Living where we do, in the San Juan Islands, the opportunities to explore are virtually endless. There are 176 named islands and most are only accessible by boat. The Gulf Islands, just across the aquatic border in Canada, have over 200 islands. This is what makes our region a popular boating destination. People, mostly in big comfortable boats, spend weeks or months island hopping and anchoring in coves and harbors.
The allure of this lifestyle was irresistible. We saw an opportunity to leave home for days at a time and explore. This would be our form of vacation travel. Almost 2 years ago, we invested in a motor boat just big enough to sleep two people and two dogs. She’s a Jeanneau NC 795 that is 26’ long with an outboard motor. We named her Novella and started the long journey of becoming more competent boaters.
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As we searched for boats, our friend LJ, a very experienced boater, reminded us of something important to consider. When you have dogs aboard, they will need to go ashore multiple times a day to relieve themselves. She said to think carefully about how that process would work. This was sage advice. For most boaters, this process happens with an inflatable dinghy that attaches to the boat when not used.
During our first summer with Novella, we borrowed a dinghy on a couple of trips and I learned to steer with the tiller of a small electric motor lent to us by our friend Will. The system worked, so we made plans to get our own dinghy for the 2024 season and store it on the roof of Novella. I named it Footnote, in keeping with our literary theme. Thankfully, Will said we could continue using his motor. We were set.
Learning never stops in boating. The basics, like driving and docking, are pretty easy. What takes time is getting all the processes and systems down for safety, comfort, and optimizing time on the water. For example, when we’re at anchor and not connected to the shore, we have to manage and conserve electricity and potable water. We need to feel confident about how we’re anchored and how the weather and tides will change over time. Every trip gives us practice and teaches us new lessons.
Our version of cruising is a lot like camping. The space and supplies are limited, and we sometimes cook with a Coleman stove. It feels like having your own little island that is completely independent. You don’t need anyone’s permission to anchor. We both love the feeling of being alone. The big difference is that your campsite could sink and you could die. That fear is in the back of every boater’s mind, and for good reason. It can happen.
A few weeks ago, we planned to spend two nights on Novella in Fisherman’s Bay, which is off of nearby Lopez Island. This trip seemed easy and more carefree. The bay has a reliable anchorage, a couple of marinas, and a classic restaurant/tiki bar at The Lopez Islander Resort.
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Leading up to the trip, we both looked forward to having dinner at the Islander and Sachi said, “I’m definitely going to have a drink Wednesday night”. I agreed wholeheartedly and didn’t think much of it. On Tuesday morning, I was reminded of something important: Wednesday was our 20th wedding anniversary. No wonder she wanted a drink! Shit. We laughed. Anniversaries have never been a thing for us.
This realization provided the trip with new resonance. We were now there to celebrate and looked forward to spending our anniversary day afloat and carefree. On Tuesday evening, just before sunset, we loaded Piper into Footnote, our new dinghy, to go ashore. Most marinas have “dinghy docks” which are low-lying docks that boaters use to access land-base amenities.
Piper and I made our way to the dock and she did her business before we made the return trip. These evening trips feel like a tiny sunset cruise and we both enjoy them.
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Just LJ advised, we’ve developed a system for getting dogs off the boat. Sachi waits at the swim step and as we arrive, she grabs a short line and attaches it to Novella so the dinghy stays close. Once that’s secure, Piper can jump out and I can prepare to disembark. When the motor is switched off, we use a longer line to attach Footnote to Novella so it floats safely nearby overnight.
On the eve of our anniversary, my return to Novella was a little different. Sachi was cooking dinner and didn’t want to leave the galley for too long. Sachi tied the short line to Novella, got Piper onto the boat, and said, “You got it?” I said, “Yep, I got it. I got it.” I then switched off the motor and unhooked the short line from Novella so Footnote could float using the long line. I stepped out of Footnote and into dinner.
We hung out for about an hour as the sun went down. With just a bit of light left, I looked at the back of the boat and it felt like lightning went down my spine. Footnote was gone. I said, “Uh, where’s the dinghy?” We both started to panic. Shit. Shit. Shit. Sachi put her head between her folded arms and took measure of the situation.
