How Lindsey Wander Left the Classroom to Build Her Tutoring Business

Lindsey Wander is a former middle school teacher who chose to start her own tutoring business when she moved to a new city. Initially, she did all the tutoring herself, but today WorldWise Tutoring has a team of more than 100 tutors. Read this interview to learn how she started and grew the business.

Tell us about yourself and your business.

I am a former middle school math and science teacher. I taught in the low-income neighborhoods of California, making it my mission to create a learning environment that was so engaging that it motivated my students to come to school. We explored, questioned, investigated, learned, laughed, and loved – all within my classroom walls. For the sake of a better word, it was “magical.” I knew I found my calling, and I knew I was making a difference. My students became my kids whom I worried about even when I wasn’t working and whom I am still in touch with to this day. 

However, there was a part of me that remained unfulfilled. While I truly loved my job, I was limited. Time and financial restraints added to endless bureaucratic red tape, prevented me from being able to dedicate the 1-on-1 time to my students who needed it. Many of “my kids” fell through the cracks, and there was nothing I could do about it.

So, when I moved to Chicago at the age of 30, I decided to start my own tutoring business. My mission was to help students of all abilities not only improve their grades and scores but also master the underlying learning and life skills to grow into confident and independent learners and, eventually, competent and conscious leaders. I sought to empower our youth with the tools to succeed in school, work, and life – so they were in a powerful position to direct their own lives. 

My methodologies were so effective that WorldWise Tutoring quickly grew beyond what I could handle alone. So I started to “teach the teachers,” guiding tutors dedicated to my cause with my best practices. I’ve since expanded to 100+ tutors who work with students of all ages in person throughout Illinois and into Texas, as well as online throughout the world.  

When the pandemic school closures began to disproportionately impact the learning of socio-economically disadvantaged students, I decided to use my experience in the education industry to found a tutoring nonprofit. Since 2020, Educate. Radiate. Elevate. has been providing high-quality learning support for underprivileged students – at no cost to their families. By providing the tools needed to grow academically and emotionally, we’re positioning the youth we serve to be successful in life and to become contributing members of society.

I found a career that I love and that makes the world a better place. My goal is to inspire my students to do the same.

What was your inspiration for starting the business?

Looking back, I realize that I had a few influential teachers right at times in my life when I desperately needed them. This is likely what lead me to become an educator, going beyond what is required of me and assuming a similar “coaching” role in my students’ lives.

But, growing up, I personally didn’t know any entrepreneurs or business leaders (though I know many now).  I think what inspired me to pursue a career as a business owner was simply that I wanted to do things the way I knew was best, and not just the way I was told to do them.

As a teacher, the school or state often mandated me to teach a certain way utilizing a specific curriculum. Even if the required approach was ineffective, politics dictated that I must stick with it. Meanwhile, I was forced to sit by and watch my students fall behind and, perhaps more devastatingly, hate being at school.

I knew I was a great teacher who could read my students well and deliver the personalized instruction they needed. So, I took the risk of leaving a guaranteed job with stability and benefits to use my talents to help kids excel.

How do you market your business? 

I work with families and their children, so word-of-mouth has been the best way to spread awareness of WorldWise Tutoring’s services in a genuine way. Because of the stigma around tutoring and because many parents are worried about their tutor not having enough availability, the most frequent situation in which word-of-mouth occurs is once the family has finished with our services. Since our goal is always to get our students to a point where they do not need a tutor, this sharing of info with others could take place even just a couple of months after a family starts with us.

It seems counterintuitive: try to get your client NOT to need you. But in doing so, that client goes out and tells everyone how effective our services are, and for the one client who moves on, we gain many more new clients. Plus, the original client often returns later as new challenges arise, such as AP classes, ACT/SAT prep, college planning, internship applications, GMAT prep, etc.

I credit clients who refer other families with free tutoring and give bonuses to tutors whose work results in those referrals. While many referrals would likely occur organically, offering these incentives gives an extra push for families to spread the word and for tutors to provide exceptional services.

What advice do you have for other entrepreneurs?

Do not be swayed by others from what feels right. In high school, I was told to just choose a career that “makes you money, since everyone ends up hating their job anyways.”

When I changed a potential career as a biomedical engineer to that of a teacher, I was told I was “wasting my intelligence.” When I left my stable job as a teacher to become a full-time tutor, I was told I was “making a huge mistake.” Yet, each time I knew that I was doing what was right for ME. So I ignored their “advice,” and I followed my intuition. 

Now, I wake up each day excited to work, and perhaps more importantly, I’m inspiring others to do the same. Your job is a huge part of your life. If you’re unhappy at work, you will be unhappy in life. Choosing what makes you happy can also make you financially secure if you’re willing to put in the work—and it’s worth all that work to be able to do something you love.

What tools do you use and recommend?

I love Content Studio for social media. I have the most basic package and use it to post on all my social media accounts at once.  I know there are many tools like this – and I probably tried them all! But this is the easiest to use right from the beginning and its customer service is amazing. I will eventually add more features once my budget allows, but for now, I’m quite pleased with how much time (and money) Content Studio saves me.

What motivates you to keep moving forward?

When in high-stakes situations that involve a lot of pressure, I first make sure I stop to put everything into perspective.  This may mean giving myself a pep talk that “This is just temporary” or telling myself that “I’ve got this!” Or it may mean reminding myself of my main life goal of helping others to reach their goals.

If that does not help, I seek outside help. I talk to loved ones whom I trust to support and guide me. I’m vulnerable with them about my worries and self-doubts. They always seem to know exactly what I need and deliver it. I’m very fortunate to have such a supportive network in my life.

Alternatively, I may simply take a break. Even though high-stress situations may seem like the worst time to step away, taking a breather always helps me return to the situation with a clearer mind.

What is your favorite quote?

Benjamin Franklin’s quote, “Tell me and I forget. Teach me, and I may remember. Involve me, and I learn,” has been my driving force as an educator for the past 15+ years. It reminds me that students need to be involved in their learning every step of the way in order for it to be effective.

As adults, we tend to underestimate kids, thinking we know better. But not a day goes by without one of my students impressing me with his/her deep understanding, perceptiveness, creativity, or empathy. Kids are wiser than we may think. They usually just need the proper support to lead them down their own path of discovery and growth.

I also recently heard “small changes are big changes.” Some of these suggested reforms can seem daunting, and they are. But even changing the language we use when speaking to kids and the opportunities we expose them to makes a huge difference in what they see themselves as capable of.

What are some of your favorite books, blogs, podcasts, or YouTube channels?

My first teacher mentor gave me a book titled “Teach Like a Champion.” Even many years later, through all my travels and cross-country moves, this is the one education resource I have held on to – it sits within arm’s reach on the bookshelf in my office to this day. I credit this book with amplifying my natural abilities to help me become an extremely efficient and engaging instructor.

As a teacher, I was always evaluated as having exceptional classroom management skills, many of which I learned from this book. Using the 49 techniques this book suggested, I was able to facilitate student-centered learning that was successful and fun.

I’m an undercover nerd who sits on the ledge between science and spirituality. So I love anything that invites me to look at the world differently. My favorite thing to do is to listen to podcasts while I exercise. There is something about having my body occupied that allows my mind to truly focus on the words I’m hearing.  My favorite podcasts are This American Life, Hidden Brain, Science Vs, and Positive Head.