Why We Can’t Relax When Life is Good: Overcoming the Fear of the 'Other Shoe' Dropping

Read time: 7 minutes

Welcome to My Musings, a (usually) weekly newsletter where I share what’s been impacting me lately, what I’ve been thinking about, and actionable ideas to help you navigate the career and life transitions that might be coming up for you.


Today’s Musing: Things have been going well lately. So why am I expecting things to not continue that way? In other words - why is it so hard to enjoy things when they are good, and then to rue for the good days when things are less than good?

Waiting for the Other Shoe to Drop - a huge shoe hanging over a small man, about to crush him.

When Everything’s Fine, Why Are We Still Waiting for the Other Shoe to Drop?

There’s a particular type of existential fear that creeps in when everything is fine. 

  • Your career is stable.

  • Your relationships are good.

  • You’re financially secure.

  • You’re healthy.  

By all accounts, you’re doing well. Yet, for some reason, there’s a nagging sense that something is bound to go wrong.

The record is going to skip. 

For me, this is usually accompanied by a voice in your head saying, "This can’t last." 

In other words, I’m waiting for the other shoe to drop - bracing myself for a disaster that may (and probably will) never come.

Why We Can’t Relax When Everything’s Going Fine

Before jumping into the analysis, it’s key to understand that these feelings are normal and are rooted in our natural human instincts to survive. 

According to a study by Harvard psychologist Dr. Daniel Gilbert, we are naturally wired to anticipate threats. Our minds have evolved to focus on potential dangers even when everything is going well. It’s a leftover survival mechanism from when our ancestors needed to stay alert to avoid predators.

So, even when things are good, we stay alert to potential threats. This may have worked in the expanse of the Sahara or the depths of the jungle - but in modern life, where real survival threats are minimal, that instinct is often a waste of the limited energy and focus that we have, and manifests as a chronic sense of unease or perpetual worry (an unfortunately overly common predicament).

In the professional context, here’s how it often plays out

You’ve worked hard to get to a certain point in your career. And, now, you have to maintain it.

What if things fall apart? What if you can’t keep up with expectations? What if it was all just a fluke?

These thoughts can be paralyzing. Dr. Brené Brown has often spoken about this in her work on vulnerability and shame, noting that many high achievers feel like impostors in their success. “The vulnerability paradox is this: It’s the first thing I look for in you and the last thing I’m willing to show you. In you, it’s courage. In me, it’s weakness.” This vulnerability to loss and failure often intensifies when we feel we have the most to lose.

Writer and Poet David Whyte speaks about fear and vulnerability as well (I’ve written about him before): “There is no life we can live without being subject to grief, loss and heartbreak.'“

The Impacts of Existential Fears on our Work

Where I find this comes up all the time (and did for me as well) is in the legal world. The margin for error feels razor-thin and you might find yourself constantly anticipating a mistake that could derail everything. 

According to a study by the American Bar Association, over 25% of lawyers report chronic stress, and many cite a fear of making a critical mistake as a primary reason.

There is a pervasive belief that if you’re not constantly vigilant, you’ll miss something critical and everything you’ve built will collapse. 

Ironically, this hyper-alertness can make you less effective, as it’s impossible to sustain peak performance when you’re always bracing for impact. Instead, it leads to overwork, and eventually burnout

I’ve worked with clients who, despite significant career success, live with this constant tension.

One client, a partner at a prestigious law firm, described it as “always feeling like I’m one mistake away from being found out.” She wasn’t talking about being unqualified—she was eminently capable and successful. But the fear of losing it all haunted her, pushing her to work longer hours, second-guess her decisions, and never feel satisfied.

How to Manage the “Other Shoe” Mentality

So, what can we do about it? How do we stop waiting for the other shoe to drop when everything is fine? 

Here are a few strategies backed by research:

1. Acknowledge the Fear

It’s important to recognize that these feelings are normal. You’re not alone in feeling uneasy when things are going well. Acknowledge the fear without letting it dominate your thoughts. The key is to observe the fear, recognize it for what it is, and move forward anyway. Dr. Kristin Neff, an expert in self-compassion, recommends recognizing your fear with kindness rather than judgment.

2. Focus on What You Can Control

One of the main reasons we feel anxious is the sense that we’re not in control. By focusing on the things we can control—our actions, decisions, and responses—we can create a sense of agency. Psychologist Martin Seligman’s research on learned helplessness suggests that feeling a lack of control increases stress. Accept that uncertainty is part of life, but remind yourself that you have the skills to adapt to whatever comes.

3. Practice Mindfulness

Mindfulness is about staying present and not worrying about future outcomes. By grounding yourself in the present moment, you can reduce the anxiety that comes from worrying about what might happen. A study published in the Journal of Clinical Psychology found that mindfulness practices significantly reduced anxiety and improved well-being. Practices like meditation, journaling, or simply taking a few moments each day to breathe deeply can help.

4. Embrace Impermanence

Instead of fearing that the good times won’t last, embrace the fact that everything—both the highs and the lows—are temporary. Buddhist and other mindfulness teachings often emphasize the importance of accepting impermanence. This perspective can help you appreciate the present without becoming too attached to outcomes.

5. Set Realistic Expectations

Perfection isn’t possible, and neither is total control. Set realistic expectations for yourself and your career. Success doesn’t mean never encountering challenges. It means being resilient enough to handle them when they come. Or, as I often try to remind myself, “80% is perfect.”

Want to Dive Deeper?

I work with people and teams to confidently meet change at work and in life; to foster cultures of mentorship; and, to hone and develop soft skills to create better leaders. Through that work, folks uncover their deeper purpose, navigate challenging transitions, and answer the call to vocation.

If you’d like to explore what’s coming up for you, get in touch.

I hope this week’s edition has been helpful. See you next week.

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Why Change Is Hard

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LIFE IS IN THE INTERRUPTIONS