There was no time for analysis or recrimination. The light was going away, and with it, any hope of finding Footnote that night. Tidal currents are constantly flowing into and out of Fisherman’s Bay. When Footnote was lost, the tide was going out and the wind was blowing in the same direction. So, we decided to try to find it.
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We pulled up the anchor and Sachi grabbed our spotlight. As I started the engine, she was perched on the bow of Novella. With everything in place, we puttered around the bay for 30 minutes in the dark, our spotlight sweeping the shore. The navigation screen at the helm was essential for avoiding obstacles and shallow areas, but it was so bright I couldn’t see anything. I didn’t know how to adjust the brightness, so I put my hat over it and leaned out of the window to see and talk to Sachi. It was fruitless. We’d returned to the same spot as before, set the anchor, and started to prepare for a restless night.
It was obvious what happened. When Piper and I returned from shore and Sachi said, “You got it?”, she was referring to me attaching the long line. I thought she meant unhooking the short one. When I stepped off, Footnote began to drift and we didn’t notice. All in all, it was my fault for not checking everything before heading inside. I was embarrassed and feared having to explain this situation to fellow boaters. I was THAT guy.
We were both exhausted and wondering what to do. Our new dinghy and borrowed motor could be lost forever. Could it have washed ashore somewhere as the tide went out? Was it now floating aimlessly in the Salish Sea? I considered using our VHF radio to alert other boaters that night. Who knows, the Coast Guard could even get involved. Nothing sounded worth pursuing until morning when we could take a look ourselves.
On the morning of our 20th anniversary, we awoke to low tide and a lot of anxiety. I started to map a path for the search using our paddleboard. We decided that the best starting point would be the dinghy dock at the marina. Could someone have seen Footnote, grabbed it, and tied it up for us? Fat chance. It was almost dark when it floated away.
As I got closer to the dock, I saw something familiar but dismissed it. Then, as I paddled closer, it became clearer: Footnote was there. OMG. A weight was lifted and I slouched in relief. A kind and anonymous boater had saved our dinghy, and with it, our anniversary celebration. I stepped in, slid the paddleboard across Footnote like airplane wings, and cruised back to Sachi and Novella like a conquering Viking with inflatable booty. There was much rejoicing and our plans could begin again.
For all the stress and anxiety this caused, it ended up being such a valuable lesson. I’ll never let a dinghy float away again. And if I see a random dinghy float by, I will do everything in my power to save it and return it to the owner. Also, I now know how to change the brightness on the navigation screen.
But more than that, it made me rethink the idea of boating being independent. Yes, we were alone, but we were also part of a community of other boaters who are motivated to help one another. Cruising can be incredibly fun and easy, but the reality remains: your campsite could sink and you could die. Because this is the case, we look out for one another. We ask for help and offer help. It’s the boater’s code and this time, we were beneficiaries. I hope some day to return the favor.
We still have so much more to learn and it will come in time and through experiences like this one. As long as we stay afloat, we’ll have a good time.
It’s been a sad phase for us lately. We lost Maybe, our 10-year-old Bernedoodle last week. The essay below is about loving, enjoying, and saying goodbye to our canine friends.
In 2013, Sachi and I considered getting a second dog. I asked her, “If you could combine two dogs, what would you want?”.
She thought briefly and said, “A cross between a poodle and a Bernese mountain dog.” I did a quick web search. This was the moment we learned about the existence of a Bernedoodle. These are large dogs, sometimes over 100 pounds, with the poodle features of intelligence, low shedding hair, and hypoallergenic. The Bernese side added goofiness, color, and good nature. It seemed like a fit.
One of the reasons to get a second dog was to have two. Our dog Bosco was 4 years old and we wanted him to have a playmate. Also, we love dogs and wanted more. A big question loomed: how would Bosco react?
The Bernedoodle puppy arrived via air freight from a family in Ohio. At the airport, we found multiple puppies waiting for new owners. Inside a medium-sized crate was a tiny black ball and we named her “Maybe”. I wish the name had a rich story, but it came from a dog-friendly hotel that listed the names of arriving “guests”. Sachi, in particular, fell in love with the name.
Bosco, a lab and springer spaniel mix, was a good big brother. He was patient with the annoying puppy and they became attached at the hip. I felt bad for him, at times, because she would NOT leave him alone. I asked a vet friend, “How long will she keep this up?” Her answer: 2-3 years. Poor Bosco.
