Dan Cullum

When leading a project or running a business, an abundance of time, capital, and talent is a luxury.

If only we had an extra week. If only we had additional budget. If only we had more engineers. Then, things would be different. We’d do better.

However, needing to succeed or die can be a powerful advantage for a team or company.

The need to survive begets creativity, it demands resourcefulness, it encourages decisiveness.

When there is an ample supply of food for the winter, where is the motivation to hunt and forage for anything better?

The tale of Oscar Figueroa is one of grit and persistence.

The 21 year old Colombian weightlifter participated in his first Olympics in 2004. At 165cms and 62kgs, Figueroa had been training and preparing since he was a teenager. In Athens, he finished a commendable 5th, but well short of his goal: a gold medal.

Four years later, Figueroa competed in Beijing but a spinal hernia prevented him from completing a single lift.

This was his lowest point. Tears. Heart ache. Disappointment.

When Figueroa walked out onto the Olympic lifting platform at London 2012, it had been 8 years since he’d successfully completed a lift on the Olympic stage. Despite setting an Olympic record on his lift, he was still beaten, and took home a silver medal.

Refusing to give up, Figueroa participated in his fourth Olympics in Rio de Janeiro in 2016. Figueroa braced himself on the weightlifting platform and propelled the 176kgs above his head. He lifted 26kgs more than his first Olympic outing in 2004 to finally win a gold medal at age 33.

Following this personal best performance, Figueroa symbolically took off his shoes and placed them on the platform to signal his retirement.

As we admire Figueroa’s journey, it’s a nice reminder to remember the grit and persistence hidden in the 4,380 days between his Olympic debut and his gold medal win.

The economist J.K. Galbraith once wrote, “Faced with a choice between changing one’s mind and proving there is no need to do so, almost everyone gets busy with the proof.”

What if our default thought was, “What if I’m wrong?”

What disharmony, frustration, or wasted effort would we avoid? What personal learning, improved relationships, and better answers would we gain?

The cost of defensiveness is higher than we think.

I’ve realised through these daily reflections that a key component of my happiness is learning, and having the opportunity to put that learning into practice.

Much of the dialogue on self-improvement is on becoming a better person. This could be building better habits, growing in confidence, or identifying lessons learned from experiences.

It also occurred to me that we spend little time and effort on removing the unhelpful habits in our lives. What would happen if we invested time in getting rid of ideas and practices that no longer serve us? This can be viewed as the process of unbecoming.

A house plant provides a good analogy. Unrestrained growth can get unwieldy and stifling. Often, we need to prune and get rid of the dead matter. This allows the plant to continue growing.

Becoming and unbecoming, to add and to remove, go well together.

Whiskey is a long term game.

It can take 200 years to get from acorn, to oak, to cask, to spirit, to whiskey.

We visited The Macallan Distillery in Northern Scotland today, and what struck me most is the long term thinking required to run a whiskey business.

The spirit they distil today will be put into casks to mature for at least the next 12 years. Their best whiskeys will be left to mature for 72 years. And the casks used for maturation are made from oak trees that are at least 100 years old before being felled.

There are no shortcuts, no quick hacks, and no quarterly short term profiteering.

It’s a pure, calculated long game.

When leading a company like Macallan, you reap the good and bad decisions of the people that came before you. You also know the product you make today will likely be consumed by people well after you’re gone.

I can’t help but be inspired by this type of long term thinking. What if we applied it to business, government, and environmental decision making?

Maybe we can learn something from, or over, a few whiskies.

Today marks 100 days of daily blogging.

For a little over 3 months, come rain or come shine, I’ve executed my three daily blogging rules:

1. Show up every day (there is magic in that)
2. Be curious and notice something in the world
3. Share what I notice in the most thoughtful and generous way I can

The experience has been overwhelmingly positive. The habit of shipping something everyday has forced me to be attentive to the world around me. Each learning or experience is now an opportunity to reflect and look at the world in a new way. Turning thoughts into succinct daily posts has forced me to clarify my thoughts.

