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Chapter 2. Dream Up Your Remarkable Life
Thereâs a book I love called The Dream Manager by Matthew Kelly (2015), a business parable that tells the story of a fictional company called Admiral Janitorial Services. At Admiral, custodians work for a number of different companies cleaning offices, workspaces, bathrooms, and so on. The job literally stinks.
Well, Admiral finds it hard to get workers to show up. And instead of trying to understand the reasons why, what does the leadership team at Admiral do? They blame the workers; they assume that the people theyâve hired lack a work ethic and donât care about doing a good job. (Have you heard this anywhere else before?)
Eventually, after the problem continues, the leaders start to get curious about it. They start investigating and discover pretty quickly that itâs not that their workers are lazy or careless. The problem is actually that most of them live far from the job sites and they donât have access to public transportation.
Once the leaders identify the actual problem, they finally start coming up with real solutions. First, Admiral invests in a fleet of vans and buses and goes to the workersâ communities to drive them to work every day. For a while, that solves the problemâbut it introduces a new, unexpected problem. The workers are finding new work at other companies.
At first, the leadership team at Admiral assumes once again that they are lazy or that the work is too hard. Finally, one of the leadership team introduces a radical idea: Because everybody wakes up each morning with some kind of dream inside themselves, what would happen if we knew the dreams and desires, the hopes and aspirations of all of our workers? Better yet, what would happen if we helped make those dreams come true? What if we invested radically in improving their lives?
With that idea, they create a new position at the company called the Dream Manager. The Dream Managerâs sole job is to sit down with the workers at Admiral, come up with a list of their dreams and aspirations, and figure out what it would take for those dreams to come true.
One woman the Dream Manager talks to wants to buy her first home, so he helps her create a plan to save the money for a down payment and increase her credit score. When she buys her house, she shares her joy and gratitude for the Dream Managerâs help with her coworkers and friends.
Interest in the company grows as more and more employeesâ dreams come true thanks to the help of the leadership team. They are happy and engaged at work, and they deliver a superior customer experience than their competitors. Other janitorial companies find their workers leaving to go join Admiral, and Admiral suddenly finds it has more contracts for work than it knows what to do with.
In education today, thereâs a similar retention problemâand itâs not just because of the money. Itâs also because of the stress. The expectations and burdens you carry are probably not what you thought you were signing up for when you decided to become a teacher. In other words, your dreams arenât being fulfilled.
The good news is that you have the power and agency to change your situation. You can be your own Dream Manager. And while you should care about your teamâs dreams as wellâthatâs the whole point of the bookâthe first person you have to worry about is yourself.
In Chapter 1 of my book Build Leadership Momentum: How to Create the Perfect Principal Entry Plan, we wrote about bringing your best self to school and taking care of your physical and mental needs. Ruckus Makers know that you canât pour from an empty cup, and you have to put on your oxygen mask first before you can help others.
The same is true for your dreams. You have to pay attention to the dreams and goals you have for your life so that you donât harbor resentment and bitterness against others when you see them achieving their goals.
The other reason to think about your dreams is that you only have this one life! Tim Urban has created a series of awesome visuals to help illustrate how short your life is. Hereâs a chart he created of all of the weeks in your life:
Take a look at this chart and figure out what week youâre in right now, depending on your age. To figure out what week youâre in, Google âhow many weeks between [your birthday] and [current date].â The answer should pop up immediately.
Itâs hard not to see the value of the remaining weeks you have when you see them like this. Tim writes:
Sometimes life seems really short, and other times it seems impossibly long. But this chart helps to emphasize that itâs most certainly finite. Those are your weeks, and theyâre all youâve got. Given that fact, the only appropriate word to describe your weeks is precious. There are trillions upon trillions of weeks in eternity, and those are your tiny handful (Urban, 2014).
Most leaders we know havenât spent enough time thinking about their dreams and what they still want to accomplish in their lives; theyâve usually been too busy focusing on making everyone else happy. Letâs change that right now with the power of visualization.
