Successfully Self-Employed
The Weekly Hotseat
Wednesday, 9 September 2026 · Issue #11
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
Another nice full room this week, cameras on, everyone showing up despite the distinct ‘not quite end-of-year’ weariness in the air.
In this session we worked through all the different ways social media can work for us in our different phases of growth, why positioning has to come before content, and what to do when the yeses arrive faster than you can hold them - all in the safe, comfortable space we’ve curated Wednesday Hotseats to be.
Key learnings and discussion points
What came up this week
Redefining social media wins, positioning before content, and saying not-yet without the guilt.
Social media isn't only a lead generating machine.
A lot of social media managers are biased entirely towards acquisition. Leads, booked calls, conversions. If it doesn't convert, it doesn't count. That's a narrow read.
Same content engine. A different definition of winning. And ensuring all involved in the social media process feel a sense of achievement from these new goals.
Positioning before content.
Nik expressed what I think a lot of us question privately - what am I? Am I a consultant, an AI strategist, an AI trainer? What struck me is that the question surfaced the moment he got stuck on content. The two are connected.
Liz reframed it nicely. It isn't about the label; they’re made up and people invent new titles every day. What matters is the problem being solved for the client or the person consuming your content.
Her analogy stuck with me: you can read how to change a pipe and still hire a plumber. Teach the how-to freely, and you can still become the implementation partner people call when they get stuck. Content built around specific scenarios, blockers and real cases earn more trust than any job title ever will.
Sometimes the problem is too many yeses.
I put myself in the hotseat for this one. I've been doing sponsorship outreach, and far more people said yes than I expected. Instead of celebrating, I froze. I couldn't reply, because replying meant saying no to a lot of them.
A few community members came to my rescue with excellent alternatives to no. This one from Liz I'm keeping word for word: “It isn't a no, it's a not-now.” Here are some of the others if you ever find yourself in a similar scenario:
● Move to first-come-first-serve mechanism
● Hold a waitlist - which also provides sponsorship safety if a sponsor drops you at the last minute
● Add tiers to your sponsorship strategy for anyone willing to do/contribute more
Throughout the group a similar fear showed up around outreach and goal-setting: the quiet worry that it works and we can't handle it. That is hardly ever the reality though, there is almost always a way to handle the success.
This week's resources & community
Needs & Leads
●Live Discovery Call Demo: I’ll be running a live roleplay of a real discovery call with Pearl on Thursday 27 September at 10am EST, 3pm UK time, 4pm SAST. If you wish to see how we ditch the pitch and turn sales calls into discovery missions, all are welcome to join. It will also be recorded for anyone who can't.
●Cape Town event incoming: I'm launching my first Notion event of the year in Cape Town at the end of October. More details to come soon.
●End-of-year sponsorship window: This is just a gut feel but corporate budgets seem to be freeing up right now, and sponsorship interest seems to be running high across a few of us. A good moment for a sponsorship drive if that's currently on your list.
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.
Skills Sharing & Development Survey
What do you need from Successfully Self-Employed next?
We're planning what comes next — the sessions, the resources, etc. This is a continuation of the recent WhatsApp poll regarding skills sharing & development.
A few short questions around areas you'd like to grow in and your areas of expertise.
| Take the survey → |
Three minutes of your time is all it'll take.
Accountability
What we're each doing in the next week or two
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