Skip navigation
From PhD to Life

Transition Q & A: Lindy Ledohowski, CEO of an educational software company


Lindy Ledohowski earned her PhD in English, focusing on contemporary Canadian literature and ethnic identity politics, at the University of Toronto, and did a postdoctoral fellowship at the University of Ottawa; she serves on the board of trustees for the Canadian Museum for Human Rights, is a member of the Institute of Corporate Directors, a member of the Ontario College of Teachers, and was both a high school teacher (at Balmoral Hall School) and tenure-track professor (at St. Jerome’s University in the University of Waterloo) before co-founding EssayJack as its inaugural CEO. Find her online at EssayJack and follow her on Twitter @DoctorLindy.

Lindy Ledohowski

What did you hope for in terms of employment as you completed your PhD? 

I had been a high school English teacher, teaching AP English and coaching debating before starting graduate school, so I was very comfortable with the teaching side of the academic profession. Throughout my PhD I taught courses, sometimes two or three sections per term, while juggling publishing, presenting, researching, and writing, and so I felt content with the idea of being a full-time, tenure track professor, balancing teaching and research.

I loved my doctoral experience, made great friends, was active in my department, respected and liked my supervisor and committee members, and I enjoyed the scholarly reading and writing that I did. If I thought about my professional future at all, I think I thought about merely wanting to extend that great doctoral experience forever.

What was your first post PhD job?

Before defending my doctorate, I was awarded a SSHRC postdoctoral fellowship which I took up just after my defense (2008). Then, partway through the first year of that two-year postdoctoral fellowship, I landed a tenure-track job at St. Jerome’s University in the University of Waterloo (2009). It is an interdisciplinary university federated within the University of Waterloo with a degree of autonomy, a focus on teaching, excellent colleagues, and small class sizes. It seemed like a perfect fit. During my campus visit, one of my U of T friends from my doctoral days – herself a University of Waterloo prof – met up with me for champagne. I distinctly remember my thoughts that night: “please let me get this job, please let me get this job, please let me get this job…” And then I got it.

Why did you leave your job as a tenure-track professor?

I was so excited when I got the job offer. And in many ways, I still love the professional academy in its best iteration. But loving something as an ideal doesn’t necessarily mesh up with the real, lived experience of love, does it? I needed to make up my own mind about whether or not I had landed in the right place.

There were a number of factors that went into my decision to leave my tenure track job, and while I can drill down into more and more personal reasons to explain the particularities of personality, desire and ambition in my case, what’s likely more important here for others in transition to note is that some of the common reasons for leaving a tenure track job didn’t apply to me:

  • I didn’t leave my job because I didn’t like what I did day in, day out;
  • I didn’t leave my job because I didn’t like my colleagues or students;
  • I didn’t leave my job because I didn’t publish enough or do well enough by university metrics (to quote my review letter: “It is my pleasure to inform you that the Merit Review Committee has recommended an award of 9.84 merit points [out of 10] for the review period and we greatly respect and thank you for all the work which you have done.”);
  • I didn’t leave my job because of personality conflicts; and
  • I didn’t leave my job because I hated it or was disillusioned.

I left my job because the very material conditions of labour – location, income, and autonomy – weren’t what I was looking for out of my professional career. When push came to shove, when the professional academy started asking me to make sacrifices I wasn’t willing to make – especially around indefinitely living a five-hour drive away from my spouse for less disposable income than when I was a doctoral candidate or postdoctoral fellow – I realized that it was not a good fit for me. It was a hard awareness to come to and took some painful moments of self reflection, but I know myself better now.

What was your first post academic job?

While I may have figured out that the professional academy in my real context (not the idealized version in my mind) wasn’t going to give me I was looking for, I wasn’t sure what would, but I knew that I didn’t want just to trade one “job” for another “job” where the value I create goes into benefitting a larger machine. I feel privileged in my education and life, and I feel a responsibility to use my privilege to make a real difference in the world (while also making a living). So I began consulting, finding interesting and lucrative professional contracts that I didn’t even know existed or that I created for myself. And I emailed the press that wanted me to turn my PhD into an academic monograph and told them I wasn’t going to go through with it. When I sent that email and felt no pangs of regret, only relief, I knew I was on the right track, even if the details of the track were still opaque to me at that point.

