You Have Financial Freedom. So Why Do You Still Feel Stuck? Let’s Go There.
A reader asks: “I’m financially secure, but emotionally stuck. Why am I still frozen?” Having savings doesn’t automatically create courage. Here's what may be keeping you from moving forward.
We talk a lot about money here — building remote income, layering revenue streams, creating flexibility. And for good reason… financial stability changes what’s possible in midlife.
But what happens when the money isn’t the problem?
Lisa from Maine wrote to me and said: “I’m financially secure, but emotionally stuck. I could make a change. I have savings. I have options. So why am I still frozen?”
We spend years telling ourselves that once we’re financially secure, we’ll finally feel free. Unless you were born into generational wealth or experienced early success, financial insecurity is often the background noise of our 20s, 30s, and well into our 40s.
We can point to it, know what it is. Blame it. Plan around it.
Once that piece stabilizes — maybe you’ve built some retirement savings, acquired property or investment wealth, grown a business or evolved into a high-paying position — the barrier gets more complicated.
It might start to sound like this:
What if I disrupt a life that’s objectively good?
What if I regret leaving stability?
What if I make this big change but nothing inside me actually feels better?
What if people think I’m nuts for burning down a decent life?
When money is tight, fear of change is external. When finances are handled, fear of change often still exists, and it becomes internal.
Internal fear is a heck of a lot harder to argue with.
That’s great, Miranda, but what can we do about it?
Let’s go there.
Let’s Go There is a candid, question-led column where we unpack the real stuff behind remote work, solo travel, and midlife reinvention. No filters… just honest answers to the questions you’ve been carrying around.
Here’s the turning point I see again and again, especially in people who’ve built solid careers, paid off homes, raised families, survived layoffs or divorce and rebuilt from scratch:
You’re not frozen because you lack options. You’re frozen because now the responsibility is fully yours.
There’s no villain. No crisis forcing your hand. You’re not standing on a burning platform, being pressured to jump off.
If you move, it’s because you chose to.
That level of agency can feel heavier and more uncertain than instability ever did. When change is forced on us by layoffs, breakups, financial strain, we don’t have to debate it. We react.
But when nothing is broken — when the life on paper looks good — making a change means admitting that comfort isn’t enough.
That’s not a practical decision. It’s an existential one.
So instead of asking, “Why can’t I just do it?” try this:
1. Identify the Real Risk
Not the financial one; the emotional one.
Are you afraid of disappointing people?
Of being seen as restless or ungrateful?
Of discovering that the change doesn’t magically make you happier?
Write it down plainly. Often, once it’s visible, it has a way of shrinking.
2. Lower the Stakes
You don’t need a dramatic reinvention. Listen, I smoked cigarettes for over 20 years and would never have quit if I’d kept catastrophizing by characterizing it as a permanent, forever change. There’s a lot of truth to that “one day at a time” mantra for kicking an addiction.
Stop sabotaging your efforts by thinking in terms of forever and always.
Maybe you can take a remote contract for three months instead of applying for permanent remote jobs.
Book a solo trip for a month without announcing it as “a new chapter” in your life. It’s just something you’re trying on.
Shift one day a week into working remote, or trying your new side gig on for size.
Treat all of this as data collection, not your manifest destiny. Big life doesn’t have to start big, and it isn’t always cinematic. It can be iterative and incremental.
3. Test Your Identity
This is the part we don’t talk about enough. For a lot of us, especially in our 40s-60s, the real thing we’re protecting isn’t the money. It’s the identity we built while earning it.
Ask yourself: if I weren’t “the reliable one,” or “the successful one,” or “the steady one,” who might I be experimenting with becoming?
That question can feel far more destabilizing than leaving a job or booking a one-way ticket, because identities are sticky.
You may have spent decades being the responsible one in your family. The high achiever. The practical partner. The calm in the storm. The person others count on to not rock the boat.
If you shift, even slightly, you risk confusing people.
And maybe more uncomfortable than that, you risk confusing yourself.
Who are you if you’re no longer optimizing for stability?
Who are you if you choose curiosity over predictability?
Who are you if you disappoint someone who prefers the old version?
Financial security can remove the external excuses, but it also takes away your shield. Now, if you stay, it’s not because you have to. It’s because that identity still feels safer than the unknown.
So instead of trying to leap into a brand-new version of yourself, experiment with your behaviour first.
Say yes to something slightly out of character.
Set a boundary you’ve been avoiding.
Introduce yourself without mentioning your title.
Spend a week prioritizing what energizes you instead of what’s expected.
You’re not falling behind, and there’s nothing wrong with you. You don’t have to dismantle the steady, competent, responsible parts that brought you this far.
But you also don’t have to let them define the edges of your life forever.
Financial security is a foundation. It was never meant to hold you in place. It was meant to give you somewhere solid to step from and build onto.
✌🏻 Miranda
P.S. Have a burning question about remote work or nomad life, particularly in your 40s and beyond? Submit to hello@midlifenomads.com and I’ll do my best.
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