Fear of Being a Beginner Again: How to Cope

For me, the most difficult thing about changing from an academic career to a career in tech was giving up my persona as an expert. And I suspect that fear of giving up one’s status as “expert” is an important reason people don’t leave academia more often. Like anyone who had been in academia for nearly as long, I’d amassed a lot of highly specialized knowledge. A peculiar feature of the ivory tower is that you end up knowing a lot about very little, but you live your life surrounded by that single topic. Even if you’re an expert in something quite obscure, you probably end up teaching it fairly often. You attend workshops on it, and you correspond with the half-dozen or so other experts. And so, you end up living as an expert, expecting others to defer to your opinion, and being able to speak authoritatively at a moment’s notice.

I moved from my niche in academic philosophy to the much wider world of the tech startup. Friends and acquaintances frequently commented that “this would be easy” for me because I’d been programming for a long time (ever since I was ten), and I already knew a lot. Fortunately, I knew enough to realize that this was not going to be the case. There is a world of difference between programming as hobby, or on simple one-off personal projects, and being a software engineer on a professional team, with responsibilities to clients. I did not know what I didn’t know, and the learning curve was very steep.

Fortunately, I landed in a very supportive environment with colleagues who were always happy to teach me new skills. So I learned more in that first year than in any other time I can remember. But even despite being so fortunate in my new colleagues, it was a sometimes difficult adjustment. For the first time in twenty years, I was learning an entirely new vocabulary, skill set, and methodology from scratch. To someone who’s used to having others defer to his expertise, this is a jarring experience. Adding to the cognitive dissonance was the fact that many of my colleagues were the same age as my students. This was a big role reversal for me.

I had to get over a lot of bad habits when I left the relative safety of the ivory tower. Most difficult for me was getting into the habit of asking for help. I’d spent my career as the only person with my particular skill set (formal logic, game theory) in an academic department. So there was literally nobody to collaborate with, and nobody to learn from. I had a very deeply ingrained habit of assuming that I had to do everything on my own, without benefiting from the experience of others. Obviously, this does not work in an environment that’s the exact opposite of a typical academic department. In a tech startup, everyone absolutely must work together, or the business will certainly fail. And as a beginner with virtually zero experience, it would have been especially inappropriate and counterproductive to do things on my own. To be perfectly honest, I made mistakes caused by my previous bad habits many times before I started to get into the right habits.

Try to find a supportive environment

Personally, I think this is the single most important piece of advice I can offer on transitioning out of academia. If you don’t have a supportive environment, you’re likely going to experience a lot of unnecessary pain. When evaluating whether to join a specific organization, try to discover during the interview process whether it’s a supportive place to work. You can find this out by asking questions like, “How do you get new employees up to speed?”, “How do your teams function on a day-to-day basis?”, “What’s your process for evaluating whether a project is going well?”, and so on. Gear your questions toward understanding what their work lives are like on a day-to-day basis. Personally, I like to ask at least one or two similar questions to different people in the organization to see if their answers cohere. I say “cohere” rather than “match” because people with different roles will certainly identify their problems and methods somewhat differently. But if it sounds like different people are describing totally different organizations, that’s a serious warning sign. A truly collaborative environment will foster general agreement about how the group functions, what challenges they face, what their plans are for the future, and so on.

Stay intellectually curious

In theory at least, you went into academia in part because you’re an intellectually curious person. Learning about a new career should be fun and intellectually satisfying. Your new colleagues ought to be a wealth of new information.

Speaking for myself, I found some aspects of the private sector much more interesting than I had anticipated. My father had been in sales and marketing, which is part of the reason I had always assiduously avoided anything having to do with sales or marketing. But when I started working at a tech startup, even though I was a software engineer, sales and marketing were very important to my work life. When our product was marketed or sold in a particular way, it was up to the engineering team to ensure that the customers were satisfied. I found myself on many phone calls with clients, trying to work out how to meet their business needs. Shockingly, this turned out to be very, very interesting, even to a former academic philosopher.

Be forthcoming about your strengths and weaknesses

It’s okay — and even quite desirable — to start a new career with very little experience and with lots of gaps in your knowledge. As assumption I’ve bet my career on is that my experience as an academic has value that outweighs my relative inexperience in software engineering. If you really take that assumption seriously (which you should), then you should feel confident about being totally up-front and honest during an interview process.

For example, during my own interviews, I was asked a couple of times about some technical issues that I had literally never heard of before. It was clear from the context that these were not normally considered difficult questions. So, after stammering for a few seconds that felt like hours, I just came out and said that I had literally no idea how to answer. But then I elaborated about how I’d go about approaching a problem that was so novel to me — where the reliable sources of information could probably be found, for example. I took a guess (and said that it was a guess) about what other technical issues might be related, based solely on the words in the question. And I also just came right out and asked what these things were. This turned out to be the right approach. Interviewers want to get a sense that they know you a little better by the end of the interview, and being forthcoming about what you don’t know is a way to make that happen.

Don’t go for perfection; iterate instead

When changing careers, your number one priority is to learn as much as possible, as quickly as possible. When you’re given a project to work on, the worst thing you can do is finish it before asking for feedback from others. If you do, then you’ve got only one learning opportunity, and it’s at the worst possible time — namely, at the end of the project when the deadlines are now upon you.

Instead, you want to have as many learning opportunities as possible. So you should think of your job as iterative. This means that you do some chunk of your current task, and then you choose a natural stopping point to check whether it’s on the right track. You assume that everything you do will end up being revised several times before it’s done. Basically, your personal work should have a “work, test, revise” cycle with as tight a feedback loop as possible. The more times you can go through that cycle, the more you will learn. You will also be demonstrating that you care about others’ opinions (which you should!), that you take their input seriously (which you should!), and it will improve the quality of the end product while avoiding any unpleasant surprises.

Work should be fun

If you’re an academic, you should enjoy learning. Switching careers provides huge learning opportunities. If you think of your new job as a big laboratory filled with fascinating experiments, and your new colleagues as potential partners and mentors, you can have a great deal of fun while providing a lot of value to your new employer.

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