If Not Now, When
Will I make it? Did I choose the right path? These fears can shape our entire lives until we name them and begin again.
Will I ever make it? Will I get the job? Will this new venture work out? Am I making the right choice moving to this city?
These are the questions I go over and over in my head.
And I know I’m not alone in this.
Why is that?
Because deep down, even if we don’t say it out loud we’re afraid we might fail.
Failure.
It’s a word many of us know intimately. If you’re a creative, a writer, or someone who lives life a little differently, you’ve likely felt it more times than you can count.
When failure becomes a theme in your life, you begin to question your choices.
There are days you regret the paths you took, even if they once made perfect sense.
You apologise too often.
You shrink back into rooms that no longer fit.
You stay in relationships that aren't right
What is fear of failure, really?
Woke up this Sunday and something felt off. I couldn’t quite explain it, but it was there — lingering. So I did the usual: made a coffee, opened my journal, and started asking questions. I wanted to get underneath the discomfort.
What I found was this: fear of failure.
I’ve been questioning my path lately. Leaving corporate. Pausing my consultancy.
Choosing a slower, more undefined way of living.
So I looked up the definition: At its core, fear of failure is the fear of trying and not measuring up.
It keeps you in comfort zones. It holds you back from growth, from risk, from realising your full potential.
And I realised, this fear has been keeping me small.
I don’t want it to lead me anymore.
Where does fear of failure come from?
Let’s name a few root causes:
Perfectionism
You try to perfect every detail. You over-edit, overthink, over-deliver. I know this one well. I’ve spent hours reworking posts most people won’t even notice.
Past experiences
You’ve tried before and it didn’t work. So now you ask, “Why try again?” If you haven’t processed that disappointment, it can become a silent belief that you’re not capable.
Low self-worth
When you don’t feel secure in your value, you try to prove it. You chase goals that aren’t aligned. You stay quiet when your voice matters. You play small.
External pressures
Culture, family, society, they shape us more than we realise. If we’re not rooted in our own truth, we can end up chasing someone else’s version of success… afraid to fail on our own terms.
What can you do?
Start by acknowledging it. Get honest about the fears shaping your choices.
Write them down.
Name them.
And then begin to rewrite the story.
My personal list of “failures” (as I once saw them)
I have one close friend in London. Just one. In a world that celebrates community and connection, that used to feel like I was lacking something.
I’m single at 38. Many of my peers are married or raising kids. I don’t even know if marriage is for me and for a long time, that uncertainty felt like failure.
I paused my consulting business to explore a slower path. I built systems, a website, a YouTube channel and yet I stepped away.
I write on Substack, while others work stable 9–5s. Sometimes I feel like I’m floating in an undefined space, with nothing to “show” for it.
If you carry similar guilt or shame, I want you to know this:
This fear, if left unchecked - will lead you to hustle for things that no longer serve you.
It’ll keep you in places you’ve already outgrown.
It’ll convince you that slowness is weakness, that rest is failure.
But maybe… failure isn’t the enemy.
Here’s how I’m rewriting my story:
I have one friend who makes me feel safe, seen, and supported. That’s not lack, that’s intimacy.
The relationship meant for me won’t miss me. It’s coming, in perfect timing.
This season isn’t punishment. It’s preparation. I’m being equipped, deepened, strengthened.
I am not behind. I am exactly where I’m meant to be.
If Not Now, When?
That’s the question I’ve been asking myself. If not now, when will I say yes to the new path? When will I book the ticket? Open to new possibilities? Stop waiting for the perfect moment?
Fear of failure might still be there and in some ways, it’s valid. It’s trying to protect you. But it doesn’t need to decide for you. You can choose differently this time.
Because even if you “fail,” that experience might hold the exact lesson you need.
Everything you’re walking through is preparing you for what’s coming next.
“If not now” is a question that moves fear aside.
Ask it next time that fear knocks on your door:
If not now, when?
What about you?
What story are you ready to rewrite?
What would it look like to name the fear and then move anyway?
You can reply here, or write it in your own notebook. I’m with you.
These are some hard, but necessary questions we need to ask ourselves in order to grow. Thank you for writing this, I appreciate it! 💜
embrace failure!! its the best way to learn and grow in life