Sportfishing Captain: Living the Realistic Dream

Maintaining the balance of passion and purpose

May 20, 2019
a sport fishing boat out on the water
Sportfishing Captain: Living the Realistic Dream Courtesy Bayliss Boatworks/Ray Matthews

The life of a sportboat captain is usually portrayed as a glamorous, adventure-filled occupation. But all too often, the reality of the job isn’t front and center for the public to see. Many dream of being at the helm of these amazing boats—backing into the scales with a tournament winner on deck and traveling the world—all without knowing the true reality of what they are wishing for.

I was there 20 years ago. Through a relentless amount of hard work and sacrifice, I am lucky. I am one of the few who, after years of trials and tribulations, have managed to not only keep my job, but also keep my family—which in this business is the hardest part. There are a thousand jobs, but you have only one family.

By the age of 25, I had traveled the East Coast, West Coast, the Caribbean and Central America, and I got paid to do it. I have worked for NBA superstars, celebrities and Wall Street moguls, living out my wildest dreams. As a younger man starting out, the endless days spent fishing and traveling from one spot to the next never fazed me. I didn’t blink—I just kept going.


And like all of us, I remember like it was yesterday: I had just finished up 10 days straight with the boss, sitting at a bar in Cabo San Lucas, Mexico, ready to unwind. I was in my early 20s, surrounded by the Who’s Who of captains and boat crews. The epic fish stories just seemed to keep coming one after another. At that point, the only thing that could have made my day better was if Jimmy Buffett came out of the back singing Son of a Son of a Sailor, then paid my bar tab. It was heaven. Little did I know how it would play out in the life that was ahead of me.

The Van Dellens, with their three children Autum, Liberty and John III, invariably live a real career/life balancing act—vowing to make it work even with John’s grueling travel schedule. Chris Rabil Photography

The Passion

Sitting at that bar in Cabo you would have thought: This is the life. How could it possibly get any better? As many old salts will tell you, be careful what you wish for, because you might just get it. At least that’s what I tell every wet-behind-the-ear greenie that I meet or bring onboard. This job—this life—is definitely the stuff dreams are made of, but we don’t get to choose which dreams we have from one night to the next.

I have had plenty of nightmares also. The truth of the matter is that the days are long and the work is endless. Between the boss, the boat and managing the crew, every minute of every day is consumed. This leaves very little time for family, rest—and honestly, there is no such thing as a vacation. After all, we live on vacation, right?


The road traveled to the bridge is a wild ride filled with ups and downs, taking many years and miles, missed holidays and daily sunburns before you know it.

Today’s sport-fishing captains will readily tell you about all the years of free boat washes just for a chance at a mate’s job, or charter fishing trips in hopes that they would take home a good tip—because hope was all they were guaranteed. Or the numerous days of commercial fishing to fill the box and pay the bills. Everyone’s ride is different, and no two are ever the same. There is one common denominator, however, and that is passion.

I have found that the biggest factor in the success or failure in this, or any other job, is the passion that drives you. Is your passion pure or is it motivated by something such as the need to be in the spotlight? The level of passion is what will make you, and ultimately break you. Without it, you will never last. The paycheck and 30,000 Instagram followers aren’t going to get you through a four-day canyon trip or the 10-day stint offshore trying to fill the fish box. It’s going to be the passion—the driving force.


We were newly married, without a dime to our name and had just moved to St. Augustine, Florida. I came home one day excited to tell my wife I had met someone at the tackle store and he wanted to go out fishing. I hadn’t been on the water in months, so I was ecstatic.

The first thing she said was, “How much is he going to pay you?”

With a blank stare, I just looked back at her and mumbled, “I don’t know.”


Her reply? “Well, figure that out.”

As it turns out, I got $500 for three days, a happy owner, and boxes full of amberjack, dolphin and a sailfish. Money didn’t drive those three days, passion did.

man in sunglasses and cap with daugher in his lap
Capt. Taylor Hansen with his youngest daughter, Teegan. Courtesy Capt. Taylor Hansen

The Temptation and Vices

Now, with some cash in hand, you’re fishing the best destinations and part of an elite group of captains and crews. That’s all grand, but after the boss is gone, the boat is clean, repaired and ready to head back out, you are faced with your downtime. You find out fairly fast that there is a reason why most people only take weeklong vacations in paradise: After a week, all the bases are covered and you’re left with a bar stool and a cute bartender.

The atmosphere in which we live and work is one of extremes and excess. The locales are as noteworthy for their nightlife as much as they are for the fishing. Coupled with a $6 million floating piece of furniture and a disposable income, you can get in a lot of trouble fast. I have seen countless captains and crewmembers fall victim, myself included. Before, trouble was never even on my radar, but now as a husband and father of three, it’s at the forefront.

The Purpose

Don’t get me wrong, I still love to travel, and I have my favorite restaurants and bars along the way—but 20 years later, I have to be purposeful. I have so many great friends who are family guys like myself. Capt. Taylor Hansen on the 68-foot Bayliss, Blue View, is probably one of the most disciplined guys I know, with a program that keeps him from home 180 days per year. After speaking to him about the routine of being on the road and having a family, I get inspired.

