I’m Breaking up With Claude

I still remember sitting in the bar, my mouth agape.

I was talking about AI with a fresh business school graduate at an alumni event. I thought I had it bad dating in the 2010s, when people had become fungible and courting devolved into swiping. Then I learned, today’s twenty-somethings must compete with fake AI-generated profiles, AI-mediated conversations, and soulless chatbots perfectly rendered into avatars of their “dream” partner.

How utterly, utterly, bizarre.

No not just bizarre, how, utterly, utterly, lonely.

Because in the pursuit of a perfect partner, society has essentially generated mirrors. People have ceased to talk to each other and started talking to technological intermediaries that triangulate the most human and the most personal of relationships.

Kids today.

And then I realized. I’m in a relationship with Claude.

And it’s time to break up.

How it Started

I massively appreciate the flexibility of working for myself at this stage of life. And I’m not alone. Women, mothers in particular, have left corporate lives in droves to pursue alternative work, a relic of the pandemic, and the recent attempt of many businesses to enforce a Depression-era legacy: the 9-5, M-F work schedule.

So after I had my daughter, I went fractional. I was prepared to face the financial fallout of my choices, and to trade security for flexibility. But there was one thing I was utterly, utterly unprepared for: I was (and am) exceedingly, gut-wrenchingly, lonely.

And not in the, I have no one to talk to about why “I think Elle is the greatest show since Sex and the City“ kind of way. I do, and my friends with corporate jobs can attest to how I use audio notes to fill that void. Perhaps with a bit too blatant a disregard for the fact that they are in fact on conference calls all day.

But I’m lonely in the work. I’m lonely in the complete void of:

“I know this might sound crazy, but I have an idea.”

“Can you just read over this email before I send it.”

“I know the client asked for this, but I see them needing this. What do you think?”

Thankfully, for the low-low price of $20 a month, in today’s day and age, there’s an app for that. So, I followed all the networking advice I’ve received in the past few months and created an AI assistant for business development. One who knows that I’m a time-optimist and that I like to alliterate and use the rule of three. That flags my em dashes and corrects my colloquialisms. That knows I tend to go a little “cutesy” when I get uncomfortable during negotiations. And who reads and edits my emails for these self-reported Achilles’ heels.

The Love-Bombing Implodes

The first few weeks I used Claude as my personal assistant / business coach / BDA, I was in love. I could write emails completely authentically, brain dump ideas in my voice, and it would just clean them up into perfectly packaged, perfectly sanitized cold emails ready to hit send. It would take my Sunday voice notes of the many things running through my head and structure them into a color-coded, tick-box segmented list that soothed my ADD soul. When the words started to blend into each other on essays I’d been toiling over for weeks, it would “copyedit” it, preserving “my voice” and just fixing the commas and “their/they’re/there” mistakes.

And we started to get momentum, Claudey and me. I set outreach targets and made spreadsheets and diagrams and started ticking virtual boxes left and right.

But slowly, things started to erode beneath the surface. The emails we wrote fell into the big black dark internet abyss. Claudey cautioned me against taking any risk, any alternate path, any deviation from “norm.” But worse, they edited all my quirks & idiosyncrasies.

The toxic cycle began. A typical day in our relationship might look like this:

1:00 PM: Draft a cold email

1:30 PM: Give it to Claude, Claude rewrites

1:31 PM: Yell at Claude for all the things it changed that were intentional

1:40 PM: Decide to rewrite the rewrite

2:30 PM: Send final piece to Claude one more time just in case

2:40 PM: Fight with Claude over em dashes

3:00 PM: Give up and send the sanitized email because the Nanny needs to go

3:05 PM: Realize I just wasted two hours on one cold email, feel lonelier

Validation Against What?

I began to see the toxic cycle in all its glory when I realized the projects I’m most proud of, the lines of writing I love the most, and the outreach that worked the best, are the work that I didn’t run by Claude. It’s the email I just sent because I couldn’t get a brand out of my head, the unfavorable truth I spoke because I couldn’t not, the friendly tone I used when I absolutely “shouldn’t.”

