The Rebel's Guide to Health Insurance
My strategic playbook to maximize benefits and mitigate risk. Plus, how to use tax benefits, coupons and AI to your advantage.
Navigating U.S. healthcare can feel like a life-or-death battle — brutal for most, except the super wealthy.
The murder of United Healthcare CEO, Brian Thompson, spotlighted a grim reality in this country: insurance is a for-profit business prioritizing shareholders over patients and doctors. The odds are rarely in our favor.
We know that we must take a pro-active approach to our health. Yet, many of us pick our plans based on premiums alone, skipping the fine print and hoping it all works out — only to be shocked when it doesn’t.
The result? A third of all GoFundMe donations now go toward medical expenses, with 250,000 campaigns raising $650 million annually for people drowning in unexpected healthcare costs.
Your health and your finances are inseparable. That’s why I created The Rebel’s Guide to Health Insurance — a strategic playbook to empower you with tools, knowledge, and a mindset shift to take back control:
Strategically select your 2025 plan
Maximize your 2024 dollars with smart year-end moves
Leverage tax benefits, coupons, and AI to outsmart Big Insurance
This isn’t just about surviving the system — it’s about mastering it.
My mission is to optimize all aspects of your health by empowering you with critical information presented in an understandable and entertaining format. Please consider upgrading to paid to support my work.
Understanding Health Insurance 🚑
We use insurance today in ways it was never originally designed for. To paraphrase Saum Sutaria, physician and former healthcare leader at McKinsey, who illuminated this point in his podcast interview with Peter Attia…
In every other area of our lives, we use insurance for random, infrequent and unpredictable events to prevent a catastrophic loss.
Yet with health insurance, we expect a majority of our expenditures like preventative care (doctor visits) or chronic illness management (diabetes) to be covered through our plans.
It’s like trying to use your car insurance (procured for financial protection against accidents) for an oil change.
Insurance today is a discount card.
Strategically Build Your Healthcare Plan 💰
Think of your healthcare spend like a budget and allocate funds for the highest ROI.
Just as in business, smart decisions come from combining historical data with future projections. The goal is to invest in preventative health interventions while mitigating risk against catastrophic events.
“If the extent of your health insurance strategy is ‘just in case,’ you’ll be sorely disappointed when it doesn’t serve you in every case.”
— Rich Sterling, Sterling Benefits
Without employer-subsidized benefits, every dollar counts — review the past, assess the present, and plan for the future. Open enrollment until Jan 31 but varies by state.
🚨 If you are a beginner, read this guide that defines all of the terms of healthcare before taking the steps below!
Step 1: Understand Your Healthcare Needs
Every year, perform this review during open enrollment.
Evaluate Current Health
Review your family’s medical history, ongoing medication and regular healthcare needs.
Keep reading with a 7-day free trial
Subscribe to In the Pink to keep reading this post and get 7 days of free access to the full post archives.