Successfully Self-Employed

The Weekly Hotseat

Wednesday, 24 June 2026  ·  Issue #1

This week's Hotseat recap: what came up, what landed, what we're each holding each other accountable to doing next.

Community Update

This week in the room

Cold Cape Town Wednesday. Most of us were in hoodies, at least one person was visibly working from a blanket. It was that kind of week — the kind where you show up anyway, and it turns out showing up was exactly the right call.

The theme that kept surfacing was the gap between knowing what to do and actually doing it. Not for lack of skill or vision. For reasons that are harder to name. We spent a lot of time in that gap together, and many a useful idea came out of it.

Key Learnings

What came up this week

This was one of those sessions where the room went somewhere real. So I'm going to be honest about what came up.

I cannot hear my gut right now, and I've stopped pretending I can.

I have a decision to make. Stay with a well-known brand, doing capacity work I can deliver but that is not what I want to build toward. Or move toward a new community-building opportunity with a founder who wants to hire me for exactly the work I care about, but needs funding first before that's a real offer.

My mentor told me to suck it up and do the hard work with the known brand. Part of me agrees. Part of me doesn't trust it.

What the group gave me was a reframe: the "90-year-old you" exercise. Zoom out so far on the timeline that the immediate stakes shrink. Someone added another layer: think back to a similar past decision and how it actually landed. I left a big SA brand a few years ago. I was scared it would close doors. It didn't. That is its own proof.

I still don't have the answer. But I know I can sit with real uncertainty instead of defaulting to survival logic. That is the shift worth noting.

Decision fatigue is not the same as not knowing what you want.

Someone in the room came in with what they called analysis paralysis. Another person in the group reframed it as decision fatigue, and they agreed immediately. They were not confused about what they wanted. They were exhausted from having to choose between too many things at once.

The suggested fix: outsource the small decisions temporarily. Coin flip. Random generator. The goal is not to optimise the decision. It is to break the paralysis and rebuild momentum. One person also built their own comparison tool that runs "this or this" rounds until a priority surfaces. I liked that they built it for other people and then forgot to use it themselves.

The distinction between fatigue and confusion matters before trying to solve anything.

A brief small enough to start is not a compromise on the vision. It is what makes the vision possible.

Someone in the group has been sitting on a creative project for years. The concept is real and the passion behind it is real. Every time they try to plan it, the scope swallows them.

What the group landed on: ask one specific person for one specific brief. One object. One material. One ask. We offered contacts, revenue angles, a roadmap call. The point was the same in every direction: the vision is not the problem. The entry point is.

Changing goals midyear is not failure. Avoiding it is.

Someone in the group ran a midyear review and found most of their January goals had stopped fitting. They came to the call having already decided: the ones that stayed were the ones worth pursuing all along. The ones that fell away had never been genuine commitments.

I am overdue for the same thing. Two months inside someone else's business tends to make that obvious.

Needs & Leads

This week's resources & community

I gave a talk on Networking out of Necessity and it's now in the resources channel. If networking still feels like a chore, go watch it — I promise you'll come out the other side an actual convert.

Watch the talk →

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.

From our partners

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