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After five years of working in the industry and two years of holding my captain’s license, last summer I took the next step and landed my first gig as charter captain. Making the transition from crew to captain can be intimidating and to add to the pressure I hired my boyfriend (who’d never worked on a boat) as my crew!

While it ended up being one of the best summers of my life, I wanted to take a minute to acknowledge that it wasn’t always easy. Here are some of the phases that I went through as a brand new boat captain:


Every bone in my body tells me that I should quit. I’m a fraud. I’m a liar. I don’t deserve this. I continue onto the boat anyway. I hop down into the engine room and roll through my checklist – shouldn’t I be fluffing the pillows? I do a visual inspection of the engine, check the coolant, lube oil and transmission fluid. I check the fuel lines running to and from the engine, ensuring we are still pulling and returning to the starboard tank.

Today is the first day that I am the captain. Today I push myself beyond holding the license, beyond having easy, comfortable jobs driving small boats. Today I really earn the title and justify it to myself.

I know I belong behind the helm but there’s an animalistic fear telling me to run for the hills. If you’ve ever started a new job or tried something that pushed you out of your comfort zone, you know the feeling. It’s that little voice saying you’re not good enough and you should give up; “Who do you think you are? You can’t do this.” Moments like these define what kind of person you will be: stay and push yourself, or cower and run. I didn’t run.

PHASE 2: TIME MANAGEMENT aka I hope you don’t have dinner plans!

Phase one was short-lived. It didn’t take long before I found my confidence. Whenever people looked at me like I was too young to be a captain or started to question my abilities, I would casually bring up crossing the Atlantic or working in the Virgin Islands and Hawaii. Having a backstory to justify my position not only raised my status in the guests’ minds, it served to remind myself that I actually knew what I was doing.

Still, I was not confident in my ability to pick an itinerary that would work for the allotted time. In the first week I was thrilled just to make it into the dock without any injuries or damage to the boat. Sometimes we’d be five minutes early, sometimes ten minutes late. I chose the same itinerary for every sail trying to keep things simple.

And then one day, guests came onboard and told me what they wanted to do – something they had done the previous year on the same boat. It was time to expand my horizons. They wanted to circumnavigate Shelter Island, located between the north and south forks of Long Island. Even though I had done this journey many times on other boats, this was a first for me on this boat… and guess what? I was 30 minutes late returning to the dock, forcing me to come back in the dark (another first!).

The critical error? On the first leg of the trip I tried to tack upwind for too long without using the motor. I should have been keeping better track of the time but I was overly ambitious – plus I HATE using the motor!

It was a crucial lesson in time management and it was the only time that I’d be that late for the rest of the summer! The guests were happy to have a little extra time and I wove gracefully through the harbor in the darkness, docking without any trouble. It worked out, but it definitely changed the way that I would sail (or… motor?) for the rest of the summer.


In five years of working as a mate, almost all of my captains have uttered a variation of this phrase: “You can’t understand what it’s like until you become the captain.” I wrote this off as a silly, somewhat condescending thing to say. That is, until I became the captain.

Suddenly everything fell squarely on my shoulders. I began keeping an internal log of how much water was onboard, how much coolant, how many drips per minute were coming from the stuffing box. These things became ingrained in my mind; information that I could access as easily as the last time I ate or drank water.

So right before a sail one day, I mentioned to Scott that we should take a fuel sounding. On this boat we do it old school. We have a large wooden dowel that we stick into the tank (like a dipstick for your oil) with markings for every ten gallons of diesel. It’s a flawless system if you check it regularly… BUT on this particular day the guests arrived a little early and I decided to push it.

Flash forward to a half hour before we were supposed to dock, about 2 miles away from the entrance to the harbor.  We were beating upwind against the current when I decided to turn the motor on. A few minutes later the engine puttered and shut off, the low oil pressure alarm blaring until I flipped the key.

OH CRAP! We were out of fuel in the Port tank. I knew that the Starboard tank had a reserve of at least 30 gallons (I mean, I’d cut it close, but not THAT close). I hopped down into the engine room and switched from the Port tank to the Starboard…if you’ve ever run out of fuel with a diesel engine, you know what comes next.

Having run completely out of fuel I had created air pockets in the fuel lines. In order to remove the air, I had to bleed the lines. I put Scott at the helm on a tack that I knew he could run forever (though it was the opposite direction of our destination) and hopped down into the engine room beneath the feet of our guests.

I called my boss and she calmly talked me through what to do. I took a photo and sent it to her before I started unscrewing the nuts around the fuel injectors. Next, I instructed Scott to push the ignition over and over while diesel flooded into the absorbent pads in my hands. At this point there was no hiding our struggle from the guests who were becoming increasingly concerned. After what felt like an eternity, the engine turned over and we were able to head home.

I was given high fives and more than anything else the guests were impressed at my ability to quickly solve a problem that could have potentially been much worse. It’s never a good idea to run your fuel tanks this low and I definitely learned another valuable lesson. Coming in on my day off to change the fuel filter in case it had been contaminated with gunk from the bottom of the tank solidified my commitment to never skip another fuel sounding! The bonus lesson learned was that I have the ability to react calmly and methodically when sh*t hits the fan. That skill is a MUST.

PHASE 4: ANGRY FEMINIST aka NO, I don’t need your help.

