My Year of Transitioning to Dad Hood: Month by Month Lessons and Life Changes

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A year and a couple of days ago this happened:

Alyssa woke me up, the pregnancy test was positive and as the old adage goes — life would never be the same again.

When I think about the fact that this was over a year ago, it’s really hard for me to process. It feels like forever and yesterday wrapped up into one weird timeline. So much has changed over the past year in our lives, from learning about the baby to pregnancy and then the first several months of Ellie’s life.

I wanted to dedicate this post to sharing what the past year of our lives have looked since we found out that we were expecting. Also, at the risk of only revisiting random life events, I also wanted to share some of the bigger lessons that I’ve pulled from each month over the past year (as best I can remember, we do have a 4-month-old after all and you can bet I’m already using that to make memory excuses).

September 2018: I’m gonna be a dad.

This month was an emotional roller coaster for us. We were halfway through a several month trip across Canada and if I’m being honest, we were burned out. We’d hauled ourselves across the world last year, spent a lot of time working on starting a new business, hosted another conference, and then topped off the year with a fast-paced jaunt across the Great White North.

We live an incredibly fortunate life and one I’m so grateful for, but burnout in any capacity is real. Once we found out we were expecting, it was almost a relief to find an excuse to be still for awhile (even though we could have easily made this decision without needing to get pregnant).

And if finding out about pregnancy was like a soft voice telling us to slow down, Alyssa becoming sick shortly after was like being screamed at through a megaphone to slow down. Every time I cooked a meal in the RV or walked around, it made her nauseous. She just wanted to relax and soak in a tub and I wanted to be able to cook a meal and not make her hurl (TMI? Probably, sorry.)

It was time to slow our roll.

Four days after we found out we were expecting, we made the decision to move to Alyssa’s hometown of Denton, TX for a year. We would spend time around family during pregnancy and take a break from the full-time travel life.

What this month taught me: You can’t plan everything (or even most things).

To quote Kevin from The Office, “I’m a textbook over-thinker”.

For months last summer, I’d stressed myself and Alyssa out trying to figure out what was next for us. Would we buy a campground? Would we travel to Europe? I was so busy trying to plan what was next instead that I forgot to live in the moment. And then, when our life situation changed, within a matter of days we had clarity.

Going through this process made me realize that if I’m constantly revisiting a major life decision without getting any clarity (the nice way of saying overthinking), maybe it’s just best to wait until that clarity hits you in the face like two pink lines on a stick.

October 2018: One last pre-baby RV adventure with friends, a major car scare, and finding a home base.

October was kind of a nuts month for us. During that time we drove from Vancouver allllllll the way across Canada to Leisure Travel Vans headquarters in Winkler, Manitoba to pick up our Brave and then alllllll the way down to Texas.

So. Much. Driving.

However, before that journey, our friends Kara and Nate flew up to visit us for a couple of weeks. Anytime we can convince some of our close friends to come and spend time with us, it’s a major win. Luckily, a Canadian friend who owns a van rental company needed transport from Vancouver to Calgary, so we were able to hook them up with some wheels.

Little did they know, they were about to become some of the first people to know about baby Ellie. After their plane arrived, I called and asked if they would pick us up some crackers and Gatorade and they were immediately onto us. It took all of 30 seconds upon arrival for us to spill the beans. We hadn’t even told our parents yet.

Over the next couple of weeks, we drove from Vancouver to Kelowna (wine country, sorry Alyssa) and up to Banff. We celebrated Canadian Thanksgiving with four adults cooking in our Leisure Van, we made tacos on the side of the road after hiking on a glacier and we drank tea on top of a mountain (now that I think about it, most of our time with friends revolves around food).

Also, Kara and Nate, being the amazing people they are, snapped some super early pregnancy announcements while in the snow (side note: as I type this, Ellie is wearing this onesie for the first time!).

One evening from this time in Canada really stands out to me.