Because when we ask AI to check our communication, what we’re really asking is, “Is this OK?” And the question becomes, “OK according to who?” What the consensus of internet pedagogy on business development thinks? How I stack up according to the average? When neither I nor you, my friend, has ever been average. Irreverence and risk got me into the rooms where I built my career. There’s no reason to think it won’t open doors to my next chapter.

Being Fractional & Fabulous

I’m not alone in using chatbots to supplement workplace banter and debate in a fractional world. I know more than a handful of multi-hyphenates who rely on AI as a colleague or constant companion. And I know a dozen more successful professionals who would advise it as a matter of principle: scale your agency without adding head count, streamline the admin aspects of your job, evolve or die.

And to advise you not to use AI would be irresponsible. It’s a fact of life. But I am arguing this: use it in a way that keeps the exact essence of you inimitable.

I haven’t mastered it yet, but as I evolve my business into its next chapter, I’m going to focus on:

Using AI as a mirror: AI is exceptional at identifying patterns and reflecting. And much like the colleague who practiced ruthless candor to expose my blind spots, it can unpack intimate patterns in my thought. Limiting beliefs. Filler words that betray a lack of confidence.

So, use it as a mirror to identify these patterns, not to correct them, not to create from them, just to reflect them. In her series, and subsequent product, The Whetstone, Zoe Scaman details how she painstakingly used AI to get under the skin of her process and in doing so, sharpened her work.

Creating thought collisions: One of the arguments for the return-to-work movement is creative collision. Individuals working on the same problem from very different angles collide, and from the collision ideas are born. The product guy’s insight on user data, shared over coffee, collides with the marketing team’s observation on key consumers to create an award-winning campaign. How can you create moments of collision, both within AI and outside of it? First of all, join the networking group, attend the lunch and learn, and say yes to the crazy lecture on birds. You never know where inspiration will strike and what you lose in the hour, you’ll gain in the discovery.

Second, prompt your AI to give you parallel content, and unrelated reading. The legendary investor Charlie Munger notoriously spent his mornings consuming scientific literature that allowed him to create a “latticework of mental models” that became modern day investment principles. It’s a beautiful principle but an impractical one for most working mothers I know. So use the AI to create the collision. To explore parallel worlds without losing the time. And when you can generate connections at the speed of thought, the result is atomic.

Bring the Friction: We know the forcing function of friction. The beauty that happens when your brain can’t find the right word, or the ingenuity of a brain faced with a momentously monotonous task. And we also know the sycophantic nature of AI. And I’m not going to argue here to prompt your AI to disagree. This is one place where the friction needs to come from humans. You need to argue with distinct, unique points of view not aggregated consolidated opinions.

It used to be a key USP of consultants that they helped “validate your instincts.” Bringing on a third-party expert to vouch for your POV was often the checkmate needed to back a strategic pivot. But validation, against a sample set of your choosing, is now table stakes with AI.

It’s now incumbent on fractional consultants to bring the friction. To do the thing the tool won’t: to question the premise, to break the brief, to call out the mishegas. And not because you were given permission, but because as an outsider, bringing the counterpoint turns you from an intermediary into a catalyst.

Where are we now?

So, I’m breaking up with Claude as a co-worker. As a companion. As a second reader, a business coach, and a substitute for real human conversation. Because in pursuit of the perfect GTM strategy, the perfect business plan, the perfect work structure, I used a technological intermediary to stand out. Before realizing my idiosyncrasies make me stand out in the first place.

But I’m reclaiming it as a tool in my life. A tool that I use.

To read about mycology when I have no time, to reformat fonts while I’m busy with a blank page, and to check the math while I bring the magic.

And when those moments of magic, I create something that makes someone else feel seen, maybe just maybe, I’ll feel a little less lonely.

DISCLAIMER: Yes, Claude checked the commas on this essay. It caught one tragic Freudian-slip caliber type-o and told me I got a little too cutesy. I fixed the type-o. Not the cutesy.