In my years of working on charter boats with mostly female captains and crew, I have had my fair share of encounters with the chauvinistic male. I’ve seen entire groups of people sit on the dock waiting for the Captain, not realizing that SHE was already onboard. It’s never bothered me much; it has always just seemed kind of funny.

Until the day a guy came out with us talking about guns and women and completely belittling his wife and daughter every chance he got. Ten beers later, he began to inquire more and more about the dynamic of the relationship between me and Scott. It was no secret that we were a couple and that I was in charge but he kept questioning my authority. When I asked Scott to quickly crank in some lines, the guy shouted, “You could say PLEASE!” in defense of Scott.

Now trust me I DO say please most of the time. Scott and I have a very healthy, loving relationship – we’ve even discussed that when things need to happen quickly on the boat it’s okay to ditch some of the niceties. When I tried to picture this guy saying the same thing to a male captain, I knew that it would never happen. It pissed me off. To me, men telling women in positions of power that they should say “please” more is completely demeaning.

Now, it definitely wasn’t just this one guy who made me angry. It was a combination of little remarks over the years that made me take this one incident so harshly. In the Virgin Islands alone, I had men whistle at my ass while I was pulling an anchor up, tell me that I’m too pretty to be working on a boat, grab my hands to feel my “sailor callouses” and one charmer even touched my lower back to “rub in my sunscreen” while I was raising the main sail. Being a woman in a completely male dominated industry can present challenges that you never expected to encounter.

Instead of using my jiu-jitsu skills to break his arm or flipping out and telling him exactly what I thought of him, I did what women have done for centuries: I smiled and nodded. The angry feminist phase lasted for maybe two sails after this, but I quickly realized that people are just people and many don’t even realize when they’re offending you. It’s better to just take the hit and roll with it because at the end of the day I don’t need to prove anything to anyone.

PHASE 5: WEATHERWOMAN aka I’m Captain, Not God.

After just a few sails I began to feel completely in tune with nature. Even on my days off I would feel a breeze on my face and notice the direction it was coming from. I started to pay closer attention to the clouds and the tides, knowing how they would later affect me. This is one of the best parts about working outside for a living – being aware of the world around you.

But just because I could read the weather didn’t mean I had any control over it!

On days with absolutely no wind I would still hoist the sails, turn the motor off and watch the boat bob in the waves just to remove all doubt. Too many times I have had guests onboard complaining about some other captain who “didn’t even put the sails up” on their last charter; I will NOT be known as that captain.

At the same time, people have to be reasonable. If we launch the sails and we’re not moving, but you also want to sail around Shelter Island without using the motor, it’s just (obviously) not possible. I don’t get what these people think. Do they think that everyone is trying to scam them? Do they think that I became a sailboat captain because I enjoy motoring more than sailing? Do they think that I’m too lazy to (tell Scott to) raise the sails? Really… I don’t get it.

In this phase I finally came to the realization that if I phrase things in a way that the average landlubber could understand I’d have much more success. I would try to convey that even though they felt wind before when we were motoring, it wasn’t actually windy. It’s like the breeze you feel through a car window – when we’re moving faster, the air is going by us faster. It’s called apparent wind, and apparently this confuses people.

PHASE 6: CHILDREN aka the best birth control I’ve ever known.

Parents listen up: I did not go through the effort of becoming a captain just so that I could watch your kids. Maybe I have the look you’d expect from a babysitter, but that’s actually not my job. No, my job is making sure we all survive this day (as in I have your actual lives in my hands, not just your rosé).

Don’t get me wrong, most of the parents that we took out last summer were pretty awesome. I mean, booking a day out on a sailboat with the kids? How cool is that?! I have no issue with parents asking for photos, sharing stories about the kids or even venting about summer camp.

What I do take issue with is when parents bring young children onboard and decide that their day will be more about drinking rum punch than parenting. We are on a moving boat people; this is NOT the time to experiment with hands free parenting! We’ve had kids smear brownies into the seat cushions, threaten to jump overboard, pull the emergency fuel shutoff and try to take the sails down. Listen guys, we all want to have a relaxing day and if you know you’ve raised a monster, bring a sitter!

It’s when I reached phase six that I knew I had officially made it. Do you remember all the way back in phase one, when I was just trying not to kill anyone??? Now I am sounding like a real salty sea captain! Hooray!

All kidding aside, working with Scott on Surprise last summer was one of the best experiences of my life. I was able to constantly push myself out of my comfort zone and tackle so many different fears in a matter of three months. Did I mention we made great money? Given our minimalistic lifestyle, Scott and I will be able to make it through the whole off-season without working again and even put a little into our retirement funds!

Deciding to become a captain wasn’t the easiest choice I ever made. Had I chosen to run away on day one I would have been able to find a safe, comfortable job in a café, at an office or a bank. Nobody would have blamed or judged me, in fact many may have found it to be the responsible thing to do. Here’s my advice for this life because we’re only given one shot: don’t chase money, don’t chase responsibility and don’t chase what you “should” do; chase your wildest dreams, chase happiness and always chase the challenges.

Pin it for Later!

I hope that you found this post encouraging. I’m dedicating this year to helping people push outside of their comfort zone in pursuit of their dreams. Leave a comment or send me an email with a fear that you plan to tackle in 2017! Don’t know what you want to do with your life? Here’s some inspiration from some badass ladies!

She Quit Silicon Valley to Captain Boats in Hawaii

Seeing the World Through the Eyes of a Sailor: Captain Bridget 

ALSO: Check out my free guide to finding a job on a yacht.


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