The Chutes and Ladders of Business: Turning Setbacks into Strategy

If you’ve ever felt like running your business is a constant game of ups and downs, you’re not alone. One month, you’re on a winning streak — clients are flowing in, systems are clicking, and momentum is strong. The next, something unexpected sends you sliding backward.

Welcome to the Chutes and Ladders of business ownership.

In Episode 2 of the R Readiness Lens podcast, Sheri Radler breaks down this familiar pattern — and how to use structure, mindset, and readiness to climb higher and slide less. Because growth isn’t about avoiding the chutes; it’s about learning how to navigate them.

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Why Growth Feels Like a Game

Every business starts with a goal — independence, impact, financial freedom, or sometimes just proving to yourself that you can do it. But the journey between starting and scaling is rarely linear.

Sheri compares it to the childhood board game Chutes and Ladders: sometimes you land on a ladder that propels you upward — a new client, a great hire, or a breakthrough idea. Other times, you hit a chute — a compliance issue, an economic shift, or a staffing challenge that sends you sliding backward.

The key, she says, is to understand the framework of the game. Big corporations already know this. They build with structure, process, and readiness in mind. But most small business owners? They’re building while they play.

“We want to bring that corporate framework down to small business owners — so you can stop just reacting and start steering your growth.” — Sheri Radler

The Corporate Framework — Without the Corporate Feel

The goal isn’t to turn your business into a bureaucratic machine. It’s to take the parts of the corporate mindset that actually work — structure, documentation, planning, delegation — and scale them to fit your size.

Think of your business as its own mini C-suite:

• You’re the CEO, setting the vision.

• Your accounting team acts as the CFO, managing the numbers.

• Your marketing team is the CMO, fueling growth.

• Your IT, HR, and operations fill in the rest of the structure that keeps it all running.
  

You may not have all those departments in-house, but you do have access to their expertise — through consultants, fractional roles, or trusted advisors. The readiness mindset simply says: use them intentionally.

That’s how you move from hustling to scaling.

Recognizing the Chutes in Your Business

Every business has pain points that create slides — and most owners can name them immediately. Sheri calls these “chutes”: the moments that drain time, energy, or revenue.

Common chutes include:

• Over-reliance on the owner for every decision

• Inconsistent or undocumented processes

• Lack of visibility into cash flow

• Staffing turnover or unclear roles

• Outdated systems that slow down your workflow
  

The problem isn’t that these happen — it’s that they catch you off guard.

Readiness turns those reactive moments into manageable pivots. When you know where your vulnerabilities are, you can build guardrails that prevent one small issue from becoming a full-blown crisis.

“You can’t plan for everything — but you can plan for how you’ll respond.” — Sheri Radler

Building More Ladders

While chutes represent challenges, ladders represent opportunities — the systems, habits, and investments that help your business climb faster.

Sheri points to a few ladders she’s seen transform client operations:

1. Leveraging Technology

Using tools like QuickBooks, Scribe, Loom, and AI-based platforms helps automate repetitive tasks and document your processes. When technology handles the “how,” you can focus on strategy and growth.

2. Building a Leadership Team

Even if you’re a team of five, designate leadership roles. Give your people authority to make decisions. The goal isn’t to step out — it’s to build a business that runs with you, not through you.

3. Creating a 12-Week Framework

Instead of yearly resolutions, Sheri encourages a 12-week planning cycle. Break big goals into small, measurable sprints. It’s easier to stay focused and celebrate progress along the way.

4. Focusing on Readiness Reviews

Quarterly reviews aren’t just for financials — they’re for systems, people, and strategy. Ask: Where are we strong? Where are we vulnerable? Then document, delegate, and adjust before the next cycle.

Real-World Story: When One Person Holds the Rope

Sheri tells the story of a client — a pediatric therapy practice shifting to insurance billing — that found itself in freefall after hitting a chute. One employee managed all insurance claims, meaning when she was out, revenue stopped completely.

The fix? Build redundancy. They documented the process, trained multiple people, and implemented software to automate key steps. Within months, cash flow stabilized, and the owner finally had breathing room.

That’s the power of systems — not because they eliminate risk, but because they give you the ability to recover faster when things go wrong.

How to Spot Your Next Ladder

Sometimes, ladders show up disguised as work. Implementing new software, hiring a bookkeeper, creating SOPs — none of those sound exciting. But they’re the moves that create momentum and freedom down the line.

Ask yourself:

• What could I automate or delegate today?

• What process needs documenting before it becomes a problem?

• What’s one area I’ve been avoiding that keeps me on repeat?
  

Your next ladder might not look like a huge leap — it might just be a solid, repeatable process that frees up your time to focus on strategy.

“We’re not building businesses on luck. We’re building ladders that last.” — Sheri Radler

Readiness Isn’t About Control — It’s About Confidence

When you adopt the readiness mindset, you start to see that stability doesn’t come from control — it comes from confidence.

Confidence that your systems work.
Confidence that your people are empowered.
Confidence that if something unexpected happens, your business keeps running.

That’s the beauty of turning chutes into ladders. Every challenge becomes a chance to strengthen your foundation and prepare for the next level of growth.

From Chutes to Strategy

If business sometimes feels like an unpredictable game, the readiness mindset gives you the rulebook. You can’t stop surprises from happening — but you can make sure your business is ready when they do.

As Sheri puts it:

“We want to build playbooks, not panic buttons.”

Whether your next move is documenting your systems, bringing in support, or simply carving out time to plan, every ladder you build now makes the next climb smoother.

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Listen to R Readiness Lens Episode 2: The Chutes and Ladders of Business.
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