Why We Can Never Stop Dreaming

It was spring of 2008 and I was struggling. I felt suffocated by a job that I had long ago realized wasn’t meant to be my path.

The harder I tried to figure out what path I ought to be on, the more frustrated, aggravated and desperate I became.

I began actively seeking answers and often turned to books as sources of enlightenment.

It was around this time I was first introduced to The Dream Manager by Matthew Kelly. I remember being fully enthralled with the idea that a manager, boss or supervisor would ever care enough about the welfare of an employee to actually ask about their dreams.

Even better, the book offered somewhat of a roadmap to writing a dream list of your own. Because I believed I wasn’t likely to inspire my current leaders to implement this as as an institutional program, I decided to focus on my dream list.

According to the book, there are categories you can consider when writing a dream list, including Legacy, Adventure, Travel, Creative and Character.

Initially, I had difficulty articulating my dreams. I realized I had never really considered what I might want to accomplish. I almost always focused on what I was likely to accomplish.

And those may be different things entirely.

Here is a sampling of things I put on my list (circa 2008, pre-kids and about four years into my marriage):

• Run a full marathon

• Become known as a mentor to others

• Get a master’s degree

• Pray every day

• Become a cash only buyer

• Buy a boat

• Learn to play the guitar

I know. Not super exciting.

But, I loved the process of writing my dream list and I reviewed it daily when I first compiled it.

Then, we moved back to my hometown. Then, I became a mom. Then, I took a well-paying salaried position. Then, I had another kid. Then, I realized I wasn’t meant for this “supposed to be the answer to all my career questions and allow me to live the perfectly balanced life in my small town” job. Then, I decided to quit said job. Then, as I was transferring company documents from my personal computer to my work computer to transition out of my role, I stumbled upon the list.

I hadn’t looked at it in nearly 5 years.

My heart skipped a beat.

I suddenly struggled to take a full, deep breath.

I felt an odd combination of resignation and anticipation as I double clicked the Word document titled My Dream List.

As I scrolled through my detailed list of 81 dreams (Yes–81!), I came to a horrible realization.

I had stopped dreaming.

For a five-year period of my life, I just rolled along, doing what I believed to be the next “right” thing and more than anything, just tried to be a successful person. And mom. And wife. And sister, daughter and friend.

I had not once stopped along that journey to ask myself what success meant for me.

It suddenly became clear to me. Back in 2008, I was asking the wrong question.

Instead of asking what path I was supposed to be on, I needed to first ask where I wanted to go. What I wanted to pursue.

What my dreams were.

Dream Wall

This past Monday, I was reminded about my dream list and felt inspired to re-engage with it again.

I had scheduled a meeting with a Northwestern Mutual branch office in Aberdeen, SD, managed by a friend of mine from high school named Derrick. I was meeting with his team to discuss the program I offer to rural communities through my speaking business.

After the meeting, Derrick gave me a tour of his office.

I was blown away when we came upon the wall in the photo on the right.

It’s a wall that showcases all of the dream lists of the people in his office.

I had never seen this actually implemented as an organizational approach to leading people. I’d only ever read about it.

When I asked Derrick a bit more about this philosophy, he told me that every single employee completes a dream list when they start and as part of their review process, each person updates their list once a year as well.

Here I was, visiting with someone who had managed to implement this dreaming process into their work environment. The Dream Lists are a part of their workplace culture.

Derrick was quick to point out that as part of their annual celebration, besides the usual “here’s what we booked in new business and here’s our year-over-year revenue growth percentage” they also measure how many dreams were attained that year.

They measure “attained dreams” as one of their benchmarks.

Maybe this doesn’t seem all that interesting or important.

I’d argue it matters a great deal.

If you’re responsible for leading people (in any capacity–think parent or coach, too) knowing (and supporting) people’s dreams matters.

Dreams provide a why. We all should start with why. If you need a refresher on the concept, re-watch Simon Sinek’s TED talk on the power of starting with why. It’s important to realize that gone are the days when the majority of people embraced the philosophy of living to work. We now work to live. People’s dreams are the key to what kind of life they’re working to attain.

Dreams create engagement. Well, not entirely on their own. As leaders, we actually have to care about people’s dreams. When we do, our people will know that we value them for more than the number of widgets they produce or the number of new clients they bring in. People who feel known, valued and appreciated outperform those that don’t.

Dreams make the tough times more tolerable. Every job involves some details or elements we don’t love. When we have a bad moment, day, or even month, if we can still think about dream list (or in Derrick’s team’s case, physically see it, every day) and know that we’re on a path to help achieve them, we can better tolerate the tough times.

Dreams provide a destination. Sometimes, we realize that the path we’re on isn’t going to get us where we want to go. And while detours and changes of direction are okay, it’s important that at some point along the path, we lift our heads, look around and ask if this is still the direction we want to move in. It’s about making sure that we are still chasing dreams worthy of pursuit and then ensuring that our current path is still a viable avenue to reach them.

In Derrick’s office, he said that knowing people’s dream lists have made it possible for him to help people out of his company. Their dreams were better chased in another job or with another company.

He harbors no ill will about it either. He places a high enough value on the concept of cultural/role fit, that he’ll help people move on if that’s what’s best for them.

This is visionary leadership.

Yes, sales numbers matter. Metrics, benchmarks and data matter. But at the end of the day, we are all in a people business and all people need to dream.

So, if you’re a leader, I challenge you today to discover the dreams of your people. If you have a significant other, sit down with them and develop a dream list together. When your children are old enough, start encouraging them to dream.

Write your own dream list.

And once those lists are made, make sure you revisit them at least once per year. As C.S. Lewis said, “You are never too old to set another goal or dream a new dream.”

Never, ever stop dreaming.