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Culture

March 26, 2026

Making the best of a bad system

BY

Teagan Miller

Feeling supported — like we’re truly valued — makes a huge difference in how well we do, both personally and as a team.

We aren’t responsible for our team members’ lives outside of work, and we don’t expect them to build their lives around us. But their quality of life affects who they are when they show up for work. As a company, we have a valuable opportunity to make our employees’ lives easier and more enjoyable by removing some of the headache from healthcare. And ultimately, to foster a better overall work environment and culture.

The backstory

You might be asking yourself (on the daily): why is healthcare related to my job in the first place?

In the US, most people rely on employer-sponsored health insurance for medical care — which is unusual among developed nations. It’s not the result of a deliberate, well-researched policy or a failed grand strategy. Rather, it’s a holdover from World War II labor shortages, when employers began subsidizing premiums to make compensation packages more attractive. For a deeper dive, check out this article from the National Institutes of Health.

We’d love to talk more about how the entire infrastructure should change (really). For today, though, your health insurance is tied to your job, for worse — and potentially for better. We want to help tip the scales towards “better.” In fact, we believe it’s our duty as employers to do so.

Health insurance and your life

For employees, healthcare is a huge part of how we show up day to day. If you’re stressed that your upcoming dental procedure might make you go bankrupt, then you’re probably not bringing 100% to the table to design a website (or reshingle a roof, or teach kindergarteners, or whatever it is you do).

For employers in a traditional sense, there’s a day-to-day cost-benefit analysis at play. Benefits like healthcare directly impact stress, trust, retention, and burnout. So, even though it would be cheapest (on paper) not to offer any benefits at all, that’s not an effective long-term strategy. It’s more expensive in the long run. 

Giving employees better benefits is also a straightforward way to show we appreciate their hard work. It’s one way to show we’re invested in their well-being and want to keep them around. And it’s a recognition that they have a big say in their quality of life: when everyone shares in the success (not just the folks at the top), it creates a system where doing great work leads to better financial results. Better financial results allow us to offer even better benefits.

At Mediocre, transparency and community — which includes the welfare of individuals within our community — are core values, and we really do try to align our actions with those values. Even when there’s no audience.

What we’ve learned as a small business

Health insurance: a mystery

First of all, we’ve confirmed what most people in America feel on some level: health insurance is confusing. There’s a lot of lingo and an underlying assumption that you should inherently and completely understand all of it.

Deductible? Yeah, pretty sure I know what that means… Coinsurance? Um, I could Google it…

All these micro-anxieties can eventually turn into a generally “icky” feeling that makes people want to just give up — or to accept the path of least resistance. That’s an understandable urge, but one that only enables the system to keep ruling our lives.

Challenging norms

When a system is built to maintain the status quo, it takes a little extra effort to shake things up. We’ve found that even the most well-meaning health insurance reps (the people who talk to the insurance companies for us) push back quite a bit against deviations from the norm. They’re just doing their jobs, of course, but it’s eye-opening to see how ingrained those norms really are.

We’ve been met with raised eyebrows, polite incredulity, patronizing chuckles, waves of dismissal, and a heaping dose of Oh, well, good on you! But also with a distinct feeling that we’re unlike most companies in our willingness to stretch ourselves financially to pursue better benefits.

Better benefits, happier team

Despite the stretch, we’ve learned there is a considerable payoff. The jump in morale and confidence in our leadership makes the challenge just as inspiring as it is uncomfortable.

To back this up with data: we send out an anonymous team poll every month, and through their responses over time, we’ve learned that better health insurance has a direct, positive impact on how happy the team is.

What we do differently

Going beyond the minimum

Companies with fewer than 50 employees are not required by law to provide health insurance. So it’s a bit against the grain for a company as small as ours to offer benefits at all. But we see it as an opportunity to improve our employees’ quality of life, just like we see the company itself as a vehicle to better our collective experiences and communities.

We enjoy finding out what’s possible with a little extra effort — it’s motivating. For instance, adding a monthly well-being stipend for health-related goals became a fun way for us all to talk about what makes us feel healthier and stronger, what’s happening around town, cool new gear, and so on.

As a company, we started investing considerable time, money, and resources into building up our internal knowledge base so we could then share it with, and guide, the rest of the team. It was uncomfortable to learn how little we knew and to understand how rough the experience can be as a team member trying to pick a plan and utilize their benefits. 

Proactive engagement

We try to be involved in each employees’ experience choosing, using, and navigating their benefits. It’s an attempt to counter what many of us have experienced — a smattering of benefits and lingo with something akin to “Hey, here’s what we got, you’re welcome. And good luck!”

What does this look like in action? We bug our reps. We poll our team. We try to make it as easy as possible for each person to enroll in, engage with, and use their benefits. We remind our team that it’s their money going towards those premiums (so use it!). We are the thorns in our reps’ sides, and in the sides of the insurance companies when necessary. We ask questions. We push the limits of what’s expected.

Benefit contributions

We’ve increased our monetary contribution year by year. We currently contribute a flat $450 to each employees’ medical insurance premium. We offer two PPO plans. And to avoid the gatekeeping lingo, PPO stands for “Preferred Provider Organization.” These plans reward you for choosing providers or doctors that are in-network (in other words, those that have a pre-existing agreement with your insurance company).

We also cover 100% of premiums for supplementary benefits, which, for us, means vision, dental, short-term disability, and life insurance.

Why we’re telling you this

We want to normalize a sentiment for both employees and job seekers: it’s okay to ask.

Raise your expectations for your employer and the benefits they offer. If you’re not happy with your current benefits, ask for improvements or suggest alternatives. If you don’t understand your options, keep asking questions until you do. 

We wanted to offer our perspective because understanding your leaders’ potential for action empowers you to demand more. The combined power of small teams choosing to elevate standards creates a strong ripple effect.

What small companies can realistically do

Focus on progress over perfection. Just start making moves toward getting better, even if they're not perfect or groundbreakingly impactful right away. Small steps can have just as much impact as big ones, depending on the context.

Second, don’t underestimate the value of asking better questions (and getting better advice). If something doesn’t feel explicitly clear, keep digging. If something seems fishy or murky, it’s probably designed to be that way. So challenge it.

Third, be willing to take risks and stretch. Investing in your team is good business, even if it involves a bit (or a lot) of discomfort.

Raising the bar

So, what’s the takeaway here? For us, it’s that being a responsible employer isn’t just about checking a box or doing the bare minimum. It’s an active choice. We’ve learned that, even as a small company, we can and should challenge the status quo when it comes to employee welfare. This isn’t charity — aligning our actions with our values of transparency and community is good business.

For you, whether you’re a Mediocre team member, a potential job seeker, or another small business owner, we hope this offers a bit of encouragement and clarity. Don’t let confusion be a reason to settle. Ask, ask, ask. Push your employers — or your insurance reps — for better answers and better benefits. Collectively, we can move the needle.

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