Here’s a neat trick that has served me well over the years.
When confronted with a seemingly lose-lose situation, instead of opting for the second worst option, I ask: “Is this a false dichotomy?”
Get into this habit of paving an ‘option 3’, and you’ll be surprised at how often this is possible.
“I don’t care about the options closed to us. Tell me the roads open to us or the grounds we can clear to make one.” – Bobby Axelrod, Billions
How does one do this?
Step one. Figure out if the lose-lose choice is a false dichotomy. This gets easier after you’re more familiar with the common flavours they come in (covered in section 1).
Step two. If there is a false dichotomy, generate alternative options (covered in section 2).
We’ll also explore the common false dichotomies in politics. Ones that tragically distract people from the core of the important political issue at stake – covered in section 3.

1. Calling out false dichotomies
The 5 common flavours.
(i) One option disguised as two
False dichotomy due to falsely assuming a Hobson’s choice.
“Customers can have the car painted any colour they want, so long as it is black.” – Henry Ford
(ii) Omitted/forgotten intermediary options
False dichotomy due to falsely assuming there’s no intermediary options.
Someone that’s only ever seen red and white flowers may never have imagined pink ones.

Oftentimes, things that occur on a continuous spectrum (e.g. amount of milk in a coffee) are intentionally reduced into discrete options (e.g. milk vs no milk), often out of convenience (since no one really asks for 37% milk). But this convenience can sometimes blind people into perceiving a false dichotomy.
We can go further. False dichotomy does not imply there needs to be a true dichotomy.
Maybe a dichotomy is inappropriate. Maybe there’s more than 2 options, an infinite spectrum of options for example. Contemplating false dichotomy vs true dichotomy itself can be a false dichotomy – a kind of meta false dichotomy.
(iii) Why not both
False dichotomy due to falsely assuming mutual exclusivity.
Someone that’s only ever seen red, white, and pink flowers may never have imagined one that is both red and white.


Basically, whenever “both” is a valid answer to “option A or option B.”
(iv) Neither
False dichotomy due to falsely assuming collective exhaustion.
This is not even picking an intermediary between the two extremes, it’s picking something entirely outside the range presented.
Someone that’s only ever seen red, white, and pink flowers may never have imagined blue ones.

If “neither” is a valid answer to “option A or option B.”
Note, combining the previous two ‘flavours’, consultants frequently use the MECE shorthand (mutually exclusive collectively exhaustive) to make sure strategic options have no gaps and no overlaps.
(v) Incorrectly defined opposites
Sometimes, defining the logical opposite is obvious: Yes-No, North-South, True-False, On-Off, Plus-Minus, Win-Lose, Ying-Yang, Good-Bad, Strong-Weak, Life-Death, Black-White, Left-Right, Pass-Fail, Go-Stop…
…Or is it?
Ask people what the opposite of fragile (breaks easily when dropped) is, chances are they’ll say it’s resilient (doesn’t break easily / stays the same when dropped). But that’s like saying the opposite of positive is neutral, when it’s in fact negative. A better answer is antifragile (becomes even stronger when dropped). More on antifragility here (one of my most popular posts).
The nuance is the correct opposite depends on the context.
A math example. In some contexts, the ‘opposite’ of the sin(x) is the inverse, sin-1(x) – function of each other gives x. Someone else could say it’s the reciprocal, 1/sin(x) i.e. cosec(x) – multiplying the two gives 1. Or maybe it’s -sin(x) – adding to give zero, or reflect along y-axis. Or maybe it’s sin(-x) – reflection along x-axis. Or cos(x) – 90 degree phase shift. And so on.
A parable
There was this scene from a Korean history drama. The protagonist is captured by this bad guy. Bad guy offers her a chance to live. She must choose one of two boxes. In one box there’s a piece of paper that says freedom. In the other box it says death.
But bad guy cheats – both boxes contain death. Whichever box she opens, she’s doomed.
The protagonist, suspecting this to be the case, opens one box and before anyone has a chance to verify what it says, immediately swallows the piece of paper.
“Now the only way to know my fate is to see what the other box says. If it says death, that means the one I chose said freedom.”
It would be more entertaining if I told you she gets killed anyway But no, he lets her go because protagonists dying like that is bad for ratings.
2. Overcoming lose-lose situations
I could end the post here and just tell you to “think outside the box” and leave you with one of these kind of cliche pictures…

…instead, I’ll briefly go over one of the most powerful frameworks on making difficult decisions.
The Opposable Mind
Inspired by all of the cool things humans can do thanks to having an opposable thumb (unlike many other animals), Roger Martin’s book, The Opposable Mind, describes a framework to develop “integrative thinking.”

