I still have the COBRA packet.
December 13, 2022. Workterra sent it to my house in Houston after I left BHP. Eleven pages of legal language explaining how I could keep my health insurance for 18 months—if I was willing to pay $2,392.04 per month.
That's not a typo. Twenty-three hundred dollars. Every month. For coverage that had cost me a fraction of that while employed.
Medical: $2,295.34. Dental: $75.58. Vision: $21.12. Total: $2,392.04.
The packet even included a helpful 12-month projection showing me exactly how much I'd hemorrhage: $28,704.48 in year one alone.
I'm telling you this because health insurance is the single biggest barrier keeping talented executives trapped in corporate jobs they hate. And I'm going to show you why that barrier is mostly an illusion—built on fear, not math.
The Job Lock Phenomenon
Gallup calls it "job lock." One in six American workers—16%—stays in a job they'd otherwise leave purely because of health benefits.
That's millions of people trading their careers for coverage.
A separate survey found that 33% of workers with employer-sponsored insurance would be "very or somewhat likely to quit" if healthcare wasn't a factor. Among workers under 35, that number rises to 40%.
But here's the statistic that should make every aspiring fractional executive pay attention:
26% of insured Americans said they would start their own company if health insurance wasn't a barrier.
"That's not a barrier. That's a ransom."
The Fear Is Real. The Math Doesn't Support It.
When you're employed, your company covers roughly 80% of your health insurance premium. You see a manageable number on your paycheck—maybe $500-600 per month for a family.
What you don't see is the full cost.
The average employer-sponsored family plan in 2024 costs $25,572 annually. That's $2,131 per month.
COBRA doesn't add a markup. COBRA reveals the truth.
You were always paying that much—you just didn't know it.
The Real Math: COBRA vs. Everything Else
Remember my $2,392 COBRA quote? That was for me and my wife—not even a family of four.
Here's what I actually pay now:
- Private PPO (family of 4): $782/month
- Dental and Vision: $92/month
- Total: $874/month
That's a $250 deductible individual, $500 family. National PPO network. Preventive care at $0 copay. Ten doctor visits per year at $50 copay. Unlimited telemedicine at $0. Full maternity coverage.
The difference? $1,518 per month. That's $18,216 per year I'm not burning on overpriced COBRA coverage.
"You were always paying that much for insurance—you just didn't know it."
Let me be clear: I didn't sacrifice coverage quality to get that price. I just stopped using the corporate healthcare system that's designed to keep you dependent.
Your Actual Options (With Real Numbers)
Here's what nobody tells you about health insurance as a fractional executive:
Option 1: Spouse's Employer Coverage
This is the most common solution I see with clients. If your spouse works and has benefits, you can often add yourself to their plan for $300-600/month. This is usually the cheapest path.
Option 2: ACA Marketplace
The government will tell you 92% of marketplace enrollees receive subsidies, averaging $536/month in assistance. On paper, your net cost can be $0-350/month.
Here's what they don't mention:
Narrow networks. Many marketplace plans restrict you to a fraction of the doctors and hospitals you had with corporate coverage. That "affordable" plan means nothing if your specialist isn't in-network.
The subsidy cliff. Earn a dollar over the threshold and your subsidy vanishes. I've seen executives scramble to manage income in December to avoid a $10,000 surprise.
Bureaucracy. Income verification. Documentation requests. Annual re-enrollment headaches. You're trading one corporate hassle for a government one.
The marketplace can work—especially if your income is genuinely low in your first year of transition. But go in with eyes open. There's a reason I chose a private PPO instead.
Option 3: Private PPO Plans
This is what I use. Brokers specializing in independent professionals can often find plans at 50-70% of COBRA costs. My plan runs $782/month for a family of four through a private PPO network.
Option 4: PEO (Professional Employer Organization)
Platforms like Justworks give you access to large-group insurance rates. Their Plus plan runs about $109/month per employee for benefits access, and you can often get coverage comparable to corporate plans.
Option 5: HSA-Eligible High Deductible Plans
If you're healthy and want to minimize monthly costs, these plans can run $300-500/month for families. Combine with an HSA where you can contribute $8,550 pre-tax in 2025 (family), and you're building a tax-advantaged healthcare fund.
The Tax Advantage Nobody Mentions
When you're self-employed, you can deduct 100% of your health insurance premiums above the line. That means you don't even need to itemize.
At a 32% marginal tax rate, a $10,000 annual premium effectively costs you $6,800.
That's not available to W-2 employees.
Add HSA contributions—$8,550 for families in 2025—and you're looking at nearly $19,000 in potential tax-advantaged healthcare spending.
The fractional executive health insurance situation isn't just manageable. For many people, it's actually better than corporate coverage once you understand the math.
"Health insurance isn't a barrier. It's a ransom—and there's a systematic way to stop paying it."
Why the Fear Persists
I've had dozens of discovery calls with executives who cite health insurance as their primary barrier. When I dig deeper, almost none of them have actually researched the alternatives.
They haven't called a broker.
They haven't checked healthcare.gov.
They haven't asked their spouse about adding them to their plan.
They've just assumed it's impossible because that's what they've been told.
Follow the money. Who benefits from you believing health insurance is an insurmountable barrier?
Your employer does. The longer you believe you can't leave, the longer they keep you.
The healthcare system does. Fear keeps premiums high and options invisible.
And yes—the government does too. Subsidies create dependency just like corporate benefits do. Different master, same handcuffs.
Career coaches do—the ones who charge you $5,000 to help you "optimize your mindset" instead of giving you actual solutions.
I'm not selling hope. I'm giving you numbers.
My COBRA was $2,392. My current coverage is $874. That's the math.
The Bottom Line
Health insurance is a solvable problem. It's not the barrier—fear of the unknown is the barrier.
I still have that COBRA packet in a drawer somewhere. I keep it as a reminder of the moment I had to decide: pay the ransom or find another way.
I found another way. So can you.
The work is serious. The life doesn't have to be.
Now if you'll excuse me, I have a tee time to keep.
Kirk Coburn created the Fractional CMO category in 2009 when he co-founded Chief Outsiders, now North America's largest fractional executive firm with 2,000+ clients served. He runs The ReTern from Nantucket and is usually on the golf course by 2 PM.