We rode the Banff Gondola up a mountain, ate candy apples and listened to a local artist play music into the night. The venue was giving away free beer and hot cider and it was one of those moments where I had to pinch myself that this is our lives. It was a great reminder that these were the little moments that are easily missed when you allow your life to be to become too busy.

After Kara and Nate departed, we dropped off the Leisure Van in Winkler, picked up our Brave and drove it all the way back to Texas (but not before nearly totaling our tow vehicle, which you can read about here).

What this month taught me: Life is meant to be lived in community.

This was one of the hardest periods Alyssa and I have ever gone through as a couple. At one point I considered putting her on a flight back to Texas to go see a doctor (luckily it didn’t come to that). Having good friends nearby during this time was a great reminder that when you go through difficult times, you need people in your corner who have your back.

November & December 2018: I honestly can’t even remember.

Other than moving into a little apartment on the downtown square of Alyssa’s hometown, I have very little recollection of November & December.

One thing I learned during this time: It’s amazing to create an income around a lifestyle you love, but creating income solely tied to lifestyle can be dangerous (because lifestyle can change quickly).

When Alyssa and I decided to settle in one place for a bit, we did an audit of our income streams. One fear we had as content creators was that our income streams would be tied too heavily to travel and that by slowing down, it would hurt our finances.

As it turns out, we’d created enough diversified revenue streams this wasn’t the case. But just going through this exercise made me realize that I never wanted our income to be tied to our lifestyle (because obviously lifestyles change without warning). This was a great motivator to go all-in on CampgroundBooking over the past year so that no matter what our lifestyle looks like, we have projects to work on and income flowing in.

January 2019: Speaking at Xscaper Bash, “Babymoon in Bahamas”, and filming a commercial for CNN & AMEX in NYC.

This month was pretty crazy for us. Once Alyssa passed the five-month mark and wasn’t sick anymore, we could be more mobile. We kicked off 2019 in the desert of Lake Havasu to speak at an Xscapers Bash. Travis and Melanie who head up the organization invited us to come and teach attendees about how to build a blog and we were honored to be a part of the event.

We don’t often get to speak together and we were able to share some of the things we’d learned about blogging over the past 5–6 years.

I don’t often think of myself as a blogger, as most of my energy the past year or two has been on growing a software company. However, working on that presentation made me realize how much we’d learned about blogging over the past few years. We easily filled up a 45-minute presentation and could have spoken for much longer.

After speaking, we flew to the Bahamas on a trip with Alyssa’s sister, her husband, and our two-year-old nephew. One big benefit of moving back to Denton for the year was that we’ve been able to bond a lot with our nephew. Up until coming back to Texas, we had spent little time around him and he didn’t really know who we were.

Over the past year, we’ve grown a lot closer to this little guy.

After the “babymoon”, we promptly hopped on a plane and flew into a blizzard in New York City to shoot a commercial (not a normal thing for us, even though I said it very cavalier).

We were randomly contacted by CNN’s production company who were shooting a video series for American Express a few months earlier. They wanted to find people who, because of good credit, were able to do something interested in their lives (i.e start a business or buy an RV to go travel the country).

We didn’t really know what to expect for the shoot but when we arrived they had built multiple full-scale replicas of our RV and even hired a little girl to come in and play Alyssa as a child (we didn’t get to meet kid version Alyssa, unfortunately).

We were the talent on set with about 60+ crew and it was probably the easiest talent job ever. We had no voice lines since we recorded voiceover in a studio the following day. None the less, I ate plenty of craft service and we made some new friends.

Here are some photos of the sets they built.

I was blown away with the wooden RV sets they made for the backdrop. I tried to convince them to ship them to us so we could use them as staging for RVE Summit but Alyssa reminded me we had nowhere to put them.

The blue trim was supposed to represent Franklin and the newer/nicer set up was supposed to be Merica (our Winnebago). I would hire their set design crew to build me an RV any day. 

Here’s the finished product, below. It was funny how many people who saw the video and shared it with us, knowing our story without even seeing our faces.

One thing I learned this month: If you don’t value your time, nobody else will.