“We start every morning with a FaceTime call,” says Hansen, which includes not only his wife Ashley, but also his two daughters, Taylie and Teegan. Every evening he’s FaceTiming again, making sure all is good at home and to say goodnight.

His purpose is evident. But, a FaceTime call every morning and evening is not going to get the family through the daily struggles or important milestones that are missed by a traveling father.

“Taylor’s schedule makes it very difficult to plan anything,” Ashley says. “Family vacations, weddings, not to mention missed birthday parties, plays and church events.”

Hansen wholeheartedly agrees, and says just being away from home is difficult—on Ashley, especially. “All of my husbandly roles get added on to my wife while I’m gone,” he says, but his wife does her best to support him, offering up this piece of advice to other wives in the same position: “Never give your husband a hard time for [doing] his job, always build him up; he’s working hard to provide for you and the family.”

Every year as I turn the compass homeward, I initially think about what needs to be repaired or what our next season might entail. But once the boat hits the dock in its home port, an even bigger task moves to the top of my to-do list. The biggest repairs I try to address are those relationships with my wife, my children and my friends.

As you come into your own—as both a captain and a man—you begin to reevaluate what is most important. Sure, your job is important because it’s your career, but for me, it’s my family.

It’s not an easy life as a captain’s wife, constantly being put through the ringer: Going through hell and back, moving from here to there, and countless days alone with the little ones. When I finally make it home, the last thing she wants to hear about is how tough the bite was, or how happy the boss was as he left the boat.

Once I hit that driveway and step through the front door, it’s game on, just like the shotgun start at the Bisbee’s Black and Blue. Time to win my girl’s heart one more time. Time to be the hero to that 7-year-old boy wearing your old visor from years past, and time to hug those little girls who roll their eyes at you—just like their momma does.

The balance of the extremes is the job. Lights Out‘s Capt. Chester Sims knows all too well the balancing act of keeping a home and a boat program afloat. He and his wife, Farron, have a 2-year-old son, Chase. They own two homes, four horses and two Labrador Retrievers. Farron’s a superwoman of a wife and probably wears a cape.

The Sims family lives in Key Largo, Florida, in the wintertime and outside Ocean City, Maryland, in the summer. To make sure everything is covered before Chester hits the road—which is often for three to four weeks at a time—the Simses rely heavily on their extended families to help out.

“When we are in Maryland, my family still lives four hours away,” Farron explains, “but they will come up and watch Chase if I need them to. When Chester is gone, I go down and stay with them so I’m not alone.” Family and friends are essential to couples in this business, especially when those couples are trying to raise a family.

“Being apart is the most difficult,” she adds, “but I am very thankful the family he works for makes sure we are never apart for too long.”

Luckily for the Simses, the Lights Out owners are very family-oriented themselves, and take Chester and his family into consideration when making their program’s plans.

Sims says his family’s safety is always on his mind, no matter where he is. And the feeling is mutual: “My biggest fear is Chester having an accident on the water, or something bad happening with Chase,” Farron says, “[but] I understand the demands of his job when he’s gone, and we both work hard to try and make things easier on one another when we’re apart.”

Sims has to be all things to everyone in his circle. He has to be successful on the tournament trail, but also wants to be just as successful at home. He works hard not only to provide for his family, but to stay in a position where his employers allow him the opportunity to do what he loves. They also grant him the courtesy of knowing that Sims is not a machine, but a real person, with a real family—just like theirs. These are the types of people that I look up to—not the guys with 30,000 Instagram followers.

The Goal

In the end, it’s not how many fish we catch or how many tournaments we’ve won, it’s about keeping our relationships healthy. This business can very easily tear your life to shreds, if you let it. From the outside, it looks so carefree, but it’s not at all. It’s hard work with a responsibility for human lives and an incredibly expensive boat that you could never replace in 10 lifetimes. This job will eat you up and spit you out, leaving you alone on a barstool in Cabo, telling old fish stories to whomever will listen.

My goal is not to scare anyone away from a career in sport fishing, or shatter anyone’s dream of taking the helm and traveling around the world, but to candidly shed some light on the realities that are rarely discussed—so future generations can not only be better crewmembers, but be better people. Keep an eye on the snares that lie in wait for you in every port, and the pitfalls that could damage relationships along the way.

I will not always be at the helm of Singularis, or any other boat, for that matter. Today could be the last day I get to feel its rush under my feet; it also could be the last day I get to hug and speak to my own loved ones. Catching hundreds of billfish is not what makes you a man, and pretentiously building self-worth based on the rig you drive, the tournaments you win or the brand sponsorships you acquire will soon have you finding out what lonely really is—and there will be plenty of room for you on that bar stool in Cabo.

So, when all these rides around the sun end, I hope before they call me a good captain, a good fisherman—they say I was a good man.


More Travel