I heard this from a client recently, and it captured something I remember feeling myself at a certain point in my career:
“I thought once I got to this level, I’d feel more secure.”
We follow this invisible blueprint: work hard, prove yourself, earn the promotion, earn the bigger title, earn the bigger pay cheque, the bigger office …because we believe each step will come with a little more certainty.
The part we often don’t consider, is that the higher you climb, the farther you have to fall.
No Safe Path
I recently read Bob Anderson’s Leadership Circle white paper No Safe Path to Leadership and knew I had to share it with The Whipp community. In it, he describes the tension between purpose and safety.
As professionals, and especially as leaders, we are constantly managing the pull between purpose and safety.
Purpose asks us to stand for something. Safety asks us to make sure we don’t lose too much while we do it.
But here’s the part I think we don’t talk about enough → both come with risk.
Purpose is risky because the moment you actually organize your life and leadership around something that matters, you step out of neutral territory and into consequence.
You’re no longer optimizing for comfort or predictability. Now you’re making decisions that can impact your security, your reputation, and the people depending on you.
As Anderson puts it, there isn’t a safe way to pursue purpose, because committing to it immediately raises the possibility of loss right alongside it.
But safety has risks too.
Safety is risky because the higher you climb in an organization (what most of us think of as the “safe” approach), the more you have to lose, not less. What looks like security on the way up (more influence, more visibility, more compensation) comes with bigger stakes, more scrutiny, and a much longer fall if things change.
As Anderson describes, the pressure to maintain approval and hold your position increases with each step upward, which means the very thing that feels like safety is often where the risk compounds.
So if choosing purpose carries risk, and choosing safety carries risk, where does that leave you?!
I see a lot of leaders try to think their way out of this ongoing tension.
“If I just prepare a bit more, build a bit more credibility, get one more win… then I’ll be able to lead in a way that feels both meaningful and secure.”
Being prepared, building credibility, and having wins are not inherently bad things to do or aim for – but only if we understand they will not solve this problem.
What Anderson names, and what I’ve come to recognize in my own experience, is that this tension doesn’t go away.
It’s here to stay.
And so over time, the work becomes less about solving it and more about noticing what is driving your decisions and deciding what risks are you comfortable with… knowing full well that leadership doesn’t offer you a risk-free lane.
And that puts the question back in your hands:
When it counts, what are you organizing your leadership around?