Quitting: Cutting the Cord That Holds You Back

Letting yourself let go so you can soar

“Quitters never win and winners never quit” is a quote that you have no doubt heard. Those who stick to something are the ones who win, and those who quit are losers, not worthy of success. 

But what if everything we thought we knew about quitting was wrong?  

Freeing Yourself to Focus on Your Strengths 

Sometimes we are our own worst enemies because we lack the ability to see ourselves as clearly as others do. We have a concept of who we want to be and what role we want to play, but that may not actually align with our strengths.  

I once worked with a product manager who was a brilliant strategist. She could take a difficult concept and simplify it, clearly and concisely, into a coherent strategy, but she struggled to get alignment with her manager, which was a cause of much frustration for her. I pushed for her to take a role in product strategy for months, but she resisted because she wanted to succeed as a PM.  

Ultimately she took the role, becoming the leader of our product strategy team. She has since thrived, getting promoted twice and running multiple new areas. Casting off her perceived identity as a PM and allowing herself to play to her strengths unlocked her career in ways she couldn’t previously imagine. Her superpower was obscured by her relationship with her manager and her role, which didn’t lend itself to her growth. Once she was free of that weight, she was able to soar. 

Breaking the Inertia of Getting Stuck

Throughout the process of interviewing amazing women leaders for my upcoming book, I noticed a common thread that ran through each of their experiences: They never let themselves get stuck. 

I went through a period after my first child was born when I felt stuck, but I wasn’t sure what to do about it. I had handed my team off when I went on leave, and since it was in good hands, I came back and took a role in Corporate Strategy. I missed the hands-on nature of being in Product, so I built out the Charity and Social Commerce Verticals at PayPal, but I still felt stuck. 

So I quit. 

I told the VP I worked for that I was out. I wasn’t sure what I wanted to do, but I knew that after five years at PayPal, I was done. This broke the inertia I was experiencing, and I was soon offered a position at eBay leading the Buyer Experience. I jumped at the chance. That brought a whole new set of challenges and insights, and eventually led me to Facebook a couple of years later. 

Quitting put my career on a whole new trajectory. It forced me to explore something new and reignited my passion for working in tech.

Cutting Your Losses 

The sunk cost fallacy often holds us back. The logic goes, “I’ve already invested x years trying to get promoted to the next level, so what’s one more?” Maybe we have been promised the next big opportunity only to see it go to someone else, so we stay in line, waiting for it to pan out. Perhaps we have something we want to build or work on, and we keep telling ourselves it is right around the corner.  

I often ask people who feel stuck in their roles, “Given what you know today, would you take this job, with this manager, at this company, under these circumstances again?” 

So many of them say no, yet every single day that they continue in their current job, they are really saying, “Yes, I would.” Quitting means saying no, cutting your losses, and giving yourself permission to start on a new path. 

Making conscious choices means actively thinking about where you are and what you value today. Those things can change over time. Your managers will change, or a company will grow from a small, intimate startup to a large corporation. Forcing yourself to evaluate where you are and whether this is still the path you want to follow can free you from overstaying and getting caught up in the sunk cost fallacy.  

Counting Opportunity Costs 

Every choice you make has a cost. In particular, whenever you say “yes” to something, you are implicitly saying “no” to something else, whether you realize it or not. Decisions have a price, and that price is opportunity cost. 

This goes beyond just your work and career. The longer you stay in a bad relationship with the wrong partner, the longer it will be before you find the right person for you. The more time you invest in a friendship with someone who doesn’t value you, the less time you have for those who can support you. The more you spend time with people who don’t bring you joy, the less time you have to find a tribe where you will truly thrive.  

Several years ago, Aileen Lee, founder of Cowboy Ventures, asked me very directly, “When are you going to go out there and start or run something, rather than being an exec in someone else’s company?” I thought about her words often over the years, but it took me a while to finally make the move. 

When I left my last role, I didn’t do it because I no longer loved the company, my team, or my work. I left because I knew that I could do more in my new role than I could in my previous one.  

We have a limited amount of time to spend on our careers, and that time is precious. Knowing what you are sacrificing ensures you make your decisions with sharper focus.  

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As I coach and mentor women throughout the industry, I have urged many to change teams, move to different roles, or go to different companies. The most challenging cases are the ones where it is clear that there is little to no path forward, whether because of a bad manager relationship or a terrible team dynamic. Some people take my advice, but many choose to stick it out. Those who do often come back months later and tell me they should have quit the first time around.  

Knowing when to quit is just as important as knowing when to double down. So many people cling to situations that aren’t conducive to their growth and success because they are afraid to quit. Right now over 40 percent of people are thinking about quitting (ref). The great thing is that if you are thinking of quitting something, you are in good company. Evaluate where you are. If you want to cut the cord tethering you to the wrong thing and weighing you down, this is the right time. Let yourself soar.