Today, a wise man asked me, “is it better to have tried and failed, or never to have tried at all?”
Immediately, I said, “never have tried!” – only somewhat joking.
Because let’s be honest… failing is a horrid thing to tackle.
When we have a dream or an idea, it’s so safe and comforting to keep it tucked away in that dream/idea zone. In that space, nothing can go wrong. Nothing can judge us. Nothing can fall apart. It stays perfect, untouched, full of possibility.
But is that really the right answer?
The original quote, of course, is “is it better to have loved and lost…” and we all know love is a mad, wild, irrational thing. We all have to be a little unhinged to step into it. There are no guarantees, no control, and yet… we do it anyway.
Why?
Because the payoff is worth the risk.
And that’s the moment we move from dream to potential. Not when something feels safe, but when something feels worth it.
The Horsey Version of This Question
In the horse world, this shows up everywhere.
- Entering the competition you don’t feel ready for
- Cantering when your confidence says “not today”
- Changing yards, trainers, or direction
- Saying “yes” to a bigger version of yourself as a rider
All of these moments come with the same quiet question:
“What if I fail?”and underneath that “Can I handle it if I do?”
A Real-Life Example
I worked with a rider who had a very clear dream: she wanted to confidently jump a course at a show.
Simple, on paper.
Except she’d had a fall months before, and ever since, her world had shrunk. What used to feel normal now felt enormous. Even small fences came with hesitation, tension, and that familiar spiral of the what ifs gremlins.
So she did what many riders do and she stayed in the “almost” zone.
- Almost entering competitions
- Almost pushing on
- Almost believing she could do it
Because in “almost,” she couldn’t fail. But she also couldn’t win.
Eventually, we flipped the question. Not “what if it goes wrong?” but:
“What if it goes right?”
What if she rode into that ring, heart pounding, and did it anyway?
What if her horse rose to the occasion with her?
What if the version of her she kept imagining… actually existed?
That became the focus – the payoff.
Not the rosette or the result. But the identity shift!
And when she finally did it (not perfectly!) the outcome wasn’t just a clear round but it was proof.
Proof that she could feel fear and ride anyway.
Proof that she was no longer the rider defined by her fall.
That payoff was worth everything.
So… What About You?
What are your current equine dreams or ideas?
The ones you keep circling.
The ones you talk about “one day.”
The ones that feel exciting… and slightly terrifying.
Now ask yourself:
- What is the payoff if it goes right?
(Not just the outcome but who do you become?) - What would trying give you that staying safe won’t?
- Are you protecting yourself from failure… or preventing yourself from growth?
- If you knew you couldn’t fail — what would you do next?
Practical Ways to Step Out of “Dream Mode”
You don’t need a giant leap. You need movement.
- Shrink the risk
Make the goal smaller, safer, more achievable but still forward. - Redefine failure
Failure isn’t the fall, the refusal, or the wrong stride.
Failure is only the deciding you’re not capable and stopping there. - Focus on evidence, not emotion
Your feelings will tell you you’re not ready.
Your actions will prove that you are. - Borrow belief
If you don’t believe in yourself yet, borrow it from your trainer, your horse, or someone who can see what you’re capable of. Totally legit to outsource some self belief on occasions.
Final Thought
Maybe it’s not about choosing between trying and failing or never trying at all.
Maybe it’s about deciding that some things are simply too important to stay in the dream zone. Because failing is uncomfortable but staying stuck is far worse.
So… what’s worth the risk for you?
And more importantly: are you ready to find out what happens if it goes right?
P.s. anyone else going to badminton to walk the grassroots course? Totally unrelated obvs. 😜