This month was more of a business lesson than life one. We almost didn’t do the commercial because it was unpaid and would take multiple days. We had to record voice over at a studio in Dallas first and then fly to NYC for four days—where we ended up needing to re-record the initial voiceover. It was taking a lot more of our time than we expected and we had a business to run (plus Alyssa was trying to catch up on projects she missed while she was sick).

We had decided since it was unpaid that it would be better to just politely decline the opportunity.

Instead, during a call with the producer, I explained the situation and that we have other projects going on, which this one is taking away from. He then happily agreed to pay us our day rate for production shoots and it ended up being a really fun shoot. The lesson for me was to simply make sure that we are always valuing our time because if we don’t then it’s unlikely others will.

February 2019: Working on CampgroundBooking, RVE meet up in Denton & time in Florence, Alabama with friends.

We hosted an RVE meet up in Denton in February!

One perk of being stationary for a bit is that I joined a coworking space a few blocks away from our apartment in downtown Denton. I can walk to the office and I’ve been able to make friends with several other local entrepreneurs.

Later in February, we ventured out to Florence, Alabama en route to RVE Summit to spend some time with our good friends. This place has become a home away from home for us in so many ways. Without realizing it or over orchestrating it, Alyssa and I realized that we’ve spent a decent chunk of time in Florence every year since we’ve been married.

Hanging out with our friend Wes and his little ones on their front porch

We first stopped in Florence during Hourly America in December of 2014. We hired an editor and rented office space there to work on our documentary for a few months in 2016. We came back for a wedding, and to see our friends’ new baby, and it’s become a consistent stopping point for us because there are so many people we love in this town. Plus, our friends Wes & Tera let us mooch their office space and put up with our shenanigans.

What I learned this month: Relationships don’t happen by accident.

This month we went out of our way to host a meet up with people from our Facebook group. We left weeks early for our conference so we could spend time with friends in Florence and I joined a coworking space as a way to get out of our house to make new friends. Looking back on this month, it was a great reminder that building relationships doesn’t happen by accident, that you have to be intentional.

March 2019: RVE Summit (number 3!)

I can’t believe we’ve hosted a conference for three years. Mind. Blown.

This year’s conference required extra logistics because we changed our venue from Fredericksburg, Texas to Guntersville, Alabama. With new venues came a lot of new worries, but in the end everything worked out and everyone loved this beautiful little state park.

One specific worry I had was that it would be weird for the campground to be separated from where sessions were happening at the lodge (it’s a short drive up a hill). In the end, everyone loved the new space and we rented it again for 2020.

I was also worried because Alyssa was seven months pregnant and hosting an event can be a lot of stress. Luckily, we hired some incredible help this year with more of an established event and production team and it made the world of difference.

Some of our core team and RVE volunteers.

At one point hosting a conference for 350 people would have sounded terrifying. Now it’s this thing we do every year. It just goes to show that when you take small steps towards a goal and also marry a former event planner, anything is possible. 🙂

What I learned during this month: Hosting people gives me a lot of energy.

One thing I’ve been thinking about this past year is how to do more work within my “genius” (as Jill Sessa says).

I don’t how if hosting events is within my genius, but I know that hosting this conference gives me a ton of energy (before, during and after). I love planning little experiences throughout the event, working with our speakers on their presentations and walking around the campground during the event just to make new friends.

April 2019: Ran my second half-marathon, visited a campground on the beach and knocked out a bunch of pre-baby to-dos!

This month Alyssa and I adventured down to the beach for one last mini trip together on the Gulf Coast. A campground called Stella Mare invited us down to stay in one of their beach houses and with this view, it was hard to turn down. Even without an RV, there’s something about RV parks that just feels like home.

This month also consisted of my first trip to the infamous Silos in Waco, Texas to run a half marathon with my buddy James. I’ve realized over the past year that signing up for races is a guaranteed way to force me to run and exercise. I’m not sure if it’s the most efficient way to stay in good shape, but hey it works.

James and I rented a van from Outdoorsy instead of opting for a hotel during our visit to Waco to run our half marathon.