Unlike conventional thinkers, integrative thinkers transcend false dichotomies, and generate alternative solutions. This takes place in four stages.
(i) Determine Salience: take a broader view on what factors are relevant
“The first difference between integrative thinkers and conventional thinkers is that integrative thinkers take a broader view of what is salient.”
Where conventional thinkers might only consider factors a, b, c, integrative thinkers would also consider, d, e, f.
Much of our perceptions about a system are merely warped constructions of reality. Our decisions are only as good as the models we construct to interpret things. Models reduce complexity to help us understand, but come at a cost of excluding certain elements that are rather substantial in certain contexts.
So continually question the boundary conditions.
Ask: What features do I see as important/relevant?
While this is more cognitively demanding, embrace the messier components to get a better outcome.
The reason why organizations find this difficult is because it encourages simplification and specialization. Every business function has an implicitly accepted range of salience. No wonder why so many organizational decisions end up with a functional optimum, rather than a holistic, global optimum.
(ii) Analyze Causality: multi-directional and non-linear relationships
“Integrative thinkers don’t flinch from considering multi-directional and nonlinear causal relationships.”
It’s common to assume uni-directional relationships: “under certain conditions, x causes y to happen.” But changes in y can cause changes in x too – i.e. there may be bi-directionality. Although beware of the causation-correlation fallacy: correlation does not necessarily mean causation.
It’s also common to assume linear relationships. Sometimes the links are right, but the magnitude is wrong.
Ask: How do I make sense of what I see?
(iii) Envision the Decision Architecture: keep the whole in mind when working on the parts
Keep the broader problem in mind while looking at the details.
See the system as an interdependent, integrated whole.
Ask: What tasks will I do in what order?
(iv) Achieve a Resolution: create a resolution of tensions
Search for a creative resolution of tensions between the two options, rather than just accepting unpleasant trade-offs.
Ask: How will I know when I am done?
“”Any situation has a certain number of alternatives, but if you are doing system thinking, even for a complex problem, and you realize what is the system, what are the subsystems, what are the sub-subsystems, and you define their interrelationship as well as you can, you will start to see some daylight, how to get out of it. The complexity – if you have some logical inputs and also have a system structure – I don’t think it looks that bad” – Kohlier, founder of Tata Consultancy Services (Indian software giant)
Example: Four Seasons Hotel
Sharp founded Four Seasons Hotel in Toronto in 1961. It had 125 rooms with standard rooms going for around $12 a night. The hotel industry at the time seemed to offer two choices:
- have fewer than 200 rooms and offer guests moderate amenities, or
- have more than 200 (usually 500+) rooms and offer extensive amenities e.g. conference facilities, multiple restaurants etc
Salience. As Sharp opened more hotels, he wanted to keep the cosiness of the smaller ones. Guests wouldn’t feel at home in big hotels. So he opened one with 220 rooms – much less rooms than a typical luxury hotel – but complete with luxury amenities. However, if he had charged similar room rates as other luxury hotels, spread of the cost of his luxury amenities across less rooms would yield unsustainably low profits. So he charged a substantial price premium, boosting revenue per room way up to a level the industry thought would not be possible.
While other hotels considered location, staffing levels, room size, and furnishings as the salient factors, Sharp also considered the broader business travel experience – wanting to feel more at home. Seeking to replace this at-home feeling, Four Seasons was the first hotel to offer shampoo, 24-hour room service, bathrobes, hair dryers, 24-hour dry cleaning etc.
Causality. Some causal relationships in the hotel business are obvious: between room utilisation and profitability, between room revenue and food/beverage revenue etc. The industry had accepted that a minimum number of rooms was required to cover amenities cost to stay profitable. Sharp instead saw a more subtle, complex relationship between hotel size and amenity level. He saw both costs and benefits to increasing rooms, while competitors only saw the benefits.
Architecture. Sharp also recognised that providing an at-home experience depended on every aspect of the hotel experience, not just the amenities. So the entire customer department was scraped. Customer service was instead made to be the responsibility of every department, and every staff.
Resolution. Sharp didn’t settle for trade-offs between: (i) big with amenities but cold, versus (ii) small without amenities but cosy. He managed to combine the best of both worlds.
Used the Four Seasons example as it’s the most simplest one from the book to follow. Four Seasons, you’re welcome.

3. Prevalence of false dichotomies in politics
The increasingly polarised electorate
Tragically, the political electorate is now more polarised than ever.

There are many reasons for this which I wont get into. Short version is: changing nature of media since 1960s accelerated by social media echo chambers in the 2010s, all incentivised to appeal to and nurture the extremes.
Political issues frequently misinterpreted as false dichotomies
And here’s what compounds the polarisation problem. Most political issues are represented as false dichotomies.
Even smart people often forget that the issues are on a spectrum, or have incorrectly defined extremes etc – taking on one of the 5 flavours of false dichotomies, as we discussed.
- Pro-life vs pro-choice?
- Intervene in Syria vs don’t intervene?
- Should we side with US or China?
- More regulation vs less regulation?
- Keynesian intervention vs neoliberal?
- Renewable energy vs affordable energy?
- Freedom of speech vs hate speech?
Such ideological extremity has contributed to increasing with-us-or-against-us behaviour.
Democrat: “Do you support Trump?”
Republican: “Yes, and the reasons why is because….”
Democrat: “He’s racist and misogynist so you must be too. So fuck you. Don’t talk to me.”
Horseshoe Theory: extremes have more in common than they like to admit
The interesting thing is the extreme ends of the political spectrum usually have more ideas in common with each other than they would like to think. Extreme left and extreme right have more in common than the political center. This is known as the horseshoe theory – distance from each other representing commonality in ideology.

Moral of the story
When faced with a difficult binary choice, ask yourself if it is a false dichotomy. If so, determine salience, analyse causality, keep the whole in mind, and resolve the opposing tensions to create a resolution.
Watch out for the landmine false dichotomies in political discussion. Be aware of your political views, and re-examine for any false dichotomies you may have accepted. You may have laid down some landmines too.
Here’s to better decisions!
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Related:
The Opposable Mind, Roger Martin, 2007
Transdisciplinarity: a case for generalism in a complex world
When surprisingly simple solutions work
Antifragility, modernity, and dancing with disorder
Ergodicity: the most over-looked assumption