Tuesday Email: What Your Calendar Is Actually Saying

Happy Tuesday!

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

We build processes for everything.

CRM workflows. Client onboarding checklists. Investment protocols. Documents for all of it.

The one thing that controls our time? We just leave it open. We let other people fill it in.

Doesn't that feel odd? The most precious, most limited resource any of us has is the one we pay the least attention to, and complain about the most. Time.

We pour energy into operational infrastructure and process-building, yet we spend almost none of it managing, organizing, or controlling our calendars. We leave them open. Free for anyone to plant their priorities on, to make their issues our issues, to pull us away from the things we actually care about.

We feel the cost of this every day. We want time, but we need money to do things with time.

Research suggests that people who prioritize time over money are happier. But here's the challenge: money funds what we do with that time. That's not a clean resolution. It's a constant internal struggle, and understanding that it is one matters.

It's not unlike what we see with clients transitioning into retirement. For 50-plus years they've been in accumulation mode: save, grow, build. Then we ask them to flip a switch and start drawing down. It doesn't work that way. It's a gradual shift, and it's hard for them. Turns out it's the same for us. We've driven our whole professional lives toward generating money. Getting out of that mindset creates a circular reference that isn't easy to break.

McKinsey research found that nearly half of executives admit they're not spending enough time on strategic priorities. Only 9% are very satisfied with how they allocate their time. These are people whose entire job is to drive strategic value, and they're still saying it. So if you feel it too, you're in good company.

But here's the thing: this isn't about laziness. There's science behind it, and understanding that science is the only way to actually change it.

A researcher named Ashley Whillans introduced the concepts of time affluence and time poverty. Having time is affluence. Not having it is poverty. And what the research consistently shows is that people who prioritize time over money, even in small, everyday decisions, report greater life satisfaction, stronger relationships, and higher intrinsic motivation.

We get it. We agree with it. That doesn't make it easier to live.

Inside our businesses, we focus on growing AUM and revenue because that's our livelihood. We need to provide for our families. And nobody's going to argue with us for doing that. That's fine. The problem is that the cultural gravity around money pulls us toward money affluence at a direct cost to time affluence. It's not ambition that's the enemy. It's the pull of that gravity.

One diagnostic tool I find genuinely useful is what I call the interest-to-calendar gap. It's a simple audit. You list what you're most interested in right now and then look at whether your calendar actually reflects that. If you're deeply interested in something, you should be able to find time carved out for it. That's the test.

Here's how to run it:

1. Write down every project you're actively working on and rate each one: low, medium, or high interest.

2. Pull up your calendar for the last 90 days. How much time did you actually spend on the high-interest ones?

3. If the time doesn't match the interest level, you found the gap.

4. Now look forward: block the next 90 days with intentional time for the things that matter most to you.

This does require willpower and intentionality. But there's another reason our calendars break down, and it has nothing to do with willpower.

We are trying too much.

Everything moves fast. Expectations are high. And in our drive toward time affluence, we end up creating time poverty by cramming more in. What that produces is something researchers call attention residue: the inability to be fully present where you are because part of your brain is still in the last thing you just left.

Think about a typical run of back-to-back meetings: client, team, leadership, client again. No breaks. We treat that as a badge of productivity. But what happens is that your attention from meeting one bleeds into meeting two, which bleeds into three. The residue stacks. I'm not immune to this. I fall into it constantly.

The solution isn't technology. It isn't an app. It's 10 minutes.

Between every meeting, before you open email or check Slack, write down where you are: what got resolved, what's still open, what you need to do next. A voice note works. So does typing. So does writing it out. Whatever sticks.

If you're transitioning from focused work into a meeting, do the same thing. What did you do? What still needs doing? I do a version of this with my own agent work. When I'm in the middle of building something and I know I won't return for a week, I have Claude generate a handoff document so I can re-enter with full context the next time. Same principle.

Research backs this up: people who wrote down exactly where they were in a task and what they intended to do next improved their performance on subsequent decision-making tests by 79%. Simple, but it requires intentionality.

Now look at how an advisor's week actually breaks down. A typical week runs around 43 hours, and only about 20% of that is direct client time. The rest gets eaten by prep, planning, business development, and admin. Research shows productivity peaks when advisors spend 35 to 40% of their time in client meetings, measured by revenue per advisor. Most aren't close.

So the question becomes: are you managing your calendar, or is your calendar managing you?

That feels counterintuitive. We're in a client service business. Shouldn't clients have access? My answer: having access doesn't mean instant access. Our protocol has always been to respond within 24 hours. But somewhere along the way, we convinced ourselves that anything less than immediate response creates risk. So one email that says "can we talk?" turns into a 40-minute unplanned call that costs you whatever you were building toward.

AI can relieve some of the prep, admin, and business development pressure. But if we're not controlling the calendar, we're just opening more space to fill it with things we didn't plan for.

Here's what I think the real problem is: the calendar isn't broken. We are. Because fixing the calendar requires things we don't want to do.

It requires us to say no.

It requires trade-offs.

It requires accepting that taking one thing means giving up something else.

We understand this intellectually. Living it is another story.

For me, the challenge has always been curiosity. Every new thing feels like an opportunity to learn, to explore, to build. Curiosity is my greatest asset and my worst habit.

There's also the belief that time is infinite, until it isn't. When I started my company before kids, before a family, I'd work 60, 70 hours a week. Weekends, late nights. And I still never felt like I got everything done. Time expanded to fill whatever I gave it.

Then Levi was born. Suddenly my time had hard edges. Morning routines, dinner time, evenings with my family. I couldn't work the long hours anymore. I spent a period reading every productivity book I could find, trying system after system, each one a little painful at first, each one getting easier before I'd tear it down and start again.

What I eventually realized was this: my hours of focus time had shrunk, and the quality and depth of what I produced had actually gone up. Having more time doesn't mean getting more done. Having intentionality, a process, a system, allows you to accomplish more in less time than you ever could just by adding hours.

That's the real takeaway here. We sit and yearn for more time. But more time isn't the answer. Constraints force execution. The question is whether we're controlling those constraints or letting them control us.

Start here: instead of an hour on social media on Sunday, spend that hour on your calendar. Write down your 15 most important tasks. Look three weeks out. Make sure time is protected for the things that matter. Then execute during the week and check back in the next Sunday.

And between every meeting and every focused work session: take five to ten minutes. Write down what you did, what you learned, and what still needs doing.

The solution to having more time is not having more time. It's having intentionality about the time you already have.

The best is ahead!

-Matt