Why I’m doing this
June 23, 2026A few years ago I got chatting to friends who attended my high school’s 10 year…
One of my favourite scenes in the tv show “The Simpsons” is where the whole town decides to take up adult education classes. You’ve got Moe the surly bartender teaching funk dance for self-defence, and the geriatric Hans Moleman teaching people how to eat an orange. His wisdom for such an arduous task is to compare the eating of an orange to a good marriage. To which Grandpa Simpson shouts back, “JUST EAT THE DAMN ORANGES!”.
The cleverness behind the joke is that to compare a task as simple as eating an orange to the complexity of maintaining a long term marriage is ridiculous. Hence Grandpa’s impatience for Moleman to just eat the damn thing. Yet, I see the complexity assigned to eating the orange as a metaphor for how we go about making decisions today. That is, massively overcomplicating them to the point that we don’t enjoy making any decisions whatsoever.
It’s clear that we have more options now than ever before in history as to how we spend our time, both our free time and what we do with our working time. On the surface having all these options available to us should be freeing. However, what we are left with is known as the Paradox of Choice. Namely, this means that the more options we have with what we do with our time, the more disappointed we are going to be with whatever we choose1. So, we are pretty much screwed from a satisfaction standpoint anyway. Still, the paradox of choice has been widely written about, and I’m not going to re-hash that point today, but I do want to talk about the problems caused by this flow on effect of having so many decisions we can possibly make.
Every decision we have to make means it gets examined to all hell to determine what is going to be the best choice. Decisions are placed side by side on a viewing platform and scrutinized like choosing two equally cute puppies to be adopted.
“This one has beautiful eyes…”
“Oh but the other ones ears are so floppy and cute…”
“This one over here has come up and spent more time with me …”
“Yes, but this one will fit nicely on the couch while we snuggle”
“This one’s fur is white so its going to show when it gets dirty”
“A bigger dog means it will do big poo…” (Alright, my mum used to say this one and I never understood the problem)
What I’m getting at is that when we’re often choosing between two very good options the definition of what we now consider to be the “best option” is the one that ticks the most variety of boxes. Or in other words, which one has the largest spread of good certain outcomes if its chosen.
Rarely is the puppy that’s most appealing quality is that it’s got incredibly large, floppy, adorable ears going to be chosen over the one that’s cute, but has got just standard floppy ears, but is the perfect size, and the breed that is known not to do big poos (seriously, what’s the big deal?). It ticks a wider range of boxes, and for that reason, is perceived to be the better choice.
Sometimes this is warranted. Its completely fair to scrutinize major life decisions, things like choosing a city to live in, or a romantic partner. But a lot of the time we are faced with decisions where choosing either of the great options are going to give us what we are after. The problem then becomes that when you start applying intense scrutiny to major life decisions it can be easy to fall into the trap of letting this same method of Columbo level detective work flow down to more trivial decisions2.
In university I worked at a specialist running footwear shop, the policy of the store was that for each customer I had to offer three pairs of runners for them to try. Being a specialty running shop the only shoes we sold were high quality runners that would be excellent for any athlete and running distance. But time after time I’d be absolutely bamboozled when a customer would love all three shoes I brought out to them, and exclaim that they loved all three pairs so now they didn’t know what to choose. And then they’d walk out without buying anything!
In these cases all that was needed was to choose one of the three pairs and the customer would have gotten a quality product that filled their needs. But instead, the fine tooth comb scrutinization of what option would be best for them led them to choose to not make a decision instead!
Making a decision about a nice quality purchase like that is that is supposed to be an enjoyable experience. These customers were aware of what the specialty shop offered, so for them to view the choice between three great options as an overwhelming and not enjoyable process just speaks to how far our desire to make decisions has fallen.
What happens when every choice is put under a microscope like this is that each decision is assessed like a value proposition. It’s treated like a business decision that the most optimal outcome has to be attained or else it’s a failure. Looking at anything this way completely saps the joy or spark out of it.
I once worked with a guy who made every decision through the lens of how it could provide the most amount of value to him. This guy was smart, wealthy and popular at the company, but he drove the most generally optimal car you could buy (a Mazda 6)3 and he didn’t see the point of travelling for work as he’d been paid to do previously, having been sent to a conference in sunny Croatia (in summer), entirely paid for, and several years later, again he’d been asked to head to Canada on a business research mission.
When he told me about his past opportunities to travel for work I was struck with awe at how unique these experiences would be compared to that of living the same hum drum life day in and day out. But he was firm that those work trips were a waste, because they were an inefficient use of his time. How rigid does your view of optimizing your life have to be if you’re disappointed at being asked to go on an international business trip that you might get asked 4 or 5 times throughout your entire career?
