From Tenure-Track Prof to EdTech Startup Founder | Interview with Lindy Ledohowski, PhD

Lindy Ledohowski, PhD, is the Founder and CEO of EssayJack, a rapidly growing software company that helps students to write better. In this interview with Roostervane, she tells the story of leaving a tenure-track professor job in English, and her journey through consulting to eventually becoming a founder. Listen to her talk about following her inner voice and where she draws meaning from.

Chris: It’s my privilege today to have with me Lindy Ledohowski. She earned her PhD in English focusing on contemporary Canadian literature and ethnic identity politics from the University of Toronto. She did a postdoc at the University of Ottawa. She’s done a whole bunch of other interesting things, as we’re going to hear about, but most notably she is the founder of a really awesome edtech startup called EssayJank, and she’s the inaugural CEO of that startup. So Lindy, thank you so much for being here.

Lindy: My pleasure Chris! Thanks for inviting me. I never know if I have anything interesting to say, but I’m happy to tell everyone my story.

Chris: Based on experience, you always have something interesting to say!

Lindy: I have something to say, and it’s up to you to decide if it’s interesting!.

Chris: That’s true, I suppose. Interesting is subjective (laughs), but it’s always very interesting to me.

So we first met around January. We had lunch in Ottawa and I was still working for the government. I had just started Roostervane, and it was getting a little bit of traction. So I was just so excited when we met! I was excited to hear your story, and it was so cool that someone had left a tenure-track job and left and started a company. And I thought, this is amazing! I didn’t know PhDs were doing this!.

And then, to this day, you’re the only humanities PhD I’ve ever met who has taken that path, so maybe my enthusiasm in thinking that I’d found a new subspecies of PhD was a little premature. But it is so good to have you here, I’m just really excited for you to share your story. I know it’s fantastic, and inspiring, and all that good stuff.

I’m wondering if we could just dive right in and if you wouldn’t mind telling us about you “The Academic,” which is a few years in the background now.

Lindy: Yeah. What’s interesting… I finished my PhD in 2008, got a postdoc right away, and then by 2009 I got a tenure-track job. So I had a two-year post doc, and I had to lose the last year of it to take the tenure-track job.

So what’s interesting in some of that, is that I now feel like, “Oh, my story is ten years old, so is it really going to be relevant to people who are newly on this post-academic journey these days?

And I feel like the part that’s important is that 2008 was the financial crisis. The entire world and the academy was crumbling. And while the context now is very different, the job market and the way people feel about it is very much the same.

And so, when I was leaving my tenure track job, there was a lot of verbiage around “You need to be grateful,” “You landed a tenure-track job,” “you’ll never get another one.”

That, I think, is very similar in today’s context. So that’s ten years ago, but I think the pandemic is not so radically dissimilar to the financial crisis when it comes to a very bleak outlook. And so, I like to be able to share my story which isn’t bleak.

But to go back to your question, to tell you about myself as an academic,… So as an academic, I’m a literary scholar by training. My expertise is Canadian literature—CanLit, as we like to call it in the biz. My area of expertise is contemporary Canadian literature, and as you mentioned, looking at identity politics. So what that means is, what do we think about when we think about what it means to be Canadian in today’s Canada? Particularly as it pertains to questions of diversity and identity.

So that’s the kind of stuff that I wrote about, and even still do write about the odd time as a full-fledged scholar. “Lindy the academic,” I first started publishing while I was still in my PhD, so by the time I was on the job market and in the postdoc I had a few peer-reviewed publications under my belt and continued to do some of that publication even once I quit my tenure-track job.

Chris: So as you alluded to in the introduction, you’ve got the dream… the tenure-track job. The thing that everybody is chasing.  The vast majority of PhDs statistically, and also anecdotally from my conversations, expect to be professors. And one of the things that struck me when you first told me your story is that you had, kind of an epiphany, I guess you could call it. So tell us a little bit about what that tenure-track professor job was like, and some of the things that led you on your journey to eventually leaving that “dream job,”

Lindy: Yeah, and what I want to make clear is that I too wanted to be a professor. That was the expectation. That’s what I worked towards. And I never thought of myself as being particularly gifted or smart when it came to academics, so I knew that if I was going to be competitive I’d need to work really hard and have a good track record, and all those things.

Prior to finishing my PhD I’d been teaching at the University of Toronto for three years of my PhD. My PhD was about 4 and ½ years, so for three years of that, I taught full time at the University of Toronto Scarborough campus while working on my dissertation. So I felt that I had a good handle on that mix of the research piece and the teaching piece and I really liked it.

So getting that job was fantastic. I’m not a religious person, but the night of my campus visit at the University of Waterloo I was in the shower at the hotel saying, “Please let me get this job! Please let me get this job!”

