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  • Writer's pictureAndrew Petty

APiD Ep. 048 | Holiday Reboot | How's the Conversation Going?

Improving Your Most Important Relationships One Conversation at a Time


As I looked ahead to podcast production around the holidays, I realized my creative juices were running low and my desire for more discretionary time was running high.

So, I cut myself some slack, and I’ve got something different cooked up for you.

This episode is the first of two holiday reboots of a previous episode, chosen specifically with the unique complexities of this time of year in mind and with some adjustments here and there to make it even more relevant to the season.

And perhaps no time of year reveals the health of our relationships better than the holidays.

This episode provides insights and tools for improving your most important relationships, derived from my own observations, personal experience, and work with clients.

If you’re willing to apply what sticks with you from this episode, it might just help you have the best holiday season you’ve ever had.

The results are up to you.

How’s the Conversation Going?

When is the last time a conversation didn’t go well between you and someone especially important to you? Or, when was the last time you avoided a conversation that you knew you needed to have--only to have it turn into a bigger and more intense conversation later when the proverbial shit hit the fan? If you’re anything like me and most of the other humans inhabiting Planet Earth, you don’t have to go back very far in your mental files to recall that conversation that went badly or the one you avoided that came back around to haunt you.

Some of the deepest regrets people experience in their last days or after losing someone they love come from wishing they’d never said that one thing or had been brave enough to say that other thing.

We ARE going to die. But we’re not dead yet. Let’s take a look at how we can improve our conversations with those we love and cherish most while we still have the chance.

Our Relationships = A Conversation

In my line of work, the relationship between my client and someone else important to them--like a spouse, partner, parent, or child--comes up frequently as a matter of concern, hurt, stress, or disappointment. And more often than not, in those situations the quality of the capitol-C Conversation in their relationship is suffering.

In fact, our most important relationships are like one big capitol-C Conversation made up of thousands and thousands of smaller conversations over the years.

That capitol-C Conversation is of course made up of the words we do say. But it’s also made up of the words we decide NOT to say and the little conversations we avoid because they’re too inconvenient or uncomfortable in the moment. What we say matters, and what we don’t say matters, too. Sometimes, there are way too many words, and sometimes there are way too few.

Make It Personal (Part 1)

Pause for a moment: Look back right now on the capitol-C Conversation you’ve had over the years with someone close to you. What’s it been like, overall? Full of honesty--sometimes to the point of doing harm? Contentious? Riddled with suspicion and one-ups-manship? Maybe it’s been playful and adventurous but sometimes lacked the gravity that it needed in order to navigate challenging seasons. Maybe one person in the relationship always “wins” and the other one always “loses.” Maybe you can honestly say that even though there have been lapses, overall the conversation has been maturing through the years.

Whatever it’s been like, though, I think we can all acknowledge that there is room for growth somewhere.

We’re not in pursuit of perfection. But we are in pursuit of even more substance and meaning and joy and satisfaction in the conversations that matter most, in the relationships that matter most.

So that when either they or we breathe our last, we can say with conviction that we gave it everything we had.

Let’s look first at common barriers to improving the Conversation in the relationships that matter most to us. Then, we’ll explore a few ways to begin improving those conversations right away.

2 Common Barriers to Improving the Conversation

ere are two of the most common barriers to improving the Conversation that I’ve observed:

  1. Our Own Stuff: Obviously, this is a big one. Maybe we dislike conflict and just expect that any attempt to improve the capital-C Conversation will create conflict. Maybe we don’t assign enough value to what we see, think, want, or need. Or maybe we’re overwhelmed by our sense of how much time and energy it will take to turn things in a better direction. We might doubt that anything we do will make much of a difference, so why try? Past attempts to improve the conversation haven’t yielded much, so what’s the point? Those are just a few of the ways in which our own stuff can stand in the way, but there are many more, and we each have our favorite flavors.

  2. The Status Quo: We get so accustomed to relating to each other in a certain way that it’s simply easier day-to-day to just stay on the well-worn path that we know--even though that well-worn path often doesn’t lead to good destinations in your relationship. And over time, it becomes a deeply rutted path with steep sides that make getting out of it seem even more challenging. Ladies and gents, the status quo is not benign. The status quo can be a mortal enemy standing between us and the best things in life. We’ll touch on this more when we get to how to improve the conversation.

Make It Personal (part 2)

Let’s pull over to the side of the road for a minute, so to speak, before we go any farther. With whom in your life is the Conversation not going as well as you’d like? More than one person may come to mind, but for now, just think of one. While you’re at it, that person might as well be someone important to you--someone with whom improving the Conversation would be a big win. After all, among other things on Andrew Petty is Dying, we’re intent on eliminating deathbed regrets.

And which regrets are most painful if not those that have to do with the most important people in our lives?

Reflect for a moment on your part in the “capital C” Conversation with the person you have in mind. Which barriers to improving the Conversation are within your ability to influence or change? Is your own stuff getting in the way, and it’s time to step up and take responsibility for it more completely than you have been? Or have the well-worn Conversational paths become so deeply rutted that it’s easier to stay in them than create new ones? What power do YOU have in the relationship to forge new paths?

