How to Dream Is Back: Season 2 Is for Anyone Trying to Build a Life They Cannot Yet See

When I created the How to Dream podcast, I knew I wanted to talk about hope. Not the kind of hope that asks us to ignore what is difficult or pretend everything will work out exactly as we want it to. I wanted to talk about the kind of hope we need when life is uncertain, or when the world feels heavy, and we are trying to figure out how to keep moving forward anyway.

That became Season 1 of the new podcast How to Dream, which I based on the work in my book by the same name.

Throughout the first season, we talked about what it means to dream as an adult, especially when life has given us plenty of reasons to stop dreaming. We talked about the myth of being ready, the danger of comparison, the courage required in the middle of a dream, and the possibility of wanting more for our lives without being ungrateful for the lives we already have. Most importantly, we talked about hope as something more than a feeling. Hope can be practiced. It can be strengthened. Hope can help us move.

The response to that first season was more meaningful than I could have imagined. People listened. They shared episodes. They reached out. They told me that the conversations were helping them think differently about their lives which was really the whole goal.

When Season 1 ended, however, I had so much fun making this podcast that I wasn’t quite ready to stop talking to you.

The Summer Journaling Series

That is how our special summer journaling series began. Over ten bonus episodes, we slowed things down and made room to think. Journaling was a natural extension of How to Dream because dreaming requires more than imagining a different life.

We have to become curious about the life we’re living now.

What do I want?

What am I afraid of?

What have I stopped believing is possible?

What am I carrying that I no longer need?

What keeps coming up when everything gets quiet?

Journaling gives us somewhere to have those conversations with ourselves.

The summer series wasn’t about writing beautiful journal entries or finding the perfect notebook. It was about creating a regular practice of noticing, questioning, reflecting, and telling ourselves the truth. Clarity does not always arrive as a lightning bolt. In fact, I would guess most of the time it doesn’t. Most of the time clarity appears one sentence at a time.

And now, all of that brings us here.

Season 2: What Do You Do When You Still Want a Life You Cannot Yet See?

Season 2 of How to Dream is going deeper.

People are struggling right now.

Some of us are exhausted. Some of us are afraid. And a lot of us are grieving. I know so many people who are worried about money, or their jobs, their family, and the state of the world, or what the future is going to look like. Some have spent years taking care of everyone else, and now, aren’t quite sure what to do next.

But they know they want something. Something different. They know they deserve something different. And that’s the tension I want to explore this season.

What do you do when you want a life you cannot yet see?

What do you do when you want something different but have absolutely no idea how to get from here to there? How do you get started when everything feels dark?

Something truly interesting happens when we feel stuck. When it seems like nothing is happening, we often find that we can’t do anything at all, so we end up doing nothing. But when we do nothing, we get nothing. Nothing changes. And that lack of change can become even more evidence that we’re stuck.

I have spent decades as a therapist sitting with people during incredibly difficult chapters of their lives. I have watched what can happen when someone who feels completely overwhelmed takes one small step. Then another. And another.

We often think that hope has to come first.

I’ll do something when I feel better.

I’ll try again when I feel hopeful.

I’ll start when I’m less afraid.

I’ll move when I know where I’m going.

I am here to tell you something: movement comes first!

One small action creates a little bit of evidence that change is possible. That creates enough energy for another action. That action reveals something we couldn’t see from where we were standing before.

And slowly, something begins to move.

That is the territory of Season 2.

We’re Going to Talk About the Harder Things

Season 1 earned our trust.

Season 2 is going to use it.

We’re going to talk about giving up on yourself without realizing you’ve done it.

We’re going to talk about age and the terrible feeling that you should be further along by now.

We’re going to talk about regret.

We’re going to talk about jealousy and what happens when somebody else gets the very thing you’ve been dreaming about.

We’re going to talk about realizing you’ve outgrown a life you once desperately wanted.

We’re going to talk about the embarrassment some of us feel simply admitting that we want more.

We’re even going to talk about something that a podcast called How to Dream has to be brave enough to say:

Sometimes the dream doesn’t happen.

What then?

Can we still hope?

Can we grieve something we deeply wanted without deciding that nothing good will ever happen again?

Can we change direction without calling ourselves failures?

Can we build meaningful lives while living in a world that sometimes gives us very good reasons not to feel hopeful?

I think we can.

In fact, I know we can, but we ain’t gonna get there by pretending.

This Will Not Be a Season of Toxic Positivity

Nobody wants that and nobody needs that. I’m not going to tell you to “just think positive.” I won’t tell you everything happens for a reason. I’m not going to tell you that if you simply believe hard enough, everything you want will happen. And I absolutely don’t want you finishing an episode feeling ashamed because you haven’t accomplished enough, healed enough, dreamed big enough, worked hard enough, or become some imaginary better version of yourself.

That’s not what How to Dream is about.

Instead, we’re going to say:

Here is where we are. Start here.

We’re going to bring evidence into these conversations. We’ll talk about psychology, behavior, hope, action, agency, fear, momentum, and the very human ways we respond when life becomes overwhelming. And every episode is going to bring us back to one question:

What can you do from here?

Not seventeen things.

Not “change your entire life by next Tuesday.”

One thing.

One tiny act that says:

I’m still the leader of my life.

What I do know about dreams is that when you move towards them they take you to places that you can not imagine before you start. We cannot possibly know where we will end up, but I know that you will never regret trying.

Why You Absolutely Cannot Miss Season 2 of How to Dream

I am incredibly proud that How to Dream is free. That is important to me because there are people who need encouragement, practical tools, evidence-based information, and a steady voice beside them who cannot purchase another program, or attend a retreat, or hire a coach, or add one more expense to their lives.

You shouldn’t have to buy hope.

And if you ever want to go deeper, the How to Dream book is where all of this began — buy it, borrow it, or ask your library to carry it, because I believe books are medicine and everyone deserves a dose.

So wherever you are, you can come sit with me.

In your car.

While you’re folding laundry.

On the train home.

On your morning walk.

Or maybe at 11:47 at night, when everybody else is asleep and the thoughts you managed to outrun all day finally catch up with you.

Come as you are.

You don’t need a five-year plan.

You don’t need to know your purpose.

You don’t even need to feel particularly hopeful yet.

Just bring yourself and maybe a pen and a journal if you feel ready for that.

Over ten episodes, we’re going to move through the darkness together. We’re going to see where we are and then say some things out loud that we’ve been afraid to say. And we’ll figure out what we actually want while we allow ourselves to begin moving toward something again.

I can’t promise you exactly what will happen. Nobody can do that. But as long as there is breath in your body, there is still the possibility of making something new.

There are decisions you haven’t made yet and people you have yet to meet. There are a whole lot of things you haven’t tried and ideas you have not dreamed up yet. There are so many places you have not seen and plenty of versions of yourself you haven’t encountered.

In season 2, we won’t pretend to see the whole path. We’re just going to talk about what it means to build a life anyway.

And by the end of Season 2, I don’t need you to believe that everything is going to work out perfectly. I want you to hold inside of you something much more useful than that.

I want you to be able to say:

I don’t know exactly what’s coming.

But I’m not done.

I am the leader of my life.

And I know the step I’m going to take next.

Welcome to Season 2 of How to Dream.

The first episode arrives Monday, September 14, 2026. Follow the show right now on YouTube or subscribe on your favorite podcast platform so it finds you the moment it drops. And if you’d like somewhere to start writing tonight, my free How to Dream Reflection Guide is waiting there too.