What do you do now? (How did you get this job?)

I wanted to take the skills that we as academics offer our students day in and day out and see if I couldn’t scale that more broadly in an ethical way. Put another way, I have always believed that with the critical thinking skills earned through textual exegesis and argumentative prose people are empowered. I used to tell my high school students:  “analyze the world around you and be empowered!” I took that mantra, and my spouse (and co-founder) and I developed a web app to help students write essays more easily and to help teachers teach essay writing more easily (we called it EssayJack). Once we tested this idea with live users in 2014, we began to see that we had to build a business to support it, so now I’m the CEO of EssayJack Inc., an educational software company, and our digital product has just been ranked as one of the world’s top English Language Teaching Digital Innovations by Cambridge and the British Council a mere six months after launching in beta. Ironically, I had to leave the University of Waterloo – itself a bastion for entrepreneurship and software development – in order to have the freedom to enter into this field!

What kind of tasks do you do on a daily and weekly basis?

This changes from day to day and week to week. I do it all. Think of it this way: we began with a blank page, and from that blank page, I have the responsibility to build both a product – and plan for a series of future products – and a business to enable this. So what do I do? Project management, bookkeeping, product development, accounting, networking, sales, marketing, human resources, legal etc. I make a million and one different decisions every day as we go from a fast-paced, messy, bootstrapping, “holy cow, what are we doing?” loose connection of folks who believe in this vision of scaffolding for writing to developing ways for this business to grow and exist beyond us. To put it another way, I find myself in a leadership role. It so happens that I lead my own company, but the skills that I am refining as a leader are those that many PhDs in transition have and can offer to other companies too.

What most surprises you about your job?

Everything is a surprise. But the biggest surprise was my utter financial illiteracy. I always prided myself on my fiscal responsibility; I’ve worked since I was 11 years old; I didn’t have consumer or student debt; I never bought a car with financing; I saved and lived within my means, and my spouse and I have always lived by Polonius’s advice: “neither a borrower, nor a lender be.” But those are merely financial intuitions, not real knowledge about dollars and cents, how to make them, how to save them, how to grow them, and how to protect them. I had been happy to trust banks or universities or governments to see to my big picture financial needs so long as I “worked hard” and was “responsible,” and I was surprised to drill down into some of those assumptions and develop a better sense of clarity around finances. To be clear, my developing financial literacy is still very much a work-in-progress, and I imagine it will continue to be something I work at for the rest of my life, but now, at least, I feel less blind.

What are your favourite parts of your job?

My favourite part is that it’s not a “job” where I am plugged into someone else’s framework. My inner kid screams “you’re not the boss of me!” whenever a context feels too arbitrarily restrictive or someone wants me to do something “because that’s the way we do it,” without a clear justification that I can support and endorse. But, now, I get to learn new things all day every day and believe in the choices I make.

Technically, I don’t know how to do any of the things that I currently find myself doing. Do I have training in building and motivating a sales team? Nope. Do I have training in building and managing a technical development team? Nope. Did I even know how to create cash flow spreadsheets, budgets, profit and loss statements, and invoices? Again, nope. What do I know about social media? Zilch. You get the picture.

And when I have low days and down days, I remind myself that when I started my PhD I similarly had no idea what I was doing, but I figured it out. When I started doctoral work, had I ever delivered a conference paper? Nope. When I started doctoral work, did I have peer-reviewed publications? Nope. When I started doctoral work, had anyone ever trained me in how to write a dissertation? Nope. But I did all those things, and so I tell myself that all the surprises that come my way now are nothing in comparison to what I and anyone else who has been honed in the crucible of a doctoral project have done already.

