S7 Ep11: Letting Go of "Should" — Rewriting Your Own Success Story

Welcome back to Your Path to Career Success, the podcast that helps you build the skills, confidence, and strategies to thrive in your career.

And can you believe it? This is the final episode of Season 7 — and what a journey it’s been! With 75+ episodes and over 1,000 downloads since we launched in November 2023, I’m so grateful you’ve been part of this growing community.

In this special wrap-up episode, we’re diving into a transformative topic that could completely shift how you define and pursue success: letting go of "should" and rewriting your own success story.

Because the truth is, so many of us get stuck chasing other people’s definitions of success. But when you release the pressure of external expectations, you create space for your own authentic vision to emerge — and that’s where real fulfilment begins.

What You’ll Learn in This Episode:
• Why “Should” Feels So Heavy — Uncover why we often feel trapped by the word should and how it subtly shapes our career decisions.
• The Impact of External Expectations — Learn how to spot when societal pressures or family beliefs are holding you back from your true path.
• Break Free from the Success Formula — Discover how to challenge the traditional, one-size-fits-all success narrative and define what success really looks like for you.
• Practical Strategies to Rewrite Your Story — Get actionable steps to align your career with your passions, values, and unique timeline.
• How to Embrace Uncertainty with Confidence — Find out how letting go of what no longer serves you can open up exciting new opportunities.

What next?
A big thank you for tuning in to Your Path To Career Success – where your dreams and your career intertwine!

🦉 Book a free discovery call to explore how my Unlock Your Career Potential coaching programme can support your leadership goals.
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🦉 You can also connect with me over on LinkedIn for more career strategy and leadership insights.

Stay tuned for more episodes focused on helping you unlock your full leadership potential!

Useful Resources:
🎧 Further Listening & Reading
• Book: Untamed by Glennon Doyle — A powerful guide to breaking free from societal expectations and living your truth.
• Podcast: We Can Do Hard Things with Glennon Doyle — Especially episodes about letting go of “shoulds” and embracing authenticity.
• Article: Redefining Success: Why It’s Time to Let Go of Other People’s Timelines — Harvard Business Review.

🧠 Coaching Tools You Might Love
• My Unlock Your Career Potential Coaching Programme — Dive deeper into confidence-building, career transitions, and creating your own version of success with tailored 1-2-1 support.

Transcript

Welcome back Your Path to Career Success, the podcast that helps you build the skills, confidence, and strategies to thrive in your career.  This is the final episode of Season 7, can you believe it?  75+ episodes and over 1,000+ downloads since it was launched back in November 2023!

I’m Kathryn, your host and I’m thrilled to have you with me today as we wrap up this season with a topic that’s incredibly close to my heart — one that can completely change how you view your own success.
 
 

We’re talking about letting go of “should” and rewriting your own success story.

So often, we find ourselves trapped by what we should be doing, by expectations, or by the way others define success. 

As Albert Schweitzer says "Success is not the key to happiness. Happiness is the key to success. If you love what you are doing, you will be successful." 

But today, we’re going to dive into the power of letting go of that “should” and creating a vision for success that’s uniquely yours and we’ll cover:

✔️ Why we often feel trapped by the word "should" and how it impacts our success
 ✔️ The pressure of external expectations and how to recognise when it’s holding you back
 ✔️ How to break free from society’s definition of success and redefine it for yourself
 ✔️ Practical strategies to rewrite your success story — aligning your career with your passions and values
 ✔️ How to embrace uncertainty and courageously let go of what doesn’t serve you

Before we jump in, grab your favourite beverage, find a comfy spot, and get ready to map out your leadership path with those lightbulb moments.

Segment 1: The Weight of “Should”

Let’s begin by unpacking the word “should.”

“Should” can feel like a heavy weight — a constant reminder that we’re not measuring up to some external standard. Whether it’s career milestones, how we should be managing our time, or how we should be achieving our goals, “should” is a word that often leaves us feeling inadequate.

There’s a quote by author and speaker, Glennon Doyle, that really resonates here:

"The thing that I wish people knew is that we are all a little bit behind where we thought we’d be, and it’s okay."

How many times have you thought, “I should be further along in my career” or “I should have a more successful business by now”? I know I’ve certainly had those thoughts. And if you’re listening to this, you might have had them too — those moments where you feel like you’ve missed some imaginary deadline or that you haven’t achieved enough by a certain age or stage.

But the truth is, life doesn’t always follow a linear path. Success doesn’t come with a strict timeline. And yet, we often keep pushing ourselves forward based on some arbitrary “shoulds” that we’ve internalised from society, our families, or even our colleagues.

