Embarrassing AI #63:1,500 Applications Later: Why I Finally Killed My Corporate Alter Ego

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Five months and more than 1,500 job applications yielding 3 interviews that whimpered like the final spasms of a spent party balloon have finally convinced me to stop trying to have my cake and eat it too.

The cake: walking away from my corporate career to pursue an academic career that I need to build from the ground up.

The eating: not shed my corporate identity just in case I need it in the future.

It’s not an insane compromise. You could even argue that it’s the adult thing to do, with two kids, a wife and a dog that rely on me to do my part in paying the bills.

And having the opportunity to work with my brother on running his startup, made punting the embodiment of my new identity both convenient and comfortable.

But that ship has sailed and necessity is truly the ultimate forcing function.

A little over a week ago I completely revamped my CV and LinkedIn profiles.

It feels strange, and scary, and the right thing to do if I’m serious about making the career switch that I’ve been talking about.

Using Claude has been central to this. Without AI, figuring out how to reframe two decades of corporate experience into something that reads as academic would have taken weeks. Instead, an afternoon of iterations and I landed somewhere that finally feels honest. Each position gets its own tailored CV. The LinkedIn is the narrative thread that holds them together.

This will change again when I’m applying to PhD programs at the end of this year.

With this weight lifted, because the identity dissonance was top of mind, I’m also working on building additional income that will not come from a regular job. The fellowships that come with history PhD programs aren’t enough to keep the lights on.

I have 18 months to make this work. The clock is running. You'll hear about all of it.

Five months into my job search, I have started to switch gears. AI has been very helpful in helping to think through this, and finding practical things to do. I’m sure I’ll be writing about it soon.

Tools I am using to fake being an expert.

1. Beehiiv (The Platform)

"I tried other platforms, but Beehiiv is the only one that makes growth feel like a game. It’s what runs this newsletter. The Deal: You get a free trial + 20% off (I get a commission to keep the lights on)."

2. Wispr Flow (The Time Saver)

"I hate typing. This tool turns my rambling voice notes into perfect text. It’s the only way I can write this much every day. The Deal: We both get a free month if you try it."

3. Emergent (The Coding Cheat)

"I am not a coder. Emergent is my 'vibe coding' partner that writes the messy parts for me. Essential if you want to build apps without a CS degree."

🧘‍♂ Last Word.

Running out of options is sometimes the clearest path to reinvention.

Making daily progress,

P.S. Did I do something totally backwards today? Or do you have a better prompt for this? Hit reply and tell me. I’m here to learn just as much as you are. (I read every single email).