

Uncharted Work: Navigating Unvalidated Paths
This Dilemma Lab is a small-group lab for people building without clear external validation. If you are building something that doesn’t fit the usual templates, this session offers a facilitated space to work with uncertainty, legitimacy, and choice-making.
Maybe it’s a business, practice, or body of work rooted in a specific community, culture, or set of values. Maybe it’s early-stage, intentionally slow, or oriented toward a future that doesn’t yet have a clear name, market, or category.
What you know is this:
there is no obvious playbook for what you’re doing.
No clean benchmarks.
No ready-made success stories.
No external validation you fully trust.
Instead, you keep encountering questions like:
“Is this too niche?”
“How big can this really get?”
“Is this a smart move—or am I being idealistic?”
“Whose standards am I actually using to judge this work?”
Candidly, what you’re really grappling with is something quieter and harder to name:
How do I continue to act with conviction and internally generated authority when the world cannot yet confirm my choices?
Uncharted Work is a Dilemma Lab designed for people sitting right inside this tension.
Not to resolve it neatly.
But to learn how to hold it without losing coherence or self-trust.
It’s about learning how to act before legitimacy arrives.
What this Dilemma Lab is
Uncharted Work is a small-group facilitated dialogue and working space for entrepreneurs, builders, and practitioners navigating unvalidated paths. That work may be:
• culturally grounded or community-specific
• early-stage, emergent, or intentionally slow
• difficult to explain using dominant market language
• meaningful, but not yet externally legible
Why this matters
When people lack support for navigating uncharted paths, they often respond in one of two ways:
They dilute the work until it becomes legible but hollow.
Or they abandon it altogether, mistaking isolation for a sign they were wrong.
Neither response is a failure of courage or competence.
It’s a failure of support for meaning-making under uncertainty.
This lab exists to interrupt that pattern, not by promising certainty, but by helping you become the kind of person who can move responsibly and confidently without it.
How the lab works
Participants come with one live, unresolved dilemma — a real decision or tension where questions of legitimacy, scale, worth, or timing are actively present.
Together, we will:
• surface the external standards you may be unconsciously using
• examine where authority is being outsourced — subtly or overtly
• work with tensions as polarities (not binaries), such as
– Legibility ↔ Integrity
– Scale ↔ Specificity
– Conviction ↔ Responsiveness
• practice staying in ambiguity long enough for clearer internal structure to emerge.
There is no advice-giving and no optimisation.
This is a collaborative space to develop your ability to see and relate to the standards, assumptions, and voices that usually operate invisibly.
What this is not
To protect the integrity of the space, it’s important to be clear about what this lab is not:
• This is not a business strategy or scaling workshop
• This is not a “quit your job and follow your passion” session
• This is not about convincing you that niche is inherently superior
• This is not a space for passive listening or inspiration-only consumption
You will be asked to reflect, map, and engage honestly with your own decision-making patterns.
Investment
Standard - $137.5
Concession - $110 (for those who need a little financial breathing room. No questions asked)
Members - all Dilemma Labs and online workshops are free for Ijeruka members. To learn more about membership, visit our website.