On June 14, 2021, we sold Fearless to another family who, like us, decided to turn their sailing dreams into reality. We were excited for them, and happy we had found someone who would enjoy and care for our boat as much as we did. But, it wasn’t easy walking away. Fearless was our home for two years. She had shepherded us through good times and bad, rocked us to sleep at night in many a strange harbor, and been our personal island sanctuary when we needed to retreat from the world. Perhaps one day we will look back on our decision to sell her and conclude we were crazy to walk away from something we had worked so hard to achieve. However, we knew we didn’t want to do this for years on end, so it seemed like a logical point to stop.
Despite the hard decision to stop sailing, there is a positive side to this that will influence us for the rest of our lives. The seal around the willingness to do something amazing has been forever broken. We actually did what we said we were going to do, and consequently unlocked the secrets of how to turn a dream into reality.
Team Fearless in Newport, RI in August 2019. We had no idea how much the world would change when we started our adventure.
Quick spoiler – it had very little to do with money.
Now that we are back on land, it’s worth sharing some thoughts about how we did it. I have already posted about the background story and why we made the decision to go sailing. In this one I talked about the intial fears and limiting beliefs we had about cruising, and in this one I gave a one-year reflective look on whether or not any of our fears came to pass.
To be sure, there were many benefits to what we did. There were also challenges, and it would be misleading to pretend they didn’t exist. With this in mind, my goal is to be as transparent as possible as I walk you through the hows, whys, and so whats. It wasn’t amazing every day, and I don’t want to give the impression that we lived a perfect life afloat. There were some tough moments out there, but it was in those moments we grew the most. The key takeaway is that the overall experience was life-changing in ways that I never imagined. We are not the same people we were two years ago. Our children have seen and experienced things that no classroom could ever hope to replicate. We became more confident, self-reliant, and worldly, and that says a lot for a military family that had been stationed overseas on multiple occasions.
Like many people, we had been following some inspiring YouTube channels featuring people who had quit their lives and gone sailing. Despite our excitement about the possibility of following in their footsteps, we were also overwhelmed by the amount of courage it must have taken them to actually do it. So, we sat timidly on our couch and lived vicariously through their experiences. At some point (I don’t remember when) we started asking ourselves some hard questions. Why not us? What is holding us back? What is the worst thing that could happen to us? What fears are standing in our way? What will it take to turn our dream into a reality?
Once we figured out we were the ones holding ourselves back, we made the decision to stop dreaming and start doing. That’s it. It’s as simple as that. We are not special. We are not wealthy. We are not blessed with superhuman qualities.
We just did it. So can you. Here is how.
2. Hold Yourself Accountable. The simplest, most effective way to start is to put dates on your calendar and honor them. Use those dates to put together a solid plan, then work hard to meet the milestones you establish in it. This is obvious to many people, yet it is the difference between talking and doing. Trust me, if you are dreaming about a mid-life sabbatical or a break between careers, you will have a lot to do. However…and this is blindingly obvious…what at first seems impossible will quickly become manageable when you can start figuring out the order and magnitude of the tasks in front of you. We needed to sell a couple cars, pare down our belongings, find a boat, survey and buy the boat, put our remaining belongings in storage, then move aboard. I had the benefit of a known ending date to my military career so I didn’t have to orchestrate my departure from work, but even that can be manageable if you make it part of your milestones. Regardless, it was still a giant transition for us, so we needed to lay out specific tasks in a well-organized timeline.
The point here isn’t to tell you how to plan your life, and I don’t want to imply that we were organizational geniuses. I merely want to emphasize there is a huge difference between a dream and a plan, and it’s very easy to put your dream on a shelf when it feels like you can’t gain traction. Once we started to check things off our list of tasks, a curious thing happened. We suddenly started meeting people who could help us. These were people with whom we had never crossed paths before, yet they were either friends of friends or people who literally lived a few houses down the street. We found ourselves asking them, “where have you have been our whole lives?” The answer is they were always there somewhere, but how were they supposed to know we needed them? The incredible part is those people enthusiastically helped us even though they were new acquaintances, and they connected us with even more people who could help us. Without much effort our cruising-focused network quickly began to fill with the right people, and suddenly we gained traction…a lot of traction. The bottom line is that until you commit to a specific start date and supporting timeline, people will politely smile and tell you how amazing your dream sounds, and that’s as far as it will go.
