Of all the high leverage leadership tools to develop people, coaching, to me, is the most beneficial and satisfying. There’s a real sense of meaning in equipping your people to go further and faster in all areas of their lives.
Whenever I’ve had the opportunity to engage in a formal coaching relationship with someone, I started with a few “big picture” questions about work, family, habits, and aspirations. And if there is one “30,000 foot” question that evokes the greatest difficulty in answering, it’s this:
“What are your dreams?”

It is interesting to me how much trouble people have answering this question — in most cases, they’ve asked for more time to think it through. Why do people struggle to dream? Is it a product of a conformity-based, performance-driven culture? Is it our education system? Is there a negative stigma associated with dreaming — something that only naive, unproductive, starry-eyed slackers do?
Whatever the reason, I believe that having big dreams is a valuable asset in developing your personal brand and living a purposeful, fulfilling life. Here’s why:
1) Big dreams = a big life. Confucius said, “Aim for the stars, that way the lowest thing you will hit is the moon.” Dreaming pushes people to heights they wouldn’t have hit had they not set their minds on something big, even if it is insurmountable. Consider the dream that launched Habitat for Humanity: “We envision a world where everyone has a decent place to live.” Will this ever happen? Not in our lifetimes, but pursuing such a lofty vision has enabled them to grow far beyond what they ever imagined and become a worldwide resource for millions of displaced people.
2) Dreaming brings out the best in people. Big dreams have led to the most important achievements in human history. From the eradication of smallpox to unmanned spaceflight to the most important technological discoveries of our age, all great accomplishments started in someone’s imagination.
3) Dreaming shifts our perspective. In a culture that overemphasizes busyness and accomplishment, there’s constant pressure to stay on life’s runway, chasing what’s directly in front of you. When all your time and energy is spent working IN your life instead of ON your life, it depletes you, causing you to settle for less. As Tony Robbins said, “Most people get caught up in making a living instead of designing a life.”
To be clear, it’s important to differentiate between dreaming and fantasizing. There is no benefit to having your head in the clouds with no basis in reality. Dreaming isn’t fantasy; it is an intentional pursuit that, if done right, will bring out the best version of yourself. To fully harness the power of your imagination in a way that adds substance and impact to your career and your life, here are five keys to dreaming big:
1) Ask the right questions. Questions have tremendous power to expand our thinking, generate ideas, and uncover our true selves. Here are some good ones:
– How do I want to be remembered? What do I want people to say about me at my funeral?
– What matters most to me? What am I truly passionate about? What inspires me?
– What activities and pursuits really engage me — where I lose track of time, where the hours seem to fly by while I am doing them?
– What would I give myself to if money was not an issue?
2) Set aside time each week to think. This sounds so counter-cultural, doesn’t it? But it’s precisely what some of the most productive and resourceful leaders build into their busy schedules. In his New York Times best selling book, Thinking for a Change, author John Maxwell advises leaders to commit time each day to uninterrupted thinking, planning, and processing ideas. One way to start: Commit 30 minutes a day to answering the above questions.
3) Commit to becoming a more curious person. Practice asking and listening. In my July 10th, 2014 post, “Learn to Be Lucky,” I summarized some interesting research findings on luck. One of them is that lucky people tend to create their own chance events by paying attention, opening their minds to noticing things and, as a result, frequently discovering possibilities well beyond what they were looking for. In much the same way, people who take the focus off themselves tend to stretch their minds, expand their possibilities, and generate new ideas — all of which are the building blocks of great dreams.
4) Write down your dreams, ideas, and goals. Eighteen months ago, at the urging of a mentor, I committed to journaling in the morning three to five times per week. While I was skeptical that I would stick with it, this small habit has become so ingrained that I truly miss it if I go even a day or two without this reflective, thought-provoking activity. In her outstanding book, Write it Down, Make it Happen, Henriette Klauser shares powerful stories about ordinary people who witnessed miracles large and small unfold in their lives after they performed the basic act of putting their dreams on paper. The act of writing down your dreams activates something in your soul that sets things in motion.
5) Spend time with people who see things differently than you. Yes, they will challenge you, but engaging with people who have different political, religious, and intellectual views will sharpen you and expand your thinking. Sadly, in a political culture that labels the opposition as the enemy, we tend to vilify people with whom we disagree instead of engaging them.
My Father, the Dreamer
Earlier this year, I created a presentation for our employees on the history of our company, which chronicles the life and career of my father, and founder of the Bill Marsh Auto Group. My dad has always been a dreamer. Below is a clip from the end of an interview with my father, Bill Marsh Sr, as he shares why:
Question: What about you? Do you consider yourself a dreamer? Why or why not? What would it mean to you and to the quality of your life if you committed to dreaming big? What holds you back? I’d really like to get your feedback.
