What I never asked my dad

What I never asked my dad

Read time: 6 minutes

Hey, welcome back.

Last week, we talked about fulfilling small promises to yourself. You can read that (and all past issues, here)

Today, I want to talk about advising my younger self:

I'd probably have plenty to say about work, money and the decisions I was about to make. I'd have questions too, especially about whether any of it worked out.

But I'd want to pick up the phone while I could still ask the people closest to me about their lives.

My dad ran a fashion business for decades. I started my company after he passed, so we never got to have the conversations I'd later want to have with him.

The questions came as I began to understand what running a business involved.

The questions I'd ask now

I would have loved to ask how he dealt with a difficult year. How he decided whom to trust. Whether he ever got used to having people depend on him.

Back in 2014, I wrote about wanting to build a business like his. He'd built a fashion manufacturing company and bought its premises with profits from trading. Some employees had stayed for decades.

I admired the care he took with people and the responsibility he carried for their livelihoods.

By then I had questions I could have asked years earlier, when I hadn't yet realised how useful his answers might become.

I would have liked to hear about the beginning, when he was still figuring things out. The decisions that worried him. What he learned through experience and wished he'd known sooner.

You can know someone for your whole life and still have so much left to ask.

A parent had ambitions before you arrived. An old friend has lived through things you only heard about afterwards. Your partner has memories you haven't thought to ask about, even if you talk every day.

Knowing the outline of someone's life can make us feel as though we've heard the whole story.

I think that's a shame, because there's so much pleasure in being surprised by someone familiar. Finding out they once wanted to live somewhere else. Hearing about a friendship that mattered to them. Discovering what they were like at the age you are now.

You get to meet another part of someone you already love.

There's always a reason to call later

It's easy to assume there'll be a better time for those conversations. You're busy, they're busy, and you'll see each other soon anyway.

You think of calling while you're walking into a meeting. By the time you leave, something else needs your attention. You remember again late that evening and decide tomorrow will be easier.

Nothing particularly dramatic has happened. Another day has passed.

Meanwhile, you can spend an hour listening to a stranger explain their life on a podcast without asking someone close to you much about theirs.

I host a podcast, so I say that with affection for a good interview. I love that we can hear people talk at length about how they think and what they've experienced.

I'd like us to bring some of that curiosity home.

Ask your mum what she wanted to do at your age. Ask an old friend what they're looking forward to. Give someone enough time to get past "all good, just busy".

Then stay with the answer for a moment.

It's tempting to respond with a similar experience of your own, especially when you're trying to show you understand. Sometimes another question gives them room to say what they were only beginning to explain.

What happened next? How did they decide? Do they still think about it?

You don't need to arrive with questions written down or turn Sunday lunch into an interview. Follow something they mention that interests you.

If they bring up an old job, ask who they worked with. If they mention someone you've never met, ask how they knew each other.

The conversation can wander. Let it.

There's also something generous about letting people tell a familiar story again. You may know how it ends, but you can ask about a part they've always skipped over, or simply enjoy hearing them describe a time they still remember with so much affection.

Some of the things you'll enjoy hearing won't contain advice or anything you can apply to your own life. They'll simply tell you more about the person sitting across from you.

That's enough reason to ask.

Make time for an ordinary conversation

I'd encourage my younger self to get curious sooner, and to make it easy to stay in touch.

A call doesn't have to wait until you have an hour free and something significant to report. You can ring because you thought of someone and wanted to hear how their day went.

You can send a photograph that reminded you of them. Suggest a walk. Ask when they're free and put the time in your diary while you're both looking at it.

Some conversations will stay light. Someone might be tired, distracted or simply happy talking about the television. Enjoy that too.

You're making room to hear whatever they feel like telling you.

Over time, those ordinary conversations give you more to return to. You remember the appointment they were worried about. You ask whether they went on the trip. You hear how something turned out because you were there when it began.

I like the thought of paying that much attention to someone.

You might hear a story you've never heard. You might discover they've been waiting for someone to ask. Or you might spend twenty minutes laughing about something that wouldn't make sense to anyone else.

All of those sound like a good use of an evening.

If someone came to mind while you were reading this, send them a message and find a time to talk.

You can start with exactly what happened: "I was thinking about you and realised it's been a while. When are you free?"

Dan

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The key insight: self-acceptance amplifies emotional resilience, while self-judgment weakens it.

📌 Quick Takeaway →

Your average days aren’t failures; they’re emotional training grounds.
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Why book a call? Some of my expertise/success:

I've built 6 startups. 3 fails, 1 win, and 2 still going.
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Podcasting: Leaders Media - Bootstrapped to #1 in business and 10M downloads
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