Four large duffel bags. The sum total of our possessions. Kelly and I walked down the dock with Nathan (9) and Violet (5) until we came to Shannon. Our new home.

Cold, overcast sky, typical Monday afternoon. No fanfare, no welcoming party - just a flock of seagulls on the covered slips eyeing us to see if we'd drop any food. A family of four loading duffel bags and boxes of toys, Legos and food onto a sailboat.

Shannon wasn't a head-turner. Just a clean, 35-foot boat almost 40 years old. White fiberglass with a green stripe running the length of the hull just above the waterline and green canvas covering the sails.

The kids were excited. Exploring every inch of their new home. Claiming the V-berth at the front as their "room."

Me? A mix of excitement that we'd actually pulled the trigger - didn't let the dream die - and apprehension. This was uncharted territory. Not just for me, but for my whole family. I'd left my job of 17 years as a software developer to chase this crazy dream. The plan was to make a living as a writer, blogger, digital nomad.

I've done wild things before and survived and as a Christian, I had faith. I didn't know how it would all work out, but I knew that it would.

The Routen family had made the leap. We sold the "stuff." and we were starting our Grand Adventure.

The dream started in 1988. I was in the Navy, stationed at a hospital on a Marine base in North Carolina. Renting a kayak to paddle on the river, someone mentioned they were looking at a sailboat to live aboard. I'd never even considered living on a boat - even though I grew up water skiing on a local lake. But the thought of living on the water, changing my location on a whim, exploring when the feeling hit... but I knew the dream of living on a boat would have to wait until I got out of the Navy.

I met Kelly just 6 months before I was scheduled to get out. When I mentioned the idea of living on a boat, her response: "That's crazy talk. People don't live on boats."

Well, I wanted her more than the boat. So we stayed together, got married and started our family.

On our 10th anniversary I booked us a dinner cruise on a sailboat on the Willamette River that cuts right through downtown Portland. While we ghosted downwind, watching the shore quietly drift by, Kelly says: "I could live on a boat like this."

My mind went into overdrive. We were going to make that happen. It was the cherry on top of a beautiful evening.

We started looking at boats. Small ones to start, but nothing really came of it. The dream didn't die, life just pushed it out of the spotlight.

Near our 20th anniversary, I'd reached a breaking point. Hated going to work every day, doing the same thing. Sitting behind a computer screen, working on software I just didn't care about anymore. I'd been passed over for promotion and I could tell I was dying on the inside.

So I reached out. Through some connections, got a spot as crew on a sailboat for the weekly races on the Columbia River. That's where I learned to sail. How to run the lines, trim the sails, steer the boat.

The dream started to feel real again.

The vision: North American coast. Panama Canal. Caribbean Islands. Not a vacation. A life.

The plan was to fund it through blogging. The whole "digital nomad" trend was really hot at the time and I figured with my background in tech - plus Navy Search and Rescue Medic, helicopter pilot, instructor, and other wild things - I should be able to make it as a blogger or podcaster. Something of the sort.

Kelly and I had always planned on homeschooling the kids, so that was never an issue. We just brought our books and laptop onto the boat and kept on going like we did at the house. Always tried to work in lessons no matter what we were doing. Now the kids were getting lessons in boat plumbing, diesel engine repair, how to organize a boat into a home.

The route: Explore Puget Sound for a few months as we got to know the boat and learned the area. Then head south down the West Coast, cross into Mexico, and ultimately through the Panama Canal to the Caribbean. Writing, creating YouTube videos, sharing our story along the way.

The math: I had $40k in a retirement account. We decided to use it to buy the boat and keep us afloat financially until the writing could support us. The boat took half of that. Okay, we didn't have a mortgage, the slip rental wasn't too bad, no other big expenses. The math made sense on paper.

When we were buying Shannon, we had a marine survey done. Like a house inspection it looks for any issues that need to be addressed. Survey came back with a few small issues, nothing that screamed "walk away."

Then the insurance company told us the standing rigging - the cables that hold the mast up - were original. Nothing above the deck would be insured until they were all replaced.

Ugh. Not sure how we missed that in the survey, but there it was.

So we spent the next three months working with a rigger. Replacing all the cables. Painting the mast while it was down. Fixing the lights and antenna that would be at the top when it went back up. Making sure the whole thing would be safe for our travels.

What I didn't realize was just how much boat stuff costs. The new rigging, the rigger's time, all the other small stuff, about $15k. There goes our savings.

No money coming in from blogging. Just a slow burn on what was left.

Once the mast was back in place, we got out of the marina. Spent the next three months exploring the islands of Puget Sound. Nights on anchor, alone in amazing coves. Sometimes in a crowded anchorage, fending off other boats as the winds changed.

On a walk on a beach, Kelly and I ran into a father and daughter visiting the area. He was the head of an American School in Israel, there with his young daughter during their summer vacation. Something in that conversation made me realize we didn't have to force the dream. We could take the experience we had up to that point and keep it as a fond memory instead of forcing our expected outcome.

