Feeling overwhelmed? Do as Challengers do and lean into your constraints.

Liston Pitman & Toby Brown

Like many of us, Challengers are no strangers to constraints, but they see them differently to most. Where the natural first response when faced with a lack of resource, experience or interest, is to limit ambition or potential, those with a Challenger mindset work hard to find the opportunity within the limits they face – to disrupt the status quo, to find a more creative solution, to gain a competitive edge. 

We’ve even written a book about it. 

But alongside these more familiar constraints, there’s another kind that we all face. One we haven’t clocked as a limitation at all. Quite the opposite in fact, as they often present as can’t-miss opportunities for us or our organisation. 

The Tyranny of the Shoulds

In the 1950s, psychoanalyst Karen Horney coined the phrase ‘tyranny of the shoulds’, referring to the tension caused by the gulf between where you are and an idealised sense of where you should be. For the individuals concerned, this was not only a source of psychological distress but also a hindrance to their ability to go on to achieve actual progress. 

When we’re pulling (or being pulled) in many directions, it’s hard to make progress in any. 

While many of us have probably felt the touch of this tyranny at some point in our individual lives and careers, we’d bet with some certainty that we’ve all experienced it at an organisational level too.  

It can be driven by factors like personal ambitions and aspirations, the cultural inertia of what we’ve always done around here and the relentless pressure to keep pace with the competition. Not to mention the constant deluge of philosophies and models we’re told we should be adopting by LinkedInfluencers and consultancies (ahem). 

Even in good times, this runs the risk of spreading our energy and resources too thinly. What are often perceived as opportunities instead begin to act as constraints – dividing attention (both external and internal), splitting resources and holding an organisation back from making real progress. 

In the tougher times many of us are experiencing, when there’s little flex in the system and a strong instinct to be trying everything, these shoulds can be even more dangerous. When mounting constraints meet unending shoulds, it starts a sort of death spiral that drains effectiveness and morale. 

The Prime Constraint

In this storm of competing demands and constraints, Challengers have a counterintuitive way to relieve the pressure – they add one more constraint to the mix: a constraint to rule all others, the constraint of brand.  

For a Challenger, brand is more than just a platform for marketing. It’s a clear point of view on the world that they use as a lens for making any decision. Instead of falling prey to the logic of the tyranny of the shoulds, what a brand should be doing or where a brand should be focusing resources, they ask, “How would a brand challenging X (or a brand about Y) do Z?”  

This gives them, to paraphrase David Ogilvy, the “freedom of a tight brief” – an unwavering sense of what they stand for and what they stand against that translates into what they should be doing, and what they shouldn’t. Or, to paraphrase our founder Adam Morgan (who’s probably also worth a mention), a clear sense of where to sacrifice and where to overcommit. 

For a great example of the former, take a past partner of ours: Tillamook County Creamery Association, a brand standing against fake food and for ‘Dairy Done Right’. In one meeting we had with them, one of us asked how they felt about missing the Halo Top opportunity – a booming sub-category of good-for-you ice cream with less cream and sugar. They gave us an answer filtered through the sort of prime constraint we’ve been writing about: How would a brand about ‘dairy done right’ handle the launch of a Halo Top-style ice cream? It wouldn’t launch it – that’s not ‘Dairy Done Right’. 

Or look to citizenM, an affordable luxury hotel chain with locations from London to Austin to Taipei. They’ve built a brand for a very specific audience mindset: “those who take the train, but drink champagne.” And so, when they were creating their hotel experience, they asked themselves over and over, “How would a brand for that person do this?” And sometimes the answer was: “They wouldn’t.” When it came to the rooms, they literally took out a red pen and crossed out all the things that type of person wouldn’t be into – no chest of drawers, no double vanity, no fluffy slippers. Ditto with check-in staff in the lobby – you’ve got this far, so you can probably manage the last few meters to your room.  Having sacrificed the things that weren’t right for their brand, they’re now free to overcommit to the things that do really matter to that audience: lightning-fast WIFI, a truly incredible bed, a lavish late night bar and more. 

