Vacation As a Product Manager

Recently, I went on a 5-day vacation. It was terrific, but not because we did once-in-a-lifetime experiences. It was terrific specifically because we did “regular” vacation things.

I planned this vacation as I do most planning as a Product Manager – I started with the requirements.


I started with coarse basics – what’s the goal of the vacation? To get away with my kids and have fun together. So I came up with a list of requirements, product management style – that is, no solutions:

  1. No flights. That’s a COVID risk I’m not willing to take yet, for a vacation. When I planned this trip a few months ago, we did not know when vaccines would be ready; as it is, by the time the vacation began, my 3-year-old had gotten one shot but was not fully vaccinated yet. Buses and trains are OK, as is driving, but nothing more than six hours or so of travel.
  2. Get away. Not a “staycation.” If we saw local sights, we should at least be in a hotel so I could be present with my kids and not worry about doing house chores.
  3. Accommodate my 3-year-old napping in the afternoons (approx 1-3 pm) and general flexibility. My 6-year-old has anxiety, and sometimes we simply have to leave. A timed experience with no re-entry means I have to be willing to go and lose the entry fee if the situation calls for it.
  4. Something engaging for my kids that they will love. They’re 6 and 3 years old, and I don’t want to spend the whole vacation trying to convince them to do something fun or listen to them complain.
  5. Focus on being active, preferably outdoors. Since it’s summer where we live, that wasn’t too difficult.
  6. Accommodations: Hotel or rental house, strong preference for a pool in the hotel, at least one bedroom that’s separated by a door so the kids can go to sleep and I can stay up without bothering them.

High-Level Solution

Once I had the requirements, I could engineer possible solutions. Requirement #1 helped narrow down what we could do. Living in Boston, we could go to the Berkshires (mountain range three hours away), New York City (four hours away), the beach, arbitrary city (Lowell MA, Mystic CT, Hartford CT, etc.), Mount Washington, amusement parks (Six Flags and Story Land)…there’s a lot of options.

However, since it is all within driving distance due to requirement #1, it was by nature something repeatable. It wasn’t a trip to Paris where I would regret not seeing the Eiffel Tower. If we didn’t see something, we could go back some other time.

I wanted to focus on an activity that was best or only possible in summer, which ruled out a lot – for example, New York City has tons to do, but summer’s heat makes everything, well, stinkier.

Accommodations were a big part of the decision – I ruled out tent camping, it’s a lot of work, and I wanted to have a vacation too. I settled on Cape Cod, basically the beach, with the second choice of Story Land because in a few years, my kids will be too old for it.

I looked for hotels or rental properties on Cape Cod, within walking distance of a beach, for the easy back-and-forth. And something that had a pool – my kids LOVE swimming and jumping into a pool. If I couldn’t find something that met our accommodation requirements on Cape Cod, we could try Story Land. I was lucky and found a beach place and booked it.

A hotel pool with blue shimmering water, and a rope with oval plastic buoys separating the deep end from the shallow end. The shallow end is in the foreground, marked as 3 FT. A three-year-old in a yellow and blue life jacket, and purple long sleeve bathing suit, is in the pool and holding on to a handrail by the pool stairs. A 6-year-old is across the pool horizontally, still in the shallow end, slipping headfirst from an inner tube decorated like a watermelon. The 6-year-old is wearing red and blue swim trunks and goggles.
Having fun in the hotel pool

My partner isn’t an outdoorsy guy, so I told him he didn’t have to come, and called my sister and invited her to go with us. This way, I’d have help wrangling the kids so I could relax on vacation too.

Things began to get complicated – my sister decided to sell her house and move while the market was hot, as her youngest is going off to college this fall. The move was nine days before the vacation, so we kept the vacation planning to a minimum until after she moved.

Tools of the Trade

Usually, we use Google Sheets to plan vacations – one sheet for ideas, one sheet with a column for each day once we figure out activities, and one sheet for figuring out who paid for what and making it fair at the end. Google Sheets isn’t lightweight on mobile devices, so I asked around and decided on a Trello board.

We liked that URLs were clickable, and things were easy to move around – we brainstormed ideas in one swimlane, then had one swimlane per day and moved around activities as we saw fit.

A trello board with several swimlanes, many activities in the 'Ideas' swimlane that did not get moved to a swimlane for any day
Our Trello Board, click to expand the image

Vacation: The MLP Version

An inflatable park sounded really co0l, but did I want to spend $100 for all of us to go for just a few hours (nap time interrupts things) and risk leaving after only an hour or so if my kids weren’t having a good time?

My 6-year-old LOVES trains, but there’s not much to do ON a train – did I really want to spend $90 for an hour on a train when my kids might get bored in the first 5 minutes?

