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When Success Stops Feeling Like Success

Michelle Sales/10 August 2026
1 minute read time

Last week, I wrote about something I've seen time and time again in my coaching. Intelligent, capable and successful people reach a point in their careers where something no longer feels right. From the responses I received, it was clear just how many people recognised themselves in that experience.

Many people shared that they had been feeling exactly the same way but had struggled to put it into words. Others admitted they had convinced themselves they simply needed a holiday, a new challenge or another promotion. Some had already started searching for new jobs, hoping that a change of scenery might be the answer.

That response didn't surprise me because it's exactly what most of us do.

When we're dissatisfied at work, our instinct is to look outward. We update our cv, browse job advertisements, message recruiters or imagine ourselves in a completely different organisation. We assume the problem must be the role, the manager or the workplace.

Sometimes it is. However, after many years of coaching people through career transitions, I've learnt that changing jobs doesn't automatically change the way we experience work. If we haven't taken the time to understand what's really driving our dissatisfaction, there's every chance we'll recreate the same experience somewhere else.

I've seen people leave organisations full of optimism, only to find themselves asking the same questions six or twelve months later. They haven't necessarily made the wrong decision; they've simply solved the wrong problem.

When we feel stuck, it's natural to want to take action. Staying where we are feels uncomfortable, so we convince ourselves that movement must be progress. Yet I've learnt that movement and progress aren't always the same thing. Sometimes the most valuable thing we can do is resist the urge to rush into a decision and instead become curious about what is really happening beneath the surface.

The people I've worked with who have built careers they genuinely love haven't necessarily made bolder decisions than everyone else. What sets them apart is that they've made more informed ones. Before deciding where they want to go next, they've taken the time to understand themselves and the life they want their career to support.

That changes the questions they ask.

Instead of asking, Where should I work next?, they begin with questions like: What has changed about me? What am I craving more of in my work? What am I no longer willing to compromise? What kind of life do I want my career to support?

Those questions don't always produce immediate answers, but they almost always lead to better decisions.

This isn't about overthinking every career move or waiting until everything feels perfectly clear. It's about recognising that the quality of our decisions is shaped by the quality of the questions we ask ourselves first. When we ask better questions, we give ourselves a much better chance of creating a career that genuinely fits who we are today, rather than continuing the one we've simply grown into over time.

Over the coming weeks, I'll share more about the approach I've developed through years of coaching leaders and professionals who wanted more than another promotion or another job title. They wanted work that was aligned with who they were and the life they wanted to create. It all begins in the same place - not with searching for the next opportunity, but with understanding yourself well enough to know what you're really searching for.

Reflect:

Before you think about what your next career move might be, pause and ask yourself this:

Am I trying to change my career, or am I trying to change the way my career feels?

There is an important difference between those two questions. Taking the time to answer the second one may completely change how you approach the first.

Michelle Sales/10 August 2026