Being a little sister, Maybe played a supporting role. Bosco was extremely connected to us in the way that labs can be. He was more human than most dogs and you could see it in his face.
The Trip, The Trouble
Within a year or so, Sachi and I planned a big trip. We would pack both dogs in our car, drive from Seattle to Charleston, SC, and stay for a few months. We worked from home and wanted to take advantage of making our temporary home somewhere else, somewhere very different. We planned for months and counted the days with growing excitement.
About 20 days before departure, Bosco was diagnosed with canine lymphoma, a terminal cancer in dogs. Everything changed. The first chemo protocol didn’t work and we faced a grim reality: he would pass in a matter of months. We were crushed.
We decided that the trip to Charleston would be his swan song. The new “rescue” chemo put him in remission and he seemed normal. We could pretend, for a couple of months, that he was fine.
The Asterisk
It was a surreal experience to be on this amazing trip with so much to see and do, yet always knowing that your dog is going to die soon. I call this “the asterisk”.
At the time I had problems with anxiety and my mind always found a way to worry or discount the future. The asterisk is the constant reminder that tempers any happiness. It goes like this: What a fun day at the beach* [Bosco is dying]. Living in Charleston is such a treat* [Bosco is dying]. The asterisk steals joy and my anxious brain could not let it go.
Just after New Year’s in 2016, Bosco died in our temporary Charleston home. He was five years old. Over the months of worry and sadness, we came to terms with the inevitable and saw his passing as a relief. He never knew pain. We did the best we could.
Maybe’s Rise
Starting then, Maybe rose to prominence in our lives. Being so focused on Bosco, I didn’t appreciate Maybe as much. She was a wallflower in a chaotic situation and it took time for her to become the star. We returned home to Seattle with one dog and a new beginning. Without Bosco around, we could experience and appreciate Maybe from a new perspective.
Maybe seemed to come out of her shell. She filled Bosco’s role and I came to know her better than before. In human terms, it felt like Bosco was the popular jock and Maybe was the valedictorian. You didn’t have to worry about her. She listens, gets straight A’s, and will go to a good school. That said, she was very vocal and always let you know how she was feeling. We called her “Maybe, Lady Barks-a-Lot, Duchess of Barkington“.
Two Dogs, Again
Within a couple of years, we decided to become a two-dog household once again. We went back to the same Bernedoodle breeder, got Piper, and the cycle started over. This time, Maybe was on the front lines of Piper’s constant attention.
Maybe was a naturally sweet and we told her that often. Her sweetness came out when she was around puppies. When we brought Piper home, we were on the floor lavishing her with attention. Without any prompting, Maybe brought over a toy and placed it gently in front of Piper. She nudged it closer and closer until Piper noticed. Then she barely moved so Piper didn’t get scared.
It was her nature to be gentle and kind to people and puppies.
Piper and Maybe became fast friends and were inseparable. Over a few years, we moved them both from Seattle to our yurt-shaped house on Orcas, a tiny guest house, and finally to Flattop. Maybe was the leader and Piper was the follower. In the human sense, Piper was the cheerleader: pretty and enthusiastic.
Her entire life, Maybe was possessive of toys. Even as a puppy, she bossed around Bosco if he was too interested in a toy. It wasn’t aggression, but assertiveness. That toy is hers and it’s her right to take it. This was Piper’s reality, too. If she showed too much interest in us, or a toy, Maybe would rush in and bark in protest. We would say “Watch out Piper, here comes the fun police.”
As of 2024, Maybe was 10 years old, and Piper was 6. When a dog reaches double digits, it becomes clear that most of their life is behind them. Maybe was surprisingly spry for a geriatric dog and able to jump easily onto the bed, into the truck, etc. She loved to chase Piper around the garden and fetch a purple ball we’d had for years. In the last six months, I noticed her fetching had become slower. She got up from naps with a bit of soreness. I could relate.
Sachi and I both wanted Maybe to last forever but knew, within a few years, we’d have to say goodbye. Having been through so much with Bosco, it filled us both with dread. Dog owners often face the same end-of-life dilemma: wanting a dog to live as long as possible, but not at the expense of the dog’s happiness and well-being. Too often, in my opinion, owners can’t let go and wait too long.
