What’s the Worst That Can Happen? Really.
We all have one thought we return to. A thought that holds us steady, that we whisper to ourselves at crossroads or in quiet moments of doubt. For Emma Simpson — wild swimmer, author, mother, and my guest on this week’s episode of A Thought I Kept — that thought is:
“What’s the worst that can happen?”
It sounds simple. Even flippant. But for Emma, this thought has been a guide — first through trauma and grief, then through healing, change, and courage.
What began as a phrase loaded with anxiety slowly became something else: a spark of freedom, a tiny rebellion, a way to say yes to the wild, unpredictable mess of life.
In our conversation, we talk about the fear that underpins so many of our decisions. The kind of fear that keeps us small, silent, stuck. We explore what it means to let fear sit beside you instead of driving the car. We talk about grief, bravery, the emotional labour of friendship, and the quiet, daily choices that shape a life.
If you’re feeling overwhelmed, unsure, anxious or flat, this podcast episode might just be the first small step (or a shift in direction or a sentence to hold onto) that you need.
From Fear to Freedom — What Shifts?
When we’re anxious or lost, our inner voice often says things like:
What if I get it wrong?
What if I fail?
What if people judge me?
What if I can’t cope?
That fear can feel so familiar it almost becomes comforting — a twisted safety net of at least I’m not risking anything. But, as Emma shares, fear doesn’t always need to be a stop sign. It can also be a jumping off point.
Because what if you changed the tone of the question?
Instead of fear, what if “what’s the worst that can happen?” came with a shoulder shrug, a grin, a let’s see energy?
So that it becomes not about recklessness, but more recognising that:
Fear doesn’t always mean danger.
You can survive discomfort.
You might even discover something better.
The Trial-and-Error Practice of Facing Fear
One of the most powerful parts of Emma’s story is how she’s come to face fear curiously — not through huge declarations or dramatic overhauls, but through presence and practice.
When she quit her job in aviation after 20 years, trained as a coach, and became a full-time writer, she didn’t do it all at once. It happened over time. Through grief. Through healing. Through honest questions like:
What am I afraid of, really?
What am I protecting myself from?
What’s on the other side of this fear?
If you’re feeling overwhelmed or anxious right now, you don’t need to do anything drastic. But you might try asking yourself:
What’s one small thing I could try today… even if I’m scared?
That one thing might be sending a message, signing up for something, going for a swim, or starting a conversation. You don’t need to feel ready. You just need to feel curious.
Emotional Energy is a Real Thing
We often talk about time and energy like they’re the same thing. But they’re not. Emotional energy is its own resource — and it can be quietly, completely draining when we’re holding too much.
Emma shared how she made the difficult decision to stop coaching — not because she didn’t love it, but because it took up emotional energy she needed to keep for herself, her daughters, and her writing.
If you’ve been feeling unusually tired, flat, or irritable — ask yourself:
Where is my emotional energy going right now?
What replenishes me?
What depletes me?
You Might Just Make a Friend
Loneliness is one of the most common themes I hear in my work — and one of the most painful to talk about. We tell ourselves we should be fine. We should have more friends by now. We shouldn’t need connection this much.
But we do. We all do.
In the episode, Emma and I talk about the challenge of making friends as adults. The awkwardness. The vulnerability. The real fear of rejection.
And yet — one of the simplest, most powerful reframes she offers is this:
“What’s the worst that can happen? You might just make a friend.”
Listen to the Full Episode:
Transforming Fear into Adventure: A Conversation with Emma Simpson
Or search for A Thought I Kept wherever you get your podcasts.
A Thought I Kept is a wellbeing podcast for anyone feeling lost, anxious or stuck and who is searching for ideas to better navigate everyday life.
Self-Reflection Prompts to Take This Further:
If you're feeling disconnected or unsure, here are three journal prompts to gently explore:
1. Where does fear show up most in my life right now?
2. What have I survived that once felt unsurvivable?
3. What might be waiting on the other side of “what’s the worst that can happen?
If You’re in a Wobbly Place Right Now...
Just know that…
You are resilient, even when you don’t feel it.
You don’t need to fix everything. Just stay in motion.
One small, brave thought can change everything.
You don’t have to leap. You just have to look up and say, “Maybe…”
