How to Break Through When You Feel Stuck in Midlife
Did you ever think you'd have it all figured out by now?
Like, you'd hit your 40s and somehow everything would just... click? The money would be handled, the career would be solid, you'd wake up feeling energized and excited about your life?
But alas, here we are. Tired. A little (or a lot) behind where we thought we'd be. Wondering what the hell happened to all those plans we had.
And the worst part? Everyone else seems like they have it figured out. Their Instagram looks amazing. They're buying houses and taking trips and talking about their investment portfolios while you're over here trying to figure out how you're going to afford new tires.
If you're nodding along right now, I got you.
I know how exhausting it is to try so hard and feel like you're getting nowhere. You read the books and listen to the podcasts and pin all the quotes, but nothing seems to change.
The good news is that you don’t actually need a complete life overhaul, or another pep talk on how you just need to just think positive and manifest it!
Because I'm about to show you five questions that might just change everything.
Why the Usual Advice Doesn't Work (And What Actually Does)
Let me guess what you've already tried.
Maybe you bought a course on starting a side hustle. Watched two videos and never opened it again. Maybe you tried the 5am miracle morning thing. Lasted three days before you remembered that you actually hate mornings. Maybe you made a budget, followed it for a week, then something came up and now it's buried in a drawer somewhere. Maybe you promised yourself this year would be different. Fresh start. New you.
And now it's February (or June, or October) and you're basically doing the same things you were doing last year.
Please don’t beat yourself up.
The problem is that all those approaches completely ignore how actual humans create change when they're already running on empty. When you're this tired, adding MORE to your plate—even if it's "good" stuff—doesn't help. It just gives you one more thing to feel guilty about when you can't keep up.
What works better are small, honest moments where you pause and ask yourself real questions.
Not the fluffy "what would your best self do?" kind of questions. And definitely not the shame-y "why can't you just get it together?" questions.
These are questions that help you:
See what's actually true (versus what you're making up in your head)
Notice patterns you keep repeating
Spot opportunities you've been walking right past
Remember that you're more capable than you feel right now
This is where journaling comes in. No fancy supplies needed. No perfect handwriting. No pressure to do it every single day. And definitely not asking to devote tons of time that you don’t have.
Just you, being honest with yourself, and asking better questions.
The 5 Questions That Change Everything
Question #1: The Thought Flip
"What's one unhelpful thought I've had recently, and how can I rewrite it?"
Okay, this one's sneakish-ly powerful.
Most of us walk around with a running commentary in our heads that we don't even notice anymore. And a lot of that commentary is... not great.
Like:
"I'm 47 and still bad with money. What's wrong with me?"
"I've wasted so much time. It's probably too late now."
"Everyone else figured this out. Why can't I?"
We think these thoughts SO automatically that we don't even question if they're true, and with this type of commentary running through our brains, no wonder we’re hard on ourselves!
So try to pay attention and catch one of these thoughts to re-work it. Here’s an example:
Unhelpful thought: "I should have my life together by now. Something's wrong with me."
Rewritten version: "I'm figuring things out at my own pace, and that's okay. I'm learning and growing, even if it looks different than I expected."
You don’t have to pretend everything is fine, or tell yourself a positive thought that feels like lying to yourself. We just want to interrupt the negative thoughts, like the ones that keep us up at 2 am, for example..
Why this works: Your thoughts create your feelings, and your feelings drive what you do (or don't do). Change the thought, change everything that comes after it.
Question #2: The "Wait, I'm Actually Capable" Reminder
"What's one thing I did recently that proves I'm capable?"
When you feel stuck, your brain does this fun thing where it completely forgets every time you've ever been competent, resourceful, or capable, and all it can remember is every mistake you've made and everything you haven't figured out yet.
This question interrupts that spiral.
It makes you look for evidence—actual, real evidence—that you're not as helpless as you feel.
And here's the key: it doesn't have to be big.
In fact, the small stuff often matters more because it's stuff you can actually repeat.
Like:
"I called the insurance company about that billing error instead of just paying it. Saved $43."
"I made coffee at home three days in a row instead of stopping at Starbucks."
"I had an uncomfortable conversation with my boss instead of avoiding it."
"I said no to plans I didn't actually want to do."
"I asked my kid's teacher for help instead of pretending I had it handled."
None of those are going to change your life overnight, but they're proof that you CAN do hard things. You CAN make different choices. You ARE capable of change.
Why this works: You need evidence to build a new belief about yourself. This question helps you collect that evidence, one small example at a time.
Question #3: The Opportunity Spotter
"Where did I notice a chance to save money or make a positive change that I might usually miss?"
This one's my favorite because it trains your brain to work FOR you instead of against you.
Most of us are on autopilot like 90% of the time. We do the same things, think the same thoughts, miss the same opportunities.
This question wakes you up.
It makes you start noticing things like:
"Oh, I'm still paying $15/month for that meditation app I haven't opened in six months."
"My coworker mentioned she needs help organizing her client files. I'm good at that. Could I offer that as a service?"