Your Dream 100 List
First, letâs create what we call your Dream 100 List. This is just like it sounds: a list of 100 dreams you have for your life. If this feels hard to you, we get it! Thereâs no rush. Take your time and start paying attention to dreams as they arise in your life, the little nudges you feel pulling you toward a specific goal. But we challenge you to (eventually) fill out all 100.
To make it a little easier, we created 20 categories of dreams. If you write down five dreams per category, youâll reach 100 in no time. Some dreams might fit in more than one category, too, and thatâs fine. For now, just fill out what you can. You can write down your dreams here in this book or in your own journal.
Here are the categories:
Physical:
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One of mine: Hike the Grand Canyon.
Emotional:
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One of mine: Continue to develop awareness of my internal landscape so my emotions have less power over my actions.
Character:
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One of mine: Respond with kindness and gentleness to my wife, especially when Iâm working.
Intellectual:
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One of mine: Learn how to fluently speak Shona, which is my wifeâs mother tongue.
Spiritual:
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One of mine: Read The Way of Zen by Alan Watts, which I finished in 2023.
Creative:
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One of mine: Write a book of poetry.
Educational:
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One of mine: Increase my knowledge regarding systems and strategic thinking.
Professional:
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One of mine: Write a bestselling book. I actually accomplished this dream in 2022 with my book Mastermind: Unlocking Talent Within Every School Leader.
Financial:
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One of mine: Generate a million dollars in my business.
Travel:
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One of mine: Visit Japan.
Adventures:
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One of mine: Rappel down canyons in Moab, Utah. (This is the adventure experience planned for my live event there in August of 2024.)
Legacy:
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One of mine: Start a scholarship for students in need.
Family:
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One of mine: Have two to five kids.
Friendships:
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One of mine: Start an annual menâs trip.
Hobbies:
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One of mine: Learn to surf.
Sports and Events:
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One of mine: Go to Burning Man.
Fitness:
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One of mine: Run a half marathon in under two hours.
Health:
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One of mine: Stay healthy so I can be alive to see my future kids marry.
Possessions:
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One of mine: Own a home in Israel and Zimbabwe.
Miscellaneous:
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One of mine: Meet the poet, David Whyte.
Once youâve created your list, you can revisit it periodically to delete anything that no longer fits or add new dreams as they arise. The other thing you can do is organize them into immediate, short-term (zero-to-three years), and long-term (three-plus years) dreams. Keep checking off dreams as you accomplish them. Itâs an incredible feeling!
Reflect: Visualize One of Your Dreams
Now letâs apply the power of visualization to one of your dreams. My recommendation is to start with an easy one and then progressively go to the harder dreams. Remember what Maria Konnikova said: Writing down your dreams prevents you from skipping steps. If it helps, set reminders in your phone for key action steps that you identify.
In your journal or the space below, respond to the following prompts about this dream:
â     Whatâs the first step you need to take?
â     Whatâs the next step?
â     And the step after that?
â     Imagine every single step it would take to make this dream a reality.
â     What obstacles might get in the way? What could possibly go wrong to prevent you from accomplishing this dream?
â     How could you respond to those obstacles?
Reflect: Define Expectations
For some dreams, the expectations (i.e., success criteria) are pretty clear. Iâll know Iâm successful when Iâve gone to Burning Man. But other dreams, like responding with kindness to my wife during work, might be a bit harder to articulate, and the signs Iâve been successful might actually come from other people. For example, I might know Iâve been successful if my wife interrupts me, and it doesnât cause a fight later that night. Try to get as specific as you can.
In the space below or in your journal, finish these sentences to help you define your expectations around success:
â     Iâll know Iâve been successful whenâŚ
â     Success with this dream looks likeâŚ
Help Your Team Dream
Cameron Herold (2020), the business-growth guru, put the Dream Manager idea into practice in real life. He owned a company called 1-800-Got-Junk. At the time, he had zero debt to his name, and by making a dream list for his staff, he learned that two of his employees wanted the same freedom in their own lives. He offered to personally mentor those employees and help them create a plan to get out of debt.
The plan worked; they both got out of debt. But eventually, one of those employees left the company to start his own business. Although while he was there, his engagement and contribution to the company increased, Herold did end up losing this high-performance employee.