Self-Application

It’s worth emphasizing here that the prime constraint is not just valuable for knowing what to overcommit to, but also how to do so. Consider Tracksmith: a running brand challenging a category it sees as so focused on the edges – couch-to-5Kers or the elite-est of the elite – that it’s lost sight of everyday, dedicated runners and the ‘Amateur Spirit’ that defines them. Making decisions using brand as a constraint has helped Tracksmith turn intractable problems into unique opportunities. For instance, ‘How would a brand championing the Amateur Spirit of running handle sponsoring athletes?’ This is a staple of the category for a reason – it’s a crucial channel for building awareness and affinity. And Nick Willis, Tracksmith’s Senior Manager of Sports Marketing & Partnerships, acknowledges that there was some internal debate at the beginning: category shoulds vs. company values. But how do you square the two? 

Enter Tracksmith’s Amateur Support Program – a scheme to support non-professional runners training for the Olympic Trials and provide them as much benefit as could be given without compromising their amateur status. This isn’t just an empty excuse to enact a version of a category staple, it turns that staple into something that reinforces what Tracksmith is all about and benefits the amateurs they exist to serve.

As Nick told us, “limited sponsorship opportunities means only the top 1-5% of athletes are able to be supported at any sort of sustainable level. That means there’s a huge chunk of athletes that are yearning for any sense of support, and not just financial, but a sense of belonging and being part of a team. They’re being blown around by the wind in the challenging space that is the wild west of post-collegiate track and field and marathon running.”

By breaking from the tyranny of shoulds in their category, Tracksmith has started to make a dent in a defining problem of their space. And, as a bonus, various iterations of this programme have given the brand some of its most viral moments: at both the 2020 and 2024 Olympic Marathon Trials, around 20% of the overall field sported a Tracksmith singlet because of it. 

It feels important to emphasise that this way of thinking is not just for mature brands and businesses – you can self-impose the prime constraint of brand from day one. Take Thursday, a dating app that launched a few years ago into an already noisy and saturated category. They had a clear point of view on what this brave new world of swiping and algorithms had delivered for their consumer: digital fatigue and dating apathy. To them, the problem with dating apps was too much time spent on the apps. 

“If you have too much of something you’d get bored of it. That may sound strange but you can have too much of a good thing.”

Matt McNeill Love, Thursday Cofounder and COO, Verdict

Why would a company that believes that launch another dating app? Or, more aptly, how would a company that believes time spent on dating apps is killing dating, design a new app? They would, as their name suggests, create a platform that only works one day of the week. Matching and messaging opens on Wednesday at midnight and deletes at midnight on Thursday, because as they say, “This is not for the time wasters.” In sacrificing the other six days and overcommitting to Thursday, they’ve created a sense of urgency and given dating a hard shove out of the digital world and back into the real one. And, beyond their app functionality, they’ve doubled down on bringing IRL dating back with hugely popular in-person events held on, of course, Thursdays. 

The tyranny of the shoulds is an ever-present pressure on the attention, focus and potential of every organisation. But adding a prime constraint, a clear and directional brand point of view, can act as an invaluable antidote to this drift and loss of focus. In the words of Patrick Criteser, President and CEO of Tillamook County Creamery Association, “It’s stopped us chasing trends and instead kept us true to ourselves.” 

So, a simple question for us all: are we clear enough on what we stand for or against and do we use that as a filter for decision-making? What’s our version of ‘a brand against X’ or ‘a brand about Y’ and can we discern what to sacrifice or how to overcommit on the basis of that alone? 

If not, might we actually need the clarity of a tighter constraint? 

If you’d like to know more about how eatbigfish can help you tackle your strategic challenge with a challenger mindset, get in touch at www.eatbigfish.com – we’d love to hear from you.