Meet Char Lessenger

We recently connected with Char Lessenger and have shared our conversation below.

Char, thank you so much for joining us. You are such a positive person and it’s something we really admire and so we wanted to start by asking you where you think your optimism comes from?

My optimism truly comes from two core beliefs that have been deeply ingrained throughout my journey, coupled with personal mottos I live by.

First, I fundamentally believe in the power of human connection and clear communication. Whether it was guiding students through complex decisions, helping clients achieve their business goals with digital strategies, or navigating new cultures while teaching English abroad, I’ve seen firsthand how clarity, empathy, and genuine connection can overcome almost any obstacle. When you focus on understanding and building rapport, challenges often transform into opportunities.

Second, I have an unwavering faith in growth and strategic problem-solving. In every role, especially running my own agency, I’ve faced unexpected hurdles. Instead of seeing these as roadblocks, I’ve learned to view them as puzzles to solve. I trust my ability to analyze a situation, adapt rapidly, and find a path forward. That belief in continuous improvement and the power of a strategic pivot fuels my positive outlook.

Underpinning all of this is my deep conviction that everything always works out for the best, for my highest good. This isn’t just a hopeful thought; it’s a belief born from experience. I’ve navigated challenging times and past shortcomings, and each instance has ultimately revealed a positive outcome or a valuable lesson that propelled me forward. It means I view setbacks not as failures, but as a confirmation that rejection is protection and redirection – clear signals guiding me toward an even better path. This mindset helps me embrace patience when things get tough, knowing that challenges are simply detours leading to even better destinations.

This blend of trusting connection, embracing challenges, and holding onto those unwavering beliefs is what keeps me optimistic, constantly looking for the best possible outcome, and genuinely excited about what’s next.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

I wear a couple of hats, both driven by a core passion for connecting people with meaningful experiences and solutions.

First, I’m the founder of a digital marketing agency, where I partner with businesses to transform their online presence and connect them more effectively with their ideal customers. What excites me most about this work is the direct impact I see. It’s incredibly rewarding to dive deep into a client’s vision, understand their unique challenges, and then craft a digital strategy that helps them not just reach, but truly resonate with their audience. We’re not just building websites or running ads; we’re helping businesses tell their story, expand their reach, and ultimately grow. My goal is always to deliver clear, measurable results that directly contribute to their success.

Beyond that, my professional journey has been a vibrant tapestry of experiences – from academic advising to teaching English in Indonesia. Each role has deepened my ability to listen intently, understand diverse needs, and guide individuals towards transformative outcomes. This background means I bring a unique blend of empathy, adaptability, and strategic thinking to every project and every team I join. I’m genuinely wired to build trust and turn aspirations into reality.

What I’d love folks to know about my approach is that I believe in curiosity-driven problem-solving. Whether it’s dissecting a client’s marketing puzzle or navigating a new cultural landscape, I approach every situation with an open mind, eager to understand the ‘why’ and uncover the best path forward. Having a mindset like I mentioned ensures I stay optimistic and persistent, always seeking growth and innovative solutions, even when facing challenges.

Looking ahead, my agency is currently focused on expanding our capacity to serve more purpose-driven small to medium-sized businesses, particularly those looking to enhance their community engagement through digital storytelling. We’re constantly refining our processes to offer even more tailored, impactful strategies that cut through the noise.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Looking back, three distinct qualities, skills, or areas of knowledge truly shaped my professional path and allowed me to navigate its diverse landscape successfully.

First, Adaptability and embracing change has been absolutely foundational. My journey has involved navigating different cultures while teaching internationally, launching and growing a business in a rapidly evolving digital world, and advising students through complex academic transitions. Each of these experiences demanded a willingness to pivot quickly, learn new systems, and adjust strategies on the fly. It taught me that fixed mindsets often limit potential, while embracing new circumstances opens up new opportunities.

Second, Consultative Communication proved invaluable. This isn’t just about talking; it’s about deeply understanding. Whether I was deciphering a client’s unspoken business challenge, empathizing with a student’s dilemma, or building rapport across language barriers, the ability to ask the right questions, actively listen, and then articulate solutions in a way that truly resonates was paramount. It transformed interactions from transactional to genuinely collaborative.

Finally, Relentless Resourcefulness has been my secret weapon. As an agency owner, there was no pre-written playbook for every challenge. I learned to independently seek out information, creatively piece together solutions, and leverage every available tool and connection to achieve desired outcomes. This skill kicked in whether I was troubleshooting a technical issue for a client, finding an unconventional solution for a student, or even navigating personal logistical hurdles in unfamiliar countries.

For anyone earlier in their career, focusing on these areas can make a huge difference. My advice? 👇

– Actively seek out experiences that push you beyond your comfort zone. This could be taking on a project in a new department, volunteering for a role where you have to learn new software quickly, or even engaging with diverse groups of people. See every unexpected change as a puzzle to solve, not a problem to avoid. The more you flex that “adaptability muscle,” the stronger it gets.

– Practice active listening every single day, not just waiting for your turn to speak. Ask open-ended questions that encourage others to elaborate, then summarize what you’ve heard to confirm understanding. Role-play difficult conversations, seek feedback on your communication style, and remember that true influence comes from understanding, not just telling.

– Adopt a “figure it out” mentality. When faced with a challenge, resist the urge to immediately ask for the answer. Instead, first try to Google it, consult online forums, or brainstorm with peers. Build a network of diverse contacts and don’t be afraid to reach out and ask for advice or insights when you hit a wall. View every hurdle as an opportunity to expand your problem-solving toolkit.

Any advice for folks feeling overwhelmed?

When I start to feel overwhelmed, my first step is always to pause and create some immediate mental space. I find that doing a quick “brain dump” – writing down every single thing swirling in my head – really helps declutter my thoughts and allows me to see everything more clearly. From there, I mercilessly prioritize, identifying the one or two critical items that will make the biggest difference. It’s about recognizing that not everything needs to be done right now, or even by me, and then focusing on what truly matters.

Beyond immediate action, my personal philosophy deeply informs how I handle overwhelm. I truly believe that everything ultimately works out for the best, for my highest good. This conviction, born from experience, means I view challenges not as roadblocks, but as detours leading to better outcomes. It also reinforces that any perceived setback is simply protection and redirection, guiding me toward a more aligned path. This mindset helps me maintain patience and a proactive, problem-solving approach.

For anyone else feeling overwhelmed, here are a few strategies I’ve found incredibly helpful:

Implement an “Energy Zone” Schedule: This goes beyond just time management. I actively try to schedule my most mentally demanding tasks during my personal peak energy hours, and save lighter, more administrative work for when my energy naturally dips. It transforms work from a constant uphill battle into a flow that respects my natural rhythms.

Conduct a “Curiosity Audit” within the Chaos: When the sheer volume of tasks feels daunting, I pick one item, even a small one, and ask: “What am I genuinely curious about within this task, or what’s one thing I could learn from this specific piece of the overwhelm?” Shifting my mindset from obligation to genuine curiosity can often unlock surprising solutions and make the entire task less intimidating.

Schedule a “Strategic Disconnect”: Beyond just taking a quick break, I’ve learned to treat scheduled times of complete unavailability – notifications off, email closed – with the same reverence as a client meeting. This isn’t just about resting; it’s about deliberately creating unburdened space for my mind to process and recover, preventing overwhelm from accumulating in the first place.

Contact Info:

• Website: https://wanderwriteagency.com
• Linkedin: https://linkedin.com/in/clessenger

Image Credits

Laxdy Sombounsy (@dy.outdoor)