Tuesday Email: The Integration Tax

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

For 5 years, I sold a product that promised to give financial advisors their time back.

Benjamin automated client onboarding, aggregated account data, and managed workflows. "Eliminate the administrative burden," we told prospects. "Focus on what matters."

Advisors bought it. Then they got frustrated.

Not because the product didn't work—it worked beautifully.

But they weren't getting their time back. They were managing flows, checking data quality, and ensuring connections stayed active.

The work had shifted from manual data entry to system oversight.

They'd expected elimination. We'd delivered transformation.

I didn't fully understand what we'd built until I closed the company and started using AI for my own work. That's when I realized: we weren't wrong about the value. We were wrong about the promise.

Most of us are hunting for the same thing—that single tool, that one integration that transforms the complex into the simple.

We want the task to disappear entirely, not just change shape.

When AI first started writing email drafts for me, I felt disappointed. I'd hoped never to touch email again.

Instead, I was still there, reading, editing, deciding what to keep and what to delete. It felt like a broken promise.

But then something shifted.

I noticed I was spending my mornings differently.

Instead of staring at a blank screen trying to remember what someone had asked me three days ago, I was making decisions.

Instead of typing the same explanation for the fourth time that week, I was thinking about whether the explanation itself needed to change.

The time didn't decrease. The task didn't disappear. But the nature of my attention had completely transformed.

This hit me hardest with these newsletters.

For years, my research process looked the same: I'd spend a week reading articles, skimming papers, collecting fragments of ideas.

By the time I sat down to write, I was exhausted. I'd already spent my best thinking energy just gathering raw material.

I had two choices: write less, or accept that my depth would stay shallow.

I chose volume.

Shorter pieces. More surface-level. Good enough.

Then I started using AI for research.

Within minutes, I could pull insights from thirty sources that would have taken me three days to find and read.

It felt like magic—until I realized what happened next.

I was still spending a week on each newsletter.

The time hadn't changed. My focus had.

I'd gone from hunting for information to questioning it, connecting it, deciding what mattered.

From gathering to distilling.

From doing work I tolerated to doing work I loved.

That's when my relationship with my own content shifted from passive to passionate.

We're operating under a fundamental misunderstanding about integration and automation.

We think the goal is to eliminate tasks.

But in a complex business—one shaped by human emotion, market unpredictability, and client relationships that can't be systematized—tasks don't disappear. They transform.

When you automate email responses, you're not freed from email. You're freed to focus on which emails deserve personal attention and which ones don't. The decision-making intensifies even as the typing decreases.

When you integrate your CRM with your planning software, you don't eliminate data management. You shift from entering data to monitoring connections, checking for errors, and ensuring the systems are talking to each other correctly.

The cognitive load doesn't vanish. It relocates.

This matters because we're building our firms like machines when they're actually more like forests.

Machines are predictable. You can optimize a fixed route—make the assembly line faster, reduce the steps, and eliminate the waste—efficiency compounds.

But advisory firms aren't assembly lines. They're complex adaptive systems. Client needs shift. Markets surprise us. Regulations change. The terrain moves underneath us constantly.

Trying to optimize a firm like a machine is like navigating a living forest with a subway map.

The map works beautifully for fixed routes, but forests don't have fixed routes. They require guides who can read subtle signs and adjust direction, not conductors who follow predetermined tracks.

There's a principle in systems design called Gall's Law: "A complex system that works is invariably found to have evolved from a simple system that worked."

You can't force integration into existence through a weekend implementation.

You can't buy efficiency.

You grow it.

Start with one small part of your business.

Rethink how you handle client onboarding, or how you prepare for meetings, or how you document portfolio changes.

Let that work. Let it stabilize.

Then build the next piece.

This isn't about being slow.

It's about being sustainable.

It's about creating systems that your team can understand, modify, and repair when they inevitably break.

Think of it like growing a bonsai tree rather than assembling furniture. You can't force a mature, elegant system into existence through intensive effort. You guide organic growth through patient, incremental shaping, where each small intervention builds upon what's already alive and working.

I understand the impulse to search for the silver bullet.

Our industry demands enormous cognitive load.

We're making complex decisions about other people's money while managing compliance, technology, staff, and our own business development. It's exhausting.

When someone promises that an integration will handle "all the other stuff" while we focus on what matters, we want to believe them.

It feels like the moment when exhausted parents discover "educational" screen time—we know, deep down, it's not solving the developmental challenge, but the promise of relief is irresistible.

The truth is more complicated: we're not finding simplicity.

We're shifting responsibility from something we see to something we don't.

Here's the paradox: as systems become more advanced, the human operator becomes more crucial, not less.

In 1983, a researcher named Lisanne Bainbridge wrote about "the irony of automation."

She observed that the more we automate, the more we need skilled humans to monitor, adjust, and intervene when things go wrong.

The automation doesn't replace judgment. It elevates the importance of judgment.

Modern air traffic controllers no longer track every plane manually.

But their role hasn't diminished; it's transformed. They're no longer data processors. They're strategic decision-makers, using their experience to read flow patterns, assess weather impacts, and manage priority conflicts that automated systems can identify but not resolve.

That's where our firms are heading.

The question isn't whether to integrate and automate.

It's whether we're preparing our team to shift from managing people to managing data and connections.

It's a different skill set.

It feels uncertain. But it's the investment that creates space for our people to do what only humans can do.

There's a thought experiment I keep returning to.

If you place a bee in a bottle with the bottom facing a light source and the top open, the bee will fly toward the light persistently. Bees are intelligent, logical insects. Light equals exit. They'll exhaust themselves trying to escape through glass because they can't abandon a pattern that has always worked before.

A fly, placed in the same bottle, will survive. Not because flies are smarter—they're erratic, almost random in their movement. But that randomness means they're not committed to a single logic pattern. They'll bump into walls, try different directions, and eventually stumble through the opening at the neck of the bottle.

In stable, predictable environments, bees win. Their logic and pattern recognition create efficiency.

In chaotic, unpredictable environments, flies win. Their adaptability matters more than their intelligence.

We're trying to build firms for bees in an industry designed for flies.

We want systems, processes, and fixed routes. But we operate in a world of market volatility, emotional clients, and regulatory surprises. The environment shifts constantly.

The firms that will thrive aren't the ones with the most integrations or the most automation.

They're the ones that build simple systems their teams can understand and adapt.

They're the ones that shift focus from elimination to transformation—from asking "how do we make this disappear?" to asking "how do we spend our attention on what matters most?"

When I was building Benjamin, I thought we were failing because advisors still had work to do.

I'd watch demos where prospects would light up at the automation, then see their faces fall when they realized they'd still need to monitor the flows, check the data, and manage the connections.

I took that as a product problem. Something we needed to fix, optimize, and eliminate.

Now I understand: we weren't failing. We were just telling the wrong story.

The value wasn't in the time we gave back.

It was in changing where their attention went—from data entry to data insight, from managing tasks to managing meaning, from doing work they tolerated to doing work that actually required their judgment and expertise.

I wish I'd understood that then. But maybe I needed to experience it myself first.

Because that's what AI has taught me.

Not efficiency. Focus.

I'm still spending a week on these newsletters.

But now I'm spending that week thinking and creating rather than searching and summarizing.

The time is the same. The work is completely different.

And that might be worth more than efficiency ever was.

The best is ahead!

-Matt