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- Always Watering: Why Readiness Beats the “When-Then” Fallacy
Always Watering: Why Readiness Beats the “When-Then” Fallacy
Serving Business Owners, Demystifying Data Lakes, and Hitting the Road with Milemarker
Jud Mackrill
June 14, 2025
Good morning from 35,000 feet.
I’ve got my laptop open somewhere over North Florida, heading back to Charleston after four packed days of conversations with people from every corner of our industry.
As I sort through my notes and thoughts, there’s a lot to be encouraged by.
And yet, the news playing on the seat back screen in front of me reminds me just how much uncertainty is out there—conflict, tension, disruption.
That’s life, isn’t it?
Good and bad. Progress and setbacks. Clarity and chaos—often all at once.
This week, I want to talk about the in-between. The day-to-day. The moments where we choose how to show up. How to be present. How to be steady when things are swirling.
So pour a coffee, tea, or whatever gets you into your zone.
Let’s walk through the moments that matter.
Always Watering: Why Readiness Beats the “When-Then” Fallacy
On the Pod: How Advisors Can Better Serve Business Owners 🎧
Workshop: What the Heck is a Data Lake?
Milemarker On the Road ✈️
Always Watering: Why Readiness Beats the “When-Then” Fallacy
My father-in-law, Rick, served 26 years in the United States Air Force.
At any moment, without warning, he could be gone for an unknown amount of time—training, deployment, assignments he never really talked about. But one thing was always clear: he lived ready.
In the Cold War, every second meant everything. Monitoring, watching, preparing were all necessary in case the world turned upside down again.
That mindset — the quiet discipline of preparation — has shaped the way I lead and think about business.
Because here’s what I’ve seen too often: the “when-then” trap.
“When the market settles, then we’ll expand.”
“When we hire the right person, then we’ll move.”
“When we close that one big deal, then we’ll finally grow.”
It sounds smart. Strategic, even. But there is a big difference between staying on your toes and being caught flat-footed.
The truth?
While you’re waiting, someone else is building.
Readiness doesn’t show up magically at the right moment. It’s built long before the moment arrives.
It’s daily. It can feel tedious. It’s usually invisible from the outside.
But it’s also the difference between firms that seize opportunity and those that miss it.
Chinese Bamboo
That’s why I keep coming back to the parable of Chinese bamboo.
In the story, it’s planted. It’s watered. But nothing happens.
For five years, the farmer sees no visible progress. But underground, a root system is forming. A foundation is being laid.
Then suddenly, the bamboo shoots up 90 feet in six weeks.
The point of the story is to remind us that the bamboo didn’t grow in six weeks, it grew in five years and six weeks. We just couldn’t see the growth until the end.
The explosion of growth is visible. The work before the growth was hidden.
Who We Are
“You have to be before you can do. You have to do before you can have.”
It’s no fault of outsiders to praise the ‘overnight success’ but if you talk to anyone who’s ever been branded one or met someone who was working on their team before they were ‘discovered’, you’ll find a very different story.
We love stories about success because we want have an inherent need to feel progress. Of course, that doesn’t necessarily mean scaling a business or growing revenue. It applies to all of the success we’re seeking. In our personal lives, it might be a successful marriage, launching fully functioning adults that we actually enjoy spending time with, maintaining our friendships with the people who matter most to us or achieving new milestones for the causes to which we give our time and energy. But having success in any of those arenas doesn’t happen without years of unseen work.
The “have” comes last — and only if you’ve put in the work, which only comes after you’ve figured out who you are.
So, who are you? What matters most to you?
Are you becoming the kind of person who can impact what matters most to you?
What are you reading? What are you watching? Who are you listening to? They’re shaping your identity.
How do you spend your time? Are you doing the things you need to do that aren’t necessarily going to garner immediate praise? Are you training for the days to come?
What will you have when growth begins? That will be wholly dependent on what you’ve spent your time on and who you’ve allowed to influence you.
The process of being prepared is designed to reveal weakness and highlight where you need to adjust systems and processes.
If you are still in preparation mode, it can be difficult when you see the flaws in your execution, but perfection is always a lie. You need courageous imperfection — and the stamina to keep going.
Because readiness isn’t only about looking sharp. It’s about showing up and inspecting.
Right now, wealth management is noisy. Fast-moving.
And for those who’ve been preparing?
It’s also full of opportunity.
So here’s to the ones who aren’t waiting; who are practicing in the quiet, who show up with faith and discipline, who water, even when it looks like nothing is happening.
Stay Ready.
______________________
On the Pod: How Advisors Can Better Serve Business Owners
Episode 097: On this week’s episode of The Connected Advisor, Kyle Van Pelt sits down with Jason Early, Founder and CEO of RISR—a wealthtech platform helping financial advisors better serve business owners. With a background in financial services, leadership, and fintech, Jason is passionate about solving complex problems and empowering advisors through data, technology, and behavioral insight.
Kyle and Jason explore why business owners are often an underserved yet high-potential client segment. Jason shares how RISR equips advisors with the tools and technology needed to navigate the complex needs of these clients—and why now is the time to tap into this fast-growing market.
(00:00) - Intro
(02:40) - Jason's money moment
(04:45) - What RISR is all about
(06:28) - Key tools and features RISR offers advisors
(08:23) - Why so many business owners go without financial advisors
(10:32) - What makes business owners ideal long-term clients”
(12:44) - How AI powers the RISR platform
(16:49) - Prospecting strategies for engaging business owners
(18:54) - The growing industry focus on business owners
(21:50) - Future trends in financial advising
(24:35) - Jason's Milemarker Minute
⚡️Bookmarks
Webinar Invite: What the Heck is a Data Lake?
If the words “data lake” make you want to call IT…
Don’t.
Just join us instead.
🗓️ Wednesday, June 18 | 12–1PM ET
📍 Virtual | Save Your Spot
Join me, Kailash Duraiswami, and Jessica Perez for a fast, no-fluff walkthrough of what a data lake really is—and how firms like yours are using them to own their data, ditch duct tape, and scale faster.
Here’s what you’ll walk away with:
What a data lake actually is (in plain English)
Why most firms think they have one (they don’t)
How to build a modern data lake without a massive IT lift
Why owning your data = owning your future
Real-world examples from Milemarker clients already winning with this
If you’re a COO, CIO, CTO, or firm founder tired of chasing spreadsheets and waiting on reports…
This is the signal through the noise.
Milemarker on the Road
Catch my team on the road at the following events or cities:
June 22-28 - Minneapolis, MN
July 11 - Nashville, TN
July 29-31 - Denver, CO
If you’re in any of those cities and want to arrange a meeting time, reply to this email, and we’ll get something on the calendar.
Jud Mackrill