The Ryan Leak Podcast

The holidays are coming, and so are the complicated family conversations. But what if the biggest problem isn’t what someone said or did? What if it’s the conversation you’ve been avoiding?

In the first episode of our eight-week holiday series, Ryan Leak explores why we talk about people instead of talking to them, how venting can become avoidance, and why addressing tension before the holidays might be the best gift you give your relationships.

You’ll learn practical ways to start uncomfortable conversations, approach conflict with curiosity, and take responsibility for your part even when the other person doesn’t respond the way you hoped.

This week’s challenge: Stop talking about one person and start talking to them. For Ryan’s latest holiday family guides and workbooks, check out ryanleak.com/holiday

What if the biggest opportunities in your life weren't just the result of hard work, but the people who opened doors for you? John Maxwell calls it Who Luck. In this episode, Ryan shares the remarkable chain of relationships that took him from a college student with a camera to stages around the world, including an Instagram Reel that caught Oprah's attention. He also explores how one invitation helped introduce Brené Brown's work to millions. The truth is, nobody gets where they are alone. Behind every success story is someone who took a chance, made an introduction, or saw potential before there was proof. You'll be challenged to thank the people who helped you get where you are and become the person who opens doors for someone else. Because you might not be the person who changes the world, but you might be the person who gives the world access to someone who will.

Negativity is everywhere. In your office, your group chats, your social media feed, and sometimes even your own thoughts. But just because the world has problems doesn't mean you have to be miserable. In this episode, Ryan challenges you to avoid the doom and gloom trap and recognize the difference between being realistic and being relentlessly negative. You'll discover why complaining drains your energy, how to shift from being a complainer to a contributor, and why optimism isn't naive. It's a choice. Life is hard, but you can still decide to enjoy it. And remember, attitude is contagious. Make sure yours is worth catching.

What if the hard thing you've been avoiding is actually the thing that's making you stronger? In this episode, Ryan explores the science behind willpower and why discipline isn't something you're born with. It's something you build. From difficult conversations to daily habits, every decision to do what matters instead of what feels good is an opportunity to grow. You'll discover why comfort can be costly, how discipline creates freedom, and why you don't get to skip hard. You just get to choose your hard. Because the life you want is often on the other side of something you don't feel like doing.

What if the thing holding you back isn’t a lack of planning, but too much of it?

We tell ourselves we’ll start when the plan is perfect, when we have more clarity, when we’ve done enough research, or when we know exactly how everything will work out. But the perfect plan isn’t coming.

In this episode, Ryan challenges the myth that you need certainty before you take action. Some information is only available on the other side of action. You can plan, prepare, and research, but eventually you have to move.

You might not need more clarity. You might just need more courage.

Make the best plan you can. Take the next wise step. Learn. Adjust. Keep moving.

Because a good plan executed today is worth more than a perfect plan that never leaves the notebook.

What if you stopped waiting to feel like it?

The truth is, you get the same results from doing hard things when you don’t feel like it as you do when you do. The mile still counts. The rep still counts. The page still counts. The conversation still counts.

In this episode, Ryan challenges the idea that motivation has to come before action. Sometimes you don’t feel your way into action. You act your way into a feeling.

Your feelings matter, but they don’t get to be your boss. They get a vote. They just don’t get a veto.

So go uninspired. Start uncertain. Show up tired. And if you can’t beat the fear before you start, do it scared.

It’s all hard. Building a career is hard. Leading people is hard. Marriage is hard. Parenting is hard. Starting over is hard. Staying the course is hard.

But some hard things get even harder the longer you avoid them.

In this episode, Ryan talks about why avoiding a difficult decision doesn’t eliminate the consequences. It simply hands them to your future self, usually with interest. The conversation you don’t have today gets harder tomorrow. The boundary you refuse to set becomes more expensive later. And sometimes, indecision is a decision all by itself.

You don’t always get to choose between hard and easy. Sometimes you’re choosing between hard now and harder later.

It’s all hard. Choose the hard that builds the life you actually want.

Getting started takes bravery. Keeping going takes resilience.