I broached the idea of bringing the sailing dream to a close and getting back on land. I think Kelly was a little relieved. Our experience didn't exactly live up to our expectations. The boat was too small. Our budget was too tight.

When we told the kids we were thinking of selling the boat and moving back onto land, they took the news pretty well. Because the boat was small and our budget was even smaller, life was pretty boring for them. Sure, we got to explore some interesting areas, but when your only vehicle tops out at 7 miles per hour, life is pretty slow.

So we asked ourselves: where do we want to go next? We didn't really have anything tying us to any specific location.

First, we had to sell Shannon.

In the largest marina on the West Coast, it wasn't exactly a seller's market. We put a large for-sale sign on the railing where the regular stream of people coming and going on the local ferry would see it. Put the word out to anyone who'd listen and listed her online.

Over the next few weeks we had a few lookers, but no one really too interested.

Now I was wondering if I had made a huge mistake. No income, no buyers. Just stuck in boat-limbo.

Day after day, watching people get on and off the ferry just across from us, wondering if anyone even saw the for-sale sign. Watching the bank account dwindle. Having mentally moved on, but physically stuck with nowhere to go. Not wanting to take the boat out and sail so we didn't break anything, but not wanting to just sit at the dock watching other people enjoy their boats.

Then, out of the blue, an older gentleman standing on the dock. "Is anyone aboard?"

Turns out his son was in college but ran into some trouble. He'd moved back home and now his father was looking to buy a boat they could sail together to help them through the rough spot. He appreciated all the work that was done. Made us a full-price offer.

When Shannon sold, we didn't have a car, didn't have a house, and only the beginnings of a plan. We considered moving to another country to do more exploring, but we quickly found out homeschooling isn't really a thing outside the US.

We decided to give Texas a try. San Antonio area was south of Tornado Alley, north of the hurricanes that hit the coast, no real earthquake activity, and a large tech community where I should be able to find work.

So we stayed with friends and family for a couple of weeks while we worked with an apartment finding service in San Antonio to figure out where we wanted to stay next.

We moved to Texas October 2013. I quickly found work as a software developer again and we settled back into life ashore.

Over the next 10 years we moved a couple of times. Ended up with an amazing opportunity to buy 10 acres with a house on it, 15 minutes from a small country town. We had a tractor and everything, but it just never felt like home. I felt more like a steward of the land than an owner. Never really felt like where we were supposed to stay.

In 2023 we sold the property and moved to Northwest Arkansas. Started R4 Digital Systems. There were four of us Routens, so R4 reflects the family effort. For the next year and a half we struggled making any headway with the business.

Then AI matured.

When I first heard an AI voice assistant that could carry on a natural conversation, I knew AI was now a tool that could have an impact on business. Not a novelty, a real tool.

Looking back at the boat days, the blogging that didn't generate income, the content that never got traction, I can see now that I was trying to create in a vacuum. I didn't have other creatives to talk with, bounce ideas off of, get feedback from. Yeah, I read a lot of other people's work, but that's only part of the equation.

Now, with AI like Claude I have a tool that pushes back, helps me see my blind spots, shows me things from a different perspective. If I had this when I was on the boat, things would have been very different.

For a while I was using Chat GPT like most other people. But I got tired of it acting like an over-excited intern, telling me that every idea I was just thinking about exploring was the greatest idea ever, running down that road before I even decided that was the direction I wanted to go.

So I moved to Claude and asked it to help me do three things: Show me my blind spots. Challenge my assumptions. Help me think more critically.

Boy did Claude take that to heart.

It's exactly what I need. I tend to have "shiny object syndrome" and I bounce from idea to idea without completing much. Claude helps me keep my focus. See my ideas in a different light. Keep me on task.

Honestly, this story is being written down because Claude helped me see my story in a new way.

The boat is still out there. The dream is still in here.

A few months ago Kelly surprised me. She said, "You know, the kids are about out of the house now. When they're gone I think we should get back on a boat."

Say no more.

I was shocked she even mentioned it. Our experience on Shannon was novel, at times exciting, but it wasn't anywhere near what we had dreamed it would be.

So this time, we're looking ahead with experienced eyes. We know what size of boat to look for, what kind of layout we want. Where we want to buy the boat so we don't have to travel all the way around North America to get to where we want to go sailing.

This time we'll have the income secured. We'll have Starlink to get us online no matter where we go. No more fighting for a slip close enough to the marina to get a Wi-Fi signal.

Sometimes the world has to catch up with our dreams. They don't have to die, but they may have to wait a little bit.

So, now you've read my story. What's yours?

What dreams are still in there refusing to die? Do you live a conventional life because doing anything else is just "crazy talk"?

What's keeping you anchored? And what wind are you waiting for that might already be blowing?

Somewhere, your Shannon is sitting at a dock waiting for you. The question is whether you'll walk down that gangway.