Learning professionals are the ultimate imposters, but in the most honest way. Not imposters because we fake expertise. Imposters because we are asked to borrow expertise at high speed, under bright lights, with a launch date sitting there like a silent judge.
We get a couple SME calls.
In those calls, we are meant to absorb what a person has been learning their entire career—years of pattern recognition, scar tissue, caveats, “it depends,” and the story about The Incident (which is always told in a tone that implies the building is still technically on fire).
Then we’re supposed to digest it, convert it, and teach it to others as if we’ve always known it ourselves.
And we do this while maintaining the facial expression of someone who owns a bookshelf.
So yes: of course we become comfortable with ambiguity.
We have to.
We make training out of fog. We build bridges while the river is still negotiating whether it wants to be a river.
The issue begins when the organization decides that “comfortable with ambiguity” is not a skill in a complex world, but a staffing strategy.
When “comfortable with ambiguity” becomes the thing you hire instead of hiring:
- a decider,
- a plan,
- a scope,
- or the slightly unsexy but essential habit of saying “not in this release.”
Enter Mac, Patron Saint of “Let’s See”
Every learning team has met Mac.
Mac is not evil. Mac is just… unpinned.
Mac says “I’m comfortable with ambiguity” the way certain people say “I don’t own a microwave,” meaning: I have transcended your small anxieties.
Mac will say it with a gentle smile, as if offering you tea.
You’ll ask, “Can we define success?”
Mac will look up thoughtfully, as if success is a migrating bird. “I don’t know if it’s that simple.”
You’ll ask, “Who is the audience we’re prioritizing?”
Mac nods. “It depends.”
You’ll ask, “Should we decide by Friday?”
Mac’s expression suggests you’ve asked him to insult a poet. “Let’s not rush to certainty.”
Mac is very open-minded. He is open-minded in a way that keeps every option alive, including the option where everyone else quietly does the work of choosing.
And here is the small, crucial detail: Mac’s comfort with ambiguity is often sustained by the fact that other people are uncomfortable for him.
When Everyone Is Comfortable With Ambiguity
This is where it gets interesting, and also where it gets expensive.
Because ambiguity, in a team, is not like weather.
It’s not neutral.
Someone pays for it.
When no one decides, what happens is not “we float serenely in complexity.” What happens is:
- someone starts sending follow-ups and feeling vaguely ashamed,
- someone starts overbuilding “just in case,”
- someone starts guessing what leadership “really wants,”
- someone starts keeping a shadow plan in their head that they never asked for.
Ambiguity doesn’t disappear. It relocates—into calendars, into late-night Slack messages, into the body of the person who cannot stop trying to make it make sense.
In learning work, that person is often the learning professional, because the job is literally: make sense of this for others.
Which means we are uniquely vulnerable to becoming the organization’s fog sponge.
We absorb uncertainty. We compress it. We produce something that looks like clarity.
And then we get feedback that the clarity is “too rigid.”
Clarity Is Not Control. It’s Kindness With Edges.
There is a superstition in many workplaces that clarity is arrogance.
That to ask for a decision is to be naive.
That to put a stake in the ground is to invite the universe to punish you for your confidence.
But clarity is not “we know forever.”
Clarity is: here’s what we mean right now.
Clarity is a temporary structure that allows other humans to do work without dissolving.
It’s not control. It’s hospitality.
It’s saying: “You don’t have to hold every possibility in your head at once. We are choosing a lane. If the world changes, we will change the lane, but you do not have to drive a car made entirely of options.”
This is the part that gets lost in the “comfortable with ambiguity” mantra: the point is not to remain ambiguous. The point is to move through ambiguity toward something usable.
Healthy ambiguity has motion.
Unhealthy ambiguity has vibes.
The Three Clarities That Save Your Nervous System
If you want to see whether a team is doing “real ambiguity” (learning, discovery, complexity) versus “Organizational Ambiguity™” (avoidance with a friendly face), ask for these three things:
1) Outcome clarity
“What will someone be able to do differently after this?”
Not “what are we delivering,” but the behavior change. The before/after.
2) Scope clarity
“What are we not doing?”
This is the fence. The mercy. The thing that prevents the project from becoming a grab bag of everyone’s hopes.
3) Decision clarity
“Who decides—and by when?”
Not “who has input.” Not “who is consulted.” Who can say yes or no in a way that sticks.
If you don’t get these, you’re not working in ambiguity. You’re working in a decision vacuum.
And decision vacuums are always filled by the person who is most conscientious, most tired, and most afraid of letting others down.
Which is a touching way to run a company, if your goal is to slowly turn your best people into smoke.
What Support Should Mean (If We’re Being Serious For One Second)
When job descriptions say “comfortable with ambiguity,” there is an ethical version of that line.
The ethical version implies: You will have support while things are unclear.
Support looks like:
- a manager who will name tradeoffs out loud,
- a sponsor who will decide,
- a timeline that includes time for discovery,
- access to SMEs that is not “two calls and a prayer,”
- agreement on what “good enough” means.
Without those, “comfortable with ambiguity” becomes a kind of cheerful warning label:
You will be judged for outcomes created under conditions you did not control. Please be pleasant about this.
It is a little like hiring a lifeguard and writing:
Must be comfortable with the ocean having moods.
Why LinkedIn Is a Mirror Here
Now, about the LinkedIn search results—why did every job that came back look like Learning?
Two possibilities can both be true:
- Learning roles really do use that phrase a lot, because learning work sits right at the intersection of SME knowledge, business urgency, and human attention spans.
- The algorithm knows you. It knows your clicks, your history, your professional orbit. It sees you coming and starts laying out familiar furniture.
Either way, it’s hard not to notice how the phrase has become a kind of corporate incense—something you wave around to make the room feel spiritual while no one picks a direction.
And that’s the part that makes you think: maybe we could do better.
Maybe we could stop converting structural gaps into personality requirements.
Not enough planning? Hire someone “comfortable with ambiguity.” Not enough capacity? Hire someone “highly adaptable.” Not enough decisions? Hire someone who can “influence without authority.”
At a certain point the job listing starts to read like:
Must be able to operate effectively in a situation where the organization declines to operate.
A Closing Thought, Offered Without a Moral
Learning professionals can do ambiguity. We do it all the time.
We can walk into two SME calls and come out with a usable story. We can translate jargon into something a human can remember. We can take a process described like a dream and turn it into steps, checks, and practice.
We can do it.
The question is whether we should have to do it as the default substitute for planning, every time, as if a lack of decisions is a weather pattern.
“Comfortable with ambiguity” is fine.
But imagine, just for comedy’s sake, if the job listings added one more line:
Comfortable creating clarity. Supported by people who will actually decide things.
And then, in small print, the part that would really make you click:
Ambiguity is shared here.
Check out the Deep Thoughts and Whatnots podcast for the audio version—complete with expanded humor 😏—on Spotify or Apple Podcasts.
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