When Your Dream Job Feels Wrong

Hello, my lovelies,

Welcome back to another edition of Ask Wendy. For those who’ve just joined us, I’m Wendy, a former corporate machine, and now your cheerleader for all things self-discovery. I spent over three decades chasing promotions, travelling endlessly, and ticking all the boxes for what I thought was success. After a journey that tested both my heart and my resilience, I realised that I’d never find belonging in a corner office. Now I’m on a mission to find the courage to be my full, messy, brilliant self.

This Week’s Question

I recently heard from a lovely soul in my #IAmMe. programme, let’s call her Michelle W. She wrote:

“Wendy, I’ve always been the one at my company who’s ‘all in.’ Loved the culture, adored my team, and it felt like a real family. But things are changing. People I care about are leaving, and the workplace doesn’t feel the same. I’m torn between loyalty to the place that once lit me up and this nagging feeling that I no longer belong. How do I figure out whether to stay or go?”

Michelle’s question is something I’ve heard time and again. Where do I belong? And how do I handle it when the place that once felt like home suddenly feels like a stranger’s flat?

Let’s talk about that, and I’ll share a story that might shed some light on this very dilemma.

A Story of Real Belonging

A few years back, I joined Salesforce. In the beginning, it felt like absolute magic. The culture was pure gold, like a neighbourhood where everyone knows your name, shares a laugh, and genuinely cares. I had lots of ideas, was excited to show up every day, glowing from the inside out. Folk would pop by just to say hello, to chat about family or the latest binge-worthy show, and we’d celebrate each other’s wins.

But as time went on, changes rippled through the organisation. Whispers, “restructuring,” people disappearing from desks that used to be full of life. Suddenly, the environment I’d loved felt off-kilter. I couldn’t shake the sense of loss. And yet, there I was, rooted to my seat, glued to that place as though if I left, I’d be uprooting the very essence of who I was.

One particularly rainy Tuesday, my coach asked, “What’s keeping you, Wendy?” I launched into a grand soliloquy about responsibilities, projects, the team, the pay, the recognition. She just looked at me kindly and said, “But that’s not the whole story, is it? This was the first place you truly belonged. It’s natural to want to cling to that.”

Her words cut through me, because they were true. I had confused belonging with becoming part of the furniture. I thought my worth was tied up in those walls. But true belonging isn’t a postcode, love. It’s a feeling you carry within.

With that, it clicked. My sense of belonging didn’t have to hinge on a corporate logo or a desk by the window. It was about being at home in my own skin, wherever I went. The real magic wasn’t in the organisation’s walls, it was in me, in how I let myself be seen and known by others.

How to Find (and Keep) Your Sense of Belonging

1. Remember: Belonging Starts with You

Give yourself permission to accept that belonging is an inside job. Write down three ways you can honour your own voice and values, right where you are today.

2. Check Your Inner Compass

If you feel that something’s off, tune in. Are you staying purely out of habit or fear? Or do you see a genuine path to rekindling that spark? Clarity often comes from honest reflection.

3. Create Micro-Connections

Even if the broader culture is shifting, you can still foster meaningful connections. Start a small group lunch, a virtual coffee chat, or a monthly ‘kindness challenge’ among colleagues. Sometimes, regrowth happens in pockets before it becomes part of the wider culture.

4. Seek Out Multiple Circles

Your sense of belonging needn’t hinge on one place. Look for other groups, friendships, or communities. They can be online and offline. Just make sure you can be your unapologetic self.

5. Have the Tough Conversations

If you decide to stay, speak up about what you value and what you’d like to see changed. Let leaders know how important community and kindness are to you. If they welcome your input, marvellous. If not, you have your answer about whether this place aligns with you.

Closing Thoughts

We all long to be part of something bigger than ourselves. We want to walk into a room and feel, “Yes, these are my people.” But just because a workplace once fulfilled that longing doesn’t mean it always will. Organisations evolve, cultures shift, and we do, too.

What I’ve learned is that genuine belonging is a gift you give yourself first. It’s in how you show up as your authentic self, whether that’s in a corporate boardroom or at your neighbour’s kitchen table. When you nurture that belonging within, no restructuring, no departmental shake-up, no sudden departures can rob you of being at home in your own skin.

Thank you for joining me for another round of Ask Wendy. Keep your questions and stories coming, my lovelies. Together, we’ll keep peeling back the layers until you discover that the real magic is, and always has been, in you.

With love,

Wendy ❤️

Corporate Survivor, On a Mission to Help You Thrive