Let me share a personal story: there was a time in my career when I was chasing someone else’s version of success. I thought I should follow a specific, pre-determined route that others had taken before me. There were milestones I felt I had to hit, promotions I “should” be striving for, and an image of what success looked like that had nothing to do with who I was or what I wanted. I became so consumed by the “shoulds” — those promotions, titles, and external markers of success — that I lost sight of what truly made me feel fulfilled.

I also experienced this pressure at the start of running The Career Owl, feeling like I had to follow a certain path to be successful. 

I’ll be honest in both my previous corporate life and also in the early days of “The Career Owl”, I ended up feeling frustrated and disillusioned, as if I was failing at something.

I can share with you a personal moment that really drove this home for me. When I first started "The Career Owl," I was gripped by all the "shoulds" — I should have a more polished brand, I should be more like other successful career coaches, I should be getting more recognition. It wasn’t until my business coach, Nicole Louise Winer, reminded me that my journey didn’t need to follow anyone else's path that I truly understood the power of letting go. She said, "Your pathway doesn’t have to look like anyone else's. It’s yours, and it will unfold in your own way." That simple, but profound, reminder gave me the courage to stop measuring myself against others, and instead, embrace the unique path I was creating.

And it wasn’t until I let go of that pressure and embraced my own definition of success that I started building a career that truly aligned with my passions and values.

Tip #1: Take a moment today to notice when “should” shows up in your life. Ask yourself: is this truly what I want, or is it a measure imposed by others? This simple awareness can be the first step in setting yourself free from a narrative that may not even be yours.

You don’t have to follow someone else’s timeline. You’re not behind. You’re just on your unique journey. And trust me, that’s more than enough.

Segment 2: The Freedom of Letting Go

Now, let’s talk about what happens when you release the “shoulds.” It’s like lifting a weight off your shoulders.

When you stop chasing external definitions of success, you open yourself up to more freedom, more clarity, and more alignment with your authentic self. But here’s the catch — it’s not always easy.

Letting go of “should” means challenging societal pressures, family expectations, or even the way the workplace defines success. It means saying no to paths that don’t feel right for you, even if they’re considered “the right way” by others. And that can be incredibly daunting.

But the real magic happens when you make that shift. You begin to realise that success isn’t a one-size-fits-all formula, and that’s when life starts to feel a whole lot more in alignment with who you truly are.

Here’s a powerful quote by Dr. Steve Maraboli that really encapsulates this:

"The only limits you have are the limits you believe."

In other words, when you stop believing in someone else’s limits for you, you unlock endless possibilities. You begin to see that the only boundaries that exist are the ones you've accepted from external pressures. And when you let go of those, you start to live on your own terms.

Let me share a story with you: I’ve worked with clients who have completely transformed their careers after realising that the path they were on wasn’t their own — it was someone else’s version of success. One of my clients had worked in a corporate job for years because she thought she should. She had always been told that corporate success was the ultimate success. There was this idea ingrained in her that this was the pinnacle of achievement, so she stayed on that track — despite feeling unfulfilled and drained.

But when she finally decided to let go of that “should,” things began to shift. She asked herself, "What if success didn’t look like a corporate ladder?" After some deep reflection, she realised that her true passion was teaching and mentoring. Now, she is building a coaching business, guiding others in their career transformations. She is finally living her true purpose — something she never thought was possible when she was tied to the “shoulds” of corporate life.

Tip #2: Reflect on the areas of your life where you feel pressure to meet external expectations. What would it look like to break free from those? What would success look like if it were defined by you, not by others?

By choosing to stop living according to someone else’s version of success, you open up a world of possibilities. You begin to live with intention, making decisions that align with who you are, not just what’s expected of you. That’s where true freedom comes from — and that's when you start living a life you’re excited about.

Segment 3: Redefining Success on Your Own Terms

So, what does it look like to define success for yourself? The beauty of success is that it’s unique to every individual. There’s no one-size-fits-all approach.

Success isn’t just about money, titles, or external recognition — it’s about the things that light you up and bring you fulfilment. It’s about finding purpose, meaning, and joy in your day-to-day life.

For me, success is living a life where I’m constantly learning, growing, and helping others do the same. It’s about building a business that gives me the flexibility to spend time with my family, pursue my passions, and enjoy moments of peace. My version of success allows me to be present in both my personal and professional life. But your version of success might look completely different, and that’s perfectly okay. We each have our own journey, our own milestones, and our own definitions of what it means to “make it.”

I’ll be honest: I spent a good part of my career chasing after a vision of success that wasn’t truly mine. I thought I “should” be striving for the same things that others in my field were chasing. I followed a path laid out by conventional expectations and external pressures. But once I stopped measuring my success by the “shoulds” and started listening to my own needs and desires, I realised that true success for me was about creating a life that felt meaningful, connected, and aligned with my passions. And that’s when my career started to take a new direction — one that truly brought me joy and fulfilment.

