after last month was the biggest month of Founder's Journal. So whether you're old or new, just write in and let's chat. Send an email to alex@morningbrew.com or DM me on Twitter @BusinessBarista with any thoughts or questions you have about the show. Thanks so much for listening to Founder's Journal and if you enjoyed, please let others know who you think would enjoy the show as well. Thanks again, and I'll catch you next episode.