When Certainty Becomes a Hiding Place

There’s a quiet trap that leaders, teams, and even individuals fall into: the comfort of certainty.

You build a model. A culture. A way of working. A way of being. And it works — until it doesn’t.

Sometimes the signals are subtle: motivation dips, friction increases, fresh thinking dries up. Other times, the external context forces your hand.

We’ve seen this recently with the changing tariff environment, a reminder that even the most robust supply chains, pricing models, and margin assumptions can be undone almost overnight. Not by mistake, but by momentum.

It’s a pattern I’ve seen often, in businesses I’ve advised and in leaders I’ve coached, where the thing that once created strength becomes the very thing holding them back.

It’s a prompt to ask not just “What’s going on out there?” but “What are we holding onto in here — in our business, our team, ourselves — that needs to be questioned?”

What’s still serving you — and what’s simply familiar?

Not a Matter of Bravery — Just Readiness

This isn’t about fear or failure.
It’s not about regret or tearing things down.

As futurist Alvin Toffler once said:

“The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn.”

It’s about being open to the idea that what got you here might not get you there. That what once felt like solid brick might now be a little more like straw, simply because the context has changed.

And it’s about giving yourself permission to look at those parts of your work or your life and ask:

If I weren’t already doing this — would I start now?

That single question doesn’t demand a decision. But it invites awareness. And awareness is where all meaningful change begins.

It takes self-awareness and acceptance to acknowledge what’s shifted and resilience to reshape it without losing your core.

When the Draft Creeps In

Often, you know something needs to shift long before you’re ready to name it. It shows up as friction. As fatigue. As that uncomfortable sense that something is no longer quite right even if no one’s blown the house down just yet.

You don’t have to have all the answers. But ignoring the draft won’t stop the wind from blowing.

Let’s Talk

If this resonates if you’re wondering whether something you’ve built still serves you, your team, or your business  I’d be happy to help you think it through.

I work with leaders and teams who are ready to rethink, reframe, and refocus — especially when what they’ve built no longer feels fully aligned.

Whether you need a sounding board, a strategic lens, or space to reset, let’s start a conversation.

👉 Reach out via Anthony.omara@aramoglobal.com or DM me on LinkedIn https://www.linkedin.com/in/anthonyomara/

Sometimes the best move isn’t holding the house up — it’s stepping outside and asking what’s next.

Anthony O’Mara is an executive coach and advisor, drawing on 30 years of senior leadership experience in global companies. He works with leaders and teams to navigate change, sharpen strategy, and lead with clarity and intent.