Each and every week the Square Holes team are deep in the bowels of a number of projects, working to mine all of the insights that we can to help grow businesses and support thriving cities.

These insights are used by businesses and organisations to innovate their offerings, move into new markets, track their impact and hone their products and output. Each week we will be sharing a broad insight that we have learnt for you to use in your own work.

Let us know what you find valuable!

Dylan: It ain’t all winning

Fresh off England’s World Cup defeat I’ve been reflecting on how one of the toughest things about watching the World Cup is seeing just how much teams put into it, only for their campaign to end in one disappointing moment. Years of build-up, expectation, training, planning and sacrifice can come down to a missed chance, a poor moment or one bad game. It can feel cruel, but it is also a good reminder that falling short does not mean the effort was wasted.

Working towards something difficult changes your mentality along the way. You build skills, strengthen relationships, learn what you are capable of and discover where you still need to improve. Disappointment may stick around for a while, but so does everything gained through the process. Winning matters, of course, but sometimes the positive is not the trophy. It is knowing you gave something a genuine shot, grew through the experience and will be better prepared when the next opportunity comes along – though it might not feel like it for the England players right now!

Mahalia: Nature of grief

I’m currently listening to a podcast about the effort to release the captive Orca, Keiko (one-time star of 90’s film Free Willy) back into the wild. It’s a story that hits close to home for me, as Free Willy was one of my childhood favourite films, igniting a lifelong passion for Orcas. They are incredible creatures, with high emotional intelligence. They have special brain cells called spindle neurons, which are also linked to human empathy – and it is because of this that scientists believe orcas feel complex emotions like love, grief, and joy just as people do. They live in matriarchal (female-led) pods, and share unique family cultures like specific hunting techniques, communication dialects, and social habits from one generation to the next. Mothers are also known to carry their dead with them for days while they mourn.

I also recently saw a clip on Instagram from a mother who kept her daughter’s body in her home for a week after her death so that people could come visit and spend time with her, as well as slowly get her body used to the loss of her child. It’s a tradition in many cultures around the world, but something viewed as foreign and macabre in many Western cultures. Maybe Orca’s also understand the need for time to let the reality of loss sink into your skin. Maybe the systems we create don’t always serve us in the ways we think they do.

Jason: Matters of perspective

Last Friday, I finished a great lunch with a business colleague who has become a solid lunch mate over time.

Nice food, conversation about work, family and life, a few beers, and that joyful Friday buzz that comes from this. A great week, lots on, and made even better because he paid.

As I left the venue, feeling joyful, I stepped outside and checked my emails after a couple of hours offline, I was ready for the walk through the Adelaide CBD back to the office.

And there it was:

“We’ve decided to proceed in a different direction for this project.”

My stomach sank. I reread it. Correct. Then again, expecting it to read differently.

I’m assuming some ‘selling’ is win some, lose some. Does a coffee shop worry when a customer goes elsewhere? But this was one where we thought we’d put in a big effort, a couple late nights, felt like we’d nailed it, and our long relationship meant I was really just awaiting the, “Thanks for your patience, Jason. You’re in. What are the next steps?”

But, no.

“We’ve decided to proceed in a different direction for this project.”

Not the Friday email I’d hoped for. It sent my mind into a pointless loop. Trying to find the gaps. What did we do wrong? How could we change the decision? Noooo. A nice email back asking if there was anything else we could do. An email to the CEO, who we’d worked with previously, saying we’re here moving forward and wishing them all the best.

It got me thinking that the more you care, the more it stings. So, the best—and perhaps only—thing you can do, if it really matters, is to do everything possible not to lose.

In the absence of competition, it is about working with the customer to find the best solution, leveraging a trusted relationship and an aligned partnership to achieve the best outcome. However, when competition steps in—a tender process—this is where it can get more complicated.

How do you stand out and win when there will inevitably be more losers?

When procurement processes are often one document competing over another, standing out can be complicated.

When it really matters, do everything you can to make the opportunity count. And, importantly, never assume you are the front-runner, have an advantage, or allow any ego about ‘being the best,’ or assume the decision is simply part of a governance process. Once the decision is made, the final whistle blows. The competition is over. There is no changing the outcome.

I’ve been watching the World Cup. Lots of disappointment, regrets and what-ifs. England being knocked out of the World Cup, going down 2–1 to Argentina in the closing minutes. The near-favourites, who haven’t won since 1966. France, winners in 2018 and again among the favourites, falling short. US President Donald Trump intervening intended to help ‘his’ team  (to have striker Folarin Balogun’s red-card suspension lifted), yet perhaps distracting the USA team and further motivating Belgium on their way to a 4–1 win. The Socceroos likely replaying the “what-ifs” after several strange penalty shoot-out decisions likely contributed to their loss to Egypt, who then faced Argentina. There are more losers than winners in the World Cup, in sport, and in business.

You replay conversations, proposals and decisions, wondering whether one small change might have altered the outcome. A somewhat pointless revision of history. I’ve spent much of the last week reflecting on what, in the scheme of things, is a relatively small loss, amongst many wins in a year. Yet, gradually, the disappointment gives way to perspective.

I’ve always believed we learn more from losing than winning. And the more you care, the more it hurts. Losing forces reflection. Losing sucks. Do everything possible to put yourself in the best position to win.

My Miss 17 has figure skated for longer than we can all remember. She’s always loved it. A girl and the ice, competing against others. Even with all the practice, losing is inevitable. It breaks the hearts of parents, but the best way to soften the sting of losing is to do everything possible to win. Even when it follows multiple losses, eventually something clicks, or you stop. Miss 17 now has an impressive medal cabinet.

Losing challenges us to improve, prepare better and work even harder next time.

Perhaps that’s the price of caring. If the losses don’t hurt, maybe they didn’t matter enough. The challenge isn’t avoiding disappointment; it’s learning from it, picking yourself up, and trying harder next time.

Yep, we lost the proposal. It wasn’t meant to be. One loss amongst many wins in a year. We gave it everything we had and learnt from the likely gaps for next time. At least we haven’t had a 60-year World Cup drought like England. Even the conquerors of the world—and the favourites—struggle sometimes.

The loses you care about sting, so try your very best not to lose.

Square Holes is a cultural insight studio.

We design mixed method explorations of people and culture beyond the category,  uncovering the patterns, tensions and shifts shaping behaviour to inform strategy, inspire innovation and enable confident decisions. Our studio model brings together the right mix of thinkers, researchers and specialists for each exploration. If you’re navigating change, entering a new market, or seeking deeper understanding of people and culture, let’s start a conversation >