We caught up with the brilliant and insightful Char Lessenger a few weeks ago and have shared our conversation below.

Char, looking forward to hearing all of your stories today. Can you tell us a story about a time you failed?

I started my career in Higher Education but after the pandemic, I felt pretty burnt out. Once I graduated with my Master’s degree in Higher Education Administration and a certificate in Teaching English as a Second Language (as a backup plan) while working a full-time job as an academic advisor I decided it was time to take the leap and try to teach abroad somewhere and get the spark back that I felt was missing in my life.
I tried for two and a half years to get a visa to China but it just wasn’t happening. Eventually, I landed in Indonesia and became a center manager in Jakarta. However, unfortunately, the man that hired me was using the center to scam teachers like myself, and schools in the greater Jakarta area. I won’t go into full detail, but needless to say I left that job pretty quickly after that realization wondering what I should do next.
I was in an unfamiliar part of the world with no plan so I thought I might consider teaching in a different country. I left Indonesia to go visit a friend in Vietnam who was teaching in Saigon to see if that might interest me. Once I got there, I realized that going back to teaching wasn’t for me.
I contemplated on the things I could do with the skills I had and came to the logical conclusion of building a digital marketing agency. This work would allow me to continue traveling while also making some money and building my business along the way.
Over the course of the next two countries; spending the rest of my allotted visa time in Vietnam and then the entire visa period in Laos building my business, I set my sights on acquiring my first client on where I’d land next which was Cambodia.
I decided to head straight to Siem Reap, Cambodia where I knew a person who co-owned and managed a training center for ESL teachers. Once there, I set up a meeting and I put together a proposal for him that included some basic projects I knew would improve his business. Right after we met he approved them and I got to work!
I was also able to negotiate a project for a hotel I was staying at in Siem Reap in return for a free stay.
Things were really looking up.
Once, I finished my visa time in Cambodia, I headed to Thailand where I’d continue working on my first client’s projects and keep chipping away at adding on another client.
By the time I had traveled through Thailand and Malaysia, I landed in the Phillippines and acquired my second client who had an online retail business. The work I did for this client was extremely rewarding because I got to take my experiences from my recent travels and put them into educational articles about how to travel responsibly in those respective places. I swear I found my Ikigai.
With my first two clients under my belt and one work-for-trade client, I was feeling pretty confident. I finished out my travels in the Phillippines and went on to check out Hong Kong, Taiwan, South Korea, and finally Japan before heading back home to Wyoming.
Once I got back home, the work shifted. I had finished out the projects for both of my first clients and was left wondering how I should continue acquiring clients either locally or globally. I was stuck in a rut, to put it lightly.
I’m an avid crocheter, so to lift my spirits, I decided I needed a little ‘yarnspiration’ in the form of a little retail yarn therapy. I paid a visit to my local yarn store and chatted with the owner of the store for a little while about this incredible journey I had just been on.
She was awestruck. She applauded me for my courage to keep going even though the adventure didn’t turn out quite as I had expected. She also mentioned that she was in need of some help marketing her own business and wondered if I would be willing to put together a proposal for her.
Now I was the one who was awestruck. Here I was down in the dumps about not having any more client work, and just through telling my story, I somehow landed another client.
And then another one.
And another.
Now, I’ve managed to gain my sea legs and I have a portfolio of clients whom I truly adore working with. Their projects fulfill my work plate in ways I would have never imagined and continue to feed my love for education in some of the most unconventional, yet inspiring ways.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I got into the digital marketing world in a roundabout way.

I had always dabbled in graphic design and even did a stint as an online editor for my local community college’s newspaper as well as ad sales for my university’s school newspaper. It’s always been something I’ve been good at but never pursued as a career until I had that unique experience in Indonesia.

I figured building a digital marketing agency was the best way to bring all of my skills together in a way that best served the next steps I wanted to take in life.

For most of my clients, the problems I solve include saving time. As business owners, some retail and some not, they’ve already got so much on their plate they have to juggle, marketing is something that usually gets put on the back burner. They get it done, but not to the level that they’d like.

Being able to meet a business owner and come in and help them in a way that levels up their marketing game while also educating their ideal clientele is something I pride myself on doing very well.

I genuinely can’t stand the type of ‘sleazy’ marketing that convinces people to buy things they don’t need with money they don’t have.

I want my marketing to address needs and educate buyers so they can make informed decisions which in turn helps me keep my integrity in tact. A big plus if you ask me.

I’ve helped my clients with anything from building sales pages, to the more obvious social media content, to the less obvious email sequencing and automation. It all really depends on the unique needs of the clients I come across.

I don’t like selling cut-and-dry service packages because 9 times out of 10 I find myself customizing them to the client anyway.

When I first begin working with a client, the first thing on my mind is getting to know them and their business, then I move into the nitty-gritty of forming a proposal I think might work for them within the confines of their budget. No pushy sales tactics over here.

Where do you think you get most of your clients from?

Boots on the ground chatting or word-of-mouth.

I have tried ‘cold-emailing’ tactics and they just don’t work for me. They’re too impersonal.

I’d say 95% of the clients I’ve acquired are because either I had the audacity to slide my business card over to them while we were having a conversation in passing or one of my current clients told another business owner about my work/services and connected them to me.

For me its more about the quality of the client rather than the quantity. I want to work with people who align with my values and who I believe will align well with my style of work. I can’t determine that through cold emails.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

It might be cheesy, but I’d highly recommend “The Slight Edge” by Jeff Olson.

After I read (actually listened, I’m an audiobook human) this book, it truly changed my way of thinking about productivity.

When I started this business, I was a “beat myself up if I don’t get everything done in a day” type of worker. Once I read this book, I understood why that wasn’t the smartest way to go and worked to build better habits around my productivity.

Seriously, if your to-do list overwhelms you, you need to read it if you haven’t already.

Contact Info:

• Website: https://wanderwriteagency.com
• Instagram: @charrawr01
• Linkedin: https://www.linkedin.com/in/clessenger/

Image Credits

Laxdy Sombounsy (@lllaxdy)