In addition to putting dates on a calendar and holding yourself accountable, there is even another, more powerful step you can take to maximize the effectiveness and results of your planning and execution.
3. Hire a Coach. Most people have heard of at least a couple famous athletes. Do you think they got to the top of their game by going it alone? Of course not. Pro athletes benefit from a lifetime of dedicated coaches at every level. A coach can make you a whole lot better, too, and there is a coach out there for just about every activity. Take cruising as an example. Some people spend years preparing for an adventure like we just concluded. We didn’t have that luxury (or foresight) to do that, so we hired coaches to short circuit the process. Coaches not only helped us become better, they also held us accountable to milestones and objectives. Most important, coaches saved us a lot of time and money. Money was certainly important, but time was even more so. For most of us, a mid-career/life adventure might be only six months or several years, but either way, it has a beginning and an end. As a result, you will want to maximize whatever time you have set aside, and nothing can help you more than hiring a coach to guide you through the preparation for, and execution of, your plan. Remember, time and money are always at war with each other. Time is precious and finite. Money is just money.
A coach might seem like an unnecessary expenditure. but ours saved us a TON of money. They used their extensive knowledge and experience to help us research boats that were seaworthy, well-equipped, and still within our budget. They also introduced us to an entire network of other families who were either preparing for cruising, or already out there doing it.
There were a number of boats we thought were great candidates that our coaches rejected because they looked good from a distance, but to the experienced eye they were trouble. Our coaches steered us away from unnecessary purchases, helped us with every aspect of life at sea, and remained committed to our success all the way through to the sale of Fearless.
A coach can be a formal or informal part of your plan, and he or she doesn’t necessarily have to be well-known or expensive. They just have to be willing to help you reach your stated goals and push you to be better. We went for well-known experts. We hired Jamie and Behan Gifford (www.sailingtogem.com), a couple who twice circumnavigated the globe on a sailboat with their kids. They helped us (virtually) shop for a boat, prepare for life afloat, and avoid many of the mistakes that upend newbie cruisers. We leaned on them heavily, and among all of their clients we still hold the record for shortest “flash-to-bang” timeline for making the decision to cruise and actually getting under weigh. The record isn’t important, and I don’t recommend trying to beat it because life was pretty hectic during the four months we took to divest ourselves of land life and buy a boat.
The point is that they helped us maximize the amount of time we spent actually cruising vice shopping, preparing, training, and so on. The coaching didn’t end with the purchase of the boat, either. We continued as their clients throughout our entire two-year sailing experience, and they continued to act as both mentors and cheerleaders for everything from hurricane avoidance to homeschooling. I was so impressed with what they did for us I hired another coach to help me with my job hunt (Jessica Sweet – www.wishingwellcoach.com). I am all about the coaching now, and I can’t believe it took me this long to figure out how coaching can benefit me and my family!!
If you have made it as far as hiring a coach, there is something else you might want to consider.
4. Have an exit strategy. This may seem like an obvious point, but it’s easy to overlook in the quest to get going. Unless you aren’t planning to return to some semblance of pre-sabbatical life, you need to have an exit point in mind. In our case, I knew that we would have to sell the boat and reverse the transition back to land; we just didn’t know when. Our initial commitment was one year. We didn’t know how well the kids would adopt to life on the boat but we knew it would take at least a year for everyone to get in the rhythm of cruising. Regardless of the lack of an end date, I always kept our exit strategy in mind, perhaps even to a fault. What does that mean? I spent a lot of time on boat maintenance and upkeep… probably too much. I did this for two reasons, though. The first was seaworthiness. I wanted to be ready to get the boat under weigh in a moment’s notice in case we had to run from weather or other hazards. The second, however, was the ever-present thought that I would need to sell Fearless when we decided to stop sailing. I wanted the transition off the boat to be as painless as possible, which meant a short list of projects, repairs, and inspections. As a result of all that boat work, I was really proud of the way Fearless looked when we turned her over to the new owners. But, I think the kids would have been a lot happier with me if I had played with them more and not worried about it so much.
