Successfully Self-Employed
The Weekly Hotseat
Wednesday, 16 September 2026 · Issue #12
This week's Hotseat recap: what came up, what landed, what we're each holding each other accountable for doing next.
Community Update
This week in the room
What an easy drop-in energy we had this week; generous back-and-forth once things got going. Less strategy theatre, more honest problem-solving. My favourite kind of session.
A few people had shipped the things they'd committed to a fortnight ago - always cause for celebration. We also cheered for the less post-worthy wins. Getting money matters in order, looking for help in unexpected places, and launching before something feels completely ready. Because the “unglamorous stuff” is all part of the journey we’re here to back one another on!
Key learnings and discussion points
What came up this week
Getting the boring foundations right, finding help where nobody's looking, and launching before it's perfect.
The launch post is whatever broke on the way there.
Simone is relaunching her website, and it may have started out as her fancying a refresh. But stumbling block after stumbling block, such as the payment portal not working on a previous version, has found her on her third rebuild this year. Yes, those are setbacks but it could also be the key to her launch campaign content.
The honest version resonates far more than the polished reveal. When I've shared the messy middle of my own work, the behind-the-scenes rebuilds and the things that quietly fell through, that's what people engaged with most.
● The setback is the story: "It broke despite my best efforts, and here's what I learned" is a post people actually read.
● A photo of the maker showing off the thing they worked hard to build tends to land better than a hard sell.
Sort the money groundwork before you scale, not after.
Dirk brought forward the question most new business owners dodge for too long: what happens with hiring, tax and bookkeeping once this actually grows? The answer the room landed on was reassuringly boring.
AI has quietly earned a seat at the research table.
Simone recently migrated her entire operation off of an old board into clean SOPs using Claude, then used it again to sort images and build website HTML. I've been running market-research reports through a Notion and Claude agent that digs into an industry, its competitors, its messaging and its positioning.
Research that used to take me days now takes minutes, and honestly it felt like cheating at first. Rebuilt SOPs and systems from old boards in an afternoon; full breakdowns on someone you’re pitching for in moments. The possibilities seem to be endless. Take a look in Needs & Leads if you have a market research request for your business and I’ll put my Notion and Claude research agent to work for you!
This week's resources & community
Needs & Leads
●Free market-research reports: As mentioned above, if you would like a Market Research Report on your business, fill in this form and I'll email your report to you when it's ready!
●Speakers wanted for online summit: Margaret is lining up speakers for a pre-recorded summit inside her community in January - The Pantry Project: Building Your Cannabis Kitchen From Scratch. If you know anyone who would be a good fit for helping home cooks build a real, repeatable cannabis kitchen, reach out to her on WhatsApp or GoKollab.
●Art experience: Simone is hosting an experiential art exhibition in Cape Town next month as she explores the different areas of her business. The exhibition is closely linked to a 3 day camping experience with the artist in a different province. For more details on the exhibition or travel experience contact her on WhatsApp or GoKollab.
Got something to offer or something you're looking for?
Post it in the Needs & Leads channel in the community and it'll get a spot in next week's newsletter.
Accountability
What we're each doing in the next week or two
From our partners
You or Your Company Should Have A Podcast
No studio. No production team. No need to figure it all out yourself.
Amaze Media Labs provides everything you need to launch a professional audio and video podcast—from strategy and recording to editing, distribution and audience growth.
Before you go
Know a founder who needs this?
If this resonated, hit forward and send it to one self-employed person in your network. That's it. No link, no form - just pass it on to someone who could use it.
↑ HIT FORWARD ON THIS EMAIL
Come join us on Wednesdays
The Successfully Self-Employed community is a peer circle for founders who want structure, accountability, and real conversations. Every Wednesday, live. No fluff.
Join the communityRefer 3x friends who join and you get a lifetime FREE membership. Send them this email as a sneak peak!
Successfully Self-Employed — structure for the self-employed.


