Getting Unstuck: A Guide for Those Who Need a Little Push

How to escape the quicksand that is trapping us

I love this Adult Swim video from several years ago, but there are bleeped-out bad words so be careful when watching it around young children. That said, it is the best summary I have seen of what it feels like to be stuck. 

Getting stuck is one of the hardest things you will experience, in your career and your life. You feel trapped in the quicksand of life, the suction slowly pulling you down. The energy you expend to try to get out only drags you down further, and your thrashing increases the rate you sink into the muck. 

I have been stuck multiple times in my career. The one that was the most painful was fourteen years ago, after the birth of my first son. I had just returned to PayPal from maternity leave, and I didn’t know what to do next. I had handed my team off to someone I trusted, and I didn’t want to displace him, so I took a new role in Corporate Strategy. I eventually made my way to a new team, where I built the social commerce and charity verticals, but the job was frustrating and unfulfilling. I didn’t see a way out, so I spent months treading water. Finally, I went to the VP and told him I wanted to quit. What happened next surprised me: He persuaded me to hold on and let him find me something new. Within weeks, he arranged for a VP at eBay to offer me the opportunity to run the buyer experience product there. I completely changed my path by forcing myself to speak up and quit a company I loved, because I felt stuck.  

Most people start to feel stuck in their jobs every few years. You feel lost and unmoored, just like I did. You still love your company, but the job feels stale. Maybe you don’t feel like you have direction about where to go next. Or you don’t have the manager support to take you to where you want to go. The path ahead looks murky or fraught. You don’t know where you should be, but you know it isn’t here. What do you do?

Understand the Traps

The human mind loves setting traps for itself. As you figure out what to do next, you have to be careful to avoid them, or risk sinking deeper into the quicksand. 

Sunk cost fallacy: Once we've invested a lot in something, we tend to feel obligated to stick it out, but that's often the worst thing we can do. If you only continue because you've invested so much already, you risk regret, resentment, and further stagnation. That is a sunk cost fallacy. The human mind doesn't want to lose. By selling a stock that has declined, you’re able to cut your losses. On the other hand, there is a cost to holding a stock that is declining, and that is not freeing up the money to invest in something better. 

Hoping things will magically change: We often fall into magical thinking, hoping that things will change on their own. But just like you can't run a marathon without actually training and working for it, there's no magic ticket to solving most situations. The trap of imagining that things will spontaneously get better will hold you back from making the change you need. 

Losing objectivity: One of the greatest things I’ve found about having a career coach is that she doesn't care about most of the excuses that I have. When we explain a problem, we tend to include all these caveats, reasons, justifications, and background details that are irrelevant to the current situation. My coach cuts through that by asking incisive questions about where I am now and what path I want to take from here. She provides an objective point of view that helps me regain clarity. 

Assess Your Situation

This seems obvious, but you would be surprised how many times I’ve met with people who are stuck in a rut and have yet to take stock of where they truly are. I recently spoke to a PM who was sold on a great job with promotion potential, only to have half her scope given to the new guy who joined the team -- the half with executive visibility, something her manager said she had to work on in order to get promoted. She was frustrated, but unsure what to do. We talked about how she got here and how her path was long and winding. At the end, however, what mattered was only that she was not going to get anywhere without resolving the current situation. She had to assess her problem and take action immediately, or she would remain where she was. 

Questions to ask yourself as you reflect: 

  • Am I okay continuing where I am for the next five days? What about the next five weeks, five months, or five years? If the answer is that you can't imagine yourself in this situation for five years, then what makes it okay for five more months? Understanding your capacity to tolerate a specific situation gives you an idea of how urgent the change needs to be.  

  • If my friend asked for advice in this situation, what advice would I give them? We often have more clarity about other people’s situations than about our own. Write down your problem as if you were requesting advice from a friend. Remove unnecessary details, and focus on the crux of the issue. Read it back to yourself. When people request advice, they say things like, “What about X?” or “What if I disappoint Y?” Stripping away the “I musts” and “what ifs” helps you assess the reality of the situation.

  • If I had to take a drastic step to get unstuck, would I be willing to do it?  It’s easy to think in baby steps -- ask your manager a question here, try a new project there. But what if that doesn’t yield results? In product, we often do maxdiff testing, where we show the most extreme option we can ship, just to see how far we can move the needle. By doing this with yourself, you can figure out how far you are willing to go and work backward from there. 

Be Solutions-Oriented 

Ask for advice: I offer myself as a sounding board for PMs in the industry. Most of the people I meet are at forks in their careers or are otherwise stuck in some way. I ask them a couple of questions, such as, “What can I do to help you?” and “Where do you hope to be in five years?” Their dilemmas come pouring out of them. Most of the time, I can understand exactly how they feel from their tone of voice or how they frame their answers. This allows me to put up a mirror, based purely on what they said. For example, “I know you feel like Job A checks all of your boxes, but you sound so much more excited talking about Job B. Why do you think that is?” 

When I hesitated to leave Facebook for Ancestry, I sought the advice of two of my friends. They immediately straightened me out by just pointing out the obvious. One admonished me to get out of my head and just do what I knew was right, and that was the kick in the pants I needed to accept. 

Flip a coin: If you are truly stuck when choosing between two options, flip a coin. Make heads one of the options, make tails the other. Commit that you will agree to go with whatever the coin says, and then flip. Does it sound crazy to make major life decisions like that? Yes, and it is. But the point of the exercise is not to actually let the coin decide; the point is to see how you feel once you are forced to commit to one course of action over another. Do you feel relief or frustration? Do you feel trapped or freed? Those emotions are data, and they will help get you out of the snare of indecision.  

Map the future: Play out your current path for a year, five years, and then ten years, based on staying where you are. Then do the same thing with a different path. What does that look like? Where does it take you? When we are stuck, we are often trapped in our own heads, unable to see beyond where we are. Things look hopeless, and we feel helpless as a result. By taking the long view, you can put yourself beyond your immediate situation. 


There are few people who don’t experience being stuck at one point or another. The factors that lead us into a rut are often beyond our control, but we can’t allow them to calcify and trap us. Getting unstuck is a choice, a process that we can initiate and own as we free ourselves from the quicksand.

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