Life won’t always cooperate with your plans. Ideas flop. People disappoint you. Opportunities disappear. Doors close. And sometimes the hardest part isn’t what happened. It’s figuring out how to move forward after it happened.

In this episode, Ryan talks about the difference between processing disappointment and parking in it, why you don’t always need closure to move forward, and what research on the “Progress Principle” teaches us about the surprising power of small wins.

You don’t have to fix everything today. You don’t need a massive breakthrough. Sometimes you just need one conversation, one email, one workout, one page, or one next step.

Whatever happened, it doesn’t get the final word.

Keep it moving.

We spend a lot of energy trying to keep up with competitors who aren't even thinking about us. We scroll through someone's highlight reel and measure it against our behind-the-scenes. We compare our chapter 3 to their chapter 20. And every time we do it, we lose. Not because we're behind, but because we're running in the wrong race entirely.

In this episode, Ryan shares the questions that actually measure progress. Are you stronger than you were last year? Wiser? More disciplined? Have your relationships gotten better? If the answer is yes, you're winning, even when it doesn't look like winning on Instagram.

The greatest athletes in history weren't obsessed with the person in the lane next to them. They were obsessed with their own time, their own form, their own preparation. That's the competition worth showing up for.

Someone says “your presentation could’ve been stronger” and your brain hears “you’re a failure.” Someone says “I think you could listen more” and your brain hears “you’re a bad spouse.” We don’t process feedback as information. We process it as judgment. And because it feels like a verdict, we defend ourselves against the very thing that could make us better. Ryan unpacks why defensiveness, not feedback, is the real enemy of growth.

In this episode, Ryan talks about treating criticism as data instead of a death sentence. Not all feedback is accurate. Some of it is projection. Some of it is jealousy. But some of it is gold. And if you reject all of it because some of it stings, you’ll miss the insights that could’ve changed your trajectory.

There’s a gap between who we think we are and how people actually experience us. And that gap is where most of our relational problems live. Ryan asks the question he uses in every coaching session and keynote: what’s it like to be on the other side of you? Not what your résumé says. Not what your bio reads. But the actual lived experience of working for you, living with you, being led by you.

In this episode, Ryan gets specific. What’s it like to be on the other side of your decisions? Your tone? Your urgency? Your stress? Would you want to work for you? Would you want to be married to you? Would you want your kids to grow up in a home led by someone who shows up the way you show up? You can’t improve what you’re not aware of. And the answer to that question might be the most valuable feedback you’ve ever received.

We’ve built an entire culture around surviving the week just to get to the weekend. TGIF. We countdown the days. We post the memes. But if you dread five out of seven days of your life, that’s not just a bad job. That’s a bad life. You’re spending 71% of your week wishing it was over. That’s not a schedule. That’s a sentence. Ryan challenges everything we’ve normalized about hating Mondays.

In this episode, Ryan asks a question worth sitting with: does your team dread Monday because of the work, or because of the environment? Everybody can look forward to a Friday. That’s easy. But what if you could create a culture people actually looked forward to showing up to on a Monday? That’s not just management. That’s leadership. And if you’re not in leadership, you still set the tone for your own week. Anyone can thank God it’s Friday. The people who learn to thank God it’s Monday have figured out something the rest of the world is still chasing.

Would you rather be right or would you rather be connected? Ryan has met a lot of people who are always right. And he’s noticed something about them. They’re often alone. Not because they’re wrong, but because it’s exhausting to interact with someone who never considers the possibility that they might be. Ryan gets personal about seasons where he won every argument and lost every connection.

In this episode, Ryan unpacks why being right is addictive, why your brain literally rewards you with dopamine when you prove your point, and why that hit comes at the expense of the relationships that matter most. Relationships aren’t courtrooms. The people in your life aren’t opposing counsel. And every time you prioritize being right over being kind, you chip away at the thing that matters most. Be right sometimes. Be kind always.

Your boss gives you tough feedback and you spend the whole weekend convinced they’re trying to push you out. Then Monday comes and they tell you they’re recommending you for a promotion. A friend doesn’t text back for days and you build a whole narrative. They’re pulling away. They don’t care. Then they call and say their mom’s been in the hospital. Ryan unpacks why the story we tell ourselves is almost always worse than what’s actually happening.

