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KAREN BOSWELLEXECUTIVE LEADER · EXECUTIVE COACH
← Thinking

By Karen Boswell

Success didn't settle it. The bigger goal won't either.

When success stops feeling like enough, the problem isn't ambition or purpose - it's that you asked an outcome to answer a question about yourself.

You got the thing: the role, the exit, the number, the recognition - and within a fortnight it’s got the shine appeal of a pair of old slippers.

This isn’t disappointment exactly, it’s something flatter, familiar almost – a bit like those old slippers. You did what you set out to do, and the part of you that was supposed to be satisfied just never showed up.

People read this disappointment one of three ways.

The first is appetite, ‘I need a bigger challenge’. The second is purpose, ‘the work has lost its meaning to me, I need to find something that matters more’. The third is exhaustion, ‘I'm tired, I'll feel good when I've rested’. None of these are wrong and each comes with a respectable remedy, which is part of why they're such appealing defaults.

I want to offer you the alternative reading: that goal you had was actually attempting to do two jobs. One was the visible one, the outcome of the result you could put in a board pack or stand on a stage and talk about. The other was private, and it was meant to prove something about you, and it was meant to shift something in you permanently.

The disappointment you felt stems from the simple learning that outcomes can't achieve that second job, not because you didn't achieve enough - you probably did - but because of what happens to evidence about yourself in the moment it arrives. Here’s what happens.

Success gets reclassified on contact. Before you achieve it, the ‘thing’ is hard, it’s uncertain and is a genuine test for you. Then the day you reach it, it quickly and quietly becomes the new baseline for all future success. It’s why athletes feel deflated when they finally win that race, get the gold medal and lift it to the crowd. None of those outcomes console the disappointment because ‘of course it happened’; the timing helped, the team was strong, the system moved your way. Anyone in your position would have done the same, you just happened to take pole.

That reclassification is fast, and it is almost invisible from the inside, so it means the evidence never accumulates clearly. You can compile an extraordinary record and still be waiting for the item that finally settles it, because every item gets downgraded to normal as soon as it's yours.

I remember the first time I landed a big chief role, it was a real milestone for me. I was really excited about the press release hitting my industry, I was called in early for a photo shoot, sent the edit for review and everyone on the inside knowledge chain was held to the embargo until the next morning at precisely 8am. I hadn’t been ‘embargoed’ before, it felt tingly. Then the news broke, and there it was… pop. My bubble gone, I got to work and focused on the job to be done. What I learned is this bites hardest at the top for a structural reason. As you’re rising through the ranks somebody else delivers the verdict to you, ‘congratulations you’ve got a promotion’, it comes with a boss's assessment, a top of the class grade and you can borrow - and question - their judgement for a while. When accountability sits at the top of your own structure, nobody hands you a verdict anymore and the judging moves inside whilst being carried out by the least generous assessor you’ll ever have.

So what do you do? You set the next thing that looks like ambition, you set the next goal, and you make it even bigger, because of course the last one clearly wasn't big enough!

Now, here’s why this thing has teeth – reaching for the next ‘thing’ is avoidance, and it is the most socially protected form of avoidance available to a senior leader. Nobody intervenes. Nobody says 'are you sure you want this, or are you just moving before the feeling catches up with you?' Drinking too much gets noticed. Withdrawing from your family gets noticed. Aiming higher gets applauded with a new mandate and a press release.

The chase is addictive, and that’s because briefly the pursuit is genuinely absorbing and the little voice scratching at the back of your head goes quiet while you're chasing your answer. However, the disappointment will follow, and the voice will come back every time, and every time it will get slightly louder.

So, the uncomfortable question is not 'what’s the next thing?' It’s: ‘what was that supposed to prove, and to whom?’

Sometimes the answer is a person. Sometimes it's a room you were in years ago, or a verdict somebody handed you when you were too young to argue with it. Often the person you're still trying to convince isn't available to be convinced, and hasn't thought about it in a decade. And nearly always the answer will hurt.

I'm not going to tell you the answer is to want less, or to find your why. Ambition isn't the problem, and you'd be bored inside a month. But I do want to share is what changes things is separating the two goals that got fused into your ambition. The business goal is real, achievable and worth pursuing, but the personal verdict is also real, and it was never going to be delivered by the business outcome. This part must be settled directly, or it will keep attaching itself to whatever you chase next and then spoiler alert… it won’t work.

Solving for that itch is slower work, and it's the work most senior people never get to, because the next goal is always available and always looks like the responsible choice.

So, before you set your next goal, ask yourself honestly; what will you finally believe about yourself that you don't believe today? And if the honest answer is 'nothing', why is it the next thing on your list?