How To Survive Life's Toughest Conversations | Men's Health Magazine Australia

How To Survive Life’s Toughest Conversations

Five guys who’ve faced up to their own test of nerve share their tactics on how to pull it off.


Tormented and off the rails, leading sports journalist Andrew Webster resolved to tell his father the truth.

The most significant conversation I ever had was with myself, and it came after staring at a wall one Saturday morning while watching Rage, trying to decide if I should jump off the balcony.

I can still remember the music video: Natalie Furtado’s. Towards the end of that clip, she falls backwards from a tree and hundreds of hands reach up to catch her.

I burst into tears. “Mate, you are fucking gay,” I said out loud. It all started from there.

But the hardest conversation of my life was always going to be with my dad.

I had played this conversation over and over in my mind since I was a 14-year-old growing up on the NSW north coast in the late Eighties and early Nineties, when homophobia was rife.

My dad loved me – and I idolised him – but this conversation was never going to happen. He was a bricklayer and surfer; the toughest man I knew. I was ashamed of my sexuality, and I buried the secret deep inside so nobody would ever know. Every time someone asked, “So, why don’t you have a girlfriend yet?”, I sent it down even further.

I had my Saturday-morning epiphany when I was 26. Soon after, I told my mum and then my two sisters, who were all supportive. I knew the day would come when I would have to ’fess up to the old man.

The thought of the conversation terrified me. I’d been out long enough to hear all the war stories about fathers abandoning their children, wiping them forever. All I ever wanted was for my father to be proud of me. I didn’t want to let him down.

The conversation was going to roll like this: “Dad, I’m gay. It has taken me a long time to get to this point to tell you. I have realised, after much soul-searching, that I have no control over my sexuality. I thought it was a ‘uni’ thing. Then I thought it was a ‘depression’ thing. Then I thought I was bi-sexual. Then I realised I just am who I am. It’s tough, because I am a sportswriter who covers footy. I would never have taken this path by choice.”

But I didn’t choose the moment of truth. It chose me.

Curled in the fetal position on the bathroom floor of my tiny studio in Sydney’s Elizabeth Bay one evening, I knew I was in trouble. I phoned him.

“I’ll come straight away,” Dad said.

He opened the door, sat me down.

“Mate,” he said, “what is it? What’s wrong?”

“Dad. I’m gay . . . ”

Big eyes, then a big smile.

“Is that it? Is that what’s been wrong with you all these years?”


Bigger smile.

“Mate, I’m not proud of you because you are gay. I’m proud of you because you are my son.”

Then we hugged and cried. I’d won the fucking grand final. My dad has been my best mate ever since.

The lesson, at least for me: don’t be afraid of the hard conversation, because you never know how magical the outcome might be.


As a young rugby league coach at the Penrith Panthers, Phil Gould handed out some tough love to a club champion,

Royce Simmons was a mate as well as a club stalwart. I’d dropped him the previous year and let him know that young blokes were coming through, but he’d backed up again because he could see we were going to win a comp.

About six weeks before the finals he came to see me at the club late one night. He’d had a few beers and was feeling a bit left out. The team had had another big win while he was trudging away in reserve grade, doing his best and trying hard but not playing all that well. He could see the first-grade side getting further and further away.

He said to me, “I’m not going to get back, am I?”

Believe me, these are tough conversations. At this stage of their career, blokes can be in denial. They all live on the thought that next week I’ll get it right. Next year I’ll be better. But it doesn’t happen.

You have to get inside their heads, because you’ve been there yourself. You say, “Look, I know what you’re thinking. These are the thoughts you’re having during the game and when you get up to go to training.” And you can see them thinking, Fuck, he actually knows what I’ve been thinking. He knows.

As a former player, you feel empathy for the ageing warrior, but it’s an abdication of leadership to ignore his decline. You can’t not speak up. This is a team game. There are too many other things at stake to allow one player to ride through on the performance of everybody else.

I said to Royce, “No, in all probability you won’t get back. And you shouldn’t feel bitter about that. You’ve had a great career and you should be happy that blokes here to whom you’ve been a senior player over a number of years have a chance to win a competition. You should be cheering them on and not feeling so sorry for yourself. Not everyone gets a fairy-tale ending.”