Even though I may not have technical training in many of the things that I do today, the most important thing that I do have training in is how to learn. I learn quickly; I know how to research quickly to find things out; I know how to ask for help; I know how to analyze things critically; and I’m confident speaking in front of various types of audiences. All those are skills that I developed throughout graduate school and that most (if not all) post-PhDs should feel confident about possess them too.

What would you change about it if you could?

I would have success come more easily and with less cost. I’m not going to lie, building a business is hard work. My days start at 5 a.m. (if not earlier), and they end when I can’t keep my eyes open any longer; I work weekends and evenings and haven’t taken a “holiday” in years. I have put three years of savings into this business, take no salary, and for the first time in my life carry debt. The responsibility is huge and terrifying and exciting, and I need to have the courage of my convictions, thick skin, and a strong stomach, and if I could change anything, I would have all schools, universities, and students in the whole world magically hear about our amazing, empowering product, and line up to get it, and it would all be easy peasy. Until that happens, I remind myself that I have long lived by the line from John Milton’s : “that which purifies us is trial, and trial is by what is contrary.” So when things aren’t as easy as I’d like, or when someone says something snarky to me about “selling out,” I remind myself of that Miltonian truism paraphrased as “tough stuff makes you better,” and then I just pull up my socks and get on with the next thing on my to-do list.

What’s next for you career-wise?

Maybe we’ll get investment money and build up EssayJack as a huge business, developing more digital writing tools and platforms for other contexts, such as corporate or government. Maybe we’ll partner with other companies who believe in the power of education, critical thinking, and the written word. Maybe we’ll be acquired by a big tech company, and I’ll go work there for a while to bring this vision to fruition. I honestly can’t say, but I’m open to almost anything.

What advice or thoughts do you have for post-PhDs in transition now?

First, my story is only my own, and I can’t say it’s a template for anyone else, but I feel that it is important to add my story to the many encouraging #postac and #altac stories out there, because often the discourse is shaped by not getting a tenure-track job. But I got the opportunity to try out the tenure track and come face-to-face with how it didn’t mesh up with my internal list of priorities, and if I have any advice to give, it would be for post-PhDs in transition to try to be as honest as possible about what your own list of priorities happens to be, because the professional academy may not necessarily be a good fit in reality, despite what it might look like from the outside.

Second, and I can’t stress this one enough, many academics (including former or post academics) don’t always know what opportunities are out there in the wide world. Many don’t know how fast the world outside the academy works, and some can tend to want a degree of certainty that doesn’t exist. So, have the courage to step out into the unknown and be confident that your graduate training has prepared you to figure things out, and don’t worry that you don’t know what you don’t know. Just start taking steps, which will lead to other steps, and then others, and then, before you know it, you’ll be halfway down a path you didn’t even know existed!

Third, in life (as in the academy) merit alone isn’t enough to secure success. Network, make connections, ask questions, and ask for help. Be clear in the kind of help you want and ask people for them. The worst thing that will happen is that they will say no.

Fourth, ask yourself whether you’re really looking for a “job” or whether you want to be an entrepreneur. Maybe you want to build up your own consultancy; maybe you want to start a business; maybe you want to develop a product or idea. Don’t be afraid to think outside the “job” box if it doesn’t fit your personality.

Finally, I have found that sometimes there’s an easy binary that is created that suggests the academy is good and business is bad (I’ve been guilty of buying into this binary), but I’ve begun to see much more nuance in my post-academic life. Don’t be too quick to judge anything or anyone, as there are loads of learning opportunities out there.

Jennifer Polk
Jennifer Polk is a career coach and entrepreneur. She earned her PhD in history from the University of Toronto in 2012. For more information and resources, check out her website:
Post a comment
University Affairs moderates all comments according to the following guidelines. If approved, comments generally appear within one business day. We may republish particularly insightful remarks in our print edition or elsewhere.

Your email address will not be published. Required fields are marked *

  1. Janet MacDonald / May 16, 2016 at 10:05

    Wow, what an inspiration! I’m revved up and ready to take on anything just from reading the article. Love her energy and positive attitude!