A lot of people have asked me "What's next?"  I will share the answer in this post; but before I do, let's take a quick trip down memory lane.  It will help set the stage for what's next.

I started sailing seriously about 5 years ago, in the Spring of 2013.  I quickly fell in love with the sport and dreamed about building a career in sailing – as a sailing instructor, charter skipper, or yacht deliverer.  Or a combination of all three.

By the Spring of 2015, I assessed my professional, personal, and financial situation and decided to focus on making my dream a reality.  To the surprise of friends, family, and colleagues, I quit my  job in corporate finance and charted a new course for my life.  I built a financial plan and figured out a way to minimize my expenses and maximize my experiences, focusing on what makes me happy:  sailing, volunteering, and traveling.

At a macro level, my schedule revolved around sailing in San Francisco during the summer (when wind and weather is favorable) and volunteering in foreign countries in the winter (especially countries in the tropics or Southern Hemisphere).  Season to season, my cost of living and my daily routine swing wildly from one extreme to the other; but on an annualized basis, the lifestyle has proven to be manageable and affordable.

The volunteering and traveling is strictly for fun; I don’t have any master plan other than to explore cultures and help communities.  Sailing, however, is a different story.  I do a plan, or at least the dream, of making a career out of it.  So, I’ve been structured and disciplined in my efforts. 

Over the last several years, I’ve taken multiple courses from the OCSC Sailing School, earned certifications with U.S. Sailing, and chartered a variety of boats on the San Francisco Bay.  Thanks to a former instructor, and now good friend, I have also had the opportunity to complete over 60 days of blue-water ocean sailing, including four ocean crossings.

In January of 2017, I returned to the OCSC Sailing School and applied to be a Sailing Instructor.  After interviews, written exams, and on-the-water evaluations (by both OCSC and U.S. Sailing), I accomplished the first part of my three-part career in sailing:  I began work as a Sailing Instructor!

That’s the recap of my journey thus far.  So, now, “What’s next?" you ask.

My goal in 2018 is to apply for (and hopefully earn) a Captain’s License with the U.S. Coast Guard.  The license will facilitate, but by no means guarantee, accomplishing the second and third parts of my dream - skippering charters and delivering yachts (and, importantly, getting paid to do so).

Currently, I’m perfectly qualified to take any friends or guests out on a sailboat for the day, the night, or an extended period of time.  However, I’m not legally able to be paid for it (unless I’m working for an organization like OCSC Sailing School).  With my Captain’s License, I can be paid directly as an individual skipper.  Thus, I could buy a boat and offer to take people out on charter tours in the San Francisco Bay or elsewhere.  

The Captain’s License will also add further credibility to my Maritime CV.  This, in turn, will hopefully make me more noticeable and marketable to experienced yacht deliverers, who may be more likely to offer me work as Crew or First Mate.  Such experience ultimately might lead to skippering my own yacht deliveries.

So the Captain’s License is an important step in building my career as a sailing instructor, charter skipper, and yacht deliverer. 

So, how do I get a Captain’s License?  Well, it’s quite a process which I’ll outline at the bottom of this post.  The short answer is I need to log a lot of time on the water, and I need to pass a lot of exams.  This means I'll have to put a hold on my travels, for the most part.  

To complete the required 360 days of “sea service” as required by the U.S. Coast Guard, I will be staying put in the Bay Area, and teaching Basic Keelboat and Basic Cruising classes as much as possible at the OCSC Sailing School.  I’ve lined up an apartment in San Carlos as home base.

In March, I’ll head to Portland, Oregon, where I’ve enrolled in a highly-reputable and intensive 10-day “Captain’s License Course” to study and prepare myself for the written exams.

In September, I’ll head to Croatia where I’ll skipper another 2-week charter in the Adriatic Sea, similar to what I did in 2015 except this time I’m skippering a catamaran!  This will be a good  addition to my sea service as it counts toward more near-coastal and 50-ton experience.