What I learned this month: Alyssa and I are water people.

I really have known this for a while. However, being mostly in one place for the past year has helped us realize just how much we value being near water and the energy it gives us. I’m not sure what 2020 looks like for us just yet, but we both agreed that we’d like to prioritize being near water.

May 2019: We met our daughter.

A few other things happened this month I’m sure, but none I will remember in the years to come. This will forever be the month we met our beautiful baby girl. She came into this world healthy at 7 lbs and now at almost 4 months, she is a very happy little baby.

What I learned this month: These moments go fast.

I know this is cheating, but since I’m writing this 4 months after she was born, it’s so hard to believe how much she has grown in such a little amount of time. As I write this we just put Ellie to bed. She’s the happiest little baby I’ve ever seen and to see how small she was when she was born melts my heart.

I’m already realizing just how precious these moments are. I’m not quite sure what key lessons I’ve learned as a dad yet, but figuring out how to be present for as many of these moments is already at the top of the list.

June 2019: Very little sleep and a spontaneous road trip to Colorado.

The first week of Ellie’s life, Alyssa and I slept on opposite ends of our sectional sofa in the living room of our apartment.

The first night we came home from the hospital we placed Ellie in her bassinet and laid down in our bed, only for Alyssa to sit up an hour later and say, “There is no way I can sleep right now I’m so stressed.”

Thus, we ended up moving the whole family into the living room and put Ellie in her travel bed so we could look over and see her at all times. I’m sure experienced parents are probably laughing at this, but we were just being new parents. Everything seemed daunting. In retrospect, when you’re operating with 3 hours of sleep per night it also feels daunting to just remember to put pants on in the morning.

We slowly found our rhythm with Ellie and after a few weeks we decided that we’d sat inside long enough and wanted to go on a road trip to Colorado (I share this with trepidation because in retrospect, I’m not sure what we were thinking going on such a big road trip with her being so little).

The main reason we wanted to go to Colorado was to visit a potential campground that was for sale. Alyssa and I have a dream of wanting to open up or buy a campground that we can operate as a base camp of sorts for us as a family and also for others, complete with coworking space, great wifi, beautiful location and all the things we’ve want in our perfect park.

A campground in Colorado popped up on our radar and it seemed to be a perfect fit, so this would be the first one for us to go look at together.

After a 15 hour haul up to Montrose, Colorado, we were not disappointed. The area surrounding the campground is gorgeous, with Ouray Hot springs nearby as well as several national parks. We could absolutely see ourselves here, but the park is a bit outside of our budget right now (plus we decided it’s probably not the best time to dive into a new business with a baby).

Here’s a photo I snagged while walking around the park.

What I learned this month: Traveling now that we have a baby is more challenging than before, but not impossible.

At one point on the way home, we pulled off the highway and exited into the only business nearby for miles—an old campground.

We needed to feed Ellie and she gifted us with a nice poop explosion, which somehow ended up all over my arms and on her head. This combined with a long day of travel had me feeling exhausted and disheartened. Could we really travel with a baby? Is this what it is always going to be like? But then after a night’s rest and seeing her cute smile in the morning, it made me realize that was just a difficult moment that would pass.

As we’ve done a few more trips since then, I’ve started mentally asking myself this question (something I picked up from the Subtle Art of Not Giving an F): What pain do I want to choose? Do I choose the pain of cleaning poop off myself on the side of the road (so we can go on an adventure) or do I choose the pain of being bored sitting in an apartment and playing it safe?

So far, when I position it like this the answer for me is obvious. I choose the poopy diaper on the side of the road (at least for now). We still have a lot of places we want to go travel to and I don’t want us to stop living our lives just because it becomes a bit more challenging.

July 2019: Ellie’s first business conference.

Prior to Ellie being born, we snagged tickets to Pat Flynn’s inaugural conference out in San Diego.

This year Alyssa and I knew that we wouldn’t be spending as much time out on the road making new friends and we wanted to prioritize meeting like-minded people and learning.

