Jessper Maquindang Travels Across America | Leadership Lessons from Visiting All 50 States

Jessper Maquindang is a seasoned leadership development consultant with over a decade of experience in optimizing organizational performance and fostering highly effective cultures. Jessper leads FamiLEAD Management Consulting, a premier consulting firm dedicated to transforming organizations through innovative leadership development and team-building solutions.

Recently, Jessper completed an ambitious journey, visiting all 50 states in the USA, from Hawaii and Maine to Florida and Alaska. He developed a strong appreciation for the value of different perspectives and learned to be more open-minded and flexible in his approach to problem-solving. This adventure provided him with invaluable insights into diverse cultures and challenges, helping him improve his managerial abilities and become a more effective leader. But how did these experiences shape his approach to leadership and development? Let’s find out.

Q1: Could you tell us about yourself, what you do for a living, and what you’re currently working on?

I am Jessper Maquindang, owner of FamiLEAD Management Consulting, a leading firm dedicated to transforming organizations through leadership development and team building.

My interest in leadership and personal growth dates back to my formative years in Southern California. I still remember wandering through bookstores and becoming fascinated as I walked through aisles dedicated to self-growth and career development books.

Early in my career, I got the opportunity to supervise employees and lead my own team directly. Simultaneously, I actively participated in many leadership workshops and seminars to gain more insights and perspectives in the field. These experiences gave me the confidence to lead others as I progressed through my career and continued to lead more teams over the years.

Fast forward to the present day, I’m a company culture consultant and leadership speaker. Taking what I’ve learned over the years, I enjoy helping leaders and managers build effective teams through leadership development assessments, team-building exercises, and executive coaching. As a believer in continuous growth, I continue to seek out new ideas and methods for team-building and leadership development.

Recently, I completed my travel to all 50 states in the USA, which gave me valuable insights into diverse cultures and challenges. Eventually, my trip around the country became a leadership development course in itself, enriching my approach and perspective.

Q2: What inspired you to travel to all 50 states?

Interestingly, while growing up, I had never imagined traveling to all 50 states. It was a goal that emerged later in life when I landed my first job at a travel company.

I was appointed as the team leader of our documentation department, where our daily operations involved creating customized guidebooks for clients who were traveling across the United States. As I flipped through the pages of these guidebooks, I was inspired by the landmarks and attractions around the country. With a spark of curiosity and wonder, I was motivated to explore what my home country had to offer.

I found a company that provided bus tours and signed up for a trip that would take me across the Southern states and the East Coast – from Louisiana all the way down to Florida, then all the way up to New York.

After that trip, I was hooked. From that point on, I felt inspired to visit all 50 states. I finally achieved that major goal upon reaching Alaska in June 2024.

Q3: Is traveling across the country an effective way to develop leadership skills?

Absolutely, I can confidently say that traveling across the country is a highly effective way to develop leadership skills.

But first, what exactly is leadership? While there are many definitions, I would describe leadership as the ability to achieve significant goals despite obstacles and challenges. It also involves learning and growing throughout the journey toward these goals, personally and professionally. This process teaches essential skills such as decision-making, communication, and adaptability.

With that said, can these skills really be developed by traveling across the country? In short, yes! Based on my experiences, traveling can provide these development opportunities when viewed in the right frame of mind.

For instance, exploring art galleries in Santa Fe, interacting with people beyond your usual circle, walking the expansive corridors of the Mall of America in Minnesota, or enjoying deep-dish pizza in Chicago are all unique experiences that can shape your subconscious mind and refine your interpersonal and leadership skills.

These interactions help you build empathy, improve communication, and develop a broader understanding of various perspectives, all of which are crucial for effective leadership. Additionally, these travel experiences provide valuable insights into decision-making, adaptability, and other essential skills.

Q4: Are there any specific skills you can gain from traveling across the country?

Without a doubt, yes! The five most prominent leadership skills you can gain from traveling are communication, planning, time management, adaptability and self-awareness.

Communication

There may be moments when you need to ask for directions. There may be moments when you need to place your lunch order with restaurant staff. There may be moments when you need to advise family members which items they’re allowed to take through to the TSA security line at the airport. All of these moments require communication in some form. As a result, your communication skills are sharpened as you interact with other people on your trips.