One of the fears you may have about helping your team members accomplish their dreams is: What if you develop them and they leave? Sure, this can and does happen. But the better question to ask is: What if you donât develop them, and they stay? The reality is that supporting your teamâs dreams creates a better culture.
I decided to put the Dream Manager idea to the test myself. I asked my mastermind members about their dreams, and I learned that one of the members dreamed of mentoring first- and second-year principals so that they wouldnât get burned out early in their careers, but she was having trouble finding anyone to mentor.
I thought, âWell, who has a large network of principals all over the world who might need help? I do!â In our coaching together, I helped her create an application, and I sent an email to thousands of school leaders inviting them to apply.
That mastermind member was thrilled; she chose one worthy mentee and spent three years pouring into that person. They developed a loving and mutually supportive connection. And guess what? After those three years, that mentee joined the mastermind as well. Now that mentee helps to mentor other new principals.
Iâm convinced that accomplishing incredible dreams is the key to living a Remarkable Life. When I work hard to achieve my goals and focus on giving generously to others to help them achieve theirs, I see the ripple effect as they are inspired to pour into others in return. It reminds me of a line from a Rainer Maria Rilke poem: âI live my life in widening circles that reach out across the worldâ (Barrows & Macy, 2005).
On that note, letâs turn your attention to the most important people in your life: your family.
Chapter 3. Love Your Remarkable Family
My friend Karine Veldhoen likes to say that âour leadership story inhabits our life story.â Karine knows this better than most. She became a leader at a vulnerable time in her life: She had a broken marriage and two preteen children. She was devastated by what felt like a personal failure, even while her career flourished and she became a principal at her school. She was in the process of building and rebuilding her life all at once.
Years later, she met a handsome man named David and fell in love again. Before they got married, they went on a visioning retreat togetherâmuch like the one youâre on nowâto co-create their vision for the Remarkable Family they would build together. The conversations were deep and sweet, and they set a strong foundation for the 14 years theyâve been married.
Since then, Karine and David have continued the tradition of going on a visioning retreat together every yearâand they have binders filled with their written plans to prove it!
The insights in this chapter come from Karine and Davidâs experience building a Remarkable Family, and they align perfectly with Remarkable Vision principles youâve been learning about. While this book is designed for a solo retreat, you may wish to replicate this experience with your partner and/or family after youâve dreamed up your Remarkable Vision!
Build Your Nest
Every year in the spring, birds build nests in odd places around my house and yardâin the shed, under the eaves, even behind the wreath on our door. Iâm always amazed at how the birds construct these sturdy little structures from materials like leaves, twigs, hair, and twine. Despite the fragility of the individual components of these nests, theyâre surprisingly strong enough to protect the eggs from a late frost and any predators that might come snooping.
Itâs kind of like life, right?
Together in community with others, you become more than the sum of your parts. And family is the glue that holds you to others and makes you stronger together than you would be alone.
Keep in mind, Iâm not talking about your blood relatives necessarily. Your family is the essential people in your life, the ones whom you trust and rely on no matter what. They might be your blood relatives, or they might not. What matters is that theyâre the people youâve chosen to do life with.
Like everyone else, you need a place to come home to, a nest. And the quality of that nest will determine how much enjoyment you get from life and how fully you can contribute to the world around you.
Karine and David identified four essential questions that they ask about the quality of their nest during their annual visioning retreats. They use these questions to help guide them toward a Remarkable Family, and you can, too.
Question 1: What Are My Familyâs Truths?
This question is often the most difficult to answer. It is an invitation to be honest with yourself and with the others in your family about what is and is not working.
The best partâthough it sometimes gets forgottenâis celebrating whatâs working. What are we enjoying? Whatâs everyone doing really well right now? Where have we seen big âwinsâ in our lives? What goals have we accomplished? Itâs so important to acknowledge all of the good things that youâve observed and experienced together to build each other up and strengthen the nest.
Then you have to get honest about what isnât working. It can be as hard to admit whatâs not working and to give that feedback as it is to receive critical feedbackâbut building up your resilience for both is crucial to maintaining truthfulness and authenticity in your nest. Karine and David have found that going on long walks during their retreat helps to make these sometimes hard discussions a little bit easier.