Knowing that Maybe was aging, we both spoiled her. She got human food when Piper wasn’t looking. She was loved and kissed and coddled every day. Her soulful eyes always seemed to send a message of love. She wanted for nothing and that was exactly what we wanted.
On Monday, August 19th, I took a break from work and took the dogs outside to play. As usual, Maybe was barking and wanting to fetch. So, I grabbed the purple ball and threw it. As sometimes happens, she picked it up and refused to bring it to me. So I walked across the garden, picked it up, and turned to Piper to get her interested. When I turned around, Maybe was lying on her side with her legs spasming, in the throes of a seizure. I felt so helpless. All I could do was say “Oh Maybe, Oh Maybe, no no no.” Within a few seconds, she was gone. No breathing, no pulse. I was frantic and not sure what to do.
I called Sachi who rushed home from work. I led her back to our bedroom where I laid Maybe down in a blanket on the floor. As she reached the floor I wanted to soothe Sachi’s emotions and said, “I was with her. She was never in pain. She was happy and then she was gone.” With tears in her eyes, Sachi said something I’ll never forget, “We should all be so lucky”.
We cried for the rest of the day and talked about Maybe’s life. We discussed the inevitability of death and that it comes for us all. In this way, Maybe was fortunate and so were we. She made it ten years and they were good ones. We had so much fun together.
The end of Maybe’s life didn’t come with an asterisk. There was never a period of worry or stress about Maybe. She was a happy vivacious dog and then she was gone. We should all be so lucky.
A new issue of my newsletter, Ready for Rain, went out to subscribers recently. It’s a short, scary story about our dog Piper disappearing into the woods on a windy afternoon.
It was about 3:45 when Piper disappeared and as we searched, I started to do mental calculations. It gets dark at about 6pm, so we have a little over two hours to find her. She is used to having dinner at 5, so maybe that will bring her home. I looked at the weather and saw low temperatures in the upper thirties. These little calculations led to a series of questions I didn’t want to have to face. What if she’s not home when it gets dark? What if she’s not home when it’s time to go to bed? What about two days from now? A week? Is it too cold? Are we going to have to make signs? I imagined Sachi spending the night by the front door, waiting.
Ready for Rain goes to a small group of dedicated readers and about 60% of them open each issue, which I find encouraging. I’d love to have you as a subscriber.
The post below was sent as an issue of my newsletter, Ready for Rain.
A little story about a dog.
The fear came in a flash. I was outside our guest house with our older dog, Maybe. As soon as we rounded the corner at the back of the house, I saw our other dog, Piper, dash into the woods from other side of the house without a leash. In an instant, Piper was gone.
I’ve never had a dog like her. At home, she is the most domesticated animal possible; a fifty pound stuffed animal who loves to lie upside down in your lap. But she has a wild streak when she steps outdoors, possibly the streak of a hunter. She trembles at the sight of deer that are constantly on the property. They must be chased and this instinct seems to override any kind of training we’ve tried. Our voices are clearly not enough to keep her close.
Even as a small puppy, she loved the game of staying just out of our reach when outside. She was prone to running out of sight and then coming back, just when we’d start to worry. Living in a place with no traffic or predators meant we didn’t have to worry too much. I figured she’d grow out of it. Maybe loves chasing deer too, but she usually gets to the edge of the yard and stops. That’s what I expect dogs to do. Not Piper.
She’s disappeared into the woods on a couple of occasions. The last time, she seemed to stay in the vicinity. She’d disappear for ten minutes, then you’d see her move through the trees at a radius that kept us from tracking her reliably. We’d stop and listen to leaves rustle and, often, hear very little. I’m sure the little jerk was standing still, watching us panic.
In one instance, she ran toward my outstretched arms and then veered off course at the last second to check another side of the property for deer. Not knowing what else to do, we remembered that Piper loves car rides. We moved the car down the driveway, opened the back hatch and she eventually jumped in, exhausted. The freedom she craved for months had finally been satisfied. Relieved, we vowed not to let it happen again.
Piper is not the kind of dog who wants to run away for days or end up miles from the pack. She seems to be oriented around home, but that doesn’t soothe our worry. Orcas Island is a rocky place with hills, valleys, and cliffs. We’ve heard multiple stories of dogs chasing deer off of cliffs and being seriously injured. That’s one of the biggest fears… in the rush of excitement, she injures herself and can’t move, or be found by us. In the past year, a neighbor’s dog chased a deer and came back with a knee that required surgery.