Gavin holding up Fearless in Shelter Bay, Panama in January 2021. We short-hauled to check the props and rudders as an extra precaution before transiting the Panama Canal southbound into the Pacific.
In the final analysis, our exit strategy was far from bulletproof. Returning to the shores of America and reintegrating into society turned out be a lot more difficult than I thought it would be. To be fair, it was hard to plan exactly when and where we would stop after we first got going, so it was hard to say that we should have maintained a residence and sacrificed the size and quality of the boat. The ocean can be a scary place in a low-quality boat and I wanted something that was sturdy, fast, comfortable, and well-equipped. Believe me when I tell you that very few people wish they have a smaller boat when they are caught in a storm out at sea. So, we made some decisions with the best information we had at the time, and because we didn’t have unlimited financial resources I opted to put more money in the boat rather than sacrifice size and comfort in favor of hanging on to land-based trappings. Of course, everybody will have different opinions and priorities, and I can’t give you a perfect solution. I can only tell you what we did and what came to pass as a result.
It’s also worth mentioning that everything we thought we had figured out changed because of COVID-19. Even though we were on a boat and seemingly far from the wreckage on land, the pandemic had a huge impact on our cruising. It affected the local economies where we were anchored or moored, the price of goods and services, and the freedom to cruise in the traditional sense of island hopping and ocean crossing. Suddenly, we couldn’t go wherever we wanted, whenever we wanted, and things got a whole lot more expensive. Who saw that coming? But, as I said in an earlier post, all you can do is make decisions then adjust to whatever circumstances unfold. It’s true for your entry strategy, and it’s true for your exit strategy.
When it came time to sell, we faced three different market forces – the boat market, the job market, and the housing market. None resembled the pre-COVID world we left behind in 2019. I wasn’t counting on significant abnormalities in any of them when we purchased Fearless, but c’ést la vís. It really didn’t matter what was happening, because the only thing I could control was the condition of our boat at the time of the sale, and the timing of its market entry. Ultimately, we sold the boat in a good market, returned to a strong job market, but got clobbered by the housing market. If we had been able to delay the sale of the boat by three months, we would have done that just to get us through the summer to avoid the competition with everyone else renting vacation homes and Air B&B units. However, we commited to the sale in February before we had an inkling the housing market would go as berserk as it did. I guess the lesson here is that you can’t control everything, and going all in on your sabbatical comes with risk. So, as you are getting started, think about the backside transition and have a good idea about the level of risk you are willing to take.
Team Fearless in the Mira Flores Locks, Panama Canal, February 2021. This was a huge achievement for us, and I never imagined going through the canal would be possible when we first started cruising.
I could write a book about the how-tos of what we did, and perhaps it is something I need to do. Plenty of people have suggested it, but I often wonder how much value I can add to the trove of information that already exists in all the YouTube channels and books in circulation. I think what makes our experience unique is that we executed our dream on a remarkably tight timeline, and despite making numerous mistakes, we set ourselves up for success through careful planning and responsible decision making. One of my conclusions about cruising full time is that there are plenty of people who talk about it yet never do it. Our hope is that we can inspire some of them to get off the couch and get going, whether it’s on a sailboat or some other form of adventure. This is why I am taking the time to offer up some tips and tidbits. We want to help. A lot of credit belongs to the people who helped us make this a reality, continued to encourage us as we stumbled through those first few months, and cheered us on as we pushed the boundaries of our sailing experience. Of course, all the cheerleading in the world didn’t relieve us of the responsibility to act – we still had to plan, budget, prepare, and eventually execute on our own.
These keys to success I shared in this post are some of the most important I could think of, even if they seem like the most obvious. The bottom line is that you have to start somewhere, and hopefully these tips help you get going. Life is short, and I guarantee you will have significant regrets about the things you never did. You are not going fail. You might stumble, and you will certainly have to deal with challenges and frustrations, but those are the moments that teach you the most and make you stronger.
Ask yourself what is the worst possible outcome of taking a calculated risk on something you have always wanted to do. Then tell yourself it is OK to let go of limiting beliefs, step through fear, and take a chance on amazing.
You’ve got this.