The 3 questions I ask before every big career decision

The offer is on the table. But it's not quite what you pictured.

Maybe the salary is lower than you hoped. Maybe it's a contract, not permanent. Maybe it means moving cities, or a title that feels like a sideways step.

And now you're going round in circles.

Why most people struggle to decide

Most people judge a job on two things: salary and title. If either falls short, it feels like settling.

Others get lost in the what-ifs. What if something better comes along next month? What if that other company comes back?

You can spend weeks theorising about things that haven't happened yet. The only decision you need to make is: is this job right for me, right now?

The three questions

I use a simple framework. I heard it years ago (I think on a podcast), and I've used it ever since.

1. Who will I meet?

2. What will I learn?

3. Where will it take me?

Who will I meet is about the people you'll work with and the network you'll build. What will I learn is about the skills and experience you'll add to your resume. Where will it take me is about the direction it points your career.

If two out of three are strong, you can't really lose.

How it played out for me

While I was still at Apple, I had the chance to set up a coaching business in Australia, alongside an experienced business partner, as an offshoot of a bigger US company.

Before I said yes, I ran it through the three questions.

Who would I meet? An experienced business partner I could learn a lot from.

What would I learn? How to set up and run a business from scratch.

Where would it take me? Closer to my goal of running my own business one day.

Three strong answers. So I said yes.

Then, that November, the US company went into receivership and the whole thing fell over. I lost some money. It was stressful.

But I don't regret it. Looking back, the relationship with my business partner didn't turn out the way I'd hoped. But I learnt a huge amount, including that I don't want a business partner. And it took me straight towards the business I now run today.

Two out of three came good, and that experience shaped everything I've built since.

How to use them on your next decision

Write each question at the top of a page and answer honestly.

The lower-paid role that gives you leadership experience for the first time. The contract at a brand you'd love on your CV. The permanent role that looks safe but won't teach you anything new. Run each one through the three questions and see what comes out. If two of the three have strong affirmative answers, you should strongly consider taking it. 

And remember, you don't fully know a role until you've been through the whole process and met the team. Let the process inform your decision.

The takeaway

Salary and title matter. But they're not the whole picture. Ask who you'll meet, what you'll learn and where it'll take you. Get two out of three, and you can't really lose.

If you're weighing up your next career move and want help making the right call, my Creative Career Level Up programme could be the perfect next step.

Check out more details, including testimonials, on our website here