I started reading Money Master The Game by Tony Robbins a few days ago. The intro is written by Marc Benioff, CEO of Salesforce, and in it he shares four questions Tony asked him early in his career.

1. What do I really want? (vision)
2. What is important about it? (values)
3. How will I get it? (methods)
4. What is preventing me from having it? (obstacles)
5. How will I know I’m successful? (measurements)

I sat with those questions for a while, and one of them stood out more than the others. Not the vision one, not the values one, but the one the obstacles.

For a long time I would look capable from the outside while quietly not fully believing in myself on the inside. It took me years to address what was holding me back, because it felt easier to focus on doing the work and staying busy than to admit something deeper was holding me back.

That’s the question most of us skip.

In this week’s blog, I want to look at why Assistants, myself included at times, avoid naming the real obstacle. Why it remains elusive and what happens when you finally ask yourself what’s actually in the way.

Ready to dive in?

Why we skip it

It’s easier to focus on the parts that feel good. The organising, the strategy, the delivering. Looking honestly at what’s holding us back can feel like admitting we’re failing, so most of us quietly avoid it.

I see this a lot when I ask Assistants what their biggest challenge is. Some will tell me straight away, no hesitation. Others will say something like “I don’t really have self-doubt” or “I’m pretty solid in what I do,” but when I read across all the responses, a pattern shows up again and again. 

• Waiting for the organisation to catch up with what they already know about themselves
• Hesitating to speak up even when they know the answer
• That tiny voice saying you should already know this

This isn’t a lack of confidence in the work Assistants do. Instead, it’s an obstacle that stays hidden precisely because we’re so capable.

What the obstacle actually looks like

For Assistants, the obstacle is rarely a skills gap. Most of us are already excellent at what we do. We anticipate needs, we connect dots across the business, we keep things moving long before anyone asks us to.

The obstacle is usually smaller and quieter than that. It’s the pause before we offer an idea. It’s running something past someone else before we trust ourselves enough to act on it. It’s tying our confidence to whether someone else notices or approves, instead of trusting what we already know.

A lot of this work happens behind the scenes, which makes it worse. When our impact isn’t always visible, it’s tempting to wait for recognition to catch up with it. But recognition was never the thing that was meant to build our confidence. Our own judgement was.

Looking at it without judging yourself for it

This is where CANI comes in, Tony Robbins’ idea of constant and never ending improvement. It’s not about fixing what’s broken in us. It’s about noticing where we keep hesitating and choosing to look at it anyway, even when that feels uncomfortable.

One Assistant described it to me as a “tiny gremlin voice” that says “you should already know this”, even when checking in is the smartest move available to us. Another described it as looking for a pattern to justify a decision before trusting it. That’s what the obstacle actually sounds like day to day. Small, familiar, easy to miss.

Growth comes from doing what most people aren’t willing to do, which is to pause long enough to ask, what am I actually waiting for right now. That single question starts to separate the real obstacle from the noise around it. Not so we can criticise ourselves for having it, but so we can finally see it clearly enough to work with it.

Your next step

Tony Robbins says change is never a matter of ability, but always a matter of motivation. I’d add one thing to that. Change also depends on whether you’re willing to name the obstacle instead of stepping around it.

You already have the vision, the values and the skill. The piece most Assistants leave unanswered is the one about what’s actually in the way. Not because it’s hard to find, but because it’s uncomfortable to look at.

Next time you catch yourself hesitating before speaking up, or waiting on someone else to confirm what you already sense is true, pause and ask yourself the question. What’s actually preventing me right now.

What’s the obstacle you’ve been quietly stepping around? I’d love to hear it in the comments.

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