I do want to make it clear that it’s not like I didn’t want it or reluctantly landed into the job.

Secondly, the job was a good job. The University of Waterloo is a good university, and I was at a smaller campus St Jerome’s University within the University of Waterloo. So I had small classes, I had good colleagues, so all of those things that you think you want when you dream about that tenure-track job… I had them.

So I want to make that clear, so it’s easy to think—when you hear the odd story of people leaving—you think, Oh, well maybe they never really wanted to be a professor in the first place, or maybe they weren’t good enough, or maybe they were in Timbuktu or something.

It’s important to say you can get all of the things that you think are right, but the lived experience of that still might not fit. In my case, I didn’t know it until I had it.

So for me there were three principle variables that didn’t live up to what I wanted.

The first, typically, is that I had the two-body problem. My husband is also an academic. He had a tenure-track job at Carleton university at the time. University of Waterloo and Carleton are a 5 hour drive apart. I’d made it clear on my campus visit that I had an academic spouse and that that was going to be something that was on the table for us to muddle our way through.

Thing number two: Kitchener-Waterloo is a lovely little place, but it’s a bit weird. My partner and I didn’t necessarily fit. I don’t want to say anything bad about the university or the town itself, but let’s just say it’s not particularly diverse. And my husband is a person of color, and we felt that there in ways that both of us coming from Toronto hadn’t experienced. So that was another thing that made us start to think, Is this a place that we could really live for the rest of our lives?

And the third piece, which is the most important and is really just depending on your personality:

In my case, my chair sat me down… we were sitting in the cafeteria and he came and joined me.

And he said, “I want you to settle in and be happy. You have enough published that you don’t need to have a lot of anxiety about tenure. When the time comes, you’ll be fine for tenure. So just enjoy this starting out period of your career.”

And it was really kind of him to say that, and I know the motivation for why he said that. But in that moment, I had this sort of sweat down my back, and I was thinking, So I know exactly what my life is going to look like for the next forty years. I know where I’ll be living. I know who I’ll see every day at work. I know exactly what my earning potential is going to be, year over year.

And so for somebody like me, because I didn’t think I was the smartest or the most gifted and so I needed to build these goals and challenge myself. And all of that was gone.

And so for me that was very unsettling, and I know for some people that would be very comforting. But for me, I was like, Oh… And so, from now on, there’s absolutely nothing I can do to change the conditions of my work. Whether it’s the location or getting my husband, or even just challenges to myself… there’s nothing I can do.

And so that’s a bit of the landscape of what it was like for me as a young, new tenure-track prof. The shine started to come off that penny.

Chris: That’s really interesting. And how many years into it did you say you were?

Lindy: Yeah, I lasted two years before I was like… See yah!

Chris: So what came next after that? I mean, where do you go? I think there’s a lot of people, even though, not all of us get a tenure-track job—I certainly didn’t. But you ended up plunging into the thing a lot of people go through when they leave academia, which is, “Where do I go next?

Lindy: You know, why I like to tell my story is partially, because I think, as you rightly said… It was my good fortune that I happened to land a tenure-track job, so I got to live that experience that maybe it wasn’t all it’s cracked up to be.

And some other people, statistically, won’t have the good fortune of actually landing that job and then feeling whether it is or isn’t a good fit. So it’s way easier to think, “Oh if I’d only landed that job my life would have been this, this, and this. And so, I’ve very lucky because, I never look back and think, Oh what if I was just a professor. Then I could have this or that… Even on my down days now, I don’t look back and say, Oh, but if I was a professor, I’d have X and Y. Because I know exactly what that life would look like.

Whereas, if I’d never had it, it’s very easy to have that grass is always greener attitude.

And so for some folks, I can’t stress this enough, it’s just bad luck. There’s nothing merit based that determines why one person lands a tenure-track job and another person doesn’t. I’ve been on hiring committees and I can guarantee you. It’s no reflection of your capabilities if it just so happens you don’t land a tenure track job. So it’s important to realize that whatever comes next isn’t just plan B, and plan A is this always   wonderful thing of being a professor.

Because I can tell you, you know, had it happened in some magical alternate universe where my partner and I both landed jobs at the University of Toronto, and got to live in a city we liked, etc., then yeah, being a professor is fantastic, but you can never know if those details would have lined up.


on consulting

Lindy: So when I left, I honestly didn’t know what I was going to do, so I started off first doing consulting. So “consulting” is just this catch-all phrase which is like, “I have a brain, so I’ll do anything you need. And I’ll find some way of making you pay me for that.”

