Embracing ambiguity: creative confidence in disguise

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Doug Kessler

12. 08. 2019 | 6 min read

Embracing ambiguity: creative confidence in disguise

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This started out as an apology.

I wanted to say sorry to the many clients and colleagues I’ve annoyed over the years because of my indecisiveness.

I do sympathize. I know it pisses you off. I know you came to me for a simple answer to a simple question.

I know that people and processes are waiting for an answer.

But I just don’t want to decide yet.

If possible, I’d like to delay my decision for as long as possible.

And, while I know this can be infuriating to people trying to make a plan, ask for a budget or actually get a job done, I find it almost physically painful to make decisions too early.

I used to think this was just the indecision of a weak character (it’s no doubt that too).

That the anxiety I experience whenever I close down options is simply a character flaw (again, guilty).

That I suffer from a crippling fear of regret. (A fear that’s all the more puzzling because I rarely if ever experience actual regret.)

That I’m less of an adult because I can’t just make that choppy-hand gesture perfected by movie presidents and say, “Normandy. Definitely Normandy.”

But as I’m writing, I’ve decided to turn my apology into a defense. A defense followed by an apology.

Because maybe what looks (and, let’s face it, feels) like mimbling* indecisiveness is actually a thing that the creativity evangelists call a “tolerance for ambiguity”.

Ambiguity rocks.

People with a high tolerance for ambiguity don’t mind the absence of a precise next step or a clear route or even, (FFS), a final destination.

I go a bit further than that.

I don’t just tolerate ambiguity, I kind of need it.

I am an ambiguiphile. (I like the emphasis on the third syllable. Takes practice.)

And, while this psychological mis-wiring can be annoying as hell (as when the waiter pivots to me, pen poised, eyebrows up, smile slowly sagging), it can also be really valuable.

Because, sometimes, what looks like a total lack of belief in one’s own judgement is actually masking a perverse kind of creative confidence.

Often, I feel really strongly about going in a general direction and that’s all I need to justify packing my bags and setting out (though I admit that others on the team, justifiably, need more than this).

Let’s say we want to make a video to promote a product that users really love. And the (admittedly simple) idea is to capture that enthusiasm by going out and interviewing end users, then editing the results into a video.

Having met real users of the product, I’m convinced that good things will happen as we proceed in this direction.

I know in my bones that, as we engage with the material and actually start interviewing users, our options will surface and the choices we make will become clearer. The best way will present itself.

And I trust that we’ll make good decisions along the way. Decisions that will be way better because we didn’t try to make them too early. We waited and listened, keeping the end goal in mind and pivoting to get there.

(Interestingly, even though indecision looks like pessimism, this kind is actually grounded in a deep optimism. That good things are around the corner even if we’re not sure which corner yet.)

I’m not a sailor but I like the word ‘tacking’ for this. It’s a kind of zig-zagging to get where we want to go, based on our reading of the wind.

Because it works better.

For me, this kind of approach isn’t just way more fun (though it’s definitely that). It’s also way more effective.

Yes, we could make all sorts of decisions up front. We could nail down, say, exactly which kind of end users we’ll interview, We could script all the questions and get them approved all the way up the hierarchy. We could plan the locations and the lighting.

The wider team would feel much, much better if we did just that.

Because the wider team includes people who have a low tolerance for ambiguity. People responsible for things like budgets and schedules and delivery. You know: grown-ups.

I do understand that, for these people (most of my colleagues and clients), ambiguity sucks. It makes it much harder to make a project plan and to execute it.

I do sympathize. And I wouldn’t put you through it if there wasn’t an upside—a set of benefits that more than compensates for the obvious pain-in-the-arseness of the “wait and see” mode.

There really is an upside.

I know that a lot of my best work really does come from this kind of directed stumbling.

Which end-users should we interview? Let’s interview a few and get a sense of what’s working. Then narrow down our search.

What questions should we ask? Let’s try a bunch and see what kind of answers we’re getting. Then create the list of questions (with some pivots built in, no doubt).

Where should we shoot? Let’s try a few different places and see what’s working best. Then we can write the pre-production plan.

Yes, we could have made all those decisions up front (my hypothetical isn’t very challenging). And we might have been right about many of them.

But we might have been wrong.

We’d probably have been wrong.

And, while making that choppy-hand gesture and barking out the orders might look supremely confident, it’s often just clinging to an inner set of conventions that will lead to a conventional result.

The high road to Wow.

It comes down to this: one of the most important jobs every marketer has is to surprise our audiences. To do something fresh. Unexpected. Delightful.

Doing that demands that we follow our guts in a general direction, then use our eyes, ears and… guts again… to pivot, tack and zig our way toward the surprises. The goodies.

In short, all that annoying, dithering indecisiveness might just be creative confidence in disguise. (Mixed with some plain, old, dithering indecision).

Yes, I do apologize to my colleagues for this predisposition.

I know it makes it harder to plan and budget and convince stakeholders.

But it’s worth it.

So if you’re saddled with an ambiguiphile, I hope you’ll be tolerant.

And I hope you’ll help them keep their options open for as long as makes sense.

That you’ll defend their fuzzy-but-real confidence as if it were your own.

If you can do that for us, we can do some things for you.

With that in mind, here’s…

The Ambiguiphile’s Pledge:

I’ll try to share with you my fundamental confidence in the general direction I’m advocating.

I’ll take that confidence into meetings with stakeholders, to help you make the “just trust us” appeal. I won’t ask you to do this alone.

When I’m not all that confident about the general direction, I’ll either hide that fact (praying it all works out), or let you in on it, so we can decide together whether to bluff or confess. Some stakeholders are cool with experiments.

When I can make a decision without closing too many of my precious doors, I will try my best to do so. Especially if we agree it’s reversible. Just kidding. (Not).

If a particular pivot will blow out the schedule or budget, I will warn everyone and wait for approval, offering a prudent Plan B in case of rejection.

Finally, I’ll stop apologizing for my indecision, knowing that you understand.


* Mimbling: Made it up. Dithering plus mumbling.

Published in:

  • ambiguity

  • creative

  • creative confidence

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  1. Henry Cazalet

    The SMS Works Ltd

    August 13th, 2019

    ‘I am an ambiguiphile. (I like the emphasis on the third syllable. Takes practice.)’

    I spent too long trying to perfect this.
    I’m now ready to deploy at the earliest opportunity.

  2. Kim Brebach


    September 30th, 2019

    Doug, you’re talking about ambivalence not ambiguity
    Ambivalent: doubtful, faltering, irresolute, questioning, uncertain, undecided, unsure, vacillating.
    Ambiguous: unclear, murky, mysterious, nebulous, obscure, opaque, vague, cryptic

    1. Doug Kessler

      September 30th, 2019

      I think I’m talking about both.
      I embrace ambiguity and that often makes me ambivalent.
      Thanks for clarifying!

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