It takes two to tango, as they say, so acknowledging how we can do better in a Conversation doesn’t absolve the other person of their responsibility. But we can’t take responsibility for the other person’s conduct in the conversation. Only our own. So stay laser-focused on doing the best you can on your end.

Keep your part in the capital “C” Conversation with this person in mind now as we pull back onto the road and explore this topic further.

How to Improve the Conversation

Alright, so we’ve touched on two of the most common barriers to improving the capital-C Conversation with the most important people in our lives--our own stuff and the power of the Status Quo.

Now, let’s turn our attention to how to improve the Conversation--things we can do starting today. This won’t be a comprehensive list, but I think the following things are high bang-for-buck and can get us all a lot further down the road.

  1. First, take responsibility for your own stuff. Do your own work. And get help if you need it. We usually lack sufficient objectivity on our own stuff to see it clearly enough to do much about it. A mentor, a therapist, a coach, or a trusted friend can help you get clearer on what’s preventing you from taking the next step in improving the Conversation and find ways to address it.

  2. Next, motivate yourself. This is critical if we’re going to shrug off the smothering influence of the status quo and create a new way forward. Envision the good things on the other side of the awkwardness and challenge of improving the Conversation. Also, allow yourself to feel the pain and regret you’d experience if you didn’t do your part to improve the Conversation when you still had the chance. And revisit the reality and inevitability of your Mortality to give you that last bit of resolve to get moving in a new direction.

  3. Then, have the little conversation now. We can pay a little now--in awkwardness, difficult emotions, etc.--or a lot later. It may feel easier to skip it for now, but that bill will come due eventually, with compounded interest. For example, maybe you feel like your spouse doesn’t communicate family calendar items to you very well. Since you’re working harder now to first take responsibility for your own stuff, you realize you’re feeling increasingly resentful about this because it can create a lot of inconvenience for you. You’re also taking new responsibility for the fact that you’ve never actually brought it up. So, the next time it happens, you break free of the Status Quo and risk having a little conversation about it in the moment instead of letting it slide by unaddressed again. One way that my wife and I have the little conversations now before they become big, hairy conversations is by having lunch together once a week. Sometimes one of us has something specific to discuss. But often, there’s no specific agenda other than creating a regular time for the little conversations to occur as needed. When we’re in this habit, the quality of our capital-C Conversation is usually much better. When we fall out of this habit, the quality typically declines, slowly but surely. Experiment with what works for you. But whatever you do, don’t put off having the little conversation now before you’re forced to have the big, hairy conversation later.


Creating a capital-C Conversation with those closest to us that we’ll be proud of in hindsight is the ongoing work of a lifetime. This work compounds over time, so the investment we make in it today matters.

Let’s recap the key points we’ve covered.

We first discussed two of the most common barriers to improving the Conversation, namely, our own stuff and the Status Quo. Then, we turned our attention to how to improve the Conversation--things we can do starting today. First, we take responsibility for our own stuff that’s getting in the way of a better conversation. Next, we motivate ourselves so we can shrug off the smothering influence of the status quo and create a new way forward. Then, we resolve to have the little conversation now.

Just One Thing

New conversations bring new results. Sometimes, those new results are immediate and amazing. But they’re not always super enjoyable, especially at the beginning, as the other person adjusts to the new conversation, too. That’s ok. Be patient, and extend grace and the benefit of the doubt to yourself and the other person. And sometimes, it’s useful to have a professional help the two of you learn how to have the conversation more productively. That’s a smart move if you’re not finding a good way forward on your own, despite your best efforts.

The goal, BTW, is not to manipulate or change the other person.

The goal is to do our part to create a higher-quality, healthier, more honest, and more enjoyable capital-C Conversation overall. That Conversation is made of thousands of other little conversations over the years. And you can begin to improve it today.

So resolve today to give a mighty heave and shrug off the smothering influence of the status quo, choose courage in the face of fear, doubts, and uncertainty, and resolve to do just one thing differently today. What will that one thing be for you?

Remember, you ARE going to die. But you’re not dead yet. So get after it!

Make It Personal (part 3)

Bring to mind again the person you thought of earlier--the one with whom the Conversation isn’t going as well as you’d like. What gift will you give them this holiday season to demonstrate your desire to improve your relationship? What investment will you make in the creation of an even better Conversation? Are you willing to be the one to break free of the old deeply rutted path and start carving out a new one?

Make no mistake: Opening up new frontiers in our most important relationships is not for the faint of heart. In my opinion, it’s some of the hardest, most important, and most heroic work we can do in our lifetimes.

I help people just like you have better conversations with the most important people in their lives. Connect with me on Facebook, Instagram, and LinkedIn, visit my website, or email me.

I’m so glad you tuned in today. I hope you and yours have a fantastic holiday season. Don’t forget to follow this show, and I’ll

see you next time on Andrew Petty is Dying.

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