Why You’ll Never Feel 100% Ready
Readtime: 4 minutes
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Now, onto today’s newsletter…
I’ve noticed something about big career decisions: we wait.
We wait for more experience, more confidence, more certainty. We wait to feel ready.
But here’s the truth: you’ll never feel completely ready.
In today’s edition, I’m sharing the story of one of the most pivotal decisions of my career – when I had to admit I was planning to leave KPMG. It wasn’t the “perfect” moment, but it was the right one.
Let’s dive in.
The Conversation That Changed Everything
It was summer 2021, and I was still a partner at KPMG when my boss came to me with an incredible opportunity.
A massive project had landed on our radar – one of the department’s biggest-ever contracts.
✅ The client’s CFO had specifically asked for me to join the team.
✅ It was a once-in-a-career kind of project.
✅ The contract was a five-year commitment for me.
On the surface, it was an obvious yes. But for me, it marked a crossroads.
Because I was already thinking about leaving to start my own business.
Committing to a five-year project felt like golden handcuffs. It wasn’t just about the project, it meant staying where I was, in a role I no longer saw as my future.
I had a choice:
Say yes and bury the ambition to build my own business.
Admit that I wanted to leave.
Was I Ready? Not Even Close
At that point, I didn’t have a detailed plan for my next step.
No clients lined up.
No clear roadmap.
No guarantees.
The only thing I had was a persistent question: What if I could align my passion for developing people with the freedom to work on my own terms?
I wasn’t “ready” to tell my boss I wanted to leave. The timing felt wrong. I worried about disappointing him, about stepping away from security, and about what others would think.
But I knew I couldn’t commit to that project in good faith. So, I told him.
Why We Wait – and Why We Shouldn’t
Looking back, I’ve realised we often wait for readiness because:
We fear judgment. What will people think if I take a risk and fail?
We fear uncertainty. What if this doesn’t work out?
We fear loss. What if I regret leaving what I’ve worked so hard to build?
But readiness is an illusion.
If I had waited until I had everything figured out, I would still be waiting.
The Rewards of Taking the Leap Anyway
Making the leap wasn’t easy, but it was transformational. Here’s what happened next:
I Got Clarity Through Action.
Once I left, I had no choice but to figure out what was next. That urgency helped me define my business model, secure clients, and create the impact I had dreamed of.I Built Confidence by Doing.
Confidence didn’t come first – it came after. Each small win reinforced that I’d made the right choice.I Created a Career That Truly Aligned.
For the first time, I felt fully in control of my time, my values, and my future.
How to Stop Waiting for “Ready”
If you’re facing a big decision, here are some ways to move forward, especially if you don’t feel ready:
1. Ask the Right Question.
Instead of asking, Am I ready? try these questions:
What’s the worst that could happen if I try?
What will I regret if I don’t try?
For me, when I focused on what I would regret not having tried, it made the decision to leave much easier.
2. Take Small Steps.
Small, intentional actions help build momentum and reduce the fear of change. Explore your next step before committing fully – through side projects, conversations, or low-risk experiments.
3. Borrow Someone Else’s Courage.
Find people who’ve taken a similar leap. Their stories will remind you that uncertainty is part of the process, not a reason to stop.
4. Remember: Readiness Comes After.
The act of doing builds the confidence you’re waiting for.
Here’s what I’ve learned: waiting for readiness is just a way to delay action.
It’s tempting to think that more preparation, more information, or more time will make the leap feel easier. But big decisions will always come with some uncertainty, and that’s ok.
You don’t need a perfect plan, all the skills, or complete confidence to start. Clarity and confidence grow through action, not before it.
The only thing you really need is the courage to begin.
In Summary
Congratulations, you now know why waiting for readiness might hold you back and how to move forward anyway:
Recognise that readiness is an illusion.
Take small steps toward clarity.
Use regret, not fear, as your guide.
Lean into action to build confidence.
Your next big leap doesn’t require you to feel 100% ready – just 1% brave.
On a Personal Note
Telling my boss I was leaving wasn’t easy. I doubted myself right up until the moment the words left my mouth. But once I made the decision, I felt much lighter.
Everything started to fall into place. It wasn’t instant, and it wasn’t smooth, but it was progress.
Looking back, the biggest part wasn’t leaving, it was realising that the “perfect moment” I was waiting for didn’t exist. And it hasn’t for the other things I’ve gone on to do since.
If you’re hesitating on a big decision, trust me: the right moment is the one where you take the leap.
One Quote to Get You Going
“You don’t have to be great to start, but you have to start to be great.”
What’s your take? Reply and let me know if you’ve ever taken a leap before you were ready – or if you’re still waiting.
As you’ve made it this far, you should probably take a look at Atomic Ambition here.