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Changing, Directions

6 min
Photo by Oliver Roos / Unsplash

Important Note For Better Questions Subscribers!

I've changed email providers, so the weekly emails will now be coming from If you think you're missing the emails, please re-subscribe here.

Last week, Better Questions passed the 5,000 active subscribers mark.

When I started this project last year it was primarily an experiment in getting myself to write more.

To say that I am surprised that there are so many people reading these things understatement.

Passing that goalpost has caused me to stop and reflect on what this project is, what it could be, and how I want the next year to go.

So this email is all about what's coming next for Better Questions. If you're at all interested in how a project like this works, then this email is for you.

(And no worries if not - we'll be back to our regular programming next week).

How It Started: Process and Experimentation

When I started Better Questions I didn't even know what I was going to write about.

The title came from an old idea I had for a piece of software. I knew I wanted to practice writing, and I knew that, for me, the key to practicing regularly was having deadlines.

So I created one: one email, every week, on Wednesday at 6am.

Deadlines, even when completely arbitrary, are incredibly useful for getting me to do the work. But would it be enough? After all, I had never written anything regularly in my entire life - and I had a full-time job, kids, and a pandemic to deal with.

I knew I would be far more consistent if people expected me to show up. I also knew from experience that financially investing in something made me far more likely to treat it seriously.

(This is nearly universal, as far as I can tell. If you've ever done anything you're good at for free, you'll know  that your "free" clients are almost always far harder to deal with than your paying clients).

But I didn't have an audience - not for this kind of thing, anyway. So, I posted on Twitter a few times and then set up a basic Facebook Ads campaign with a 10$ a day budget.

Now that I was fully committed, I started writing about...well. Pretty much anything.

I wrote about anything and everything because I had no idea what I wanted to do, and that was the point.

Better Questions was always a process, not an outcome. If I had raced to define what it was about, and who I wanted to speak to, and how I wanted to run it, then I would closed off any number of possible paths that I had no idea existed.

Uncertainty begets possibility. We almost always seek to eliminate uncertainty too soon, preventing ourselves from discovering new and exciting ways of being.

Not to put too fine a point on it:

"The certainty of misery is preferable to the misery of uncertainty."  Virginia Satir

Rather than shutting off possibilities by making too many decisions too early, I made small investments in a number of different things to see how they would work.

I launched a private member community, first on Facebook, then on Circle.

I started a monthly Book Club.

I started a YouTube channel.

I streamed a new video every day.

I posted regularly on Twitter.

I posted Deep Dives videos on that week's email topic.

I created three different online courses.

I experimented with 1-on-1 coaching, taking on 5 clients.

Some of these worked great (people really loved The Art of Mastery!), while others did not (about 4 people a week watched my Book Club videos).

And that's the point.

If you never try, you'll never know. Some things worked great, but ended up being too much work, or not to my liking. Other projects were incredibly fun, but seemed to resonate with exactly no one.

Only by this process of trial and error was I able to find something of a sweet spot between things I liked doing and things people like consuming.

And that brings us to now.

How It's Going: Practice and Focus

I started writing Better Questions because I was bored at work and needed something to challenge me.

What I didn't fully appreciate, however, was the impact that teaching would have on my life.

I view these weekly emails as a form of teaching - of passing on interesting things that I'm learning or am curious about.

That became codified in my unofficial motto: Learn, Make, Teach. Partially stolen from the excellent Epsilon Theory, Learn-Make-Teach means:

That iterative structure of "learn a cool thing, incorporate it into a fun project, then teach what comes out of that" has resulted in multiple quantum leaps in my personal life, health, and career.

It's made me better at everything that I do. That, and nothing else, is the core benefit of writing Better Questions each week.

You know I'm telling the truth, because I pay to write this email. I still pay for ads every week, because a growing audience keeps my motivation high. I've paid out thousands for software, hosting, tools, etc. I could've done it much more cheaply, of course, but I enjoyed the experimentation along the way, so why not?

Better Questions is a money-losing enterprise...if viewed through the typical lens of a start up. But that's not what this is.

Better Questions is a process for continual self-improvement...AND a way for me to try and effect positive change in the world.

For that, I am happy to pay.

That said, it's time for Better Questions to move into a different phase of it's life cycle.

While I'm still going to be experimenting, I have a better sense of what I do well - and what I enjoy.

I also know that if I want to keep my intrinsic motivation high, that means challenging myself to more value. What can I improve? What can I do better? How can I have a greater impact?

At the same time, it's critical that I keep the structure of this project as simple as possible. One of the side-effects of doing lots of experiments is that you tend to leave a lot of half-finished projects lying around. There's been a fair amount of confusion about the email list fits together with the blog, and the online community, and the courses, and so on.

In order to address all these issues (greater levels of focus; working on new and challenging problems; simplifying the structure), I'm going to be making the following changes.

I've unified the project behind a single name and domain:

Before we had for email sign ups, then No Less Than for the blog. I'm just going to keep everything under the Better Questions name.

I've migrated both the blog and the email list to Ghost.

Ghost is a blog publishing platform that can also handle the email list simultaneously. Not only do I appreciate Ghost's backend functionality and open-source ethos, the switch will save me nearly 200$ a month (I was paying close to $300 a month for Active Campaign to send emails alone).

Better Questions is now Member-supported.

The weekly Better Questions email is, and always will be, absolutely free.

For those who want to support my work here, for $5 a month (or $35 for the year), you'll also receive:

There's zero pressure to pay if you don't feel like it, and all of my Better Questions posts will be archived for free on the blog.

This structure seems like a simple and sustainable way of bringing in some money to help defray my costs, keeping me committed mentally, and encouraging readers to invest in the community I'm trying to build.

P.S. If you're an existing Dan's Secret Society member, you get grandfathered in to paid membership for free.

That's about it for now.

There's going to be a long period of wonkiness, as is typical whenever a change like this occurs. I'm sure some people won't get the emails for a while, some people will get unsubscribed or re-subscribed by accident, the old posts will be broken for a bit, etc.

But this feels like the right move. I'm doubling down on what I love about Better Questions - the sense of intellectual exploration, the open and welcoming community, the direct interaction with people like YOU

...And cutting out a bit of the complexity.

Here's to another wonderful year, folks.

Thank you so much for being here.



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