Borrow everything I've learnt from launching a retreat
The Good, The Bad & The Hype of trying to create a new income stream
Next weekend, I’m hosting my first in-person creative writing retreat at Rêve Retreat, Limoges, France.
It’s been a hard slog to get here and I wanted to share the messy middle. Where the self-doubt crept in, and lessons I’ve learned on this journey that can help you, whether you're launching a retreat, product or any new income stream.
In case you’re a last-minute Larry, there's still one cabin available for next weekend (5th-8th September 2025) £1,100 for solo occupancy or £1,400 if you’d like to share with a friend. Several guests have already booked extra nights before or after the retreat to make the most of the experience.
The Good
- Choosing the right location. I already knew Rêve Retreat having stayed there myself on a co-working retreat. This made me feel more confident in selling the picturesque element of the place. It’s a good reminder that being familiar with your space or technology can make promoting it much more confident and authentic
- Choosing a complimentary partnership. Gemma & Jammer at Rêve have a complimentary skillset to what I offer. Whilst I have explored collaborations with a few other partners, this was the one that flowed with ease which I think is always a good sign.
- Terms of Agreement / Scope of Work. We set clear expectations upfront to avoid confusion later. A written agreement was popped in place to ensure everyone is on the same page, particularly when it comes to responsibilities and payment. My focus was on the learning design of the retreat and the promotion.
-Respond to demand. Quite quickly, people were messaging me to say that it was of interest but they couldn’t make that date. I reacted by speaking to Rêve about having an alternate date option and then checking with those who were interersted to which alternate dates would work for them.
-Tailored emails. There were 7 people who had expressed interest in a second date. 4 of these booked on for June 2026 when I offered it to them first before going out to the main list. Then, when I was focused on promoting the retreat next weekend, a surprising side effect was I sold out for next June 2026!
- Retreat Design. I have loved creating the programme and trying to come up with creative and thoughtful ways to surprise my guests. I rarely do in-person events so my main goal is to really do this as well as I can.
While there have been some wins there were some real moments where I was tearing out my hair that I think might be helpful to share.
The Bad
The desert. If you don’t know the desert. It’s that part in between when you first launch and before the flurry at the end where you start questioning if you are going to be able to sell it at all. It’s the time when you start to question if the product is right, the price is right and contemplate giving it all up.
This phase always feels like a test of resilience. Remind yourself that this happens to everyone. I know this from my panic texts and tears to my business coach and close friends. My advice? Take a deep breath, keep promoting, and remember it’s a phase, not the end.
Current lack of email segmentation. On Substack, you can see who has clicked on a post but you can’t segment for a follow-up email in an intelligent way. Segmentation could have made follow-ups more targeted. If you're starting out, invest in a way to track interest early on so you can reach out to people who are genuinely interested without spamming your whole list
August. Could be controversial but I think it is a terrible month to try and sell something unless its ice cream. I wish I had given myself more of a run up beforehand. Moving forwards I want to give myself at least 9-12 months in advance of the event to promote so I am not in the last minute scramble position again.
I recommend having a 12-month wall chart and planning in your key moments.
Waitlist. In an ideal world, there would be a waitlist so that if I did have a dropout I could quickly refill it. Instead of which when there were dropouts I didn’t have any time for a backup plan for myself.
The Hype
- Promote in a way that feels good to you. Even as a seasoned promoter. It is really hard repeating the same message again and again. And worrying it is just your friends watching and you are not reaching the right people. Ironically, the post I hated making the most was my most engaged which teaches me I need to get back to chatting on camera again.
- Personal circumstances. I did not take into account that there would be drop-outs. Sadly, three of the reservations needed to be cancelled for very valid personal reasons. With only a small group, that isn’t an insignificant number which is hard to navigate with only a little time left until the event itself and a learning curve for me.
-Does it really matter? It took my business coach to remind me that I’ve done well for a first retreat. Technically at two points I did sell out all cabins. And maybe I still will yet as I’m as hopeful as a labrador puppy that I can reach the the right guests last minute 🤞🏻. Am I less successful if I don’t sell out first time round?
- Overachiever pressure. I was holding myself on an an unrealistic pressure to sell out whilst I was on holiday at the location in August and could create content whilst I was there. On reflection, I almost wish I had visited at a separate time to do nothing but that for a day or two instead. As I was combining it with my coworking family holiday I was constantly checking DMs and emails to see if I had done it and didn’t fully switch off.
Topline behind the hype:
My Audience Size
Substack: Paid 450 members, Free members 12,750
Instagram: 16,3k
LinkedIn: 9,000
The Stats - Here’s a quick breakdown of the promo efforts I’ve put in (excluding any promo from Rêve Retreat :
Standalone emails: 7
Instagram Posts: 22
- Instagram Carousels: 6
- Instagram Reels: 16
Instagram Stories: 138
Substack Notes: 12
LinkedIn Posts: 22
Most engaged Substack note:
Most engaged Instagram post: (I actually cringed doing the talking to camera but it performed the best)
Launch emails:
1. I offered it on early bird to my paid community first. It is important to me that with anything I do, that my community get preferential treatment.
2. Secondly, I offered it on early bird to my full email list (a fortnight later).
3. One week after all emails recipients received, I start promoting the early bird offer on my other social media channels.
4. Before early bird finished I did a final social media push and sent out an email to let people know it was ending
5. Final email reminder of what the offer was to remind people
6. I guess arguably, this is a final attempt at promotion by sharing the journey.
Full guest disclosure: I’d heard that often people invite influencers or media for free when hosting their first events or retreats. I am paying for one of my old colleagues to attend and film social media content. I wanted to be fully transparent so this sort of thing becomes normalised. I also thought it will help me with fresh content to promote future retreats.
My top five takeaways:
Plan at least 6-12 months ahead.Allow enough time for anticipation and promotion. This also gives you time to pitch to traditional press.
Create a waitlist. Even if you don’t have a product or service fully set, having a group of interested people gives you momentum.
Segment your emails. Don't blanket your whole list. Use segmentation to target those who are most likely interested.
Don’t rely on family holidays for promotion. Keep work and personal time separate to avoid burnout.
Maximize your promotional materials. Use all available channels (like email signatures and social media banners) to highlight key offers.
And remember the way I promote myself does not have to be how you do it. Find a way that feels good to you. But I can 100% guarantee you could be doing more.
Last but not least, this is a free to read post from my ‘Borrow Everything I Know’ series. If you found it helpful. Please consider giving me a comment or a share. I’m still bouncing back from deletegate.
Keep on hyping.
Lucy x
Over to you
Any launch questions? What has been your biggest launch learning curve? Meet you in the comments.
Thanks for being so honest here, Lucy. It truly is helpful to read your reflections and to know what you’ve gone through. On a much, much smaller scale I am organising a day creative workshop event in London in October and I’m definitely in the desert right now! And I launched it in August which was probably a mistake. More info here:
https://chezhanny.substack.com/p/an-invitation-to-you
As always, extremely helpful advice here. I’m considering a small event at some point and know that I’ll be returning to your wisdom along the way.