2023 was my first full year running the chilled investor and, while some of the lessons were new, some of them were really re-learnings of old lessons from 2022. Proving that you have to stub your toe on the exact same wonky slab until you learn to hop over or fix it.
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New lessons for 2023
It’s as hard to sell a cheap thing as it is to sell a higher-priced thing.
I don’t understand this at all but it repeats itself every single time. In fact, though selling is never easy, I’ve sold my highest-priced thing (The No-Stress Money Plan) more times than any other offer, even the 9€ ones, and more easily.
Now, maybe this is because the number and ratio of mentions and promotions of the beginner course are greater and more consistent, plus have been going on over a longer period of time (since May 2022) so people have had time to make the decision. I suppose I must also be being more consistent and clear about the value proposition i.e. what you get out of buying (all the skills and knowledge to grow money through investing).
B-u-u-u-t to confuse things is that, this year, I’ve also sold that higher-priced thing to “colder” people i.e. people who weren’t even on my mailing list or direct connections on LinkedIn and haven’t, therefore, spent as long gaining “like, know and trust”. It should, in theory, be harder to sell things to “cold leads”. I don’t know quite what to make of this. You’d think cold leads would buy smaller, cheaper things first. But maybe it is just that the consistency and duration affect both warm and cold leads. I admit I don’t really understand!
If this is the case, then I need to:
- make sure all my lower-ticket offers have equally clear value, equally clearly spelled out.
- be much more consistent about promoting them instead of letting them fade away and focusing more on what’s working. These newer offers all came into being in 2023, from February onwards, so have had between 2 and 8 months’ less airtime.
- set the price that feels like a true reflection of the value the course or resource provides and not set it based on feeling I need a pricing ladder or cheap entry points. After all, if not many people buy a lower-priced thing, it’s not an entry point.
Competitors are just collaborators you haven’t worked with yet
At first, when Ben Shearon of RetireJapan got in touch in autumn 2022 I was a bit … intrigued but perplexed. He teaches courses very similar in topic and scope to mine but specific to the context of retiring in Japan. He wanted to chat, so we did a couple of times but I admit my initial reaction was “Oh no! I’m not first/the only, surely this is going to compete.”
But, not only did I properly understand the potential of collaboration in 2023, I’ve learned and created concrete things because of him (the upcoming Smart Money course, for example), and been inspired to learn new things as a byproduct of working together.
We’ve established a really nice working relationship that benefits both of us and THEREFORE the people we’re trying to help. First, in spring, Ben and I did a LinkedIn live about National Insurance because we both bang on about it and have the same belief that making up overseas contributions if you’ve lived in the UK for 3 years during your lifetime is a no-brainer.
Then, in winter, I helped him build his Basics in Personal Finance course (which I recommend if you’re living and retiring in Japan). A lot of the content from that he’s very generously let me adapt for my course, Smart Money, which is great because I could see how brilliant and solid the material was and had meant to put together some sort of something about budget. This is much better than that vague idea.

But on top of that, and this is why I love, love, love collabs, in writing the workbook for his course I remembered that I’d seen something about making Google workbooks beautiful and fillable. So I learned how to do that and tested it out on the workbook I had created for his course. The result is so beautiful it wowed Ben and even I kept the tab open on my computer for a couple of days because I enjoyed looking at it so much.
That’s a whole new skillset I’ve added to my toolbox, and I’ve already implemented it on one of my own courses (Make friends with your money monsters), and adapted the Smart Money workbook, and the existing worksheets and homeworks on the No-Stress Money Plan so it has a one-stop workbook that is both gorgeous and practical.

Participating in bundles is better than summits and conferences for growing a mailing list
I’ve been in 2 summits this year, one last minute and one with plenty of warning to prepare and promote, and 2 bundles, one of which was Lizzy Goddard’s mammoth Christmas Party and doubled my list. And I’ve done some webinars for people in their group/forum/conference.
