I am pleasantly surprised that my boat experience and captain’s license are paying off with some fun, often challenging gigs.

A lot of folks criticize me for (or are in awe of) the number of “irons I keep in the fire.” Simply said, I have a lot of interests and when something really strikes my fancy, I dive in headfirst and do what I need to do to become an “expert.”

That’s how teaching myself how to use computers in the early 1990s paid off with a career as a computer how-to book author, speaker, and educator, freeing me, once and for all (at age 29), from the 9 to 5 grind of corporate America.

That’s how learning to fly helicopters and eventually jumping through the hoops required to get a charter (AKA Part 135) certificate got me a third career as a helicopter pilot, which started climbing to its peak in 2012, right around the time people stopped buying computer how-to books.

That’s how accumulating cabochons at rock shows led to making jewelry which led to getting good silversmith training and setting up my own fully-equipped studio and making/selling sterling silver jewelry at art shows. When I sold the helicopter and my two helicopter businesses, I really thought silversmithing would be my fourth career (and first retirement career) and I suppose I can still count it as that.

But I never expected my boating activities to lead to paying gigs on both coasts, bringing in retirement income just as silver prices skyrocketed and the economy led to people not spending much money on things they didn’t need. After a dismal winter art show season in Seattle and the Phoenix area, I’ve pretty much set my silversmithing activities aside to better explore this fifth career as a boat captain.

Getting into Boating

What started as me musing, back in 2012, whether it was possible to take a boat on a trip from the Intracoastal Waterway near my mom’s old house in St. Augustine all the way up to the Erie Canal, somehow ending in the Mississippi River and looping back to my starting point in Florida, eventually culminated with me doing that trip, the Great Loop, mostly solo in my own boat. I started in Chicago in October 2022 and ended there in August 2024. (I was still working as a pilot in the summer so I couldn’t do the summer part in 2023.)

I’d been boating on and off most of my life. Back in the summer of 2011, I bought a little jet boat. It wasn’t much and it wasn’t fast, but I eventually took it on outings in the Columbia River, Colorado River, and Lake Pleasant (Arizona).

My little jetboat was extremely well travelled. In the winter of 2017/18, I took it south with me to Arizona and beyond. This picture was shot at Capitol Reef National Park in October, when I drove through on my way to a side trip in Colorado.

My life got turned upside down in 2012 and I spent the next few years rebuilding it the way I wanted, with a new home and new priorities. I’ll just say this: life is good when you don’t have anyone holding you back from enjoying it. (‘Nuff said, eh, Jim?)

By 2021, I was thinking about that boat trip again. I found a boat captain doing the trip in his 2017 Ranger Tug R-27 who was looking for two crew members. I signed up for a portion of the trip: 8 weeks from Jersey City to Chicago. It was a mostly great experience, although I did clash with the other crew member and wound up leaving the boat after 5 weeks. We traveled up the Hudson River (where I’d boated with my family as a child) through the Erie Canal, and along Lake Erie and Lake Huron. It was great experience.

After that trip, I was approached by another boat captain, this time in a 1985 Aft Cabin Carver 35, who was doing the trip at his own pace and needed at least one crew member for at least two weeks. I signed up for 5 weeks, returning home just in time for my summer work. This time we were on the Atlantic Intracoastal Waterway between Charleston SC and New Bern NC. (John cruised at a much slower pace.) Again, it was great experience.

I was almost ready to buy my own boat, planning to do the Loop at my own pace starting in 2024. I had one more season of summer flying to do with my helicopter and then I planned to sell it. But weird stuff happens and I got an offer I couldn’t refuse for the helicopter in May 2022. I’m not an idiot; I sold it. I wound up leasing a helicopter — long and crazy story there — for my summer work.

But that big fat helicopter payment was eating at me, telling me to buy a boat that summer and start the trip sooner. After putting off looking for most of the summer, I finally succumbed and started a search. I found the right boat in August 2022, made an offer, had it accepted contingent on the survey, got it surveyed, and completed the sale just after Labor Day weekend.

What followed was a bit of training, a bunch of days cruising around Puget Sound, and a trip across the US to Chicago where the trucking company I’d hired launched it. My friend Janet joined me for the first 3 weeks on the Loop. My friend Alyse joined me for the second 3 weeks on the Loop. I did a bunch solo and also did about 60 days with my friend Jason and another 3 days with my friend Cheri. This was all over the course of 22 months, with time home to work when I had to.

Becoming a Captain

Along the way, I stopped in Oriental NC to attend a 7-day OUPV captain course. I got my Captain’s License from the USCG in October 2023. I put that license to work in May 2024 in the Baltimore area on two separate training gigs: 3 days for a brand new boater planning to do the Loop solo starting that summer (!!) in his 2015 Ranger Tug R-29 and 1 day with a couple who had stepped up from a pontoon boat to a really nice (and relatively new) Ranger Tug R-29.

If I had to identify one thing that has helped me stay financially secure doing interesting work throughout my life while retaining a healthy work/life balance, it’s my ability to recognize and take advantage of opportunities that come up as they come up. While many people — including too many I know — will make excuses to support why they can’t do something, I look at what I need to do to make things happen.