But at the end of it I said, “It’s a funny game – things can turn quick. There might be something else you can provide. All you can do is keep yourself fit.”

Royce took all this with a sense of resignation, but I also felt he was looking for a bit more encouragement.

As it turned out, Royce did make it back into the team. After a soft performance a month out from the finals, I felt the team needed an injection of leadership. In the Grand Final against Canberra, Royce scored two tries and inspired his team with five tackles in a row after we had a man sinbinned. Penrith won its first-ever comp and Royce got his fairy-tale ending.

It’s funny. I still get emails and letters from blokes I’ve had that “time’s up” conversation with. They say, in effect, “You were right to tell me those home truths”.

Royce has never thanked me for it exactly. But he took over from me as coach at Penrith, and he’s talked to me since about how hard it is to have that conversation with an ageing player. He’s also said that, looking back, he knows now that he was gone.

Babe, I Have Herpes

How do you tell a woman you’d like to start having sex with that you have an STI? Adrial Dale* found a way.

When I got herpes about 10 years ago I was terrified that it would mean the end of my love life. And for many years I didn’t date because I was so deep in shame.

One winter’s day I went to my local coffee shop, and the moment I walked in I saw this woman sitting alone reading a book. I chose a nearby table and just sat there thinking, My God! I have to go up and talk to her! I was beating myself up for not having the courage to do that.

I got up to leave and was almost out the door when I had this “movie moment”. I’m like, No! I have to do this! And I literally turned around and walked directly up to her table. I made eye contact with her, sat down and commented on her book, and we launched into this conversation about life and feeling lost in life.

In the end I asked her out, she said yes, and I walked out of that coffee shop on cloud nine.

We went on a few dates and we had this connection. One day she was at my house and we were cuddling and flirting. I started to get nervous, because I knew I wanted to tell her this secret of mine. Previous times when I’d had the herpes talk, it had felt like I was throwing a hand grenade over a wall and ducking for cover. But this was different. I was still scared shitless, but I was also seeing this as an opportunity to get closer to her.

I looked in her eyes and said, “Hey, I want to talk to you about something that’s really important. It’s also really scary for me. Are you up for talking?”

She looked a little surprised, and curious, but she said, “Yeah, let’s talk. I’m open.”

We sat up and I said, “First thing is, I’m so appreciating getting to know you. I’d also like to know what you’re thinking about our relationship, about where it might be going. Part two, and this is the scary part . . . before we start getting more intimate – because I’m really attracted to you – I wanted to share with you that I have herpes. I wanted to talk to you about it, see what you already know about it, and see if I can answer any questions.”

She looked at me and smiled, and you could see she was kind of stunned, but in an appreciative way. She actually said, “You’re shaking! I get that that was hard for you to do, but I so appreciate you sharing that with me. It has shown me some deeper qualities about you that I really like.”

That set the tone for us to have a beautiful relationship. It ended up not working out, but not because of the herpes. We broke it off still appreciating each other, but realising this wasn’t the relationship for us.

The experience rammed home for me that there is something more powerful than our fear of rejection. You ask any woman out there what is the sexiest thing in a man, and in a tie with a sense of humour, it’s integrity.

Honey, I’m Leaving You

Having endured a hollow marriage for years, Peter Scott finally told his wife he wanted out

Looking back at the end of my marriage, two conversations loom large. They happened about seven years apart. Both were in Sydney restaurants with my (now) ex-wife.

The first was on a wet Thursday night in March. I was still a banker in those days, on close to $1 million a year. Oh, poor fuckin’ you, you might sneer. Fair enough. But I was falling apart in mind, body and soul. Unless you’re a robot, 20 years at the pointy end of the commercial rat race can do that.

Late in the meal, after the best part of a bottle of red, I opened up to Helen. It was totally unplanned – more fool me. The subject wasn’t exactly new, but I must have sounded more earnest than before.

“I honestly don’t think I can do this work much longer – even if I wanted to, which I don’t. Please could we start thinking about a change?”