To get clearer on your own definition of success, think about these key elements:

• What excites you? What are you passionate about, and how can you incorporate more of that into your career and life? Success isn’t just about checking boxes — it’s about creating a life that makes you feel alive.

• What brings you peace? Success isn’t only about hustle and achievement; it’s also about finding moments of stillness, balance, and inner peace. If your definition of success is tied solely to external accomplishments, you may miss the satisfaction that comes from inner calm and personal contentment.

• What makes you feel proud? Not the external achievements, but the inner satisfaction of doing something that aligns with your values. It’s not always about the accolades or recognition — it’s about knowing that you’re living true to yourself.

As I mentioned before, when I stopped measuring my success by the “shoulds” and started listening to my own needs, my career took on a new direction. And that’s the beauty of rewriting your success story — it’s never too late to make changes that bring you more joy, peace, and fulfilment.

Tip #3: Take some time this week to define success on your own terms. Write down what truly matters to you — not what others expect. Then, set one goal that aligns with your version of success. 

Whether it’s starting a new project, making time for personal growth, or simply prioritising your well-being, take that first step towards a version of success that’s uniquely yours.

Remember, success is a journey, not a destination. It’s about creating a life you love, one that’s defined by your own terms and values. So let go of the “shoulds,” and start living the life that’s waiting for you.

Segment 4: The Courage to Let Go

The final piece of the puzzle is the courage to let go. Letting go of “should” isn’t just about releasing the expectations placed on us by others; it’s about trusting ourselves enough to carve our own path. 

It’s about finding the strength to step into the unknown, to embrace uncertainty, and to move forward without relying on the crutch of external validation or approval.

As the famous author and speaker, Mel Robbins, wisely said, "When you let go of the 'shoulds,' you create space for your own power, for your own path, and for your own greatness." This is where the magic happens — when we stop waiting for someone else's approval and start taking ownership of our journey.

It’s easy to stay stuck in a loop of “should” because it feels safe. But the truth is, staying in that space is limiting. The real freedom comes when we have the courage to release those “shoulds” and trust ourselves to take the leap — even when the path ahead is unclear.

When you let go of the “shoulds,” you allow space for creativity, for growth, and for the possibility of something even greater than you imagined. You free yourself from the weight of comparison and external pressures, and in doing so, you step into your true power.

Tip #4: Take a moment to reflect on the “shoulds” that are holding you back. What’s one thing you can release today — one expectation that no longer serves you? And once you do, embrace the courage to take the first step toward a path that feels right for you, even if it’s not the one you thought you’d be on.

Letting go of the “shoulds” isn’t always easy, but it’s always worth it. When you trust yourself and step into your own power, you’ll find that the road ahead, even though uncertain, is full of possibilities — and it’s yours to navigate however you see fit.

Conclusion: Wrapping Up Season 7

As we close out this final episode of Season 7, I want to thank you for being part of this journey. 

Letting go of “should” and rewriting your own success story isn’t just a career shift — it’s a life shift. It’s about creating space for the things that truly matter to you and trusting that your path will unfold in its own beautiful way.

Let’s quickly recap everything we covered:

1. The Weight of “Should”
“Should” can feel like a heavy burden, constantly reminding us that we’re not measuring up to some external standard. It’s important to notice when “should” shows up in your life and ask: is this truly what I want, or is it something imposed by others?

2. The Freedom of Letting Go
Releasing the “shoulds” opens up more freedom, clarity, and alignment with your authentic self. It means challenging societal expectations and carving your own path. When you let go of the limits others place on you, the possibilities are endless.

3️. Redefining Success on Your Own Terms
Success isn’t one-size-fits-all. Take the time to define success for yourself, focusing on what excites you, brings you peace, and makes you feel proud. When you stop measuring success by others’ standards, you can start building a life and career that truly fulfil you.

4. The Courage to Let Go
It takes courage to step into the unknown and trust yourself. When you let go of the “shoulds,” you create space for your own power and path. Trust in yourself and take the first step toward a future that aligns with your true desires, not someone else’s expectations.

This episode was all about releasing the weight of external expectations and defining your own version of success. Remember, your path doesn’t have to follow anyone else’s — it’s yours to create, with the freedom to shape it however you choose.

Thank you so much for listening throughout this season. Season 8 will be just around the corner, and I can’t wait to continue supporting you on your path to career success.
 
 

If you found today’s episode valuable, hit that subscribe button, leave a review, and share it with your network. You can also connect with me on LinkedIn—just search Kathryn Hall, The Career Owl.

Until next time, keep rewriting your success story — and I’ll see you in Season 8!