So while I was on a flotilla with five other boats (all larger than mine) going to Desolation Sound, and one of the owners of the charter company asked if I’d ever considered training people how to drive boats, I not only said yes but told him I had some experience doing it. (He had been impressed that I docked the boat solo at every stop; basically having the boat tied up before his wife hurried over to help.) And then I took the certification classes required to qualify as an instructor for their company. The following spring, I was teaching for them.

I have to admit that the highly structured classes they were teaching to give students American Boating certification was not what I enjoy doing. It was nice to make money while boating with strangers, some of whom were really great people, but I’m not a fan of teaching to the test, especially when the test covers information not in the course material or really not necessary to know. (I’d offer an example here, but I literally tossed out those old tests two days ago when cleaning out my instructor binder.)

I’d prefer to teach just one or two (a couple) people at a time, focusing on what they need to know to be safe boaters and get started building skills. And that’s what I got to do twice on my own boat last summer. I took a future Ranger Tug owner and his friend on an overnight trip in the San Juan Islands where they could see whether the boat would meet their needs; they stayed in an AirBnB on Orcas Island near Deer Harbor. And I took another future Ranger Tug owner who plans to do the Loop on a four day trip in the San Juan Islands, focusing on soloing skills — which is something the training organizations don’t want me to teach for them. I was tickled pink when he picked up a mooring ball by himself on the first try!

Later that summer, in August, I accompanied a new boater and his friend on his 2024 Antares 11, a twin outboard boat he planned to do the loop in. They had to move the boat from the Florida Panhandle to Jacksonville. We had two weeks to do it and needed almost every day because of engine issues along the way. It was brutally hot and humid in Florida, but the boat had air conditioning in the staterooms so sleeping was tolerable. It wasn’t my favorite Captain gig, but it’s always nice to get out on the water, especially when someone else is picking up the tab.

This Year Is Shaping Up

Fast forward to this year. Things are shaping up nicely. It’s just March and I’ve already done one gig, have two more under contract, and a third penciled in on my calendar. These are all gigs in a client’s boat or in my boat.

In two cases (for the same female client), I got the gig partly because I’m a woman. So that’s a welcome twist.

In the other two cases, the client wants to experience cruising in a Ranger Tug. So although my boat is in a charter program with San Juan Yachting out of Bellingham and used by others when I’m not on board, I have enough time for myself reserved so I can offer a few training cruises in it. I love teaching people how to drive Ranger Tugs, especially in my own boat. I know it so well and am still excited about it, even after 3 1/2 years of ownership. I want to make them excited, too.

And I’m also doing day trips and shorter overnight trips for clients. You can check my boat’s availability calendar here. And, of course, you can charter it for yourself if you meet the charter guest requirements at San Juan Yachting. Or you can charter it and request me as your on-board captain for custom training as you cruise.

The point is, I’m able to do work I love — boating and teaching people how to boat safely — and be paid for it. And I have to admit that the work pays a lot better for the amount of effort than my silversmithing “career,” even though it’s not as creative and personally rewarding. I guess the bottom line is this: doing work as a boat captain pays the bills; doing work as a silversmith/artist pays to do work as a silversmith/artist.

Winter 2026/27?

At this point, I’m leaning hard toward towing my boat back to the Great Loop in mid October or November, probably launching it in the St. Louis area. When I did the Loop, I sped through the southern half of the Inland Waterways in December and the trip was not as good as I think it should have been. I want to do it again and then cruise on to the west coast of Florida, perhaps with another stop in the Keys.

Heck, I towed it home from Chicago in August 2024. Why not tow it back to St. Louis in October 2026?

The boat would be available for passengers interested in learning more about the Great Loop or Ranger Tugs. Due to the size of the boat and stateroom limitations, I prefer to take solo cruisers, but I could probably make room for a couple. We’ll see.

What I do beyond that really depends on what plans I can make for Summer 2027. Right now, it’s too early to share my thoughts about that.

It’s All about Skills

I just want to end this post with a quick discussion of skills.

I have built multiple careers — some of them very successful — by learning skills and making those skills available to people willing to pay for them.

• I wrote about computer books for more than 20 years, earning quite a bit of money with my ability to write and to explain how to perform tasks on a computer.
• I took passengers for hire and did contract work in a helicopter, eventually earning a good living with my ability to fly the way a client needed me to fly.
• I’ve earned money with my silversmithing skills, although I haven’t had to depend on the income from that endeavor (see the previous two points).
• I’m earning money with my boating skills, teaching people how to safely maneuver their boat.

I have numerous other skills that serve me well:

• Computer skills for building websites, creating marketing materials, and making videos.
• Marketing skills for selling myself and my services.
• Accounting skills for taking care of my own finances.
• People skills that recognize the client is always right (even if he’s wrong), among other things.

I don’t learn skills because I plan to turn them into a career. I learn them because they interest me. But being able to monetize them makes it possible for me earn a living doing the things that interest me. In addition to the ones I’ve covered here, I’m also doing things with bookbinding, leather work, carpentry, photography, sewing, and more. I’m interested in a lot of things so I do a lot of things.

I guess the point I’m trying to make is this: building skills can never be a waste of time. You never know when that skill you’ve been honing because you really enjoy the work might be the skill that turns into a lifeboat if your life goes sideways one day.