I spent about 2 hours researching ideas. In the end, we didn’t do most of them, we spent most of our time in the pool, at the beach, and playing games together – my 6-year-old’s current favorite is Mille Bournes.

Playing in the sand at the beach.
We dug a river in the sand at the beach
An adult and child playing a card game on a coffee table in a hotel room. The child is kneeling and looking at a card holder with 6 cards in it. The adult is pointing to cards on the table in front of her, while a 3-year-old sits on her lap. The 3-year-old is holding a pink doll.
Playing Mille Bournes with my sister

Thursday, we arrived too late to see the Japanese paper theater. Sunday, it did not rain, but my 6-year-old developed swimmer’s ear, so my sister took my 3-year-old to the beach near our hotel while I took my 6-year-old to Urgent Care. We then met them at the beach. Unfortunately, we couldn’t go to Gina’s beach, but that also meant less driving around. Monday, we packed and left since checkout was 10 am; we found a local playground and then had lunch. We avoided the pool to avoid more swimmer’s ear.

MLP stands for “Minimum Lovable Product.” In the MLP that was this vacation, M stands for “minimal” – my kids are super happy swimming or playing in the sand, so that’s what we did. For food, we had free breakfast in the hotel, went to a supermarket a few times for lunch supplies and snacks, had dinner al fresco at a restaurant, or got food delivered to our hotel room.

We did make it to story time at the library on Friday morning, and we did one excursion – to the Heritage Museums and Gardens. We found the maze, looked at a Wampanoag wetu, saw art sculptures made from trash, spent time in a lily garden with a waterfall, and played in the Hidden Hollow and Treehouse. We were hot and tired after a few hours so we stopped by the indoor, air-conditioned automobile exhibit on our way back to the car. We left lots unexplored, including the labyrinth and carousel – which we can do next time.

A 6-year-old kid with short brown hair in a salmon-colored tie-die shirt and black shorts operates a water pump. The water coming out of the pump is coming near a small galvanized metal bucket being held by a 3-year-old kid with long curly dark brown hair wearing a purple tie-dyed dress. Both kids are barefoot. They are standing on rocks and slate in a shallow water feature, with rocks and greenery in the background.
Playing in the Hidden Hollow
A 6-year-old with short brown hair in a tie-dye shirt, black shorts with a green stripe, and socks and slip-on shoes points to a 1950's dark blue Ford. A 3-year-old with long black curly hair in a purple tie-die dress with a unicorn on it and tan crocs looks at the 6-year-old.
“Look, Mom, it’s Doc Hudson from Cars!”

Unexpected Extras

As minimal as it was, there were some unexpected extras that happened, mostly good ones:

  1. I thought I booked a 2-room hotel suite. As it turned out, it was a 2-bedroom hotel suite, complete with a separate living room, full kitchen, and full bathroom. I decided to invite my mother along, as she also needed a vacation, and we had the room. She carpooled with my sister and really enjoyed relaxing and doing nothing.
  2. It was handy to have other adults around, so I could take one kid to urgent care when I had to.
    A selfie with a 6-year-old with short brown hair, blue shirt, and red cloth face mask on the left. On the right is the author, a person with brown hair tied back, sunglasses perched atop her head, white N95 mask covering her chin and nose, in a dark blue shirt with a geometric diamond pattern in orange.
  3. My mother and sister took my kids to the beach one morning and let me sleep in. I got an extra TWO hours of sleep!
  4. My mother and sister babysat the kids Saturday evening while I had lunch with a friend who has a family house on the Cape.
  5. My kids wanted to sleep with me, and I learned that my 6-year-old tosses and turns ALL NIGHT. A sleep chart showing 8 hours and 3 minutes of sleep from 11:30 pm Friday to 7:33 am Saturday, with 10 'Awake' periods interrupting sleep every few hours
  6. My partner invited a friend over and had a great weekend without family responsibilities. Win/win!
  7. I brought my computer “just in case.” I did not open it once. I did no work. Some of that was luck, and some of that was my awesome coworkers covering for me.

After the trip was over, I carved two small stamps to commemorate the occasion. Like the vacation, they were simple, easy, and filled me with happiness:

Two VersaFine Clair inkpads, in pink and purple, dominate the top half of the image. They rest on a small spiral notebook with unruled pages. On the lower half of the notebook page are 2 hand-carved, blue stamps depicting a beach shovel and bucket. In the lower right quadrant of the page the stamps have been impressed on the page, showing a pink shovel laying horizontally just to the left of a purple bucket.
I carved minimal stamps to commemorate my minimal vacation.


So, what’s the tl;dr on how to I had a good vacation? I set core requirements and met them – minimally.