This was actually the first business conference we’ve attended together where we weren’t volunteering or speaking or hosting, which was fun and 100% more low key. Pat emphasized that his conference would be family-friendly, so we took that to heart and brought our two-month-old daughter.

I wasn’t sure how much of the event we would actually be able to attend (pending Ellie), but between handoffs between Alyssa and I, we roughly were able to listen in on 75% of the sessions and speakers. Alyssa would hold Ellie in a carrier and bounce her if she started getting fussy or step outside.

Personally, I was more than a little nervous of being those people with a baby at a conference. I knew everyone paid to be there and I wanted to be respectful. Luckily, it wasn’t a problem in the least.

What I learned from this month: Bringing a baby to a conference is a great way to meet new people because everyone loves a cute baby (lol, joking except not really because it’s true).

August 2019: My first business trip away from Ellie & Alyssa.

I don’t want to make a habit of traveling away from the girls, but I needed to fly up to Canada for five days in August. We were nearing the end of a big year of growth for CampgroundBooking and I wanted to spend some in-person time with our parks.

We’ve now been working on CampgroundBooking coming up on 3 years and this year was a big year for us. We signed on quite a few more parks and more importantly, we were able to get our campground software to a place where it is handling a large volume of bookings every day. We also hired a salesman & support person who have been amazing.

However, there’s only so much you can learn from Helpscout (the customer support software we use).

I wanted to spend some time in the front office of campgrounds to better understand what we could do to improve our system moving forward. I ended up writing about 15 pages of notes during my two campground visits and in the past month we’ve implemented about 70% of those changes already. Being at the campgrounds in person helped me clearly see what we could do to improve our reservation system.

What I learned this month: Never underestimate the power of in-person time with customers.

This trip was so influential in our product and with our customer relationships. Paul and I decided that moving forward we’re going to make this something we do at least twice a year.

September 2019 (that’s this month!): Getting ready for our next big adventure in Italy.

A trip to Europe has been on our bucket list for several years. We’ve talked about it seriously now since 2016 and life has a way of creating resistance for big dreams like this. However, earlier this spring I received an email from my friend Nate’s company called Faredrop that read “Round trip tickets to Venice, Italy for $472”.

Faredrop is going to get me in trouble. It sends you email + text alerts for awesome flight deals.

Our daughter wasn’t yet born. I had no idea what our plans would be this fall. But I instantly went to Delta’s website and sure enough, we could get two round trip tickets for less than $1,000 to Italy. I called Alyssa and told her that I currently had two tickets to Italy sitting in my cart on Delta’s website.

Keep in mind, at this point we’d been sitting still in our apartment for quite some time and Alyssa was eight months pregnant. The idea of traveling to Italy for a month sounded like just the thing for us to look forward too after Ellie was born.

“Let’s do it,” she said.

And in typical fashion for how we make major life choices, I grabbed two tickets and as of tomorrow, we are flying out of Dallas for a one month trip to Italy (we’ll be shooting some vlogs on our Youtube if you want to follow along).

Ellie has her passport and we invited our friends John and Peter (of RVGeeks) to come along with us. We’ll be renting a campervan for half of the trip and staying in AirBnBs for the other half.

It will be my first trip to Italy and I’m so pumped.

What I learned this month (so far): Having something big on the horizon to look forward too is so important. This year I worked a ton on CampgroundBooking and Alyssa and I spent more nights inside watching Netflix than we ever have before. As much as I was feeling burnout towards the end of 2018, this year we both felt bored at times.

As we look forward at the next few chapters of our lives, we’re both aiming for something in between full-time travel and sitting still in an apartment. We want to give Ellie a life of adventure, but also have some kind of place to come home to around a community. We’re still navigating what this looks like for us, but I feel we’re asking the right questions and I know we’ll land on something that makes sense for our family.

If you made it to the end of what turned out to be a 5,000-word behemoth, you are truly amazing (and please drop a comment below to let me know you made it!). I hope the rest of your 2019 is an adventure as well.