The Dog that Caught the Car: Defensive Pessimism and Preparatory Optimism in the Job Hunt

It’s a strange time to say this, but I’m learning to be an optimist. 

I’ve always considered myself a defensive pessimist. When I was an academic preparing to make an argument in a paper or presentation, I would go through it and try to poke holes in it in order to strengthen it. When pulling together an application, I tried to identify and remedy all the reasons why it might be rejected.

This strategy served me well. By envisioning the ways in which x, y, or z might not work, I was able to more thoroughly prepare, which helped me succeed.

This approach has worked less well outside academia.

I had an informational interview a few months back that went better than expected. As anyone will tell you, the golden rule of informational interviews is “Don’t ask for a job!”. I had internalized this rule to such a degree that I stumbled once when (I think) my interviewee said, “You should come out and work with us!” 

I was the proverbial dog who caught the car. 

What I wished I had said was, “I don’t know if you’re serious or if you mean I should come out to x city or y industry, but, if you’re asking whether I’d be interested in working with you at your company, I absolutely would be.”

To this day, I don’t know whether this person was opening up a potential job offer to me or if they were simply suggesting that there were opportunities where they lived or in their industry. Maybe there was a way to reach out and ask, but I couldn’t quite find the words for an appropriate followup. I don’t remember exactly how I responded; I just remembered stumbling over my words. 

I made the mistake of not being optimistic. 

I did better recently when an informational interview turned into a prospective ghostwriting job. Ghostwriting is high on my list of dream jobs. I love longform writing. I love figuring out issues like structure, style, voice, audience, etc. 

In the interview, my interviewee half-jokingly asked if I would like to write a book. I responded that I didn’t know if they were serious, but that, yes, I would definitely like to write a book. 

The project may come to fruition and the conversation went well. I had learned my lesson, but maybe I could have learned it even better. What if I had prepared for an unexpectedly good outcome? Perhaps I would have developed a stock plan for writing a book, my typical budget and schedule, etc. Perhaps I would have read up on communicating with potential clients in order to finesse my style of communication. 

I say this not to rake myself over the coals (I reserve that for those 2am moments of insomnia). Rather, I think it’s important to learn from the past and adapt to new conditions.

There is, to be sure, a place for optimism and pessimism. But, perhaps in these dark days, we all ought to invest just a little bit extra psychic energy towards envisioning the best possible outcomes so that we can capitalize on them when they unexpectedly arrive. 

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