How to Dream [Again] After You Face Disappointment

One of the hardest things to do when you face disappointment in life is to dream again. And if we’re honest, 2020 has been a dream killer

face disappointment

One of the hardest things to do when you face disappointment in life is to dream again. And if we’re honest, 2020 has been a dream killer, a year of setbacks, letdowns, and disappointments. There are unmet expectations everywhere. Recently I preached on how to face disappointment and setbacks and dreams again. Maybe you are in that place where it is hard to dream. You are just trying to make it through the day, and how do you even know if your dreams will come true. Here’s my encouragement, check out the sermon, and then take some time to get curious and dream again (if you’d like a really creative version of this that our incredible team put together, go here to download it). I believe that God will meet you there and help you move forward with what he puts on your heart. 

In his book Dream Big: Know What You Want, Why You Want It, and What You’re Going to Do About ItBob Goff lays out some helpful questions to help us dream.

  1. Who are you?
  2. Where are you?
  3. What do you want?

I want to encourage you as you go through this exercise to write things out and dream. We edit our dreams too quickly and miss out on what God has for us. So before you ask ‘how’ questions, take some time to pray and dream. 

We’ll get to the editing and how questions at the end. Right now, it is important to dream, to write, to let your mind wander. As children, we are good at this, but the older we get, it is easy to limit ourselves. Limiting ourselves is how we end up with regrets, face disappointment, and cynicism. More than likely, if you’re like most people when it comes to dreams, reality thinking isn’t the problem. It is dreaming that is the struggle. 

Broken Dreams

Before we get to dreams, let’s take a look at our broken dreams. Many of us get stuck in life, and rightfully so because we dreamed and nothing happened. We went after a goal, a hope, a dream, only to have it shattered. Our lives get shattered by the actions of others, and this keeps us where we are.

Larry Crabb has some helpful insight on this: Shattered dreams are never random. They are always a piece in a larger puzzle, a chapter in a larger story. The Holy Spirit uses the pain of shattered dreams to help us discover our desire for God, to help us begin dreaming the highest dream. They are ordained opportunities for the Spirit to awaken, then to satisfy our highest dream.

Don’t just speed through those dreams or that season. What is the Holy Spirit doing in you from those dreams? What is God showing you? Growing in you for His purposes?

Now, if you’re ready to face disappointment and take that step and dream again, read on…

Who are you?

What makes you, you? This is about getting an understanding of your story. What makes you tick? What makes you unique?

All of us have different gifts, personalities, talents, ambitions, and histories. God doesn’t waste any of those. If you grew up in a broken home or grew up in poverty, that has an enormous impact on what God might want to do in your life and future. 

Take some time to write down moments that have impacted your life—both high and low. 

Ask God, what does that say about me? My story? Is there anything on that list you want me to pay attention to? Were there any limiting beliefs in your family growing up? Anything in particular from your family story that you need to pay attention to?

Here are a few other questions that might jog some ideas: What are your strengths, gifts, and things you are good at? How has God uniquely wired you so that you can contribute something special? What do you do without having to think? What do people ask you for advice in or seek out your help with?

Where are you?

This is more about your stage in life than your geography, although geography does matter when it comes to dreams. 

What is your life stage? Did you make a big change in your life: marriage, children, retirement, new job, new school, or new house. Are you about to make a big change in life? Or maybe you would like to make a big change in life. These are important to the stage you are in. 

I’m a dad of 5 kids, two of who are teenagers, so there are dreams I have today that aren’t for right now. That’s okay. This isn’t about limiting yourself or your dreams, but having an honest assessment of who you are and where you are. Just because we can’t do something today doesn’t mean we can never do that thing. It just means, today may not be the time. 

So, be honest: where are you in life? 

What do you want?

Even though we love the idea of dreams, it can be difficult to attach words to them. But list out what do you want in life. What do you want to be known for? What things do you want people to say about you at your funeral? What stories do you want people to tell about you? Do you want to travel somewhere? Do something you’ve never tried before? What legacy do you want to leave in your life? Recently I heard a pastor in his 80’s say, “More people need to ask, ‘What kind of old person do I want to be?’” That really struck me and has caused my wife and me to think differently about our lives and dreams. 

If it helps to think backward, write out where you hope to be in 5 years. For many of us, we have put this on hold this year because of how hard it has been, but this is a moment to take that back and dream again. 

Don’t edit this yet. Don’t start to “how” your list and try to figure out how you’ll get there or get it done. Just list it out. 

Now What?

Take a moment to look at what you’ve written down. Bring those things before God in prayer. Ask him what things he truly wants you to focus on this week, this month, this year, or in the next decade. Not everything on your list is for now, and that’s okay. Dreams don’t always happen fast. 

Depending on your personality, you might look at your list and see some impossible things, that is great. Continue asking God for his help. Maybe you see some overwhelming or scary things, continue bringing those before God, and ask him for courage and guidance. Ask this person to pray with you as you move forward with your dreams. 

Let me give one helpful insight: The dreams that help people, that are meaningful to you and others, that line up with your personal values, those are the ones that will draw the best out of us. Whether 1 person knows, we accomplished it or a thousand. Those numbers aren’t important. 


This article on how to face disappointment originally appeared here, and is used by permission.

Joshua Reich
Joshua Reich is the Lead Pastor at Revolution Church in Tucson, AZ. Revolution is an Acts 29 church that dreams of saturating the city of Tucson with gospel-centered church planting churches. Josh has a B.S. in Pastoral Leadership from Lancaster Bible College and an M.Div. in Organizational/Missional Leadership from Biblical Seminary. In addition to writing here, some of his writing also appears at Church Leaders. Josh’s new book, Breathing Room, comes out September 2015.