My Solopreneur Framework for Making Tough Decisions: Weighing Opportunity vs. Red Flags
I’ve had my business for 7 years.
And I’m just now realizing that the way that I think about my business changes the results that it generates.
If I had asked myself better questions in the past, I would have avoided huge mistakes — like working with red-flag clients.
You know what I’m talking about.
An amazing opportunity comes up.
But, there were some glaring red flags. You feel stuck.
On one hand, the potential upside is huge.
On the other, if things go south, you’re stuck in a not-so-fun situation.
Now that I understand the questions I ask myself determines the success (and chaos) of my business — I created a systematic way to think through this.
I developed a framework, using AI as my thought partner.
Here’s how it works:
1. List out the facts
First, I brain-dump everything I know about the situation.
No judgments, just facts. I asked Claude to help me categorize them:
• What are the concrete, verifiable facts about this opportunity? • What are the assumptions I’m making? • What are the unknowns?
This helps me separate reality from my own projections.
2. Identify the opportunity cost
It’s easy to get caught up in the potential gains. But what am I giving up by pursuing this?
I prompt Claude with:
• If I don’t take this opportunity, what else could I do with the same time/resources? • How does this align (or not) with my long-term business goals?
This gives me perspective on whether the opportunity is truly unique or just shiny.
3. Red flag deep dive
Next, I dig into those red flags. I don’t want to dismiss them out of fear, but I also don’t want them to paralyze me.
For each red flag, I ask:
- What’s the worst-case scenario if this red flag becomes a real issue?
- What’s the likelihood of this happening?
- Are there ways to mitigate this risk?
Claude helps me think through each scenario objectively.
4. Seek diverse perspectives
I don’t have a board of advisors (yet), so I used AI to simulate different viewpoints:
- How would a risk-averse investor view this opportunity?
- What would a growth-focused mentor say?
- How might my biggest competitor approach this situation?
This highlights angles I haven’t considered.
5. Time-travel thought experiment
I imagine myself one year in the future, having taken the opportunity. Then I imagine not taking it. I asked Claude:
- In each scenario, what am I most likely to regret?
- What unexpected benefits or drawbacks might have emerged?
This future-focused thinking clarifies my true priorities.
6. Gut check
After all this logical analysis, I tune into my intuition. I asked myself:
- How do I feel emotionally about this decision?
- Is there any nagging doubt I’m ignoring?
I’ve learned not to discount my gut feelings, even if I can’t fully explain them.
7. Define my walk-away point
Finally, I set clear boundaries. At what point would I walk away? I work with Claude to define specific, measurable criteria:
- What key metrics need to be met for this to be successful?
- What red lines, if crossed, would make me exit immediately?
This gives me confidence that I can pursue the opportunity without losing control.
After going through this process, I always feel much clearer.
The decision isn’t easy, but I can feel confident in my choice.
I’m keeping this framework in my back pocket for future tough decisions.
Remember, as entrepreneurs, we’re paid to make tough calls with incomplete information.
Having a solid process doesn’t guarantee success, but it does help you sleep better at night knowing you’ve done your due diligence.
Want to see how Claude can be your on-demand business strategist and thought partner?
Check out my free 3-day Think Retreat:
- Copy-and-paste prompts to use as thought exercises with Claude
- Each prompt is crafted on hours and hours of researching psychology, mental models, and perspectives from successful entrepreneurs
- The prompts are written to make sure your conversation is useful and valuable without AI going off the rails or giving you low-quality responses
