Stop Making Million-Dollar Mistakes: How to Make Decisions When Nothing Is Certain
- Bailey Proulx
- Jul 13
- 6 min read
The Uncertainty Problem No One's Talking About
Here's what's happening in businesses right now. You're being pressed to make big decisions with incomplete information:
Which AI platform should we commit to?
Should we overhaul our pricing structure?
Is this new marketing channel worth the investment?
And everyone around you seems to expect a clean, confident answer. "Just tell us what to do," they say.
But here's the reality: In a fast-changing market, certainty is impossible. The traditional approach of exhaustive analysis to find "the right answer" is a recipe for either analysis paralysis or expensive mistakes.
I've seen this pattern repeat in education businesses, agencies, and consulting firms. The owner feels trapped between making snap decisions or waiting forever for perfect information. Neither works.
What's actually happening is that we're treating all decisions as if they carry the same weight and require the same approach. They don't.
Why Your Current Decision-Making Is Costing You
The typical approach to business decisions goes like this:
Identify a need (new platform, process change, etc.)
Research options and choose one
Commit fully with a big implementation
Hope everything works out
This all-or-nothing approach creates two massive problems:
First, it's painfully slow. When every decision requires the same thorough process, you end up spending too much time on minor choices while delaying critical ones.
Second, it's unnecessarily risky. By making full commitments before testing assumptions, you're betting the farm on your initial analysis being right.
Even established strategy guides from McKinsey and Harvard Business Review acknowledge that uncertainty varies dramatically by situation – and your approach needs to adapt accordingly.
The Strategic Decision Model That Drives Results
Instead of treating all decisions the same, start by classifying them based on a concept Amazon uses internally: one-way doors vs. two-way doors.
Two-Way Doors (Reversible Decisions)
These are choices you can easily undo if they don't work out:
Testing a new email sequence
Trying a different project management tool
Creating internal process documentation
For these decisions, the rule is simple: decide quickly and learn. The cost of being wrong is minimal, and the cost of delay is high.
One-Way Doors (Irreversible or Highly Costly to Reverse)
These are choices that will be extremely difficult to undo:
Implementing a core data architecture
Restructuring your client contracts
Making significant brand positioning changes
For these decisions, you need a more deliberate approach: stage your commitments, set explicit exit criteria, and keep options open.
Once you make this distinction, everything changes. You stop treating small decisions like existential choices, and you stop treating major commitments like casual experiments.
Making Smarter Bets: The Real Options Approach
For any significant business initiative, stop thinking in terms of all-or-nothing projects. Instead, treat them as a series of options – the right, but not the obligation, to take further action.
Here's how it works:
Stage 1 (Small Bet): Run a limited pilot with clear success criteria
Stage 2 (Medium Bet): If Stage 1 succeeds, expand to a limited rollout
Stage 3 (Large Bet): If Stage 2 succeeds, scale fully
At each stage, you have three choices:
Continue (if results are positive)
Pivot (if you learn something that changes your approach)
Stop (if the initiative isn't working)
This approach dramatically reduces risk while accelerating learning. You're not hoping the future cooperates with your big plan – you're building a plan that adapts as the future reveals itself.
The Six Elements of Quality Decisions
Even with the right framework, you need a way to ensure your decisions are well-structured. This is where the concept of Decision Quality comes in.
A quality decision has six essential elements:
Appropriate Frame: Are you solving the right problem?
Creative Alternatives: Do you have multiple legitimate options?
Reliable Information: Are you working with the best available data?
Clear Values: Have you defined what success looks like?
Sound Reasoning: Is your logic connecting the dots correctly?
Commitment to Act: Is everyone ready to implement?
Your decision is only as strong as its weakest link. If any of these elements is missing, you're setting yourself up for failure.
When facing your next one-way door decision, score each element from 1-10. Anything below a 7 needs more work before you proceed.
Know When to Stop Researching and Start Deciding
One of the biggest decision traps is endless research. Here's a counterintuitive truth: sometimes more information isn't worth the cost of getting it.
This is where the concept of the Expected Value of Perfect Information (EVPI) becomes powerful. Before launching another study or pilot, ask:
"What's the maximum amount this additional information could change our decision's value?"
If your pilot costs $10,000 but could only possibly improve your outcome by $5,000, it's not worth running. Make the decision now with what you know.
Conversely, if a $10,000 pilot could improve a $500,000 investment by 20%, that's information worth buying.
This mathematical approach to valuing information cuts through endless debates about "needing more data" and forces rational choices about when to learn and when to decide.
The Hidden Danger: Path Dependency and Lock-In
Here's something most businesses overlook entirely: early choices create paths that are increasingly difficult to change.
This is called path dependency, and it happens through mechanisms like:
Learning effects (teams get trained on specific systems)
Coordination routines (processes get built around certain tools)
Data structures (information gets organized in particular ways)
Once these mechanisms take hold, switching becomes exponentially more expensive. That's why it's crucial to:
Recognize which early choices could create lock-in
Design explicit interfaces and exit ramps
Document how components connect so they can be replaced
Negotiate contract terms that preserve flexibility
The businesses that maintain agility aren't the ones avoiding commitments – they're the ones making smart commitments with clear escape hatches.
The Practical Approach: Your Week of Better Decisions
Here's how to implement this framework immediately:
Monday: Create Your Decision Inventory
Take 30 minutes to list your top 10 upcoming decisions. Tag each as a one-way or two-way door and rank by potential impact.
Tuesday: Frame Your Biggest One-Way Door
For your most significant irreversible decision:
Write the exact decision you need to make
Force yourself to generate at least 3 credible alternatives
List the values and trade-offs involved
Define what information is absolutely required
Wednesday: Design Your Option Chain
Convert your big initiative into 3 distinct stages with explicit go/kill criteria for each. What specific business outcomes would make you continue, pivot, or stop?
Thursday: Price Your Learning
For any pilot or test you're considering:
Estimate what it costs to run
Calculate what it's worth if it succeeds
Determine what it's worth to learn this information
Proceed only if the value exceeds the cost
Friday: Prevent Lock-In
Document:
Exit terms (data export rights, contract clauses)
Interface specifications (how components connect)
Decision rights (who can decide to scale or kill)
Bonus: Run a Pre-Mortem
Take 30 minutes with your team to imagine the initiative has failed completely. Work backward to list all possible causes, then add mitigations to your plan.
The Questions That Transform Your Decision-Making
Next time you're facing a significant decision, ask:
"Is this a one-way or two-way door decision? What makes it so?"
"What's the minimum first stage that buys us the right, not the obligation, to continue?"
"What's the value of the information we'd gain from this pilot, and what's our maximum reasonable spend?"
"Which choices today could create lock-in, and how do we maintain flexibility?"
These questions force clarity and prevent both unnecessary delay and reckless commitment.
The Far-Reaching Benefits of This Decision System
Traditional decision-making treats uncertainty as the enemy. This framework embraces uncertainty and turns it into an advantage.
By classifying decisions correctly, you'll:
Move quickly on reversible choices (80% of decisions)
Apply appropriate rigor to irreversible ones (20% of decisions)
Stage investments to learn before committing
Value information properly to avoid analysis paralysis
Prevent costly lock-in that limits future options
The most successful businesses aren't the ones with perfect foresight – they're the ones with the most adaptive decision processes.
Remember: In a world of uncertainty, the goal isn't to eliminate risk. It's to take the right risks, at the right size, in the right sequence, while preserving the option to change course when the facts change.
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