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- #159 - AI at Work: The Good, The Bad & The Ugly
#159 - AI at Work: The Good, The Bad & The Ugly
Let's all take a breath.

Welcome back to On the Fly!
Today's goal is to present an impartial view of AI. Hence, the title: The Good, the Bad, and the Ugly. But even that saying is a little slanted. Two negatives and only one positive? That math doesn't work for me, so I'm adding one more: The Beautiful.
I know it doesn't have the same ring to it, but you get the gist.
Since the beginning of OTF, I've been an AI optimist, but I'd be doing you a disservice if I only talked about the highlights. So I'm going to keep it real — what I've experienced when things felt bad, when things got ugly, and then what makes this whole thing good and even beautiful.
And instead of ending on a sour note, we're flipping the script. Bad and Ugly first. Good and Beautiful to close it out.
Everything you're about to read comes from my own experience. No theory. No headlines. Just what I've seen, felt, and learned firsthand.
This is also part one of a series. Today we're talking about AI at work. More to come.
Time for takeoff.

The Bad & The Ugly
Let's rip the bandaid off.
People are worried about how AI is going to change the workplace. Whether they'll have a job 12 months from now. Whether layoffs are inevitable. Legitimate concerns without a doubt.
Two months ago, I was having lunch in NYC with some colleagues. The person sitting to my right was genuinely concerned about how AI was going to impact the insurance industry, and more specifically, his job. He's an ex-lawyer turned insurance broker. I won't get into all the specifics, but when he shared his point of view, it wasn't just what he said — it was the emotion behind it. You could feel the raw concern piercing through his words.
The table got quiet. A little awkward, if I'm being honest.
Not because he said anything wrong, but because nobody knew how to respond. I've noticed (and it's been this way for months if not years), the media throws extreme takes at us constantly. AI is either the greatest thing ever built or it's coming for your career. When that's all you hear, conversations start to feel like you're picking a side instead of having a discussion. That's a problem.
But here's what I think was really going on: he didn't know how AI could actually work for him. In his role, human-to-human interaction is everything. That's not getting replaced. But the hours spent on research, documentation, and prep? AI could give him that time to do more of what he's already great at and become even more productive.
The real "bad" isn't AI itself. It's the uncertainty. Not knowing what's coming or where you fit in.
Now if The Bad is the emotion, The Ugly is the evidence.
I read a newsletter recently by Ed Elson, who writes a newsletter called Simply Put, that broke down what AI is actually doing to the job market. The following data points stopped me in my tracks:
Entry-level job postings have dropped 35% in the past two years.
More than two-thirds of enterprises say they're slowing entry-level hiring.
A recent report found AI was responsible for 5% of layoffs last year.
If that doesn't sound significant, consider the fact that more than 1.2 million job cuts were announced last year, the highest number since the pandemic. Consider also that we're only a couple of years into AI.
These are ugly, and when you read this type of data, it's tough not to get worried. Clearly AI is affecting how we work, but it's also affecting who gets to work.
If you're feeling uncomfortable right now, that's normal.
The Good & The Beautiful
Now let's flip it.
I work in insurance. I've been in this industry for 10 years. Zero technical background. And yet AI is becoming one of the most useful tools in my day-to-day.
My company has its own LLM, and I use it regularly. When I'm underwriting a company, I use it to research the business, find any concerning or litigious articles, and break down complex websites so I can better understand the risks involved with the company we're looking to protect. Sometimes when we receive a submission with a bunch of information about a company, it's still not enough — so having our LLM do the digging where I'd otherwise be scrolling through Google saves me a ton of time.
That's the good. It's not replacing what I do. It's helping me do it better and faster. The same thing my colleague at that lunch table was worried about losing — time, relevance, job security — is exactly what AI is helping me strengthen.
If you're in a role where you're spending hours on research, prep work, or trying to get up to speed on something complex, these tools can give you that time back. And that time back means more energy for the stuff that actually requires you. The human stuff.
Now, here's what I think is the beautiful part of all of this.
It's not just about using the tools. It's about taking ownership of how they get used around you.
I've communicated to senior management at my company that we need to put together a plan to incorporate AI more intentionally into our workflows. Not mandating it, but heavily suggesting that our company's LLM becomes part of how we onboard and develop talent. Entry-level workers are coming into the workforce with experience in these tools. We should be meeting them where they are.
I've also pushed internally for a subject matter expert in underwriting for AI. Someone at the underwriting level who can be the point person when other underwriters, whether they're just starting out or in the middle of their career, have questions about how to leverage AI in their role. I've offered to help facilitate that plan.
I'm not sharing this to pat myself on the back. I'm sharing it because none of this required me to be an expert. It just required me to care enough to speak up. And honestly, I'm still figuring it out too.
But here's what I know: the people who start asking questions now, even imperfect ones, are going to be in a much better position than the people who wait for someone else to figure it out for them.
So if you're sitting in a role wondering how AI fits into your workplace, start the conversation. Raise your hand. You don't have to have all the answers. You just have to be willing to start.

Dan’s perspective about the concerns and the potential of AI in the business world are interesting. My line of work is obviously different, but I’ve still seen plenty of each - Good, Bad, Ugly, Beautiful - that I won’t go into because it won’t be relevant to anyone outside academia.
What I will say, though, is relevant to all of us: it’s not helpful to bury our heads in the sand. Focusing on the positives of the “old way” and the negatives of the new will only hold us back or make us replaceable. It’s okay to be worried or even afraid, but let those emotions inspire action. Figure out how to balance the best of the old with the power of the new will make all of the difference.
To that end, I recently made the decision to advance my AI use. Not in frequency, but in quality. I upgraded to the paid tier of Gemini (Google One, I think it’s called) in order to integrate Gemini into my Google Workplace and gain access to tools like Notebook LM. I’m still learning how to maximize the efficiency of this integration / upgrade (Notebook LM can actually teach you anything you want, and I’m using it to teach me about itself and Gemini at large), but I see great potential in these tools helping me with both my teaching and achieving my sabbatical goals.
I’ve also upgraded Perplexity to a paid tier (there’s a discount for teachers, so I couldn’t resist) because both Gemini and Perplexity informed me that Perplexity is better for deep research. Perplexity also has Chrome Extensions, so I’m learning how these two tools can work together to enhance each other.
At this juncture, I know very little. Until a week ago, all I’d ever used AI for was to search. I’m just getting started with my deeper dive. But that’s Dan’s point - getting started is, perhaps, the biggest step, and I’m glad I’ve taken it. I can already see its potential and am excited to learn more.
Before You Go!
Thanks for reading. I appreciate your support deeply.
This is part one of a series. Over the next few weeks, we're going to keep looking at AI through this same lens — The Good, The Bad, The Ugly, and The Beautiful, but through different angles.
Teaser: The next one being about AI in your personal life. Stay tuned.
As always, see you next Tuesday.

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