So that was everything from editing, to workplace training… I did diversity training because, as I said, for my dissertation I worked on identity politics in contemporary Canada. So there are diversity and equity questions that you can explore in literary arts, and those can also be workplace questions—if you stretch that a little bit and if you then decide, “Okay, well there are these workplaces and they may care about diversity and equity and hiring practices and what that looks like. So what’s that about, and what can I offer in that space.?”

So that’s what I did at first, and what was really fantastic about doing that experience of consulting for a little bit is that, first of all, I learned how to charge for my time and efforts, to not just work for free. And that didn’t always come easily, because as an academic you get trained to do a ton of stuff for free.

So for example, even after I quit, because I was supervising a student and she hadn’t finished and she had about six months left, and it didn’t make sense to pass her project on to anyone else. So I just finished supervising her for free for six months.  In academia, that makes total sense. That’s what you do.

But if you ask anybody else in any other job to just work for free for another six months on a project, it’s laughable. It’s ridiculous. But you do peer-review for free, etc., there are all these things you get trained to do for free. So then as a consultant, for me to say, “No, I need to allocate time and money for these things.” So that was a really important learning for me.

The second important learning was confidence in my own ability. Because the other thing that, I think, happens to lots of academics… it certainly happened to me, is that I wasn’t all that confident. I felt like, I don’t know anything about the rest of the world at all. Everyone I know has a PhD… Everything I can do, they can do.  

So being a consultant, and being in businesses and having to say, “Here’s how I can help you do what you do, better…” and then deliver on that, and have people pay and be grateful and be happy and see the value in what I was able to do helped bolster that confidence.  

So in the post-academic moment, for people leaving the tenure track either by choice or by force, getting out there, getting consulting, or whatever the gigs are… part of it is just to help boost that confidence, even if the thing you’re doing isn’t want you want to do forever.

Because I had that consulting phase, between being an academic and what I do now, it gave me that confidence to get into educational technology. As you said at the beginning, there aren’t a lot of humanities PhDs who get into the tech startup world… there aren’t a lot of English PhDs who say, “Okay, let’s start a tech company.”

It was that period of building confidence in between that made me say, “Okay… I figured that out, I can figure this out.”


on founding a startup…

Chris: So as you’re going through this consulting career, I remember you telling me before that the consulting was going pretty well. So where did the journey end up taking you that you decided to go from a freelance consultant to an edtech startup?

Lindy: So I made a mistake when I started consulting, and I’ll share this with you. My mistake is that my consulting “brand” was “Lindy Ledohowski, PhD, so that’s what I had to offer. And that was great, but it meant that, as I started to have more work than I could just do myself in hours of the day and days of the week, I would try to bring on assistants. Ultimately, because so much of the brand was me, any clients that I had built up a relationship with, if I was like “Hey, here’s this assistant. She’s gonna do your project,” they were resistant to that. They were like, “No, we hired you to do this. We want you to be the one to deliver on this project.”

So I had run into a problem of scalability. I was not scalable, there were only so many of me. And because I had created this brand around me, it meant that I could work from Monday to Friday for forever, and I could probably continue to drum up enough work. There were busy times and quiet times when it came to cashflow, but overall—on an annual basis—it was fine, and I could have kept doing that forever.

But I could never grow.

So I started to have this moment where I was like, “Okay, this is a service based business that I’m running. I need to somehow get into a product-based business, where the product can then scale outside of me. So that was really, as I started to think about what the next step was going to be. And that product could have been shoes, books, or whatever it was going to be.

And then, it so happened that my husband who had become an assistant, then an associate professor, so he’s tenured. And we’re still talking about the fact that students can’t write, and it’s this perennial problem, and you can essentially spend your entire life saying, “ARRGGHHH KIDS CAN’T WRITE!”

But we thought there was probably technology out there that could help.

So as I was doing research into what the technologies were in the writing space that maybe I could use as a consultant, or that I’m starting to think about as I think in terms of product, there wasn’t really what we were looking for.

So we asked ourselves, “How hard is it to build?” So that’s what started us on the EssayJack journey and coming up, on September first, it’s five years since we launched a very shaky beta product in the market. By 2019 we had a fully integrated, institutional product. It integrates with blackboard and canvas and D2L, it has Google Sign in so you can sign directly in with your Gmail. It has educator accounts, student accounts, automatic feedback, all kinds of things in it. But at its core, it began its life as a tool to help students write essays.

So it breaks the writing process down into small, manageable chunks that take away the anxiety and gives tips and prompts, and it just does that through technology.  

Interview has been shortened for length. For the full interview, watch the video.

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 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.

If you want to hear more stories about leaving academia, check out my interviews with Carrie Brubaker and Alaina Talboy.


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