When we both saw Piper disappear into the woods, we knew that we had stepped into the unknown again and nothing would be okay until she returned safely. It’s a terrifying feeling. There are no houses within a fifteen-minute walk and over 100 acres of moss-covered forest.
Looking back, I know exactly what led to her finding this freedom. It was a very windy day, the kind that drowns out sound and causes small branches to litter the driveway. I intended to take Maybe outside and attached her leash as Piper watched by the door. I stepped out with Maybe and pulled the door closed behind me, I thought. Then, just before stepping off the porch, I looked back and saw the wind had blown the door open about 18 inches. I looked inside and there was no sign of Piper. I figured she had gone back to Sachi inside and I closed the door. I can now see that she, instead, sprang to action the moment the door blew open and I had no idea. Sneaky.
It’s an utterly powerless feeling to yell Piper’s name into the woods. She’s out there living her best life and seems to care little about our needs at the moment. With the wind blowing at thirty miles per hour, our voices were virtually camouflaged. What else could we do?
The property sits on the top of a hill and we both walked around all sides of the property, yelling for Piper. I grabbed Maybe and we walked deep into the woods on the side where she ventured out. I got Maybe excited so she would bark and possibly attract Piper. Sachi parked the car at the edge of the forest with the hatchback open. She slammed the car doors and honked the horn. Watching from afar, I could tell it was futile. The roar of the wind was too much. I checked my phone incessantly, hoping to see a text from Sachi with good news.
It was about 3:45 when Piper disappeared and as we searched, I started to do mental calculations. It gets dark at about 6pm, so we have a little over two hours to find her. She is used to having dinner at 5, so maybe that will bring her home. I looked at the weather and saw low temperatures in the upper thirties. These little calculations led to a series of questions I didn’t want to have to face. What if she’s not home when it gets dark? What if she’s not home when it’s time to go to bed? What about two days from now? A week? Is it too cold? Are we going to have to make signs? I imagined Sachi spending the night by the front door, waiting.
Unlike our previous experience, Piper never popped up to make an appearance once she entered the woods. It was like she vanished. We both took turns driving around the area. I texted a couple of friends to look out for her. After returning from a drive, I met Sachi in the driveway with a look on her face that seemed like deep concentration. Sachi doesn’t ever lose her cool. In a situation like this, she thinks her way through. About thirty minutes had passed and I wanted to comfort her.
“She’s going to be fine,” I said. “It’s dinner time soon and she’ll come back for that.”
“Not if she’s fallen off a cliff and broken her leg”, she replied. Point taken.
Not knowing what else to do, I put Maybe back inside and I drove down to a trailhead that leads by the property. If Piper had run straight downhill she would eventually hit the trail. About ten minutes down the trail, I met a neighbor whose property borders the woods of the property and showed him a photo of Piper. I got his number, just in case.
A bit further down the trail, I veered off into the thickness and tried to get a higher vantage point. After scrambling thirty yards uphill, I ended up on a small knob and surveyed the area. I called for Piper and looked for movement. Nothing. Then I checked my phone, expecting the disappointment of silence. But there in my text messages were two words from Sachi that made everything okay. “Have her!” I let out a big sigh and sat down for a moment to collect myself. It was over. I made my way down the trail toward the car. Just in case, I read Sachi’s text message again. What if it was a question instead of a statement? Nope. She’s home. It was 4:30.
I arrived at the guest house to find Sachi washing Piper in the tub. She was muddy and full of thorny sticks and branches. Being a doodle, with hair instead of fur, she collected tangles of the forest. It’s plausible that she could get permanently stuck in a bramble. But she didn’t.
Sachi said Piper simply appeared from the forest at the point where she entered. Once she saw Sachi, she ran at full speed to her, as if she was a little panicked herself. Who knows what she had been doing all that time? What was that little canine brain thinking while on the lam?
As Sachi washed Piper, she said to look at the kitchen table to see evidence of Maybe’s poor behavior. Confused, I looked around and there it was, a freshly baked loaf of bread, still warm, 80% gone. While we were chasing Piper, Maybe was feasting. Bad dog.
