"I'm stuck in a situation that's comfortable but not fulfilling…”
How can you distinguish between legitimate caution and fear-based excuses?
"I'm stuck in a situation that's comfortable but not fulfilling. I know a big change would probably be good for me, and I've read Chris's posts about how 'no one wishes they'd made a change later.' But I keep finding reasons to delay: I'm not ready, the timing isn't right, I need more security first. I've developed elaborate justifications for staying exactly where I am, even though I'm not thriving. How do you distinguish between legitimate caution and fear-based excuses? What's helped others finally make the leap when they've been stuck in 'preparation mode' for too long?" -ETERNAL PLANNER
Dear Eternal Planner,
First, let's acknowledge the obvious: everyone's situation is different, and change is hard! Our circumstances, resources, and support systems vary enormously, and there's no universal playbook for making big life changes.
Our brains are wired to prefer the predictable, even when that predictable situation is slowly draining our soul. That's not a character flaw—it's just how we're built. So if you're finding it difficult to move forward despite wanting to, you're not broken, and you're definitely not alone.
That said, I generally think that being pro-change is often a good starting point. As noted, no one ever says, “I wish I’d made that change later.” (But often they wish they’d done it sooner!)
Here are some approaches that have helped others bridge the gap between WANTING to make a big change and actually making it happen:
Start with Tiny Experiments
Instead of making a dramatic leap, try designing small, low-risk experiments to test the waters. Considering a career change? Take a weekend workshop or shadow someone in your target field. Thinking about moving to a new city? Visit for a few days and pretend you live there (skip the tourist stuff and try to find the best local coffee shop instead).
These experiments serve multiple purposes:
They give you actual data (instead of just letting your imagination run wild)
They build confidence (by showing you can navigate new territory without the world ending)
They create momentum (which makes it easier to do bigger things!)
Get Specific About Your Fears
When we say vague things like "I'm not ready" or "the timing isn't right," there's usually a more specific fear lurking underneath. Try to name exactly what you're afraid of. Is it failing in front of people you respect? Running out of money? Disappointing your parents? Discovering you're not actually as good at your dream job as you imagined?
Once you've identified your fears, you can address them directly instead of just feeling generally anxious.
Create Deadlines with Accountability
Open-ended timelines are the perfect breeding ground for "I'll do it someday" (which often means "never"). Many people find it helpful to set a specific date for taking action and then tell someone who will follow-up if it doesn’t happen.
This doesn't mean you have to completely transform your life by that date—maybe by then you'll have just taken one concrete step forward. Having someone who'll text you "Hey, didn't you say you were going to apply for that program by Friday?" can provide the nudge needed when motivation inevitably dips.
Notice Your Personal Narrative
We all have stories we tell ourselves about who we are. Sometimes these narratives include limiting beliefs like "I always play it safe" or "I'm just not a risk-taker."
Pay attention to these stories. They might have made sense at some point in your life, but they don't have to define your future. You might find it helpful to deliberately create a counter-narrative that highlights times you've successfully navigated change in the past, even small ones.
Deal with Decision Paralysis
Sometimes we get stuck because we're trying to make the perfect decision with complete information—which happens approximately never in real life. Two approaches can help:
The "70% rule": If you're 70% confident it's the right move, that's enough information to proceed. Waiting for 100% certainty means waiting until you're dead.
The "reversible decision" framework: Ask yourself, "Can I UNDO this decision if it doesn't work out?" If yes, you can make it with less agonizing, knowing you can adjust course if needed.
Final Thoughts
Change doesn't happen in one cinematic moment where the music swells and suddenly your entire life is different. It's messy, incremental, and rarely follows a straight line. Most people who've made significant changes can point to a series of small decisions that eventually created a new path—not one heroic leap.
Perhaps the most powerful shift happens when you stop thinking of change as something you need to be "ready" for and start seeing it as the process that makes you ready.
What small experiment could you begin this week? 🤔
P.S. In addition to my new book TIME ANXIETY (which comes out one week from today!), I also encourage you to check out my dear friend Gretchen Rubin’s new book, Secrets of Adulthood. It’s a collection of aphorisms to help you manage the complexities of life.
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"Create Deadlines with Accountability" THIS! Is what I need to start doing. Thank you for another great read.
This is epic, Chris! We deeply need methods to address fears of change so we can be the self-actualized people we long to be!
One technique for fleshing out fears and addressing resistance to change is the conference table.
Make a circle on a piece of paper. Draw lines to create sections. Then go around and write all the different worries or concerns about the change, one at a time, in each pie slice of your table.
Getting this tangle of voices out of your head and out in front of you on paper is a great way to get traction about the issue!
I don’t want to be smarmy by adding a link here so I won’t, but if anyone wants a printable conference table they can find it, with more directions on how to use it, by googling “conference table ifs.”