If you’re not sure what the difference is, a summit is basically an online conference where the talks are often, but not always, pre-recorded. A bundle, on the other hand, is where customers sign up to a main package in order to access free or cheap offers and they then sign up individually for the ones they want. As a summit participant, you submit a recorded talk to the host who puts in in their event or you do a live talk during an event, in which case it’s the same as a conference or giving a webinar and only the host gets the email address of people who sign up. As a bundle participant, you give free, limited-time access to a product you’d usually sell but, crucially, both the host and you get the email addresses of people who sign up for your thing.
While I need to get MUCH better at tracking where new email subscribers and buyers come from originally and I have had people say to me that they heard me talk at a thing, the bundles were a hundred times better at getting people actually subscribing to my email list even compared with when I had an optional freebie people could sign up for if they listened to my summit talk. The bundles might have had bigger audiences too as I think summits and webinars demand a lot of the audience’s time and commitment at a specified and concentrated time period, whereas a bundle only requires signing up within a window but the products are then yours to use forever. So, not only do I plan to be in more bundles next year but I want to run something myself. I intend to have elements of both summits and bundles and it will involve collaboration as I’ve seen how great that works out.
The temptation to call it a Bummit is so fierce you can’t imagine.
Old lessons, learned again in 2023
The power of upskilling
In 2022, I took courses to learn the foundations of a business, how to build a website in WordPress, start a mailing list, use LinkedIn properly, and deliver a course online (not teaching any more means I missed out on learning how to use Zoom etc when everyone else did), and how to make and edit video. I figured there would be things to learn in more depth on all of that – and there were e.g. creating email automations, streamlining course delivery, using a platform to sell and deliver courses (I now use and love Thrivecart) and a load of other things I’ve forgotten – I kind of thought I was done on the new skills I’d need to do this business thing.
I was wrong and I’m so glad.
In 2023, I’ve learned about Everything Pages (2025 this is no longer an everything page!); what is and how to set up a Trip Wire and pop up offers (not implemented the latter yet as I need to buy Convertbox first); how to create gorgeous, fillable workbooks in Google docs and better spreadsheets; learned-by-doing to build courses and sales carts in both Thrivecart and Teachable; how to market according to someone’s money archetype/personality; a load of other things I’ve not implemented yet like Instagram 9-grids and how to run course credit programs. I also taught myself to write Press Releases for a client and while I scored him a press placement, I’ve not attempted to do this for myself yet. I do this instead of watching Netflix at bedtime which is probably just as bad sleep-hygiene-wise but I lack the concentration to watch TV shows all the way through these days and courses fill the gap.
Listen to other people less
It’s not that I don’t take on board what other people say or teach – because I learn a ton of things that way – but people teach you the way they run their business and it might not necessarily be exactly what suits you. Or they later change things up for themselves as their ideas and businesses evolve and the viewpoint they gave you reflects a moment in time, not one you should carve in stone for yourself. I’ve learned to trust that what I want to do is right for me and anything might or might not work. The only way to find out is to give it a go.
This sort of applies to asking people what they think of an idea or pricing. You’ll get their opinion – great since that’s what you asked for. But you’ll also get all their beliefs and personality type with it and their opinion is only as useful as your understanding of where they’re speaking from. Where I veer from that is about logos and how understandable and persuasive copy is. Convergence of opinion on those from a variety of people is always right.
It’s much harder than I think it’s going to be
It’s harder to sell, it’s harder to launch, it’s harder to ride the ups and downs. But, the bits I like make it worth it. For me, the bits that make it worth it are the moments when ideas hit and then map themselves out in my head. That feeling is everything. If that stops, I’ll have to find something else to do, no matter how much money I make.
No amount of money is out of reach
Two of my business mentors hit 6 figures this year. Another hit a million. I pay attention to people who disclose their figures in sectors similar and dissimilar and regularly see people who report earnings higher than I’ve ever earned at any job ever. I make a point of reminding myself there’s nothing magical about them or their businesses and anyone can learn and achieve the same.