Some days, it was a struggle. I felt uninspired, tired, and worried the well had run dry. Other days, new ideas came thick and fast, and I was able to pen down 2-3 posts in a sitting.

What I do know is that I’m going to keep it up. I set myself the goal of 100 days to make sure daily blogging was something I enjoyed. With that confirmed, I’m going to spend the next 100 days figuring out where I want to take it.

Finally, I can’t fail to acknowledge the inspiration Seth and Rohan have been in 1) inspiring me to begin, and 2) helping me to build this habit. When I see them turn up every day and say something meaningful and generous, it’s forged a path I’m thrilled to follow.

We’d be better off if we removed the word “obviously” from our day-to-day language.

Our world is complex. Conclusions and insights are, more often than not, non-obvious.

Using “obviously” in our responses implies that we know better than others and that we hold the truth. It removes objectivity from discussions. It eliminates the possibility that we may be wrong.

The best people I’ve worked with were always willing to see a problem from a different angle. They held opinions loosely. They knew that at any moment, and in any discussion, they could be wrong.

They didn’t use “obviously”.

On the contrary, they often introduced a point with, “I could be wrong, but how about this idea…”

“Obviously” risks alienation.

“I could we wrong…” leads to open, honest, and truth-seeking discussion.

I’m currently on a roadtrip in the Scottish Highlands with my sister, her husband, and my 1-year-old nephew.

After 3 years of living in the UK, I’m thrilled to have my Kiwis finally visiting.

When you’re separated by a 40 hour door-to-door journey, time together is scarce and precious.

Life is so rich; and this week, I’m hyper conscious of remembering that on our travels.

The dimly-lit Edinburgh pub was filled with silent Kiwis this morning as we watched the All Blacks lose in dramatic fashion to a romping England.

Despite the myth, folklore, and expectation surrounding the All Blacks’ quest for a third consecutive Rugby World Cup victory, the better team won today’s semi-final.

England were ferocious. The All Blacks, a shadow of their usual selves.

Thus marked the end of 12 years without a World Cup loss for the All Blacks. The end of dominance.

I’ve written quite a few posts (here, here, and here) about the All Blacks in recent weeks, and have been reading much about their psychology from the excellent book, Legacy, by James Kerr. Understandably, I had great expectations for a win today.

However, seeing their defeat helped me realise that no matter the preparation, the planning, the dedication, the mindfulness, the focus, the belief, or the courage; sometimes you get outplayed.

And that’s okay. That’s sport, and that’s life.

One match, mistake, or failure, doesn’t define you; even if it does hurt a bit.

Last week I wrote a post about Derek Sivers on how he has the best “About Me” page on the internet.

I’ve since been exploring his other content, and one blog post that stood out to me was his process for keeping a daily diary.

Derek has kept a daily diary for more than 20 years, and has structured his files to easily search and explore his ideas from many years ago. He claims being able to reflect on how he felt (often years) in the past helps him make better decisions in the present.

Since committing to daily blogging, almost everything I’ve written has been publicly posted on this blog. I don’t have any record or collection of private writing.

So for the past week I’ve been following Derek’s daily diary writing process, and I’ve been surprised as how helpful it has been.

There are two things that have stood out to me.

First, the private nature of the writing means my standards are a lot lower. I don’t think as much about the structure or being to the point. I just let the thoughts fall onto the page in whatever form or format they come out in. This is liberating.

Second, I follow Derek’s advice of writing until I have penned down all of my thoughts or emotions. It’s like a weight is lifted once I’ve externalised all the thoughts I’ve had on an idea.

I’m going to continue experimenting with the private daily diary and report back on what I’ve found.

I’d recommend having a read of his blog post and seeing if there is anything that you’d like to try. At the very least, it’ll likely make you think twice about writing or keeping a record of your thoughts.

There is much written about the benefits of saying no, and focusing our limited time on our most important work.

So when I see a new way to think about this idea, it grabs my attention. James Clear did just that this week.