Planning

When organizing a trip to other states, there will always be some planning that goes into it. How will you get there? By airplane, car, or train? Where will you stay? At a hotel, friend’s apartment or beach house? Who are you going with? Solo or with family? Even for the spontaneous traveler, you’re making decisions on the spot, which is still a form of planning. As you’re figuring out the details for your trip, your leadership repertoire expands.

Time Management

When you’re traveling, it is important to be mindful of how you’re managing your time. If your flight to Salt Lake City departs at 4:50 PM, you need to get there at least one hour earlier to check in and go through the security lines. If you’re going to a Broadway show in New York City, you need to get there early enough to find your seats and enjoy the full show. If you’ve signed up for a bus tour in Boston, you want to make sure you get there on time so you don’t get left behind. In the realm of leadership, developing your time management skills through travel can help you become more effective in how you prioritize your tasks and responsibilities.

Adaptability

Travel plans can change at any time. Unexpected situations can happen. What do you do when you arrive at a popular restaurant in town but discover it has a long line with a 2-hour wait? What do you do when the Wi-Fi connection loses its internet connectivity at your hotel? What do you do when all of the nearby roads to a highly recommended museum are closed due to construction?

It’s easy for many people to panic and get overwhelmed at the moment. But worrying is not going to be productive. Take a deep breath and consider other ways to make good use of your time. When you continue to explore, there’s a good chance that another great event or attraction can be found nearby. These are opportunities to try new things. When traveling across the country, these moments of adaptability will help you build your effectiveness as a leader.

Self-Awareness

Self-awareness is the ability to form a clearer understanding of your values, beliefs, feelings, thoughts, and actions. Traveling around the country will help you develop that clarity. Will you gain a deeper appreciation of country music when you arrive in Nashville? Will you get energized by the fast-paced lifestyle of New York City? When you make dinner plans in San Antonio, will Tex-Mex become your new favorite cuisine? Visiting other states can help you gain a better understanding of what works well for your preferred tastes and anything that doesn’t work well for your preferences. When you have a better understanding of who you are as an individual, you will become a better leader.

Q5: How did you handle moments of uncertainty or crisis during your journey, and what lessons did you draw from these experiences?

There are many benefits to traveling across the country. It is certain that the good times will outweigh any bumps along the way.

For most trips, major disruptions are uncommon. But when uncertain situations do happen, it is important to pay attention to the valuable leadership lessons they offer. As Rahm Emanuel, former mayor of Chicago, said, “You never want a serious crisis to go to waste. And what I mean by that is an opportunity to do things that you think you could not do before.”

As a leader, it is vital to appreciate every moment while traveling, even the challenging ones.

New York City

I arrived in New York City in 2012, unexpectedly caught in the midst of Hurricane Sandy. Many services and attractions were shut down. Power outages, uprooted trees, flooded streets, you name it. For safety reasons, everyone had to stay indoors, but you were still able to hear the strong gusts of wind blowing through the area. But after the storm was over and the sky was clearing up, I still wanted to explore New York City.

This was my first trip to the Big Apple, after all. Although public transit was down, I was still able to access ride-sharing services and explore some parts of the city on foot. Although the full New York experience was unavailable at the time, I was still able to do some sightseeing in Times Square and other places that could reopen safely.

Fortunately, I would return one year later for vacation with family members to get a more comprehensive experience of the city – Statue of Liberty, Central Park, New York-style pizza, everything.

Leadership Lesson: When things don’t go according to plan, learn to adapt. You might have an overarching goal in mind, but then, lo and behold, disaster strikes (perhaps literally, as in my case). You could sit back and miss the opportunity to gain something valuable from the experience. Or you can step up and find ways to make the most of it.

Alaska

I had just arrived at the Los Angeles International Airport (LAX) to catch my flight to Anchorage. As I was walking to the boarding gate, my phone received a notification. “Ding!” However, it was a message that no traveler ever hopes to receive: DELAYED. I had a connecting flight in Seattle, and I would miss that flight with this delay. Even worse, I had to be in Anchorage at a certain time, so that delay would have made me miss the day’s important events. I walked around the terminal to see if any other flights were heading to Alaska. Indeed, I found a direct flight to Anchorage that was leaving soon. However, the gate agent there informed me that I could only make the change directly with the gate staff from the original flight. That team had not yet arrived. The original flight was delayed, after all.

