When did you last update your definition of success?
Years ago, when I’d been promoted and was telling one of my sons about it, he listened and then asked me a question I wasn’t expecting: “But will you be happier, Mum?”
I gave him some version of a standard answer – more interesting work, more responsibility, better pay. He moved on to something else, apparently satisfied, but his original question stuck with me for a long time, and in fact it’s something I still come back to now.
The honest answer, if I’d sat with it properly at the time, was that I didn’t really know. I’d spent years working towards the next level and the level after that, and somewhere along the way I’d stopped asking whether where I was heading was actually where I wanted to go. The destination had become self-evident, the kind of thing you didn’t question – of course you aimed for the next promotion, of course success meant advancement, and of course the organisation’s framework for measuring progress was a reasonable proxy for your own.
It took me longer than I’d like to admit to recognise that I’d inherited that definition rather than chosen it. That distinction between the definition of success we absorb from the systems and views around us, and the one we actually arrive at ourselves is really what this edition is about.
The presenting problem
Most people don’t arrive at a career reflection point thinking “I need to revisit what success means to me.” That framing rarely occurs to anyone, because it isn’t how the problem actually shows up. What tends to surface instead is something more like:
- I’ve been looking at roles and nothing quite feels right
- I’ve been approached about something and I can’t work out if it’s the right move
- I feel as though I should want the next level but something is making me hesitate and I can’t name what it is.
These are all real and legitimate things to be wrestling with, but they can be very hard to resolve if you’re working without a robust sense of what you’re really trying to achieve. You can compare options against each other indefinitely without making progress, because what’s missing isn’t more information about the options themselves, it’s a clear enough picture of what you’re actually looking for in the first place.
Why the framework does the thinking for you
In corporate environments there’s often a very efficient system for telling you what success looks like – a grade ladder with criteria, an annual performance cycle, a promotion process and expected timelines. These structures can be genuinely useful in many ways, but they can also do something subtle over time, which is to become a proxy for your own thinking about where you’re going. You don’t have to decide what you’re aiming for because the organisation has already decided, and you trust that the destination it points towards is the right one.
The difficulty comes when the framework quietly stops fitting – when you reach a milestone you worked hard for and feel oddly flat, when you find yourself looking at the next level and feeling something closer to dread than ambition, or when something in your life has shifted and the map you’ve been using no longer matches the territory. What I often see at that point is people trying to solve it by thinking harder about the options in front of them, when what would actually help is stepping back first and asking whether their criteria need updating before they can make any real headway.
When the starting point isn’t the obvious one
I worked with a client a couple of years ago who’d arrived at exactly this juncture – senior, capable, and by most measures doing well. Her role had evolved significantly and she’d become a mother during that time, and when she sat down to think seriously about what she wanted next, she kept going round in circles. The roles she was considering didn’t feel quite right but she couldn’t say why, and nothing was obviously wrong in a way she could point to and address.
What helped wasn’t spending more time on the roles themselves. We started with different questions:
- What did she want her working life to look like at this stage, given everything that had changed?
- What mattered to her now that hadn’t before
- What was she genuinely prepared to trade off?
Once that picture was clearer, evaluating options became considerably more straightforward. Some things she’d been ready to give up she didn’t have to, while others genuinely needed to change.
She told me afterwards that the most useful thing had been simply being asked to think about her career in the context of her whole life, rather than as a separate problem to solve on its own.
One thing worth saying
Revisiting your definition of success is not the same as lowering your ambitions, and I think it’s worth saying that directly because the fear is live for a lot of the women I work with. The worry that if you examine what you’re aiming at too carefully, you might find you don’t want it enough, or that others will draw that conclusion.
In practice, it tends to go the other way. The work usually surfaces something more specific, more genuinely yours and often more interesting than the inherited framework you’ve been operating within, and the ambition doesn’t shrink so much as it gets a shape that actually belongs to you.
If you’re at a decision point at the moment and finding it hard to get traction, it might be worth asking whether the question you’re trying to answer is the right starting point, or whether there’s a layer underneath it worth looking at first. Sometimes the most useful move is stepping back to ask when you last properly updated your own answer to what success actually looks like – not the inherited version, but yours. If that resonates, I’d be happy to talk it through and share some helpful ways to start structuring your thinking.