Obviously I recently launched paid subscription support. Good ol’ Lextra Credit.

And now I’m faced with the constant decision: What’s paid, and what’s free? This is the torture of every freemium business, every newspaper website, and on and on. you want to share your good stuff. But you also want to reward paying subscribers. It’s tricky.

All of us have to make this subjective decisions all the time. There are recipes and decision flows you can use to decide which choice makes sense when, but it mostly comes down to gut.

Some folks — my former employer Amazon among them — use a great analogy, about one-way and two-way doors. If you’re making a decision that you can revert on quickly, that’s a two-way door.

Let’s try that button in red — two-way door. If it doesn’t work, we can go back to blue.

Let’s pivot to video — one-way door. You do that, you’ve pivoted to video. A new pivot would mean tons of wasted time and money and energy and morale.

Launching a paid version of this Substack — kind of a one-way door. If I stop offering it, do I refund my paying subscribers? Do I just make them hate me for life? One-way door. I did it. Now I must feed the beast.

I like the one-way/two-way door method of thinking. Penn & Teller, in their book Cruel Tricks For Dear Friends, talk about the rule of No Permanent Damage. If they can do something, even something crazy, and it won’t permanently damage/harm them, they’re in. I like that mentality.

Having paid posts in addition to free ones is hard, and maybe alienates some freeloaders free readers, but it’s a fun challenge, no permanent damage.

Find a rubric that makes sense for you. What’s your decision making approach that feels natural? Doors? Damage? Coin flip? As long as you’re comfortable with your approach, make it work for you.