When you say no, you are only saying no to one option.

When you say yes, you are saying no to every other option.

It’s easy to say yes to one person’s request. But would we still make that decision if we had to say consciously say no to everything else?

It puts things in perspective huh?

When I was 9 years old, I played a game with friends called “The Prickle or The Green”.

This simple game has some surprising learnings about the art of decision making. Here’s how it worked.

Two competitors stand at the front side of a house (think farm house with a wide amount of space surrounding it).

One of the competitors kicks a rugby ball over the roof from the front yard to the back yard.

As soon as the ball is kicked, the competitors race around the house, and the first person to collect the ball gains a point. The game is repeated until one person reaches 5 points. At this point, they win the match.

Now, this game may seem a little lame, until you learn that this particular house, on this particular farm, had two ways to get from the front yard to the back yard: the Prickle or the Green.

The Prickle was the faster route, but you needed to contend with, you guessed it, prickles or small thorns.

However, the Green, despite being an easy run across the lush grass, required the runner to cover a much larger distance.

The trade-off looked like this.

If you were fast, the Green was generally your best bet. At the very least, it was the pain-free path.

However, if speed wasn’t on your side, the Prickle gave you a shot at winning, but you’d need to endure the prickles that would cover your feet.

It’s was a simple game, with a simple trade-off, and that’s why it’s an interesting model for thinking through decisions.

Here are some of the lessons from the game that apply in broader contexts:

1. Before you begin, size your opponent, task, or challenge; have a clear idea of what it is you’re up against
2. Assess the probability of winning with a given strategy (the Prickle or the Green)
3. Once you’ve picked a strategy, you need to commit. Turning around and going back is certain failure, so you need to see it out until the end and adjust your tactics in the next game
4. No pathway forward guarantees success. You either take the long and safe road, or the thorny, fast route. Both have their risks.

We’re often faced with trade-offs that can be boiled down to two competing alternatives; much similar to the Prickle or the Green.

When looking at a world map, our eyes instantly focus on landmass.

We’re usually hunting for a route between two places, or perhaps we’re looking for a new country to explore.

Almost none of our attention is given to the ocean; yet the ocean accounts for 71% of the earth’s surface.

This habit of ours got me thinking: what if we approached problem solving in the same way we approach maps?

What if we only focused on 29% of the known problem space? What if we ignored the other 71% because it’s outside our experience or realm of understanding?

Unless you’re a sailor, there are no consequences to ignoring the oceans. However, when working on complex problems, there are severe consequences to focusing on a limited part of the problem space.

Looking at the whole map, the whole world, and the whole space, helps us navigate more effectively when compared with focusing only on that which we know.

H/T to Maru for helping me think differently about how we look at our oceans and maps

While traveling the Mississippi River, we had both a fuel tank for our outboard motor and a battery system for our electronics.

Petroleum and electricity don’t mix well, so in our design we kept the tank and the battery on separate sides of the boat.

Both powerful. Both essential. Both useful. But both better, and safer, when separate.

Sometimes lumping two good things together isn’t the best path forward.

Fish and steak rarely go well together, but are heavy hitters when served separately.

Two decisive leaders charged with making decisions for the same team can lead to more harm than good. But when deployed to two different teams, magic can happen.

There is such a thing as too much of a good thing.

It’s the role of the leader, manager, designer, architect, mechanic, engineer, artist, parent, or teacher to recognise and select for a balance of strengths in any situation.

Today was the first time this autumn I was struck by the changing colour of the leaves.

On our walk through Primrose Hill and Regents Park, I began reflecting on how our natural surroundings are a gentle reminder of change.

They shape-shift imperceptibly until, one day, they pop, and we notice we’re in a new reality.

It’s colder. It’s warmer. We’ve made new friends. Created memories with old ones. Changed jobs. Read new books. Learnt new skills. Tried new cuisines.

Much happens against the backdrop of the budding, browning, and falling leaves.

It’s nice to have nature be a reminder to reflect back on all that has changed this year.