My husband's job changed last fall, and it changed the way we travel. He has not been able to come with us since, and somewhere in the middle of all that I had to decide whether his schedule was going to be the reason we stopped going on these adventures. It was not. So in January I loaded up the Jeep with the four of them, all of our stuff and a cooler, and we headed to Chicago.
I could have skipped it, and I want to be honest that skipping it was definitely on the table for longer than I would like to admit. Was it truly in the budget? We could wait until things settled down, and we had just had a really crazy winter. Wait until somebody could come with me, and by somebody I mean my husband, because in reality nobody else is coming with me. We are down here in Tennessee on our own. There is always a version of that sentence that sounds responsible when you say it out loud.
But we went anyway, and that one decision is the reason this whole year has looked the way it has.
It started because my mom wanted everyone in one room
After losing my brother, my mom really wanted all of us together for Christmas. We do not do this often. The last time we managed anything like it was Thanksgiving years ago, when all of my brothers came down to us. My other two brothers are up in Minneapolis now and we are down in Tennessee, and Chicago sits more or less in the middle of the two, so Chicago is where we did it. Three weeks late, in a hotel in Schaumburg, with wrapping paper all over the floor and everybody talking over each other and nobody in any hurry to leave.
While we were in Chicago, I knew there was one thing I really wanted to do. I went to American Girl Place as a little girl and I still remember the escalator and the red carpet and how enormous the whole thing felt back when you are small enough for a store to count as an event. My girls and I are obsessed, all of us, and I had been quietly waiting for them to get old enough to actually remember going. This one is the original, the very first American Girl Place that ever opened. We had already been to the DC store and the Nashville store and the Orlando store on other trips, so we got to the first one last, and New York is the next one on our list.
The doll store, and then the LEGO store next door, which is the only reason my son agreed to any of it.
Then Do-Rite, which they still talk about
My youngest brother lived in Chicago for years, so we let him decide where we ate, and he walked us down Michigan Avenue to Do-Rite Donuts. He said it was one of his favorite donut shops in the city and it did not disappoint. The donuts were so good.
What I did not expect is that this would end up just as memorable to them as the doll store I had been planning for months. Sometimes the most ordinary part of a trip is the part everybody keeps bringing up afterward, and you do not get to pick which part that is going to be.
Four kids, four completely different approaches to a donut.
I was worse than the children
On the walk to the donut shop I found out that the Harry Potter store had opened a few blocks away, and at that point I stopped being the adult in this situation entirely. I have been reading Harry Potter since it first came out, which means midnight showings, preordered books picked up at midnight from the bookstore, and twenty-something years of being like this about it. So when we walked in I was, at absolute minimum, as excited as my kids had been at the doll counter an hour earlier, and I would love to tell you that I played it cool.
We ordered butter beer in the cafe and sat down with it like it was a normal Tuesday afternoon, which it was not. We have made the DIY version at home a hundred times and it is not the same thing, it is not even close. And of course we had to have the Bertie Bott's every flavor beans, which is how we ended up with some pretty disgusting ones. My son got the one that tastes like grass and he has not forgiven us yet. We loved every single minute in that store. If you are ever in Chicago, go in and get a butter beer. That is the whole recommendation.
Michigan Avenue in January. Worth the cold.
Everyone went home. I went to work.
My brothers had jobs to get back to, so after a couple of days we hugged everybody goodbye in a Starbucks parking lot and then it was just the five of us again, driving north to Janesville, because the other half of this trip was work and I had three meetings waiting on me.
The first was Jennifer Piala, over lunch at Truk't in Beloit, going line by line through the Faith and Finances workbook. That project is finished and out in the world now, which is its own kind of satisfying, but sitting across a table from somebody while she marks up pages you designed is a completely different experience from emailing a PDF and hoping. You catch the half second where something is not landing for her, but you also get to see the excitement and what she is loving. You cannot pick up on those vibes in an edits comment thread.