"The store has my usual staples on sale. If I buy extra now, I won't pay full price next month."
"There's a free webinar on exactly the thing I've been trying to figure out."
"I almost bought lunch out again, but I actually have leftovers. That's $12 saved."
None of this is about becoming obsessed with money or pinching every penny until it screams.
It's just about paying attention and looking for opportunities that you’re used to overlooking.
When you start actively looking for opportunities—even tiny ones—you'll be shocked at how many you've been missing.
Why this works: What you focus on expands. When you train your brain to look for possibilities instead of just problems, you start seeing more and more of them. And that builds momentum.
Question #4: The Money Reality Check
"Did my money choices today move me toward the life I want, or keep me stuck? What could I shift tomorrow?"
Deep breath. This one is NOT about shame. We are absolutely not going to beat ourselves up for buying a coffee or ordering takeout or whatever.
This is about gently checking in with whether your money is working for you or against you.
And here's what makes it work: the second part.
"What could I shift TOMORROW?"
Not "what massive overhaul do I need." Not "why am I so terrible with money."
Just: what's one small thing I could do differently tomorrow?
Here's what this actually looks like:
"I stress-bought stuff on Amazon because I was avoiding dealing with that email from my boss. Tomorrow, I could take 10 minutes to just write down what I'm actually worried about instead of shopping it away."
Or:
"I transferred $20 to savings even though it felt almost pointless. But that's $20 more than I had yesterday. Tomorrow I could do it again."
The magic is in making it about tomorrow, not yesterday.
Yesterday is done. Tomorrow is a fresh chance.
Why this works: It creates awareness without judgment, and it focuses you on what you can control (the next choice you make) instead of what you can't (choices you already made).
Question #5: The Gratitude Check (But Make It Real)
"What's one thing I'm grateful for today?"
I know. You've heard this one a million times.
But stick with me, because I'm not asking you to pretend everything is perfect or gaslight yourself into fake positivity.
I'm asking you to notice one good thing, even when things are hard.
Because here's the truth: both things can be true at the same time.
Life can be really hard right now AND there can still be things worth appreciating.
You can be stressed about money AND grateful that your best friend texted you today.
You can feel behind AND appreciate that your body still lets you go for walks.
Here are some examples of what I’m talking about:
"I'm grateful I woke up today with the awareness that I want things to be different. Not everyone gets there."
"I'm grateful for the coworker who made me laugh when I wanted to cry."
"I'm grateful my car made it through another week without breaking down."
"I'm grateful I have hot water and a working fridge."
This isn't about pretending your problems don't exist.
It's about not letting the hard stuff become the ONLY thing you can see.
Because when everything feels dark, you stop believing change is possible. And when you stop believing change is possible, you stop trying.
Why this works: Gratitude literally rewires your brain. It doesn't fix your problems, but it keeps you from drowning in them. And that makes all the difference.
What Actually Happens When You Do This
I'm not going to lie to you and say these five questions will solve all your problems. They won't.
All we’re trying to do here is start recognizing patterns, catch those negative thoughts in real time, shift them, and eventually let this all lead us to making different decisions that support the life we want- instead of driving the automatic habits that keep us stuck.
How to Actually Stick With This (Without Adding Overwhelm)
This is a perfection-free zone. You don't need to journal every single day. Whenever you can still counts. Here are some additional tips:
Keep it short. Set a timer for 5-10 minutes. Answer whichever questions feel most relevant that day. Bullet points are totally fine.
Pick a time. Morning with coffee. Lunch break. Before bed. Whatever. Just pick one time and try to stick with it because routine makes it automatic.
Use whatever's easiest. Notes app on your phone. Google doc. Voice memo. Scribbled in a notebook. Whatever lowers the barrier.
Don't judge what comes out. This is just you being honest with yourself. There are no wrong answers. Nobody's grading this.
The goal isn't to become a "journaling person."
The goal is to give yourself space to think clearly so you can make better choices and stop feeling so damn stuck all the time.
Want to Go Deeper? I Made You Something. . .
If these five questions resonated with you (and I'm guessing they did if you're still reading), I have something that might help.
I created The Breakthrough Journal specifically for women like us—women who are done with the BS advice and ready for something real.
It's got:
Daily prompts (like the ones above) that take 5-10 minutes and actually help you build momentum
Weekly reflection exercises that help you spot patterns and celebrate progress (even small progress)
Goal tracking that breaks things down into actually doable steps instead of overwhelming you
Space to work through your money stuff without shame
Achievement logs to help you remember you're more capable than you feel
This isn't another "manifest your dreams!" journal filled with sparkles and empty promises.
This is a practical tool for creating real change when you're tired, overwhelmed, and don't have energy for anything complicated.
And it's completely free because I know exactly how it feels to be where you are right now.
Grab your free Breakthrough Journal here
Save this post so you can come back to these questions whenever you need them. And if you know another woman who's feeling stuck right now, send this to her. We're all in this together.
xo
Maggie