In this episode, Ryan challenges the habit of assigning motives to people based on incomplete information. What if your coworker isn’t stealing your idea but just excited about it? What if your spouse isn’t criticizing you but just said it wrong? Before you build the case, ask the question. You might be surprised by what you find when you stop fighting people who were never fighting you.

“I’ll start when I’m ready” might be the biggest lie we tell ourselves. I’ll start the business when I’m ready. I’ll have the conversation when I’m ready. I’ll write the book when I’m ready. And then the thing you were preparing for passes you by while you were still getting prepared. Ryan breaks down the difference between preparing and hiding, and why “I’m not ready” is often just a dressed-up version of “I’m scared.”

In this episode, Ryan shares his own journey of starting before he felt qualified and explains why confidence isn’t a prerequisite for action. It’s a byproduct of it. The perfect conditions you’re waiting for aren’t coming. But this morning is here. And sometimes the only thing standing between you and the life you want is the willingness to start messy.

Nobody’s going to send you an invoice for being distracted. But research says it takes 23 minutes to fully refocus after a single interruption. Multiply that by a dozen times a day and you’re losing hours. Not minutes. Hours. We’re more connected than we’ve ever been and less focused than we’ve ever been. Ryan unpacks the hidden cost of the thing we’ve all normalized.

In this episode, Ryan challenges you to do an honest audit of where your time is actually going, not where you think it’s going. Because distraction doesn’t just steal your productivity. It steals your presence. And the people you love deserve more than a distracted version of you.

Someone you love comes to you with something heavy. And because you care, you immediately start solving it. You’ve got a plan, next steps, practically a spreadsheet. And you watch their face close. Because they didn’t come to you for a solution. They came to you to be felt. Ryan unpacks the mismatch that ruins more conversations than conflict ever will.

In this episode, Ryan breaks down the three things people actually want when they share something vulnerable: to be helped, to be heard, or to be hugged. The problem? They rarely tell you which one. And we rarely ask. Whether you’re a fixer who needs to learn to listen or a sharer who needs to learn to name what you need, this episode gives both sides a job to do.

There’s a word most people have never heard that describes something most people do every day. It’s called ultracrepidarianism, giving opinions on things you have no real knowledge about. Ryan unpacks why we feel pressure to have a “take” on everything, why ChatGPT access doesn’t equal a PhD, and why the smartest people he’s ever been around are the ones most comfortable saying, “I don’t know.”

Here’s the irony: we all feel pressure to be a know-it-all, but nobody actually likes being around one. So we’re chasing the very thing we can’t stand in other people. In this episode, Ryan gives you permission to be a know-it-some, and explains why “I don’t have enough information to have a strong thought on that” might be the most powerful sentence you say this week.

Only 34% of Americans believe most people can be trusted. The average person has about five people they’d truly lean on for anything. And yet Ryan has never met a single person who thought they themselves were untrustworthy. Nobody’s ever said, “Hey, whatever you’re about to tell me, I will absolutely use it against you in three months.” We all think we’re the vault. But almost nobody trusts the vaults around them. The math ain’t mathing.

In this episode, Ryan unpacks the broken trust economy and challenges listeners with two questions: What does your side of the trust equation actually look like? And how much are you letting past hurt determine the quality of your current and future relationships? You’ve got plenty of reasons not to trust people. But you might also have plenty of reasons to try again.

In 1989, a 23-year-old social worker started teaching classes and researching a topic nobody wanted to touch. For 21 years, almost nobody outside her department read her work. Then she gave a 20-minute talk, and it changed the conversation in boardrooms, classrooms, and living rooms across the world. Ryan unpacks her story and the timeline most people never see behind the breakthrough everyone celebrates.

If you’re a teacher wondering if your students are listening, a parent who can’t tell if anything is landing, a pastor whose sermons feel like they’re falling on deaf ears, or a creative whose work gets 12 likes, this episode is for you. Sometimes you get to see the difference you made. Sometimes you just have to trust that it’s happening anyway.