Workbook edits over lunch at Truk't.
The next morning I headed to Contour Consulting at their office in the Workspace at Grey Goose and got them set up on my content system. We worked through my Clarity Map together first, because until you have settled what you are actually here to say, everything after it is guesswork. Once that was down we could work out what they wanted to be saying on social and how they wanted to say it.
Then a two day media day with Trick Chassis at their fabrication shop in Beloit, and January in Wisconsin is exactly as cold as that sounds.
Media day at Trick Chassis, and the Contour content system session at the Workspace at Grey Goose.
And if you were wondering where the kids were
We stayed with my sister-in-law and my brother-in-law works from home, so they were at the house with family the whole time, although if I am being honest about it my oldest is old enough to babysit now and he was really the one doing the job.
Day two of the media day was different. We had not gotten everything we needed the first day, so I went back for a second morning on our way out of town and they came along with me. That is the morning in the snow photo below. They waited in the car with snacks and a tablet, which is not a sentence I am going to dress up into something prettier than it is. And then CJ came inside and helped me shoot. Not to keep him occupied, and not so he would feel included. Because I am teaching him. These are skills he can use inside my business one day if he wants them, or carry into whatever he ends up building for himself. He knows what I am looking for now, he knows to search for the right angles, and he is getting good at it.
This is the part I have been hoping for all along. They are never the thing I am working around. And now more than ever, I want them to be part of the work.
Back to Chicago, through the snow
Then my sister-in-law said she wanted to take my niece to American Girl. We had talked about doing it before the trip, and we were only an hour and a half away, and I have never been any good at talking myself out of a good idea. She drove her own car down and we met them there.
It had snowed hard overnight. We drove down to Beloit in it, shot for two hours at Trick Chassis, and then got back in the Jeep and kept going south. The road stayed white most of the way to Chicago, and then somewhere on the edge of the city it started to clear up.
My nephews came too, so by the time we got downtown it was two of us and seven of them. We did the doll store again, walked around, and by dinner every single one of us was cooked. We wanted Giordano's, but the wait is always brutal and nobody had that in them, so we went to the Smashburger just off Michigan Avenue because it was quick, and by then quick was the only thing any of us cared about.
The thirty seconds I keep thinking about
We were the obvious target and I knew it while we were sitting there. Two women, seven kids, food coming out, everybody talking over everybody else, coats and bags piled on every chair. There was a man sitting near us and we assumed he was waiting on a ride.
Something in me would not put my purse down, and I have no better explanation for it than that. Maybe it is the military. Maybe it is the years we lived out in the Chicago suburbs. Maybe it is just the thing that lives in the back of your head when there are seven kids at that table and only two of us counting them. Either way I kept it strapped over my shoulder and sitting in my lap while we ate, and I felt slightly ridiculous about it the entire time.
My sister-in-law tucked hers under her jacket next to my nephew, which is what any of us would have done in a burger place at dinnertime. Then she got up to go get ketchup. He was gone with it before she made it back to the table, and we did not notice until we stood up to leave and realized her purse was not there. Her car keys were inside it.
The manager pulled the footage for us and we stood there and watched it back, and you can see him go for my jacket first.
She set hers down for thirty seconds. That was the entire difference between us.
Her car was in the garage at Water Tower Place and there was no getting it out. No spare key. No tow company that would come get it. No locksmith we could find after hours who could cut and program a new fob, and Honda on the phone telling us it could not be done at all, which is how two grown women end up standing in a parking garage in January seriously wondering how long a car is legally allowed to just live somewhere.
I got her a discounted room downtown. And then I left.
That is what solo actually means, and it is the least glamorous sentence in this whole post, because I could not stay and fix it with her. We had somewhere to be. She found a locksmith the next morning who programmed a new fob and she drove herself home, and I got the text about it somewhere on the road south. We have told that story over and over since. It left an impression on the whole trip.
All that to say, stay aware in cities and be situationally aware. Not to scare you. We are just speaking from experience now.
