Brave Conversations Open Up a Happier Life

What conversations make you feel nervous? Which ones would you rather avoid?

These are the ones you need to work on.

It is so important to keep working on your ability to have tough conversations if you’d like to live a life that really expresses you and your values.


👉 It could be that you’ve decided to move to a new city, and it’s time to break the news to your family and friends. 

👉 It could be that you’ve decided to make a career switch, and it’s time to tell your boss and colleagues. 

👉 It could be that you’re taking a sabbatical break and it’s time to tell everybody at work – and your family and friends.


Now, sometimes people are just plain excited and happy to take their leap and have no problem announcing their news to the world.

But this is not the case with everyone. It definitely wasn’t the case with me when I decided to take a leap in the form of a year-long sabbatical!


Fearing the Big Conversations

I was very nervous about the conversation, even though I was working in Communications. 

I had held roles in both external and internal communications – and in very high-pressure contexts near conflict zones, natural disasters and the C-Suite and Board room. 

I had given interviews on radio, NBC television, and even took NPR’s Jason Beaubien and Nicholas Kristoph from the New York Times around post-earthquake Haiti. 

I had a major A-ha moment when I realized I could use all this experience to communicate my own leap, and keep going to have my own tough conversations that allowed me to have the much more happy and aligned life that I have today. 


I want to share all this with you because if you can get better and be more consistent at having conversations that make you nervous but are the right ones you need to have … They will improve your life and help you grow. 

What’s tragic is if the fear of telling other people about the risks you want to take in life keeps you from doing them at all. 

We have to counteract that.

Now on the surface, it might seem like I’m exaggerating. 

Like – who would be SO worried about what other people think that they would not doing something that they want to do in life. 

This is SO common though. 

I’ve worked with more than 75 people through their leaps and it’s a more common concern than anyone would let on. 

Often, we don’t even realize it about ourselves because we’ve buried the fear beneath all the other reasons (or excuses) about why we’re not making a change in our life. 



Why Some Conversations Are Hard

It’s important to recognise for yourself why some conversations seem so hard, and what a huge impact it can have on your life when you successfully can get through them, instead of avoiding them. 

Pause a moment and think about the last time you knew you needed to have a conversation with someone and you put it off or avoided it.

Think about your reasons for NOT doing it.

Here are 3 common reasons why we avoid uncomfortable conversations and some reasons why you might bravely have them anyway:


💬 Reason #1

Fall out. It’s as simple as that. We worry about the consequences. We fear facing someone’s displeasure or anger with us. I know this one quite well. It really can have a lot to do with your family dynamics and what you learned early on in life. 

I came from a household that avoided conflict and didn’t communicate well and waited until it all came out in one big outburst. As I got older, I realized from my friendships and romantic relationships that this was something I didn’t want. It wasn’t healthy. I wanted to unlearn it, and learn a new way. 

So I’ve worked for years to be brave. Bravery is one of my core values – to me, choosing bravery means doing the right thing, even when it feels hard. Communication is often an area of bravery for me. 

So here’s the thing about fall out – it can happen. People can get angry and displeased. But it’s important to remember that our fears are often worse than the reality. And even if the worst does happen, we will survive. 👇

When I was in my early 20s, when I gave notice to my boss, she actually ordered me into a conference room so she could yell at me. In fact, it was a family business, and she had her husband come in so they could both chew me out.

I now realize this was seriously messed up and unsafe and I never should have gone into a closed-door conference room with them, but guess what, even though literally the worst-case scenario happened, I survived. 

I’m here. I’m okay. Important lesson learned about how to protect myself in the future. 

It can be painful to have people get mad at you or be displeased with you, or even disappointed, but it’s important to remember that: 

1)  It’s not all about you. They have their own things going on. 

2) It’s your life and you need to do what is right for you. Sometimes, when we make an important change in life, people aren’t going to come along with us. They aren’t ready, or they don’t want to, or maybe they’ll come around later. 


💬 Reason #2  

Judgment. We worry about what people think of us. We fear their judgment. 

If you have a history of people-pleasing, this can be a big one. If you have a history of feeling like you need to prove your worth through achievement and other’s approval (and this is another one that comes up in a family of origin, especially in my Asian background!), then even your sense of self-worth can be impacted by what others think of you. 

We worry about whether people will think we’re foolish, ridiculous, arrogant, an imposter … the list goes on forever. 

Here’s the thing: I’m not going to say, “Stop Caring what people think!”. That’s so pat. So easy to say and difficult to do. When I read sassy quotes about how people stopped caring about what others think, I’m sceptical. Maybe they’ve achieved it, but more likely they’re also still working toward it.  Let me tell you, I would love to be that person. Maybe after another 25, or 30 years of working on myself, I will be that person. I doubt it though. I have a lot of things built into me and my history that probably will keep that from happening. I care. 