Reflect
Reflect on the following questions about your family. Write down your responses below or in your journal.
â     Whatâs working well? What do you want to celebrate?
â     Whatâs not working well? In which areas of your family do you want to see change?
Question 2: What Is Our Dream?
On their first retreat, Karine and David wrote down bold and vulnerable dreams. As theyâve seen some of these initial dreams come true, evolve, and become even more meaningful, theyâve been emboldened to dream even bigger. This is a no-limits conversation; they both know that they can bring up anything they want, and itâll be received with openness and love by the other person. Together, Karine and David dream about their personal lives, children, friendships, extended families, business and professional lives, spiritual lives, and every other category we covered in the Dream 100 List.
While this retreat usually happens annually, your dreams donât need to be limited to what you can accomplish within a year. For example, one year, Karine and David dreamed of giving away $1 million to charity in their lifetime together. Many of your dreams may take much longer than a year to complete, and thatâs OK. What matters is that youâre regularly reviewing your dreams and celebrating the progress that youâre making toward them.
Because you made your Dream 100 List, you likely already have a good start on some dreams for your Remarkable Family. Now letâs visualize what one of those dreams could look like in the future. If you chose to visualize one of your family dreams for the last chapter, pick a different one to meditate on in this chapter.
Reflect: Visualize Your Remarkable Family
Imagine itâs a year from now, and youâre on another retreat. What dream accomplishment do you want to be celebrating?
Envision the faces of the people in your nestâyour family. Think about each person, one at a time. How does this person feel about this dream? What might excite them about this dream? How could this dream improve their life?
Now, what questions or concerns might they have about it? What might arise as a challenge? Imagine their voices as they tell you their thoughts. How can you respond in love and with grace and understanding for their perspective? Write down your reflections below or in your journal.
Question 3: What Are Our Rituals?
Your rituals are the repeated events, milestones, and landmark moments in your familyâs life together. These rituals might be breakfast on Saturday mornings, gathering for holidays, attending religious services, having family meetings, or maybe going on an annual visioning retreat together.
One of the rituals Karine and David maintain is reviewing and updating their marriage mission statement during their visioning retreat. This idea comes from The 7 Habits for Highly Effective Families (Covey, 2022).
The mission statement is a declaration of your intentions and goals as a family. You certainly donât have to have a mission statement for your marriage or your family, but many people find them helpful.
Hereâs Karine and Davidâs mission statement:
We will nurture unconditional love in every season. We will:
â     Dream, pray, and love.
â     Work hard and invest wisely.
â     Serve.
â     Play and laugh together.
â     Live healthfully.
â     Communicate honestly and respectfully each day.
Reflect
Consider the following questions and write down your responses below or in your journal:
â     What rituals do you already have in your family?
â     What rituals do you want to adopt?
â     Do you have a marriage or family mission statement?
â     Write a simple statement of intention for your marriage or family.
Question 4: What Are Our Practices?
Your practices are the daily acts of love that help to maintain a strong bond between all of the people in your family. Karine and David do what they call âcoffee and cuddlesâ every morning during which they spend about 15 minutes with their youngest daughter and cuddle together while they have their coffee. They talk about the practicalities of the day ahead and take time to connect in a peaceful environment.
Another practice they hold is meeting monthly as a family to discuss finances without judgment. Itâs just to ensure that how theyâre spending money is aligned with their goals.
These kinds of practices are also helpful ways to repair a relationship when stressors or disagreements arise, as they inevitably do.
Reflect
Consider the following questions and write down your responses below or in your journal:
â     Does your family have any regular practices that help to build and maintain a strong daily connection?
â     If not, what practices would be easy to start right away? What do you think everyone would enjoy?
Get Intentional
Most of us donât intentionally plan for the kind of family we want; we just live our lives and hope that it happens organically. But what Karine and David and many others have found is that great relationships donât just happen; they are always the result of hard work and intentionality.
Spending time reflecting on your vision for a Remarkable Family is the best way to get started building this intentionality. It might feel awkward at first, but with consistency and time, youâll reap the rewards.
And guess what? The same wisdom applies to our relationships at school, too.
If this landed for you, here are a few ways to keep going.
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