Nashville, where it all fell apart in the nicest way
It started snowing again on the way down, which was a bummer but not a surprise, so we stopped partway, slept, and drove the rest of it the next morning. One night in Nashville, just long enough for dinner with my friend Emily, and then breakfast and coffee the next morning with her and one of my mentors, Brian, before we left.
City hotels are my nemesis. You cannot just park somewhere and quietly carry your things in like a normal person, you have to pull up to the valet and unload at the front door in front of an audience. By that point in the trip the car was a catastrophe. Christmas presents from my mom and my brothers, every doll the girls had been allowed to bring, CJ's LEGO boxes which are roughly the size of a small suitcase, and all of the shopping stacked on top of it. My kids came out of that car like a clown routine, all four of them wanting to carry their own things and none of them actually willing to carry anything, shopping bags splitting at the seams, our stuff going out onto the pavement in front of everyone. They were overtired and completely done, ready to be home and play with the things they had been hauling around for a week, and honestly so was I. It had been go go go the whole time. Shopping, then meetings, then driving, then more driving, and not one afternoon in there where we just sat.
Then we hauled all of it upstairs, opened the door, and the room was dirty.
So back down I went. The hotel was genuinely lovely about it, moved us, comped us a meal, and I sat down in that restaurant feeling like I had been hit by a bus. It was not my finest moment as a solo traveling mom. Dinner with Emily was worth every second of it anyway. She had not seen my babies in a very long time, and she got some extra snuggles from my littlest one that evening. Then breakfast and coffee with her and Brian in the morning before we pointed the Jeep home.
Emily, at the end of it.
What actually makes this work
I want to be careful here, because it would be easy to read all of that and think I am somebody who is naturally good at this. I am not. We have just had thirteen years of practice.
We have lived in Tennessee that long and my family is in Wisconsin, so my kids have been making that drive several times a year since they were babies. Then we moved into the motorhome and they learned the rhythm of it properly, what a driving day actually feels like, when we stop, what to expect out of a hotel, how to be in somebody else's house. They are good in the car because they have done it their entire lives, and that is not a personality trait any of us were handed. It is repetition.
So if you want to do trips like this with your kids, here is what I would actually tell you.
You travel at the pace of your weakest link
Whoever is in that car with the shortest tolerance is setting the schedule, not you, and I mean that kindly. If you have a baby, the baby is in charge. You get the hours the baby is willing to give you and then you stop and you rest, and arguing with that will always cost you more time than pulling over would have.
For us it is two people. The toddler, and me. I have a back injury and a knee injury and there is only so long I can sit in a driver's seat before I am no good to anybody, so an eight hour drive turns into two days and I have made my peace with that. We have ignored it before, because we wanted to get to the beach, and we bombed it. That is the Florida post, and it is coming.
Snacks are not a nice extra
I do a Target pickup order on our way out of town, every single time, because gas station prices for the same four things are offensive and I refuse to participate. The cooler comes with us so we have cold drinks the whole way. Bottled water, a few juice boxes, some Gatorade so there is variety, and snacks they do not normally get at home, because novelty buys you about forty miles.
Then something that actually fills them up. Cheese sticks, a Lunchable, Uncrustables. Because if the little ones fall asleep right at lunchtime we are not stopping, we push as far as we can and stop when they wake up, and everybody else still has to be fed in the meantime.
And sometimes you are just a mess
Normally I would tell you I pack well, and normally that would be true. This trip I had my camera bag and all my work gear, the girls had their dolls because we were going to the doll store, and CJ had LEGO boxes the size of a suitcase plus Christmas presents from his uncles and from his godfather. It was not typical, and it is exactly why Nashville looked the way it did.
It was a relief to get home. It was also worth every mile of it.
I did not need a second adult, a perfect plan, or a tidy car. I needed to decide we were going, and then go.
Building a business that travels with you?
That is the whole point of how I work. Tell me what you are building and where you are stuck.
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