“I don’t think this is my dream company. Should I stay?”

Today I’m analysing the situation of Sienna. Sienna recently reached out to me on LinkedIn, curious about my Creative Career Level Up programme.

What’s the challenge?

Sienna had just had her freelance contract extended until the end of the year. On paper, it was a fantastic role — in FinTech, with exciting growth, and working alongside a supportive head of marketing who clearly valued her input.

But she was wrestling with doubts. In her words: “I don’t think this is my dream company. What if they can’t offer me the right compensation or role title?”

She admitted she was falling into the trap of wondering if she should hold out for something more “perfect,” instead of recognising the opportunity right in front of her.

How can she move forward?

The real question Sienna had to answer wasn’t whether she was at a ‘dream’ company. It was whether her current role gave her what she truly wanted: meaningful work, recognition, growth, and alignment with her values.

Her challenge was reframing her perspective. Instead of questioning whether this role ticked some idealised “dream job” box, she needed to start asking: does this role actually give me the career and life I want?

My advice

1. Redefine “dream job”

A dream job isn’t about the name of the company. It’s about how the role fits into your life and career.

I told Sienna: “It’s not about a specific company. It’s about an environment that shares your values. It’s about a boss you enjoy working with. It’s about being challenged, fairly compensated, and recognised for your contribution.”

Lots of people land jobs at companies they once thought were “dreams” and end up unhappy. Because prestige doesn’t equal happiness. What matters is the day-to-day reality.

2. Pay attention to the signs of fit

In Sienna’s case, the signs were already there. The head of marketing was asking for her strategic input, not just her execution. Her work was recognised at a quarterly business review. She felt her perspective was valued.

I reminded her: “These are exactly the things you said you wanted — a role where your voice is heard, your skills are recognised, and you can grow as a senior marketer.”

3. Don’t let old narratives hold you back

Sienna admitted some of her doubts were a “trauma response” from past experiences where roles didn’t turn out how she hoped.

That’s normal — but it’s important not to let old disappointments block new opportunities.

Instead of saying, “It’s not my dream company,” she needed to start asking, “Does this role give me the growth, challenge, and recognition I want?”

4. Focus your energy where it counts

I encouraged Siena to put her energy into making the most of this contract.

“Think of this as a long interview,” I said. “If you act like the senior marketer you want to be, bring insights, and show the value of your role to the wider business, you’ll make yourself indispensable. And from there, the permanent opportunities will follow.”

The truth is, a dream job is rarely about a logo. It’s about building a career that excites you every day. Siena already has the foundations — now it’s about leaning in and recognising them.

💡 If you’re in a similar situation to Siena, I’d love to help you get clarity and momentum. Apply to work with me on my Creative Career Level Up programme, and let’s build a career you’re excited to wake up to every day.