MO | Edition 9 – “Don’t Be Debbie”: Why Waiting Is the Most Expensive Strategy of All
Let’s have some real talk.
We’re living in a moment of massive shift—where AI, automation, and smarter systems are rewriting the rules of business.
And yet…
We keep meeting smart, talented business owners stuck on the sidelines.
Paralyzed by indecision.
Running in place.
Telling themselves stories that sound logical… but aren’t.
This week, we’re calling it out.
Because the cost of inaction is rising. Fast.
Let’s dive in.
Why We’re Talking About This
You know that old SNL character “Debbie Downer”?
The one who shows up, hears great news, and immediately squashes it with doom?
A lot of founders are doing a version of that… to their own business.
They want growth, freedom, better margins.
They say they’re ready to lead at the next level.
But when it’s time to take action?
They default to delay.
They play small. They stall. They self-sabotage.
And often, they don’t even realize they’re doing it.
Let’s Look at the Data (and the Excuses)
Here are a few real stories from business owners we’ve talked with recently and the patterns we see everywhere right now.
(Names have been changed to protect the innocent)
The Tired and Talented: Dan at Crenshaw Architects
Been in business 20+ years
$3M in annual revenue (same number for years)
19 employees (heavy payroll),
Renowned for high-quality design and long-standing client relationships…but thinning margins
No systems…still managing prospects and clients in Google Sheets
Dan is a master of his craft.
Clients trust him.
His team respects him.
And the work is exceptional.
But the business? It’s stuck in an old operating model that’s quietly wearing everyone down.
Proposals take hours to assemble... cut, paste, revise, reformat.
Every single time.
Project management happens in a disjointed system with full manual interaction at every step.
The old systems that got Dan here are now slowing him down.
And the real tragedy?
He’s spending less and less time doing the work he loves; creative leadership, building client relationships, visionary design.
Instead, he’s stuck reviewing proposal drafts, chasing down timelines, and fighting fires.
He knows they need more marketing and business development to fuel growth. He even says it’s a top priority.
But they “don’t have time” to do it…
So they keep doing things the old way. Even though deep down, everyone knows it’s unsustainable.
Meanwhile, more innovative firms are adopting tools that auto-generate proposals, manage projects in real time, and convert leads with less manual effort.
The market is shifting.
Budgets are tightening. Clients expect more with less.
And Dan’s firm is becoming less and less able to adapt.
There’s no strategic vision. No real-time data. No operational resilience.
If nothing changes, it’s not just growth that stalls. It’s survival that’s at risk.
The business will fade, not because of talent, but because the systems didn’t keep up.
The Nodding Head: Robert at Radiant Roofing Company
Been in business 17+ years
Revenue has dropped 60% Year over Year for 3 years straight
The original partner has left the business…remaining partner is holding on
Business assets are dwindling
We’ve been talking with Robert (a good friend) for 18 months about leveling up his roofing company.
Every conversation ends the same way:
“Yep, yep. Totally makes sense. I’ll circle back soon.”
But then… nothing.
No systems. No CRM. No change.
Meanwhile, storms hit.
More agile competitors show up.
They follow up faster.
Automate better each time.
Communicate tighter.
Robert’s getting fewer deals.
Not because he’s worse…he’s just slower.
He’s literally falling so far behind that he can’t compete anymore.
At this rate, he’ll have to pivot careers or pray someone buys him out (spoiler alert: they won’t).
The Worn-Out Winner: Lisa at Sterling HR Advisors
Boutique HR consulting firm serving mid-sized companies across the Southwest
12-person team with deep expertise in compliance, leadership development, and employee relations
$2.7M in annual revenue, flatlined for the past 5 years
Still managing proposals, client onboarding, and project tracking manually—email threads, spreadsheets, and paper forms
High client satisfaction, but internal burnout is growing and turnaround times are slipping
Lisa built a firm with a stellar reputation.
For years, her word-of-mouth referrals kept the pipeline full.
Clients love her. Her team trusts her. She's known for being on it.
But she’s also the bottleneck for everything.
She still reviews every proposal.
Every scope doc.
Still jumps into client delivery because the team lacks clear systems and roles.
Still signs every check.
She keeps telling herself, “Once I get through this quarter, I’ll finally have time to upgrade our ops.”
But the quarter never ends.
So, the flawed logic is…
“I’m overwhelmed now, so let me keep doing what I’m doing so that times get easier…so that I can stop being so overwhelmed.”
Meanwhile, larger firms are winning more RFPs.
Startups are entering the space with AI-driven tools and seamless onboarding processes that make clients’ lives easier.
Lisa's team is loyal, but they’re exhausted.
Lisa's clients are happy, but they’re noticing delays.
Lisa herself is starting to feel the weight of a business that no longer gives back what she’s put in.
If she keeps going this way, the consequences aren’t just personal—they’re existential.
There will be no business to sell, and little of transferable value to pass along to her kids (if they even want it).
The firm is Lisa.
Without documented systems, centralized knowledge, or scalable workflows, there’s no asset, just effort.
She doesn’t need to work harder.
She needs to build smarter.
Because at this point, doing nothing is the most expensive decision of all.
The Real Risk
In every one of these cases, the biggest threat isn’t the economy. It isn’t AI. It isn’t competition.
It’s complacency.
And we’re seeing it more than ever.
Owners who are burned out.
Teams that are disengaged.
Companies that are fragile, because the only system is the founder’s brain.
And too many are just hoping it’ll all magically fix itself.
That’s not strategy. That’s slow-motion failure.
But Here’s the Good News
We’ve seen this pattern before, and we’ve seen what turns it around.
It’s not some moonshot pivot.
It’s not buying 10 tools you won’t use.
It’s a decision.
To lead.
To simplify.
To systematize.
To act.
The founders who win are the ones who keep moving—even when it’s messy.
They pause just long enough to reset, then take bold steps to fix what’s broken.
They build systems while they scale.
They design businesses that support their energy, not drain it.
They stop being “Debbie.”
Final Thought: Don’t Let This Be You
If you’re still reading, you’re not checked out.
You care.
You want more, for your business, your people, your life.
And maybe, deep down, you know you’ve been waiting to take serious action.
So let this be your nudge.
Don’t wait for a slow down.
Don’t wait for a cash windfall.
Don’t wait until your business screams louder than you can ignore.
Because the longer you wait, the more it costs.
Let’s fix this. Together.
You in?
You Won’t Scale Your Company Just By Reading, You Have to Put it Into Practice
You can read all the growth playbooks in the world, but if you’re not turning these steps into real growth, real revenue per staff member, real operational efficiency….you’re just spinning your wheels.
That’s why we created Modern Operators, a hands-on, tactical program built for founders who want to stop being the bottleneck and start growing.
We’ll take a look at your systems and help you map a plan to real modern growth
Implement an operational foundation that creates speed and predictable scale
Help you get understand where issues are happening and how to fix them before they become a problem
Schedule a time to meet with us if you want to audit your operational system to help you scale in a big way this year.
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