That's So Mid #8: When You Can’t Afford a Crisis But Can’t Afford Not to Change
Exploring why midlife isn’t about crisis but about honesty, shedding armor that no longer serves you, and embracing who you truly are—even when the economy says you can’t afford it.
First off, another warm welcome to all the new subscribers who've recently joined —I'm thrilled you're here! If you're just finding your way around, this is "That's So Mid," my monthly reflection on what's been catching my attention and stirring my thoughts. Today, instead of making any rec’s about what to watch or read I’m offering a free worksheet for those of you who might be interested ❤️
If what you read resonates with you, there are a few ways we can go deeper together:
Check out my website for information on 1:1 coaching if you're ready to break free from feeling stuck or stagnant and rediscover what you want.
Consider becoming a paying subscriber for access to all posts, exclusive journal exercises, reflection prompts, and quarterly Zoom meet-ups where we can connect as a community.
Founding members receive all of the above PLUS a private 1:1 Unfucking Midlife coaching session with me to address your specific situation.
That said, I'm happy to have you here regardless of how you choose to engage.
Let’s face it, Midlife is a mind fuck and sometimes just knowing you're not alone is all you need.
For those curious about what you'll find behind the paywall, I've unlocked a few previous posts so you can get a feel for what goes on behind the scenes:
A few days ago, I dropped what I thought was just a couple of ‘notes’ into the digital void on Midlife: First, the idea that 'most midlife crises are just people finally getting honest about what they actually want'
and then, 'the most disruptive act in Midlife is leaving behind the version of yourself you created to survive.'
Turns out, it wasn't unpopular at all. The notes blew up on both Substack and Threads, with the comments section overflowing with personal stories, insights, and confessions.
This is precisely why I started talking and writing about entering Midlife— no matter what kind of life you've built, you hit this point, and the questions start rolling in.
When I first created my website offering my coaching services related to this time, I borrowed from Chip Conley that midlife is a calling, not a crisis. And many of the comments touched on that very theme; Midlife is an awakening, rebirth, a coming home and I couldn't agree more.
Like birth, it's uncomfortable—even painful—especially if you resist the process. The 'it' is a transformation, metamorphosis, manifestation of Self.
Yet many of us feel constrained from fully stepping into this shift.
The reasons always make sense on paper—responsibilities, expectations, the roles we play for others (hence the "crisis").
But what was the most common constraint that came up on Threads?
Money.
Nobody Has Time for That
The most repeated sentiment across all those comments? Variations of "Who has time for a crisis in this economy?" People joked (but not really) about Midlife awakenings being a luxury when just keeping up with rent, responsibilities, and protein intake feels impossible. (Okay, nobody said anything about protein.)
The idea that contemplating how we want to spend the second half of our lives and putting ourselves first is a privilege—second only to the notion that it's selfish—comes up often.
I'd be remiss in not saying that factors like socioeconomic security, health, supportive relationships, and gender absolutely influence one's ability to respond to Midlife's calling.
And yes, it does seem like a luxury when you're barely keeping up with the basics.
But here's the thing: It's not about money, and you can't afford not to reflect on your life. If anything, it's something we owe ourselves.
Because you're right—we are in Midlife, and time is of the essence.
I would argue that the examination itself—the willingness to face the hard questions—is available to anyone, regardless of circumstance.
Our brains instinctively calculate immediate financial costs while completely overlooking the emotional and energetic tolls of staying put. We get locked in familiar patterns not because they serve us but because of what lurks beyond them: fear of failure, instability, judgment, and the unknown.
Here's the most perverse part of our neurobiology: our brains will choose familiar suffering over unfamiliar possibility every time. Pain, when consistent, becomes the baseline. Discomfort, when predictable, becomes preferable to change. Your body and mind have adapted to your current circumstances—even if they're slowly draining your life force—and will fight to maintain what they know. The ego does not fuck around.
This is how decades pass. This is how people wake up at 65, wondering where their lives went.
Tim Ferriss popularized an exercise borrowed from the Stoics called "Fear-Setting." Unlike goal-setting (which most of us know how to do), fear-setting forces you to articulate exactly what you're afraid might happen if you made a change. It asks you to get specific about what taking action might actually cost you—emotionally, financially, and relationally.
But the genius of this practice is what comes next: What will it cost you NOT to make the change? In six months? One year? Three years? Five years?
This question breaks the spell. We're wired to avoid immediate pain at all costs. But something shifts when forced to project forward and witness the slow accumulation of regret. The math changes. What once seemed like an unbearable risk suddenly becomes the only sensible choice.
The cost of staying put is always calculated in missed life. (I’ve included a PDF for you below!)
Let's Unfuck It
This month, my That's So Mid rec isn't a book, movie, or podcast.
It's for a practice: Find five minutes each day to ask yourself what you want. Not what you should want, not what makes sense, not what's practical or expected or responsible, just what you want.
Write it down. Don't judge it. Don't immediately explain why it's impossible. Just acknowledge it.
Here are some daily prompts to get you started:
Monday: What did I want to be when I grew up that I've completely forgotten about? What elements of that dream still resonate?
Tuesday: If no one would judge me, what would I change about my daily routine tomorrow?
Wednesday: What part of my "armor" feels heaviest right now? What would happen if I set it down for one day?
Thursday: What am I pretending not to know about what I truly want?
Friday: What small pleasure have I denied myself out of practicality that I could reclaim today?
Saturday: Which relationship in my life needs more authenticity and less performance?
Sunday: If my future Self looked back on this period of my life, what would they wish I had been brave enough to begin?
The truth is, we can't afford not to ask these questions. We can't afford to keep carrying versions of ourselves that no longer fit, keep wanting what we were told to want, or keep armoring up when what we really need is to be seen.
Are you hearing Midlife's calling right now? How is it speaking to you, and what is it asking you to embrace or release?
Share in the comments below.
FREE TOOL FOR ALL READERS: I've decided to share my detailed Fear-Setting Exercise with everyone this month—a tool I typically reserve for my private coaching clients. Based on Tim Ferriss's powerful methodology (with my Unfucking Midlife twist), this worksheet walks you step-by-step through identifying what's truly holding you back, creating contingency plans, and—most importantly—calculating the real cost of staying put.
It's one thing to acknowledge intellectually that change is necessary; it's another to see clearly what remaining stuck will cost you in 1, 3, or 10 years.
Hi, I enjoy your posts and listened to the pod with Julia Louis Dreyfus. But I feel a little excluded. I am nearlly 60 and dont feel it is too late to start this work. Even if you do "wake up" at 65 it is not too late. I have not woken up thinking its too late. I think Julia was very good on this as is Miranda July who lays bare her characters feelings about older women only to change her mind. It really is never too late to prioritise your needs.
I'm new to substack and I was interested in the free sheet you are offering but cannot see where to find it? Could you please give me a pointer?