What’s in the Box?

In his book entitled Halftime, the author Bob Buford uses the metaphor of “the Box” to help define the single priority at the centre of your life. In the first half, most people fill their box with success-driven goals (career achievement, money, recognition) often without ever questioning whether those pursuits truly matter. Midlife (in my experience, at least) exposes the disconnect, creating restlessness and a desire for deeper meaning.

Halftime, then, is the moment to pause and intentionally choose what belongs in the box for the second half of life: the one thing you want your decisions, energy, and legacy to revolve around. Whether it’s family, service, spiritual impact, or community transformation, clarifying your box shifts your focus from success to significance and becomes the North Star that guides every meaningful choice ahead.

I have been reflecting a great deal on my life as I write these articles each week. Each piece feels like I am pulling on a thread of some giant Gordian knot, trying to untangle and make sense of the ideas floating around my head. Of course, we know the way to unpick the Gordian knot is to cut through it with a blade, which leaves me wondering. What’s my blade? What’s the one central idea that helps me cut through the tangled mess and make sense of all my interests and various pursuits? What’s in my box?

One word. Community.

I owe you an explanation

I have enjoyed a moderately successful career. I have never been the smartest guy in the room, but more often than not I was prepared to work harder. Plus, I have enjoyed more than my fair share of luck. But honestly, whatever corporate success I enjoyed never truly brought with it a deeper sense of meaning or purpose, beyond the necessity of providing for myself and my family.

Early in my career I was quite ego-driven and reactive. I felt responsible for having all the answers. I was a classic micromanager. I often thought in terms of “my” career and “my” success. I thought in terms of the sovereign individual, not the power of the collective. I failed to invest meaningfully in relationships.

It took a painful shock to help me find a better way. I went through a divorce 12 years ago, something for which I take full responsibility and I am sorry to this day for the hurt we all suffered. Yet it felt necessary at the time for reasons I am only now beginning to understand.

A selfish act

In the immediate aftermath of separation my weekends without the kids were horrible, my identity stripped bare. I set about my filling my days any way that I could, and I landed upon volunteering. I ran an internet search and found some places where I could start to make use of my empty hours on weekends. Shout out to Kids Giving Back and Streetwork, both fine Sydney based charities, for giving me a chance.

Please understand, this was a massively selfish act. Yet it proved to be the wellspring of something far bigger and far more meaningful than I ever could have imagined. The people met didn’t know my background, nor did they particularly care. They were just happy as I was there to lend a hand, and I was grateful to do so. For sure, volunteering was a welcome distraction, but it over time I realised that it felt good to give back and be part of something.

I began to realise that even though I had nothing, I still had something to give. My time. A helping hand. Friendship. And as I started to volunteer I realised that it could also serve as a way to reconnect with my kids after the trauma of divorce.

I took my youngest son along to Kids Giving Back and for the first time in a while we were able to just hang out together and enjoy a ‘normal’ father-son relationship, without a dark cloud hanging over us. My eldest took up football refereeing as part of his Duke of Edinburgh award, and I signed up too. Again, it gave us something I common to talk about and enjoy together. A new space, and a community of like-minded people.

A new identity

It felt good, and I started to do more volunteering with different organisations. I found myself meeting all sorts of interesting people with a very different perspective on life, one that was not self-centred or self-oriented, but oriented towards being of service to others.

It started to shape my outlook on life, to change how I perceived my worth. I began to move through the world in a different way. Others must have noticed, because before too long people started approaching me with ideas for fundraising or volunteering activities. And most often I said yes because it felt good. It became intentional. And that intentionality eventually led to the greatest gift that has ever come my way in my professional life.

I was Group CEO of a privately held IT services company in Australia at the time. We were planning to IPO. It was an exciting time, and I was highly motivated. We were growing fast, profitable, acquiring companies. Then I got a call.

A former colleague was stepping up to become CEO of a large enterprise software firm. He was looking for a regional leader for Asia Pacific and Japan, as well as Middle East and Africa. He was offering good money, but he knew what I was up to with the planned IPO.

More importantly he had witnessed my growing interest in volunteering and played his trump card. “I am shareholder knife” he declared over breakfast. “You are stakeholder fork”. I was intrigued. He told me he had observed my growing interest in volunteering and needed someone not just to run the region (which felt like something of a step down from Group CEO) but also to build out the company’s corporate social responsibility program. He wanted someone to establish an independent entity that could serve as charity of choice for the company and unite the global workforce behind something meaningful.

Let’s just stop right there for a moment. Sales 101. He baited the hook and knew precisely what would grab my attention. Chapeau to my new boss.

