This is not a drill

Hey Lyle Letter #001

Today I’m introducing a new experiment for this newsletter. An experiment you can be involved in.

Every so often, I’ll be writing an advice column called Hey Lyle. It’s inspired by the author Cheryl Strayed’s Dear Sugar letters, which she recently started writing again on Substack (and I highly recommend checking out).

Hey Lyle letters will be based on an anonymous question from anyone (it could even be you!). Your question can be about anything—something you’re struggling with in your personal life, an issue at work, a rant about an annoying neighbor, or anything else you need some advice on. Tell me a little story about it and how it makes you feel. The more descriptive, the better.

If you’d like to submit a question, please click the big blue button below and fill out the anonymous form. I’d love to hear from you.

Ask Me For Advice

Without further ado, here’s the first installment of Hey Lyle.

Hey Lyle,

My wife is due with our first child in a few months and I’m feeling a combination of excitement and sheer terror as the due date gets closer. What kind of preparation should a first-time dad be doing during the third trimester?

Thank you,

Anxious Father-To-Be

Hey Anxious,

Two months before the due date for my daughter Em, on the afternoon of Easter Sunday in 2018, I hit the road from my home in Sonoma. I had exactly an eight-hour drive ahead of me. My destination? Bandon Dunes, a resort with six breathtaking golf courses, some of which border the cliffs of the Oregon coastline.

A golf pro friend of mine organizes an annual four-day trip to Bandon and I had been wanting to join for years but never felt like I could justify the cost. It’s not as expensive as Pebble Beach in Monterey, but it’s not exactly cheap either.

Let me tell you, Anxious, it was well worth the money.

The solitary time to think during the drive was precious, the time with friends—both old and new—was filled with laughter and friendly banter, and the views were spectacular and unforgettable. My golf game, on the other hand, was just okay. But that didn’t matter and I didn’t care.

A couple of weeks later, I flew to Seattle to meet up with my dad and brother for a guys trip. We rented an overpriced VRBO place right on Puget Sound. I don’t recall going on a trip with only the three of us ever before. My mom was always with us too when we were kids. And life and vast distances between our homes made it hard to do in adulthood.

About a year and a half prior, my dad was diagnosed with prostate cancer. There was a very real possibility that this trip would be the last time we’d be able to pull it off. He’s still with us today, thankfully, but that wasn’t clear at the time. We knew traveling would become more difficult for him as time went on and his pain got worse.

We ate great food at a new restaurant each night. We did the tourist thing and watched the fish throwing at Pike Place Fish Market and visited the Museum of Flight. And we laughed and talked about life, work, and family late into the night. The time together was priceless and I won’t ever forget it.

Now, Anxious, you might not be a golf nerd like me. You might not have a father with cancer either. And you might not even have a sibling at all. But the first thing I would tell you to do is to spend some time away from home. Rent an Airbnb for a few days on your own. Go camping with some good friends. Whatever.

The point is to find time to breathe for a bit on your own because you’re going to need every breath you can spare once your little one arrives.

Back in 2005, I was living in Santa Barbara and playing poker for a living. I played mostly online at home, but occasionally I would travel to play live poker. In March, I hopped on a flight to Reno to try to qualify for the $5,000 buy-in World Poker Tour event.

I was flying direct to Reno from the tiny Santa Barbara airport in one of those small, puddle jumper jets where I have to duck my head a few inches so I don’t hit the ceiling. My fellow passengers and I listened to the flight attendants give their typical pre-flight safety announcements—the ones that anyone who flies regularly tunes out—and then we took off without any issues.

As we got closer to Reno, the pilot came on the overhead speaker and told us we would be experiencing some turbulence as we descended. He wasn’t kidding. The plane proceeded to get tossed around like a rag doll by the eddies of rising and falling air in the mountains. We would suddenly drop and I’d instinctively grab my armrests. I’m not usually one to get motion sick, but I’m telling you, Anxious, I was not feeling well.

I remember thinking at that moment about those safety announcements I’d heard countless times before. My seat belt was securely fastened and anchoring me to my chair, which meant holding onto the armrests was mostly pointless. I knew we weren’t over a body of water and wouldn’t be needing to blow up our life jackets with the little red straw or use our seat cushions as floatation devices. But I was ready for the oxygen masks to come hurtling down from above at any moment. And you bet your ass I was putting on mine first before helping the kid across the aisle with his.

The masks never came down. But the pilot did miss the landing and had to pull the plane back up and loop around for another try, which meant another twenty minutes of turbulence and me trying not to puke.

Anxious, your first child is due in the next few months and you’re excited and daydreaming about the future. You’re about to go on a trip like you’ve never been on before. Consider me your fatherhood flight attendant because I have some pre-flight safety announcements for you before you take off.

First of all, buy the book The Expectant Father, if you haven’t already. It’s a best seller for a reason. Read it as the months go by leading up to the due date. It’s great at explaining your partner’s experience carrying your child and what you can do to be helpful. And, of course, you should absolutely do all the typical prepping things like getting the nursery set up and having the supplies ready for the trip to the hospital. All the standard things.

But there’s one more thing I want you to spend time doing before the due date arrives.

When my daughter Em was born, she wasn’t breathing. For this trip, the oxygen mask really did come out. It wasn’t a drill and I wasn’t prepared. I hadn’t been given the pre-flight safety announcement about what to do in case it all went wrong. I was completely blindsided.

A few weeks before the due date, my wife Allison said she was nervous about the birth. She’s more of a worrier than I am. I said, “Don’t worry, it’s going to go great.” I said it to make her feel better, sure, but I also truly believed it. Allison is the picture of health—she’s a dietitian so she eats impeccably, exercises way more regularly than I do, and I’ve seen her drink a total of maybe two glasses of wine ever since I’ve known her. So what was there to worry about?

In a way, I’m lucky because my daughter made it. Yes, she has cerebral palsy, which is a life-long disability, but she’s alive and otherwise healthy. Some parents aren’t so lucky and for about thirty minutes there, I thought I was one of the unlucky ones.

In the US, the infant mortality rate is about one-half of one percent. It’s tragic and heartbreaking. And it’s also not zero percent. It means that tens of thousands of families have to live with the grief that comes with it.

It’s a crazy process to grow a human inside another human. Allison’s body changed an incredible amount in order to fit Em in there. I can’t imagine what it feels like to give birth to another life. I’m amazed childbirth doesn’t go wrong more often.

So, Anxious, take some time to think about the possibility that things could go terribly wrong. I know it sounds morbid, but stick with me. The idea isn’t to ruminate on it incessantly. No, that’s a recipe for depression. Instead, the idea is to be aware of the slim chance of a complication. Just sit with it for a moment and think about how you might react. How would you want to react? By mentally preparing, you’ll be one step ahead and more ready to deal with it so you can focus on being there emotionally for your family.

When Em was born, I did a decent job, considering how unprepared I was. Sometimes we rise to the occasion in the most difficult moments. But I wish I had spent time considering the worst-case scenario beforehand. It wouldn’t have changed the outcome, of course, but the gut-punch wouldn’t have caught me off guard so much.

And Anxious, the beautiful thing is, if everything goes smoothly—which it almost certainly will—you’ll appreciate your healthy baby that much more. Be excited, but also be vigilant.

Wishing you the best,


You can find The Expectant Father and other favorite books of mine in my store 👉 A portion of your purchase at goes toward local book retailers. And, full transparency, if you click through my link and buy any book while you’re there, I’ll receive a percentage.

Thank you to Sasha, Simon, Rishi, Kyla, Rhishi, and Grant for their excellent feedback.

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