No, not this Maverick, but I did grow up in the ’80s.

I was in Austin this week to do a panel at SXSWedu about lessons from the pandemic. Derrell wore it better.

After the panel a few principals came up to say how much they agreed with a couple of points I made about data and transparency (the idea of “street data” is being used as a smokescreen to mask the woeful performance of too many schools during the pandemic, more on that later) and also about building better community between public schools and homeschoolers. There is a reason I’m not identifying them further – it wouldn’t do them any favors.

You have some school leaders who have taken big risks and disruptive steps. Some are people with careers in other fields – say Joel Klein or Alan Bersin – they can return to. Some are independently wealthy or have other sources of income. Some are just mavericks.

But let’s be honest, if you’re a longtime educator deciding to tack in a new direction or even to speak out against whatever fad has seized the field at any moment that can carry real costs. When Don Shalvey, for instance, stopped being a district superintendent and launched public charter schools it cost him professional relationships and had other consequences. Howard Fuller had an impactful career in education but the public school establishment turned on him after his time in Milwaukee – today hardly anyone remembers he was a public school superintendent.

Now if you’re a regular on the conference circuit you’re supposed to say things like, ‘there are 13,000 school districts and I know there are 13,000 Don Shalveys or Howard Fullers out there!’ OK. And we all know that’s not the case. There are, though, certainly say 500 or 1000 district leaders who could be path breaking innovators if they were turned loose. There are principals and teachers, too. In other words, there is a lot of untapped talent.

Yet getting loose is not straightforward. People have mortgages to pay, kids to put through college, family members to look after. It’s easy to romanticize risk taking, but it’s not attainable for everyone at any moment in time. Especially if you don’t come from money. And life happens for people and creates various constraints.

So I’ve sometimes wondered what kind of “maverick insurance” you could create to help people take big risks. And here it’s worth noting that while there are some big paydays in education when companies are acquired or go public, that’s not always the case given the market. Not everything is going to have a successful exit. And while you won’t go broke in the non-profit world, you don’t have those big life altering transactions. So the risk -reward profile is different that way, too.

Yes, some will argue, despite all that the idea of insurance and being a “maverick” are inherently at odds. Maybe. But people have life considerations. They sometimes have to listen to their inner Goose. It’s why there is always the backchannel.

Obviously, you don’t want to totally shield people from consequences and create perverse incentives that way. But what would it look like to make it a lot safer for someone with say 15 years toward their pension, kids in high school, and a big education idea to take big risks? In other words, what kind of maverick insurance could say a philanthropist offer to people with promising ideas? Especially a philanthropist with an interest in inclusivity and diversity and elevating fresh voices?

You know where I’m going. I was thinking about all this the other day and discussing it with a colleague in the context of all the MacKenzie Scott money raining down on the sector. A lot of people are quietly asking if it’s going to have an impact – speaking of the backchannel. That seems like a good question we should discuss more! (Bellwether offered some advice on spending that kind of money, you can read my take and others here.)

Regardless, in addition to no-strings attached money or organizations – perhaps what we need is some money to support risk takers, help the mavericks. There are fellowships, sure, and even some successful initiatives on certain issues – Darryl Cobb’s work is an example. Overall, however, there is not a lot of robustness for mid- and late-career professionals across a range of issues.

Organizations have value, of course but that’s definitely not where all the pent up energy is.

The actual Maverick in the picture above was accused of “writing checks [his] body can’t cash.” Maybe we’d get more innovation and energy if we didn’t ask talented educators to do that, too?