What I do feel like I can work on though, is again, bravery. To get myself to do the things that are hard, because I know it’s important. For me and for other people. To give it a social purpose.

When I was in college, I heard a This American Life episode with Mr. Rogers (episode 184), that really made this idea concrete for me. The episode was recorded a few years before he died. 

The producers of the show asked Mr. Rogers how he would approach a neighbor to talk about how their loud music was bothering them. 

(I was living in New York City at the time, and I could relate to how hard it felt to bring a complaint to a neighbor in my somewhat rough Brooklyn apartment building..) 

He said, “I can tell you what I would hope that I would do. I would hope that I would be brave enough to visit. It's so easy to condemn when we don't know. And if I would visit you and find out that you are a reasonable person, I could tell you about my sensitivities and see if it would make any difference to you.”

The interviewer asked Mr. Rogers what he thought it was that made people afraid to have conversations like this. 

He said: “Perhaps we think that we won't find another human being inside that person. Perhaps we think that, oh, there maybe are people in this world who I can't ever communicate with. And so I'll just give up before I try. And how sad it is to think that we would give up on any other creature who's just like us.”

I think he’s right. 

That the ultimate fear we have about judgment is that someone just won’t get us. Maybe they won’t. But it’s important to try. 


💬 Reason #3

Risk and vulnerability - we avoid conversations because they are about things that we’re still uncertain about within ourselves, and about ourselves. We might feel unsettled inside and it’s making us question our own judgment

That uncertainty might make us feel like it’s too early to act, that we should wait for certainty before we speak to others. 

  • We might feel afraid of failure.

  • We might feel afraid of what it means for us to say something.

  • It might represent a shift in our identity. 

  • It might be a first that we are standing up for our own ideas and decisions.

You can’t always wait for 100% certainty before you make a move in life though. You’d never get anywhere. 

So what this comes down to ultimately is your relationship to risk. 

Yes, tough conversations can be risky. They can leave us feeling vulnerable. 

Brene Brown, who has centered her work around the study of vulnerability says, 

“Staying vulnerable is a risk we have to take if we want to experience connection.” 

And also, she writes in her book “Daring Greatly,”  

“Vulnerability is the birthplace of love, belonging, joy, courage, empathy, and creativity. It is the source of hope, empathy, accountability, and authenticity. If we want greater clarity in our purpose or deeper and more meaningful spiritual lives, vulnerability is the path.”

Vulnerability, I’d also say, is the birthplace of growth. Representing yourself more authentically in your conversations is going to stretch you. You’re going to experience growth. Plus, every time you do it, you’re going to feel more capable and confident in doing so. 

As you go along, GIVE YOURSELF GRACE, maybe you’ve never spoken up for yourself and what you want in this life in this way. You probably won’t do it perfectly, but you did it. And that is what you need to remember and celebrate. 

Commit to taking some risks that are good for you, and take you closer to an authentic expression of yourself – including in your conversations. 


I often bring my expertise from my communications career to my coaching to help my clients. 

Here are some recent situations where this helped: 

A client was ready to quit his job and take a 4-month sabbatical. His job had given him many opportunities and really shaped who he was – he was grateful and he was also ready to move on. He was scared of his boss’ reaction; they were very close and he was afraid to let her down. We worked on a script that he could use just to get through the conversation – and he did it! He took his break and started at a new job that was a better fit for him. 

Another client who has been trying to find a full-time job in her very niche field wanted to approach someone she had met at a conference as a potential mentor. We worked on an email to ask her for a meeting. The potential mentor agreed to the meeting and is now making an introduction for my client at her company.

Another client was ready to leave a job to make a career switch, and she was gearing up to see a lot of her colleagues at an internal company event; she would have to break her news to a lot of them and even say goodbye to them. We worked on how she would explain her departure so she could begin the process of saying goodbye. It wasn’t easy, she reported later, and she would have liked to have done it better, but she did it, and it was over. She can now focus on her break. 

These are all uncomfortable conversations. They take courage. And as you can see from the results, they can have a huge impact on the direction of your life. 

If you see yourself reflected in any of this – you’re not alone. I hope it has helped you to be aware of what might be holding you back. 

Having a life that is self-directed and intentional … requires that we get better at tough conversations. 

The truth is, many people take a life path that is not quite right for them, because they’re afraid to speak up, afraid to take a stand on their own ideas and dreams, and because it feels easier to please others. 

So, if you want to make the shift to a life that better expresses you and your values, start cultivating the communication skills that will help you get there.

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7 Steps to Prepare You For Having Brave Conversations

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