How Do I Un-Stuck Myself?

Candid conversations about the messy middle

Careers are often looked at as journeys, with destinations sprinkled along the path as we navigate towards what is in theory, a destination of sorts, achieving a goal you’ve set your sights on. But along that path, there are often conflicting signs telling you to turn both left and right and also somehow straight ahead at the same time. You look for guidance as you find yourself entirely stuck in the spot you’re standing: faced with the fear of judgment from others, or worse, yourself.   

Career roadblocks may present itself as feeling that you’re not quite where you want to be or where you thought you’d be at this stage or age. It might look like you’ve chosen a job to get closer to that end goal only to discover it’s not the right fit, the right scope or the job just isn’t what you expected it to be. It could be that you think you may want to change course and pivot to something else. Maybe, it’s a little bit of everything, over time. You know you need to unstick yourself, but with so many “what ifs,” knowing where to start and how to get unstuck can feel overwhelming.   

To tackle this topic with actionable advice and candid insights from those who have been there, we invited Sadira Furlow, CMO of Happy Money, and Adweek Executive Mentees Kelly Byrd Marín and Andrew Almendras to share their perspective and guidance on how to move through it. The following are highlights of what we learned that we hope can help anyone get unstuck.

Three easier said than done ways to quiet the voice inside your head, free yourself from the dizzying anxiety spiral, and get a plan on paper.

1. Embrace reasons to say yes vs. searching for reasons to say no

Learn by looking within

What we already know: Careers naturally hit inflection points as your goals, role or life more broadly, evolves.  

Hot Take: Turn the “what ifs” into the “what abouts” and embrace the possibilities vs. getting stuck in the quagmire of questions (which often have many right answers).

Take it from someone who’s been there: 

  • When stuck searching for my next role, I had this strong case of the ‘what ifs’ or, the ‘what abouts’ as I call them. This is that voice that gives you all the questions and the reasons when facing big decisions that make you nauseous and giddy at the same time. Change is hard, and it’s exciting; we need to figure out how to quiet the voice and get a plan on paper. Ultimately, I got unstuck by focusing those ‘what ifs’ into ‘why not.’ Why not go do this? Why not take this leap? What if I actually focused on the best thing that could happen in making that change vs. all the things that might go wrong or that I was a bit scared about. To answer, I did three things. I wrote down my brand positioning story. I crafted a strategy and criteria—putting down what’s important to me in my next role—the culture, the work and third, I tapped my network, identified five companies on LinkedIn that I would want to work for and started to reach out to folks. —Sadira 
  • You almost have to disconnect from everyone and sit there. What I found was that journaling and writing those thoughts down and going, ‘what is it exactly that I want?’ If you’ve ever seen a crab or lobster molt, there’s this very uncomfortable moment where they have to squirm themselves out of their older shell. Then they’re in the state of two days of vulnerability where their shell hardens before they’re into their new bodies. This is much like the unsticking process where you have to uncomfortably unlearn old habits in order to grow. —Andrew
  • I kept trying to tell my story and articulate my background, but I felt stuck. I felt very typecast as the account person, the relationship person. I put together a presentation and pitched myself to take a product marketing role. I knew I needed to get my story right, but I also knew if I had an opportunity to start from where I was and get myself back in marketing, that was the most important thing. —Kelly
  • There’s this idea of optionality in your career and acquiring different experiences, capabilities and skills that maximize your optionality so that you continue to have choices as you progress. I don’t want to be typecast into one position, I want to have versatility. I want to maximize my value on the team by being able to step into a variety of positions. You’re only able to do that when you’ve made choices throughout your career to get that exposure and that experience that allows you to have that elasticity. —Sadira

2. Observations lead to options. Comparison leads to consternation. 

Learn by observing outside yourself

What we already know: Comparison is the thief of joy.  

Hot Take: Objective, thoughtful observation of the landscape can bring light to potential avenues out of the “stuck place.”

Take it from someone who’s been there: 

  • I was the catcher playing competitive softball growing up. My leadership style and how I approach navigating my career is very much like continuing to be an athlete, a corporate athlete, but also many things from being a catcher. As the catcher, you have the most differentiated point of view or perspective on the field. You are the only one looking out at the entire team while everyone else is focusing on the batter, and they have their back to each other. When I look at my career, I’m looking at all of the different options. I’ve gotta think about this at bat, the next the entire game overall. In your career, acquiring different experiences, capabilities, and skills maximizes your optionality so that you continue to have choices as you progress. —Sadira 
  • Part of what the Adweek Executive Mentorship program clarified for me in terms of my career path was that I wanted to put myself on a path where CMO could be an option. I wrote my personal brand story with the support of a lot of mentors and also fellow Adweek mentees. That was really helpful for me because I even struggled to say, well, how does it make sense that someone with a mostly PR, content and agency background, work in product marketing? —Kelly
  • You’re so much more than your resume and your title. In a career, you’re struggling with questions like, “Am I dipping into the right area? Am I unlocking the right doors?“ You oftentimes need to reinvent yourself taking into consideration the growth you’ve experienced … lean into what makes you special.” You should always make it a point to ask yourself questions about your organization, team and perhaps a new opportunity that include, “Do we align on mission? Do we align on values? Do I enjoy your company? Do I enjoy what I get to do” and most importantly, ask yourself, “Am I at the right place at the right time?” And if the answer is “no,” you have the power to change it. The most important part is to lean into what makes you unique and to be your honest self throughout the process. —Andrew

3. Perspective comes from re-focusing your actions 

Learn by doing—but do something else than what’s got you stuck

What we already know: You can’t control everything and everyone.  

Hot Take: The tense energy from being mentally stuck in one area of your life can be turned into a release if focused in the right area.

Take it from someone who’s been there:  

  • I decided to sign up for the LA marathon nine weeks prior to the marathon. I ended up running one of my best times because I needed something from start to finish that I had influence over. At work, you don’t necessarily have influence over everything – the product or even your professional relationships. But you do when you’re doing something for yourself—sports, creative or otherwise. For me, that physical manifestation was such a powerful win because as I turned a corner to the finish line, I felt like that was a turning point. —Andrew 
  • To build necessary influence in new roles, I book 25 min intro calls with my peers. This not only allows me to build necessary influence, but is a great opportunity to practice telling my story and invite them to share theirs in a way that allows us to learn from and understand each other. —Kelly 
  • This is maybe a little bit more unpopular or provocative, and I’ve learned it probably a little bit later in my career. I think it’s important to focus a little less on control and instead on how to continue improving on influence. Influence is a thing that we don’t necessarily spend a lot of time teaching or building as a capability, but the more matrixed and complex our work environments become, the much more rare it will be that you have full autonomy or independent control. So, I’ve tried to invest more time exploring, how do I expand my influencing skills? How do I figure out what the currency is in this relationship to try to help, to move through something? —Sadira 

Getting stuck is normal, so let’s start to normalize it. We can often be our own worst critics and lose clear perspective on what matters in the scope of the ethereal “why”; why we’re chasing after what we’re chasing, why we feel burnt out or behind, or why things look different than the picture we had envisioned five months or five years ago.  By learning through introspection, external observation, and forming an individually tailored plan of action, the feeling of being stuck won’t feel quite so uncomfortable, it may in fact feel like it’s what you’re meant to experience, because from discomfort, from the unknown, from the “what abouts,” comes incredible growth and possibility. 

This article is part of The Gray Area, a new series that embraces the discomfort of the messy middle career moments we all have through candid conversation among professionals in our Adweek community. Are you squarely in the gray area? Share your experience with us. It may inspire a future topic and bring about even more commonalities and camaraderie.