Fear doesn’t always stop you from starting. Very often, it shows up after you’ve built the thing, launched it, and made it real.
In this episode, I unpack a pattern I’ve lived with for years: loving an idea, taking action on it, creating something meaningful… and then suddenly doubting it the moment it’s visible and open to judgement.
From my first six-figure launch back in 2011, to our Amazon business, to courses I know are valuable but haven’t fully promoted, right through to launching This Big World travel challenge cards, this episode explores what’s really going on when the urge to pivot or start over appears.
You may think it’s your perfectionism talking, but really it’s about exposure, self-trust, and learning to stay with something long enough to let the market, not fear, give you the answer.
If you’ve ever found yourself wondering whether you picked the wrong idea, this episode will help you pause before you tear everything down and ask a more useful question: do you actually need a new direction, or do you just need to stay put long enough to see what this one becomes?
What You’ll Learn in This Episode
Why constantly starting over quietly erodes self-trust
How “bright shiny object syndrome” is often fear dressed up as strategy
Why doubt tends to show up right at the finish line
The difference between backing potential and backing yourself
When quitting is clarity — and when it’s avoidance
How long you really need to commit before deciding something doesn’t work
Why confidence only comes after evidence, not before
The 5 rules I’m using to stop starting over
Key Takeaway
If you keep starting over, you never collect the evidence you need to trust yourself.
Time-Stamped Guide
00:00 – Why fear often shows up after you start
01:12 – The pattern: creating confidently, then doubting once it’s live
02:07 – The Social Networking Academy launch ($117k in 7 days) and what followed
03:48 – The Amazon business I nearly sabotaged
04:48 – Courses, journals, and the “not quite ready” trap
05:33 – Launching This Big World and the doubts arriving on cue
06:38 – What my GPT coach “Goggins” helped me see about fear and exposure
08:08 – Rule #1: Why doubt at the finish line isn’t feedback
09:19 – Rule #2: Let the world evaluate first
10:34 – Rule #3: Fulfilment vs funding
12:49 – Rule #4: When quitting is avoidance
14:09 – Rule #5: How long to commit before judging results
16:08 – Why bright shiny objects feel safer than backing yourself
17:53 – “Back yourself” — the Sainsbury’s story
19:31 – The uncomfortable middle most people leave
20:43 – Why fear often means you’re closer than you think
21:07 – $5,000 Dream Holiday giveaway + This Big World launch
Resources Mentioned
This Big World — $5,000 Dream Holiday Giveaway - Buy a pack of the travel challenge cards and be in with a chance to win a $5,000 dream holiday — one Willy Wonka–style golden ticket hidden in the first shipment.
The 50+ Nomad on Substack - Weekly reflections, side-hustle ideas, and honest conversations about funding freedom after 50.
Join the Conversation
Have you ever started over because doubt crept in just as something became real?
Are you in that uncomfortable ‘exposed’ place right now?
Share your biggest takeaway from this episode, and what you’re committing to stay with a little longer.
Loved this episode? The biggest compliment you could give me, would be to share it, restack it or send it to someone else who would love it! Thank you so much! 🙏
🎉 Win a $5,000 Dream Holiday as Part of my Brand New Ecom Launch! 🎉
As I said on the podcast, I’m launching a new brand called This Big World, a collection of travel-inspired products designed to add more fun, curiosity, and adventure to life on the road.
The first release is The Travel Challenge Scratch-Off Deck. 50 playful prompts to help you see the world with fresh eyes, meet new people, and say “yes” to more spontaneous moments.
To celebrate the launch, I’m giving away a $5,000 Dream Holiday!
✨ Join the Early-Bird Insiders List ✨
As a member of my Substack community, you’re getting first access, before I open this to the public. Join the Insiders List now to be one of the first to grab your deck and secure your chance to win the $5,000 Dream Holiday.
Because life’s too short to travel small! 🌍
