What if it works out?
Our complicated relationship with success
December is arguably the most wonderful time of the year.
Maybe it’s because we finally slow down and take stock.
Maybe it’s because we reconnect with family and friends.
Maybe it’s the Christmas lights - or something softer in the air.
Whatever it is, I love it.
But for some people, December feels different.
It’s a reminder that the things you planned didn’t work out.
A reminder that you didn’t hit every goal you set.
Personally, I didn’t achieve some goals this year. But I’ve learned far more lessons than I thought I needed - and sometimes, that’s enough for certain seasons.
So as you reflect, review, and begin sketching out 2026, here’s one question I want to leave you with:
What if it works out?
It’s a question most of us don’t ask nearly enough.
We rehearse failure like a script we’ve memorized. We set subpar goals.
We run through every possible disaster - every way things could fall apart, every door that could slam in our faces.
We call it “being realistic.”
We call it “preparation.”
But really, many of us have a complicated relationship with success.
Because success isn’t always about smashing goals.
Sometimes it’s about building foundations that will hold the weight of what you’re dreaming of.
The Fear We’ve Normalized
There’s a reason you default to thinking more about failure than success:
your brain is wired to brace for impact.
According to research, our brains love predictability. So much that anything new - even good news - can make us anxious. Growth, success, recognition… they all stretch us, and our brain sometimes confuses “new” with “unsafe.”
So sometimes, you accept the worst-case scenario before it even happens because somewhere deep down, you believe that if you see it coming, it won’t hurt as much.
You stop short of your full potential because of three questions that haunt you in the quiet moments:
What if I fail?
What if it hurts when I fail?
What if I lose everything?
You worry about what people will say.
You wonder if you’ll recover.
You calculate every risk and convince yourself the math doesn’t favor you.
The worst-case scenario gets so loud that you forget to ask the most important question:
What if it works out?
Here’s my challenge to you:
Stop rehearsing your failure.
Act like it’s already done. The universe responds to confidence.
Start asking the question that changes everything: What if it works out?
What if you launch that business and it thrives?
What if you write that book and it touches lives?
What if you step into that leadership role and excel?
What if you bet on yourself - and win?
You deserve to find out.
And just in case no one has told you lately:
It will work out.
I’ll be slowing things down for the rest of the year. Throughout December and January, you’ll get these newsletters every other week.
But before we get into that flow, I’d love your feedback on one thing:
Thank you for your input!
See you in 2 weeks.
Keep growing 💜



You wrote this specifically for me, Wamide. Thank you so much.
Gosh, I've been doing this without even realising it (a friend noticed the same thing and told me yesterday as well), so thank you for yet another reminder. I'm going to be optimistic and move in that optimism because EVERYTHING WILL WORK OUT FOR GOOD FOR ME!