By the time it was all over, nothing really mattered but the pack being together again. We wish that Piper was better off-leash and that Maybe was less of a pilferer, but it goes with the territory. The positive role the beasts play in our lives far outweighs the moments of disappointment, worry, and exasperation. They may not be perfect dogs, but they are ours.
As a kid, I spent time reading skateboarding magazines. At the time, ads often included a line at the bottom that said, essentially, “Send us a dollar and we’ll send you stickers.” I can clearly remember how much I anticipated those stickers in the mail. Stickers have an appeal that goes beyond graphics, paper, and glue.
Today, I’m planning to send people my own sticker and this is the story of how that sticker was designed and how I’m planning to use it.
Why a Create Sticker?
Before my book, Big Enough, hits the shelves, I will encourage people to pre-order it, which means purchasing it before it is officially released. This way, when the book finally arrives, all those sales transactions happen in the same week and the book will hopefully make a bigger splash than it would otherwise. In this scenario, it helps to offer people an incentive for pre-ordering the book. If they (you?) preorder the book and send me the purchase receipt, I will send them stickers, and maybe more, in the mail.
Designing the Sticker
I am not a graphic designer, but I love working with designers and thinking through design projects. Once the idea of designing a sticker arose, I was pumped to work on it. The French bulldog on the cover of the book was my starting point. He’s symbolic of the Big Enough attitude: small and tough. I’ve come to call him “Big-E” and loved the idea of people having a fun, illustrated version of Big-E on their laptop or water bottle.
Instead of using the live-action image, I imagined a stylized cartoon version of Big-E and asked my publisher for the photo from the cover to use as a starting point. Then, I searched for dog illustrations in a style I liked. I found one that was close to what I wanted. It used flat colors and bold shapes that felt cool and modern.
Then I went to Upwork, which is a service I’ve used for years to find freelancers for small projects. I created a new job called “Digital Illustration of a Dog Based on Photo”. I included a description of what I wanted, attached the photo of Big-E and the example photo. I also said the illustration had to include the book website: bigenough.life
Next, I reviewed 15-20 profiles and invited a handful of people from around the world to apply. I’ve had good experiences working with international talent at affordable rates. I connected with a guy named Vadym from Ukraine and hired him. He got started quickly and provided a promising start.
But then, out of nowhere, he said something had come up and that he couldn’t complete the project. Such is life in the freelance market. Disappointed, I went back to finding designers and stumbled upon a profile of a woman named Brooke Braddy who had an affordable hourly rate and illustrations that looked promising. This image from her portfolio gave me confidence that she had worked in the style I wanted:
Brooke agreed to start the next day and estimated it would cost under $100 to complete the project. I was hopeful.
The project turned out to be incredibly satisfying. Over two weeks and about 40 messages back and forth, we tweaked the colors, fonts, padding, size, and more. Brooke was a good listener and had great skills. I enjoy working with people like Brooke who are independent and putting their skills to work from home.
Here are examples of how the sticker evolved over two weeks:
What I appreciated most was the iterative process of making the sticker exactly what I wanted. Every time Brooke sent a comp, another part of the design would grab my attention and kick off more changes. She took my feedback and made it work. For me, that’s how design happens. It’s a process of always asking “what sucks the most now?”
A couple of days ago, I deemed the sticker design complete. Brooke’s initial estimate didn’t anticipate the scale of my feedback, so I gave her a bonus for the extra hours. We were both happy.
A couple of days later, I thought back to those days of getting stickers in the mail and how I loved getting multiple stickers. Sure, I could send pre-order customers three of the same sticker, or I could create a set with different colors. Collect all three!
I went back to Brooke and she quickly whipped up a couple of color options. With just a bit of design time, I now have a set of three stickers for the kind souls who pre-order a copy of Big Enough. Here’s the set:
If you’d like to be notified about the pre-order campaign, you can sign up here.
About Me
I write books and run a company called Common Craft. I recently moved from Seattle to a rural island. Here, I write about online business, book publishing, modern home construction, and occasionally, dumb jokes.
I write books and run a company called Common Craft. I recently moved from Seattle to a rural island. Here, I write about online business, book publishing, modern home construction, and occasionally, dumb jokes. 