Yes, the money was good, and the relocation to Singapore (while challenging) would help me recover financially post-divorce and ultimately enable me to support myself, my kids and my parents, which matters to me. But the reason I decided to join was crystal clear. My intentionality had found an outlet, a purpose.

Purpose and meaning

The IFS Foundation, the charity I helped found and which I still have the privilege to chair, helps kids in rural Sri Lankan communities get access to a decent education. If you want to find out more, please visit us (and donate) at www.ifsfoundation.org.

Now, setting aside the shameless plug, what matters is that is a community-led initiative that has become a source of deep joy and meaning. We partner closely with the communities we serve. We look for what is already strong in those communities, and we seek to build on those strong foundations. Along the way we remove the many obstacles that children face while promoting sustainable development in a way that is firmly grounded in a sense of community, the power of the collective.

On a personal level, volunteering continued when I moved to Singapore, first through Willing Hearts. It was the time of COVID and lockdowns. I felt desperately alone in my apartment. I needed a sense of connection. Willing Hearts gave me that opportunity.

I took the 5am — 8:30am shift, cooking 10,000 portions of rice each Saturday and Sunday in giant pots. I would regularly get scolded while pulling the hot metal pots out of the cookers and would occasionally get scolded by the aunties packing the food if my rice was not up to scratch. Ah but it felt good to lend a hand. I had a willing heart. I was part of a community, a group of like-minded people all working with common purpose, in service to others. I felt like I belonged.

After a while, I started to feel like I wanted to make better use of my business skills through volunteering. I intentionally went in search of skills-based volunteering opportunities and that is when I discovered the wonderful team at TalentTrust.

I did a stint helping a small charity with some strategic planning. That, in turn led to me being asked to contribute to a masterclass that TalentTrust was running in partnership with The Majurity Trust. Suddenly my eyes were opened to the wider world of philanthropy, and I was hungry to learn more.

I didn’t take much convincing

Again, being intentional, I knew I had knowledge gaps, so I signed up for a course with the Wealth Management Institute, and before long I found myself having coffee, by accident, with the CEO of The Majurity Trust (a sure sign that the universe has a plan). Since that day I have been volunteering with The Majurity Trust, and once again not only does it give me the opportunity to put my skills and experience to good use. It also provides me a strong sense of community.

At its heart, The Majurity Trust holds a desire to see every Singaporean thrive, regardless of age or status in life. I love my work there. I value the many friendships I have formed. The work keeps me grounded.

What really matters

The common thread in all this is quite obviously community.

The more I unpack this idea, the more I feel an urgent and persistent connection to my core values. I fundamentally believe the world is made up of decent people. I believe in the power of the collective. I value being of service to others. These things matter to me.

Today, I have started up a new business with a good friend. At its heart is the building of a community for men navigating midlife. I am part of a music club, a community of likeminded lovers of live music. I just completed the Distinguished Senior Fellowship Program at National University of Singapore, a program grounded in community. I invest time and energy in relationships that matter.

Today, every decision I make is informed by the idea of community. It serves as my North Star. It’s why I will soon launch a podcast called The Giving Habit, as a means of contributing to a community of like-minded people and to help grow the giving pie.

While I am still learning, I hope this clarity serves me well in the second half of my life. But enough of all that. Dear reader, what about you? What’s in your box?

If it helps, here are some of the core reflective questions Bob Buford encourages each of us to ask to clarify what belongs in our “box” for the second half of life. These aren’t always listed as a single set in Halftime, but they represent the themes, prompts, and diagnostic questions he uses throughout the book and in his coaching.

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1. What matters most to me — really? Strip away titles, income, and accomplishments. What remains?

2. What do I want my life to stand for? If someone summed up your life in one sentence, what would you hope it said? Buford sometimes refers to this as what you would want written on your epitaph (and no I am not talking about Spike Milligan’s decision to write “I told you I was ill” on his gravestone!)

3. What gives me the deepest sense of meaning or joy? Not momentary pleasure, but rather sustained, soul-level fulfilment.

4. What would I pursue if I were not afraid? Fear often hides the deeper calling.

5. What am I uniquely wired or gifted to do? Your box should align with core strengths, not just obligations.

6. Who are the people I most want to invest in? Family, a cause, future leaders. Who matters most?

7. What is the contribution I want to make in the world? Buford keeps asking: Where can your life make the greatest difference?

8. If everything else were taken away, what must remain? This is the “pressure test” of your true priority.

I hope the answers to these questions, and the conversations they inspire, will promote intentionality. I hope you find the process of reflection as rewarding as I have. Want to talk it through? Please feel free to reach out. I would love to hear from you. We are in it together.

And to Bob Buford, if you’re reading this, thank you.

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This post was previously published on The Wisdom Vault.

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