Stop “Shoulding” on Yourself: Rewriting the Rules Around Timelines, Success, and Self-Worth
July 2025
Hello, Community —We’re officially halfway through 2025… wild, right? Take a moment to pause… Take a deep breath… Then take another one…
How does it feel to be halfway through another year?
For me, a lot of things come up—all at once. A mix of:
Wow, so much has happened already
Fond memories of travel
Pride in both personal and professional milestones
And sheer panic that there are only six months left and I’ll be turning another year older
If similar things are bubbling up for you, you’re definitely not alone. It’s okay to feel all of it—excitement, gratitude, anxiety, urgency. They can coexist.
This summer, I've been teaching a yoga intensive at John Jay College of Criminal Justice in NYC—think of it like a 5-week retreat woven into a college course. Alongside movement and breathwork, we’ve been reading the Yoga Sutras and journaling together.
On Day 9, I gave my students this prompt:
“Reflect on one inner obstacle you face regularly. How does it show up, and what helps you move through it?”
When I sat down to write my own response, the words came fast and clear:
“The belief that I’m behind for my age—personally, professionally, financially, romantically. That I should be further along.”
So in today’s newsletter, I want to explore a theme I return to often in my life—Timelines. Something my therapist lovingly reminds me is a tender spot, especially when reality doesn’t match the timeline I think should be happening.
Stop Shoulding on Yourself:
Rewriting the Rules Around Timelines, Success, and Self-Worth
In my journal reflection, I wrote about how this belief—that I’m behind—shows up in my body and mind. It often feels like a knot in my stomach, tight and unrelenting, while my thoughts spiral in every direction.
It feels as if I’ve done something wrong. Like I’ve failed. Like I’m not enough.
There’s this heavy mix of shame and urgency—an anxious drive to make things happen faster, to catch up to some invisible pace. A hunger to control things, while simultaneously feeling completely out of control.
It gets worse in certain moments—like during a mindless social media scroll or even while I’m with people in real life but have mentally checked out; lost in my own head. The common thread in both scenarios? Comparison.
While grief plays a part in all of this, it’s the comparison trap that really fuels the fire. It creates a false sense of urgency—a belief that I’ve somehow fallen out of sync with the master timeline everyone else is following.
That’s when my inner critic—my gremlin (and yes, she has a name, but we’ll just call her A)—gets the loudest. She whispers forcefully:
“You’re too late.”
“You’re not enough.”
“You missed the deadline.”
“You’re being left behind.”
But…what deadline? Where did it come from? Because I certainly don’t remember agreeing to it.
Whether we realize it or not, we’re all conditioned with certain beliefs—about success, age, milestones, gender roles, and more. These beliefs come from many places: family, school, culture, society, and yes, social media.
Sometimes, these beliefs support us and help us grow. Other times, they quietly hold us back.
I’ve clearly internalized some deep conditioning around Timelines and when things are supposed to happen.
But here’s the truth: Timelines are made up.
During one of those not-so-healthy comparison scrolls, I came across this Instagram post that stopped me in my tracks. It reminded me that I get to choose what models I follow. I can compare myself to people who make me feel “behind,” or I can choose models that remind me of what’s possible.
And the beautiful thing? I don’t have to look far to find inspiration.
I see it in my own family—each of them breaking molds and rewriting what life “should” look like.
My mom started running at 65 and has since completed races in multiple states. In retirement, she became the co-manager of a thriving thrift store and has essentially given herself a third master’s degree in painting and art. I joke that she’s on track to become the next Grandma Moses.
My dad, now 75 and with two knee replacements, still referees basketball games and umpires softball games. This year marks his 31st year doing it—what?!
My sister returned to undergrad at 34 (Go Cougs!) after a successful career as a tenured teacher. She followed her passion for nutrition, became a registered dietitian, and—like me—started her own business: Hanley & Simpson Nutrition Counseling.
You may be thinking—Ok, Stephanie, but what do I do when the “shoulds” and my inner gremlin start screaming?
“I should be married by now.”
“I should have a higher job title.”
“I should be making more money.”
"I should own property."
“I should have it all figured out.”
These thoughts might sound familiar. I hear them all the time. Not just from friends or on social media, but from my clients —high-achieving professionals, executives, creatives, leaders. These are smart, compassionate, successful people who still feel like they’re falling behind.
The pressure of a “prescribed” timeline creates false urgency. Your brain interprets it as danger. Your body responds with stress—tight chest, racing thoughts, fear, over-functioning, or shutting down. It becomes a downward spiral.
Here’s the truth: You can’t control some imagined future timeline. You can’t rewrite the past.
The only timeline you can influence is the present moment.
And that’s where the work begins.
In my coaching, I often guide clients through the four components of stress:
Source Management: Which stressors are in your control—and which aren’t?
Stress Prevention: What habits, boundaries, or systems are you using (or not using) to protect your energy?
Thought Management: What stories are you telling yourself about success, timing, and worth?
Regulation: How are you caring for your nervous system in real-time?
These tools help shift people out of urgency, comparison, and control—and into clarity, confidence, and presence.
We also explore mindset through the Energy Leadership™ framework—which helps people identify the unconscious beliefs and emotional patterns that drive their behavior.
Are you operating from fear and scarcity (Level 1 or 2 energy)?
Or from curiosity, creativity, and possibility (Level 5 and above)?
When you raise your awareness, you create more choice. You stop reacting from someone else’s story, and you start leading from your own.
You can stop focusing on the voices that say “you’re behind” and choose to focus on the ones that say “you’re just getting started.”
When I do that, I can clearly see all the ways I’ve already broken free from timeline conditioning:
At 21, I drove across the country to pursue my creative and performance dreams.
At 32, I started running—and went on to complete four marathons, three of them World Majors.
At 36, I left a secure full-time job to scale my own business.
And now, at 40, I’m continuing to stay open—to new opportunities, to growth, and to the magic of what’s still unfolding.
Every day is a work in progress. And one mantra I return to again and again is:
“I am exactly where I am supposed to be. Everything is unfolding in the perfect time and space.”
I invite you to explore your relationship with timelines:
What are the “shoulds” you’ve been carrying about your timeline?
Whose timeline are you comparing yours to—and why?
What’s one example (famous or personal) that proves it’s never too late?
Where might you already be right on time?
Let’s stop “shoulding” on ourselves. Let’s breathe into where we are. And let’s honor our own unfolding.
P.S .If you or your team are working through a transition, questioning old definitions of success, or untangling from external timelines—I’d love to support the process through coaching, workshops, or speaking.