20 issues in. Here's what I didn't expect to learn.

Work was busy this week. The kind of week where the calendar fills up before Monday is over and you surface at Friday afternoon slightly confused about where the time went.

This is the week I also hit 20 issues of Four Kids Later.

Twenty Sundays in a row of sitting down — tired, sometimes distracted, occasionally running on fumes — and writing something honest about this life. About being a dad of four in 2026. About money and Montana and soccer in Bend and a cattle ranch in Grass Range and a gravesite in Lewistown and a 1923 T bucket at Flathead Lake and 17 people on the Snake River in Wyoming.

Twenty issues. Busy week. Newsletter went out anyway.

That's actually the whole story of this thing.

I started Four Kids Later because I thought I had something useful to say about family finances. I work in corporate finance. I have four kids. I know what it costs to raise a family and I thought other parents would find that useful.

That part turned out to be true.

What I didn't expect was everything else.

I didn't expect writing to feel like this.
I've written 20 issues now. Some of them were straightforward — here's what back to school actually costs, here's how to read your benefits package, here's the sports budget math nobody does. Useful. Practical. Fine.

But the ones that landed — the ones that got forwarded, that got replies, that people mentioned to me in real life — were never the finance ones. They were the ones about my dad. About the gravesite in Lewistown. About watching my daughter play soccer on a broken foot. About sending my son bow hunting without me and spending an hour in the garage checking his gear because that was the only useful thing I could do.

I thought I was writing a finance newsletter. Turns out I was writing a dad newsletter that happens to talk about money. That pivot didn't come from a strategy session. It came from paying attention to what actually connected.

I didn't expect it to be this clarifying.
Twenty weeks of writing about your own life forces you to look at it. Really look at it. What matters, what doesn't, where the money actually goes, what the kids are actually doing, how fast it's actually moving.

I wrote about my dad's birthday in September and realized I hadn't fully processed some of that grief in years. I wrote about junior year soccer and realized I was already mourning something that hadn't ended yet. I wrote about the road trip and realized we'd done something genuinely great that most families never get around to doing.

The newsletter didn't create any of those things. But writing about them made them real in a different way.

I didn't expect it to be this hard to grow.
Honest truth: the subscriber count is not where I wanted it to be at issue 20. I had visions of hockey stick growth and viral Reddit posts and a waiting list for sponsorships.

The reality is slower and more interesting than that. The turning point for most successful newsletter creators isn't a viral moment — it's when they stop treating it like a side project and start treating it like a real newsletter business. I'm still working on that part. The writing is consistent. The systems are still being built. The growth is coming but it's coming at the pace of something real, not something hacked.

I'm okay with that. Mostly.

I didn't expect to still be doing it.
This is the one that surprises me most. I started this in the margins of a full life — full time job, three kids still at home, a dog, a wife, sports schedules, all of it. There were weeks when writing this felt impossible. There were weeks when I genuinely considered skipping.

I didn't skip. Twenty issues. Every Sunday.

That's not nothing. That might actually be the whole thing.

Since this is a milestone issue I want to be straight with you about where things actually stand.

What's working:

The writing is better than it was at issue 1. Significantly better. The dad life sections — the gravesite, the garage gear check, the drive to Bend — those are things I'm genuinely proud of. They're honest and specific and they couldn't have been written by anyone else. That's the whole point of this thing and it's working.

The content framework is solid. Every issue has a real life moment, a main story, a money connection, and a dad life closing. That structure took a few issues to find and it's the right one.

The products exist. A free activity budget spreadsheet. A sports cost calculator. A Etsy shop. A Gumroad page. The infrastructure is real.

What isn't working yet:

Growth is slower than I'd like. Reddit was supposed to be a big channel — karma requirements made it nearly impossible to post. Pinterest has one pin. The AI tool on Carrd hasn't been properly promoted yet. There are ten things on the to-do list for every one that gets done because this is a side business built in the margins of a full life.

That's honest. That's where we are.

What comes next:

More dad life content. Less finance for finance's sake. The issues that connect are the ones that feel like something a real person wrote about a real life — and that's what I'm going to keep doing.

More consistency on the growth side. Pinterest pins. Quora answers. The things that compound slowly but actually work.

And issue 21 next Sunday. Because that's how this works.

I've written about budgets and benefits packages and sports costs and road trips and back to school and life insurance and HSAs and open enrollment.

The financial lesson that surprised me most wasn't in any of those topics. It was this:

The most expensive thing most families do isn't a purchase. It's a drift.

Drifting through a year without a vacation budget and then being shocked by the credit card statement in August. Drifting through open enrollment and auto-renewing the wrong plan. Drifting through kids' sports seasons without a line item and wondering where the money went in November. Drifting through Christmas without a plan and carrying the debt into February.

None of those are discipline failures. They're attention failures. Life gets busy — work gets crazy, sports schedules fill up, the week disappears — and the financial stuff drifts because there's no system holding it in place.

That's what this newsletter has been trying to be. Not a lecture. Not a guilt trip. Just a system. A Sunday morning reminder to pay attention to one thing before the week makes it impossible.

Twenty issues in that still feels like the right goal.

Twenty issues. A gravesite in Montana. A cattle ranch in Grass Range. The Grand Tetons at 6am. 17 people on the Snake River. A daughter playing soccer on a broken foot in Bend. A son's first bow hunt. A 1923 T bucket at Flathead Lake. A graduation. A birthday my dad didn't get to have.

That's what twenty issues looks like when you write about a real life instead of a perfect one.

I started this because I thought I had something useful to say about family finances. I still think that. But what I've learned writing it is that the useful part was never really the spreadsheet. It was the Sunday morning of paying attention. Of writing it down. Of noticing the things that matter before they're gone.

If you've been reading since issue one — thank you. If you found this recently — welcome. Either way I'm glad you're here.

Issue 21 next Sunday. As always.

Back to the regular rhythm — whatever the week brings, written honestly. Soccer season is winding down. The holidays are getting louder. And there's always something worth paying attention to if you're looking for it.