Her reaction was one of horror – then cold, pitiless fury. She kept her voice low in the restaurant, but really let rip on the ride home. Absolutely. No. Way.

“And if you think I’m going back to work, forget it.”

We’d been married, then, for more than 15 years – and raised three kids. We were decent parents, but I’d known for a long while that our marriage was hollow. 

Even so, her sheer lack of empathy that night was gut-wrenching.

I let things lie and resigned myself to battling on. Within a few years I’d had a nervous breakdown and – on doctor’s advice – left banking for good. Helen fumed. Her worst fears had been realised: our income plummeted.

We were hardly on the breadline. The kids were still at private schools. I’d begun a new, less taxing career – working for myself. But regularly she’d scream: “You’ve ruined my life!”

Of course, by this stage, the marriage was as good as over. In my mind, at least. I grieved, but mostly silently. If Helen sensed the depths of my despair, she evaded the subject. We co-existed.

I came to hope that Helen would leave me. But she was in denial. Finally, I resolved to leave her. Which brings me to the second conversation.

This time I planned it carefully. A crowded restaurant at lunchtime to minimise the chances of an ugly scene. Separate cars to ensure a smooth getaway. I steeled myself for anything.

She arrived oblivious. I greeted her civilly.

We were led to a table. I even ordered drinks. I felt guilty about the turmoil I was about to cause, but wry and detached as well. The moment had arrived. It was surreal.

Then I said straight out: “Look, I’m sorry, but I want a divorce.”

I waited for a nuke to explode . . .

Talk about an anti-climax. There were no histrionics. She muttered something I didn’t catch – then upped and left. I sat there for about 10 more minutes, in a daze, before paying up and driving to my sister’s place.

Sure, years of bitter recriminations followed – nasty battles over money and custody, and plenty of rewriting of history. But the vital conversation had proved easy. 

And I can honestly say that everyone is happier now.

You’re Sacked

As a newly re-elected Premier, Bob Carr would tell loyal and trusted colleagues to move aside.

There is just one candidate for my hardest conversation, and it’s a conversation I had perhaps 10 times.

Imagine this. You’re Premier, and you’ve got to tell a valued and fond friend that you cannot take them back into the ministry with you. This is a person who stood with you during seven years of opposition; who gave you good advice and unstinting loyalty; who served with you in government.

But as leader you have to think of an even greater loyalty, and that is to your party and your government. There must be, for the health of both, a turnover of personnel after each election. You’ve got to have seasoned warriors giving way to youngsters itching to prove their talent.

I would have these conversations face to face. They’re entitled to hear it from you direct. This is not something you can delegate to a chief of staff or a senior colleague. Managing personnel is part of leadership.

I would always put myself in the position of the other person. But I steeled myself by thinking of my greater responsibility. It would have been easier for me in just about all of these cases not to make the hard decision. That would have saved the hurt, but it would have transferred the hurt to promising people on the backbench who wanted their opportunity to serve.

I would say, “Colleague, you’ve done nothing wrong. Yes, you’ve been a good minister. You can be proud of your public service, proud of the lustre you brought to your time in public life. But I’ve got a backbench bristling with talent, and if this government is going to go on and have another big win, we’ve got to show the public we’re not just the same old team, term after term.”

You see, you’re never more authentic than when you’re simply telling the truth, and that was the truth.

Reactions would vary. Sometimes a colleague would say, “I understand. I’ve had a good run.” Other times, “This is surprising. This is unfair!” In one case there was a more emphatic objection still.

I noticed one little thing. Sometimes it would be personnel from a particular ethnic culture who found it harder because of a focus on “loss of face”. On occasion I said, “Listen, I’ve sustained ritualistic loss of face every day I’ve been in parliament. Public life is a day-by-day humiliation – don’t talk to me about face!”

These conversations can mark the end of your personal relationship – that’s true. But that’s got to be their decision, not yours. Your job as leader is to make it possible for them to stay rusted on.

There’s nothing like running your own government, running your own show – that’s why I enjoyed being Premier more than being a Foreign Minister. But the downside is you’ve got to make the hard personnel decisions. Your friendships can’t count compared with the long-term viability of the institution you lead.

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