I took another lap around the terminal to search for the customer service office, but I could not locate it immediately. Time was running out. I realized another option: I decided to contact the main customer service line by phone. As soon as the agent on the other line picked up, I asked, “My original flight is significantly delayed. I’m going to miss my connecting flight. What are my options?” The agent pointed out the direct flight to Anchorage that I noticed earlier. Fortunately, there was still room available on it and the agent updated my booking on the system. Wow, I wished I had thought about making that phone call earlier, but better late than never, right?

Leadership Lesson: Know your options. Whenever you find yourself in a less-than-ideal situation, remain calm and be proactive about searching for alternate solutions. With time constraints in consideration, keep looking around until you find the most effective solution available.

San Diego

One weekend, I was on my way to San Diego for a special event. On the drive there, the warning light on my car’s dashboard began to flash. I was arriving at my hotel soon, so I was not too concerned about it at the time. After a long day, I decided to head to bed early. The next morning, I got up and started to get ready for what I was expecting to be an exciting day with the events ahead. Unfortunately, the worst thing to discover when you approach your car is a flat tire. Worse yet, I did not have a spare tire available.

I thought to myself, “What now? I have to be at this event in 15 minutes. That’s not enough time to fix this.” After pondering the situation for a few minutes, I decided that I could leave my car at the hotel parking lot for the afternoon, book a ride-sharing service to the event venue in the meantime, and then call for towing service upon my return to the hotel. Fortunately, I made it to the event on time and I was able to remediate the situation with my car when I came back.

Leadership Lesson: Make sure you have backup plans in place. In the event of an emergency in your personal or work life, you want to make sure that your projects or processes can still operate smoothly despite any disruptions or interruptions. When backup plans are ready to implement, the rest of your day can flow much more smoothly.

Q6: What advice would you give to someone who wants to develop their leadership skills but might not be able to embark on a similar cross-country adventure?

The advice I would give to someone is to explore your neighborhood and participate in community events. But go to the parts of your community that you have not yet visited. Is there a bus route that you have not taken before? Is there a nature trail that you haven’t explored yet? These are useful opportunities to sharpen your ability to respond to new, unfamiliar situations.

Understandably, exploring your neighborhood won’t give you the full experience of visiting another state. But it’s a good start to build up your sense of inquiry and wonder for the world around you. When you’re genuinely curious about the world, you will gain the motivation to experiment and try new things. When you experiment and try new things, you learn what works and what doesn’t work for you. With that understanding, you are developing your skills as a leader who wants to innovate and unlock the possibilities out there. Be open-minded about observing your surroundings.

Your curiosity will lead you to become a more effective leader.

Q7: How do you balance your adventurous spirit with the responsibilities of your professional life?

Finding this balance can be challenging, especially with the very ambitious goal of reaching all 50 states. I’ve been using my vacation time or other time off strategically, planning my trips ahead of time so I can reach the key areas in the appropriate amount of time once I’m there. In addition, whenever there is some spare time waiting at the airport or downtime waiting for a special event at the destination city, it gives me an opportunity to catch up on any work on my computer.

Another common approach is to complete tasks ahead of schedule so that your workload is completed before you leave the office for your trip. It’s also helpful to delegate your work so that your backlog doesn’t fill up too quickly upon your return. If you work with a team, this is the perfect opportunity to practice your delegation skills. Hopefully, it should now be obvious that leadership development opportunities can be gained from traveling.

Q8: Which state left the most lasting impression on you and why?

The small but mighty state of Rhode Island. Growing up in a much larger state like California, I never knew what the New England state could offer. But as soon as I stepped foot there, I realized there are wonderful places to explore in the Ocean State. I spent the entire day exploring the Gilded Age mansions, such as The Breakers, Marble House, and The Elms, taking a scenic hike across Newport’s Cliff Walk, and marveling at the views of the Atlantic Ocean from Easton Beach. For a smaller state, my time in Rhode Island would be a very productive trip that I can recommend to others.

Also Read: Themed Escape Rooms: Exploring the Best Concepts Across the USA

Q9: What hidden gems do you think more people should visit in the USA?

I’ve always enjoyed beach trips since growing up in California. In regards to hidden gems, I would recommend Gold Beach in Oregon and Cocoa Beach in Florida. I was captivated by the calm, serene nature of Gold Beach, and I was fascinated by the beautiful white sands of Cocoa Beach. Another hidden gem can be found in my home state. There’s a Danish village in the city of Solvang, located in the Santa Ynez Valley. Walk around, and you’ll feel like you are in Europe.