There are a finite number of optimal decisions, they’re generally going to be in the same vein, and you’re generally choosing these decisions because you’re able to predict what the outcome will be. I believe a large part of why people choose decisions that are made with optimization in mind is to leverage the most certainty from the outcome of their decision. In that they aren’t in the business of learning anything new, just trying to get the most spread of “good results” from their decision.
But sometimes you’ve already got a lot of great stuff going on in your life and you’ll still be upset if you haven’t optimised as well as you could. I did a 3 month euro trip with a friend, we went to incredible places across that time, yet he still lamented that we booked one too many nights in Switzerland and that how could we have not seen that the better decision was to book one extra day in Paris so we could have squeezed in Disneyland. Again, this is optimisation rearing its head in an already near perfect trip.
Choosing to not optimize opens yourself up for more possibilities that you can’t anticipate. And sometimes these will be a pleasant surprise. It may completely change your perspective on something that was otherwise rigid.
Who knows what opportunities and possibilities would have presented themselves to my former colleague if he didn’t view those business trips as a burden. Maybe he’d have seen that Croatia was a beautiful country he’d like to explore more of, or that he really liked the work culture he’d seen in Canada. Hell, imagine if the guy brought a car that wasn’t as dull as a Mazda 6, and whatever he purchased instead he realised he liked other elements of the car, like how generally fun it is to drive, or its giant ass sunroof.
There’s no way you’d be able to choreograph that you’d enjoy elements like these in your car if you just optimize for the best overall choice. In general, humans are remarkably poor at predicting what will make us happy in future4. Choosing for optimisation in my view is just humanity’s way of hedging its bets and trying to control certainty for what they think will make them most happy by giving themselves a wider spread of “good outcomes”.
But who’s to say that giant sunroof wouldn’t bring the biggest smile to your face?
It seems that somewhere in recent history making a big decision and being wrong became heavily stigmatized. Of course, we all want to make the right decision. But sometimes even the best-intentioned decisions end up not working out. But the issue is now people won’t make any decisions at all out of fear of fucking up.
A large part of it is shame, that omnipresent social driver. There are large elements of social shame we feel for things that don’t work out. As if people seem to love ripping into others about their failed decisions. “Why would they choose to date that person”, “well you chose to start that business”. These comments are unhelpful. It is important for someone to take responsibility for their own decisions, but comments like this come out as though that person is being shamed for their choice.
I remember talking with a friend about someone we mutually knew who’d switched jobs after being with same company for years. He was made redundant from his new job maybe 6 months into it, and we felt bad for him of course, but what stuck with me was the comment from my friend “did he choose to switch jobs?” As though it was his decision which put him in the unfortunate position of unemployment.
Similarly, when talking about my decision to move abroad, particularly about the challenges I face, and the worries I have, I’ve had comments such as “well you chose to do that” in reply. My decision to move abroad is in the minority, but to have comments indicating any difficulties I face are consequences of my own decisions just further propagates the stigma against decision making. Making a decision that goes against the majority should not be a barrier that stops people attempting to empathize with you.
Self-critical decision paralysis isn’t something I’m immune to either. Just the other week I was torn between taking the overnight train to the coast for two days, or staying at home and doing life admin. I chose to stay at home but that was just as much choosing not to take action about going to the coast, despite checking the train tickets 8 times per day and going so far as having them in my cart at checkout.
The problem eventually becomes that the stigma one will face around getting a decision wrong, whether from external or internal criticisms means no one wants to make any decision at all. So in the end we are stuck in the same situation, just choosing the path of least consequence whether those consequences are good or bad.
I firmly believe that the solution is just to make more decisions, and extra credit for making more decisions that end up being bad decisions. Not that I want anyone to suffer. I’m certainly not going to laugh at anyone’s decision.
By making more decisions you’re going to have little wins that inspires future confidence5. And even the decisions that don’t work out you’re going to realise aren’t going to kill you (well, in most cases anyway). If you’ve survived everything you have up until this point then I’d take a good bet you’ll survive a few bad decisions.
Especially any decision that results in an action (like someone deciding to just book that overnight train…) is especially commendable, irrespective of if it results in a good or bad outcome.
We need to destigmatize and deoptimize every decision and view it through the lens that actively choosing to do something of consequence in your life is better for you than sitting on the fence. If you sit on the fence for too long, the paling starts to dig in. What begins as a comfortable safety point will eventually keep you stuck, and less able to make future decisions. So just go out and make a decision, and see what happens.
In other words, JUST EAT THE DAMN ORANGES.
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