Don’t Wait for Tomorrow: The One Conversation You’ll Never Regret

I was asked a question today that I’ve heard a dozen times before, yet for some reason, this time it stopped me in my tracks. “If you could sit on a bench and talk to anyone, who would it be?” Usually, people give the standard answers - a famous world leader, a legendary musician, or perhaps a brilliant philosopher. But as I sat there, the only face that came to mind was my dad’s.

It hit me with a physical weight. I realised in that moment that there are so many conversations I still wanted to have with him. So many questions about his life, his challenges, and his perspective on the world that I never got around to asking. The lesson I took away is one I want to share with you today: have those conversations now. Don’t wait for the ‘perfect’ moment, because tomorrow is never guaranteed.

The Question That Changed My Day

The park bench metaphor is a powerful one because it strips away the noise of our modern lives. There are no pings from a smartphone, no urgent emails, and no project deadlines. It’s just two people, a bit of fresh air, and the time to truly listen. When I thought about that empty seat beside me, I didn't think about the business deals I’ve closed or the property developments I’ve completed. I thought about the gaps in my own story—the parts that only he could fill.

I lost my dad not too long ago, and while we were close, the finality of that loss brings a very specific kind of clarity. In my book, The Rock Bottom Paradox, I talk about how hitting your lowest point—your own personal 'rock bottom'—is often the moment the map disappears. You’re forced to look at your life without the usual distractions. For me, one of those moments was realising that my 'why' for working so hard was often rooted in making my parents proud. When that person is gone, you have to reconcile all the things you meant to say but didn't.

We often live as if we have an infinite supply of 'tomorrows'. We tell ourselves we’ll have the deep chat at Christmas, or when the work project is finished, or when life feels a bit less chaotic. But life is never less chaotic. If we wait for the silence, we might find ourselves sitting on that bench alone, talking to a memory instead of a person.

The Myth of 'Perfect' Timing

The reason so many of us delay these meaningful connections is what I call the ‘Arrival Fallacy’ or the ‘When I...’ Trap. We think, “When I’ve made my first million, I’ll take Dad on that trip,” or “When I’ve scaled the business, I’ll have time for those long Sunday lunches.” We treat our relationships as something to be ‘dealt with’ once the ‘real work’ of success is done.

But here’s the hard truth I learned from my mentor: Success isn't just a number on a balance sheet. True wealth is the freedom to spend your time with the people you love while they are still here to enjoy it. If you trade your best years for a bank balance at the expense of your closest bonds, you aren't building an extraordinary life; you’re just building a very expensive form of regret.

In my recent work on The Extraordinary Millionaire Blueprint, I emphasise that mindset is the foundation of wealth. Part of that mindset is recognising that 'abundance' includes a wealth of connection. When we are at rock bottom, we are stripped back to our core. We realise that the fancy cars and the status don't mean much when you're grieving. What matters are the conversations, the shared laughs, and the feeling of being understood. Forgiveness, which I explore deeply in Step 4 of the Blueprint, is also a huge part of this. If there’s a wall between you and a loved one, tear it down today. Don't let pride steal your time.

Three Steps to Close the Gap Today

It’s easy to feel a bit of guilt when we realise, we’ve been neglecting the people who matter. But remember, guilt is a 'bad debt', it costs you energy without giving you a return. Instead, take responsibility. Turn that realisation into action. Here are a few gentle, practical steps you can take this week to make sure you’re having the conversations that count.

1. Schedule a 'Bench' Moment You don't need a literal park bench, but you do need to remove the distractions. This week, pick one person you care about—a parent, a sibling, an old friend—and invite them for a walk or a coffee. Crucially, leave the phone in the car or at least in your pocket on silent. Give them the luxury of your full attention. Ask them one question about their childhood or their greatest dream that you’ve never asked before. You’ll be surprised at what you discover.

2. Ask the 'Uncomfortable' Questions We often stick to the surface level: work, the weather, the kids. We avoid the deep stuff because it feels awkward or heavy. But those are the stories that stay with you. Ask your parents what they were afraid of at your age. Ask them what they are most proud of. Don't wait for a milestone like an anniversary or a birthday. The most profound insights often come during the most ordinary Tuesdays.

3. Express the Gratitude Now In The Rock Bottom Paradox, I talk about gratitude as a tool for survival. But it’s also a tool for connection. If you appreciate someone, tell them specifically why. Don't just say "thanks for everything." Say, "I really appreciated it when you did X, it meant a lot to me." Vocalising your appreciation closes the distance between people. It creates a 'win-win' in the relationship where both parties feel valued and seen.

The Journey is the Destination

Life is an undulating journey of peaks and valleys. When we are climbing the mountain of our careers, it’s easy to get tunnel vision. We focus so hard on the next foothold that we forget to look at the person climbing beside us. My dad was one of my biggest supporters, and while I can’t sit on a real bench with him today, I can honour his memory by encouraging you to sit on one with the people you still have.

Don't let your success be a lonely place. Rebuild your life, grow your wealth, and chase those extraordinary goals—but bring your people with you. Make the time. Pick up the phone. Drive the extra twenty miles for a visit. We spend so much of our lives trying to 'get somewhere,' but often the most important place we can be is right where we are, listening to the story of someone we love.

If this thought has hit you as hard as it hit me today, please don't just 'like' this post and scroll on. Let it be the nudge you needed. Tomorrow is a beautiful idea, but today is the only reality we have to work with.