By the end of the calendar year, I hope to have all of the documents, exams, and sea service required for submission to the U.S. Coast Guard.  Then I'll wait for the USCG to review and approve.  Or not.   

If all goes well, I'll begin 2019 as Captain Dan, less than four years after I hung up my hat as Corporate Dan.   It will a tough year of work, study, and discipline, but I feel good about the path, the process, and the prospects for the future.  


For those interested, here’s a brief description of and requirements for a Captain’s License, which is a type of “Merchant Mariner Credential” with the U.S. Coast Guard.

Application, Fee, and Oath

I submit an application, pay a fee, and repeat an oath to the U.S. Coast Guard.  With my application, I submit proof of all of the following:

Transportation Worker Identification Credential

I need to apply for this credential, which is a very straightforward process including an online application, a fee, and an in-person appointment for fingerprinting.

Physical Exams

As you might expect, I’ll have to pass multiple physical tests to prove I’m physically capable of operating a vessel.   These include drug test, eye test, hearing test, and strength/balance test in additional to routine physical exam.

Written Exams

These cover a variety of topics like Rules of Road, Navigation, Deck Safety, and Deck General.  Since I want to be a captain on sailboats, I’ll also need to pass the Sailing exam, which is another series of questions.  There is no “practical exam” or “driving test” for the credential.  I guess the USCG assumes you can drive a boat if you’ve achieved your sea service time.

First Aid and CPR Training

Although I’m already certified, I have to re-certify so that my certification is within one year of my application to the U.S. Coast Guard.

California Boater Card

This is a new requirement rolling out in 2018 in California.  It requires an online course that takes several hours. It seems to target motorboat and jet ski operators, but it has useful rules-of-the-road information for sailors, too.

Character References

I’ll be searching for three people who are willing to submit brief, notarized statements declaring that I’m a responsible, capable person. 

Sea Service Form

I have to submit paper records documenting at least 360 days of “sea service” time.   This is why I’ve been keeping a logbook!  This is tough though.  A “day” is 4 hours.  But so is 8 hours or even 24 hours!  Even a 10-day passage from New Zealand to Fiji (sailing 24 hours a day for 10 days) is only 10 days despite being 240 hours!  This makes the accumulation much more time consuming.  Even days in San Francisco where I’ve done a day sail with one group, and a night sail with another group, is still only 1 day of sea time.  I’m approaching 300 days now, targeting to get to 360 by the end of the calendar year.


After gathering all of the above, I then submit the package to the U.S. Coast Guard.  They will review, and if all goes well, they’ll issue me a Merchant Mariner Credential

The specific type of credential I'm applying for is the Boat Captain Credential, and even that credential has a few subcategories.  The two big ones are:

  • Operator of Uninspected Passenger Vessel

This refers to a basic license I could get that would enable me to carry up to 6 paying passengers on a vessel.  So even on a 10-person boat, I can only carry 6-paying passengers.  This license is commonly referred to as “6-pack” and is typical for skippers driving a water taxi or launch. Not bad, but I ultimately would want to upgrade to “Master” which enables me to carry any number of paying passengers, up to the vessel’s capacity.

  • Master Credential

The Master credential will remove the “paying passenger” restriction.  There are multiple variations of the Master credential based on Range (Inland, Near Coastal, Ocean) and Tonnage (25-, 50-, or 100-Ton).  These will be determined by the experience (called “sea service”) that I submit, which documents the vessels and locations that I have sailed.  I will initially qualify for Inland, 25-Ton, or maybe 50-Ton.  I'm ultimately targeting Near Coastal, 50-Ton. 

So that's it.  That's my plan for 2018.  It will be a year of focus and discipline to advance my career and enhance my future!  Like I've said, there is no guarantee but I'm going for it.

 Aboard SV Avalon, somewhere in the South Pacific Ocean.

Aboard SV Avalon, somewhere in the South Pacific Ocean.

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