Skipper Trick #2: Ask for Help

Meet Vincenzo and Angelo Messina, seen here giving their skipper father a leg-up.

Meet Vincenzo and Angelo Messina, seen here giving their skipper father a leg-up.

As a skipper, you may consider yourself a cowboy, a rugged individualist, a workhorse, etc. You’re the kind of man who builds empires on sweat. But slow down, there, Andrew Carnegie. You’re probably a little more like the father of Vincenzo and Angelo in the picture up there. An Italian immigrant, he built a bakery from the ground up, and by 1917, it was running all the time. But he wasn’t the only one running it. Vincenzo, age 15, and Angelo, 11, worked long hours to help their dad make it.

Asking for help is tough. It makes you feel powerless. Humiliates you.

Help from others is one of the most important aspects in a skipper’s life. Learn to deal with it. Take some advice from famous skippers of yore:

William F. Buckley, Jr.: You are already dependent.

WFB’s parents were incredibly wealthy and gave him every advantage. Instead of taking his natural leg-up for granted, Buckley went to work like crazy, publishing his first book to national headlines at the age of 26. He worked tirelessly until he died. The Heritage Foundation offers this little anecdote about him:

Reagan speechwriter Peter Robinson recalls when he was doing research for Buckley on his latest book. “Bill,” he said one day, “you were born wealthy and you’ve been famous for 30 years. Why do you keep working so hard?”

A surprised Buckley replied: “My father taught me that I owe it to my country. It’s how I pay my debt.”


Buckley saw his good fortune neither as something to be denied nor as a mark of shame. Rather it was a call to work even harder. He recognized that he was already receiving support from others. This is lesson one in asking for help: You are already dependent.

Sir Francis Drake: You can’t stall in your ventures.

Sir Francis once wrote to his comrade-in-first-names Sir Francis Walsingham the following:

There must be a beginning of any great matter, but the continuing unto the end until it be thoroughly finished yields the true glory.

Having pillaged the Spanish Armada, Drake didn’t stop and rest. He knew that taking control of the oceans was no one-battle venture. However, he couldn’t do it all with his own little fleet. And he didn’t have time to wait until he could; the Spanish would rebuild if he did.

You, too, don’t have time to wait. As a skipper, you’re taking advantage of every bit of time available. But you may not have cash, or a truck to carry things, or a car seat, whatever. But if you wait until you have them, you’re not skipping. You’re taking the average route.

John Quincy Adams: A powerful move is good, but the right stand is better.

A separate post on JQA is forthcoming. What a skipper!

In a letter to his father, John Quincy Adams wrote the following:

My toast would be, may our country be always successful, but whether successful or otherwise, always right.

You’re young. You’re inexperienced. You’re working as hard as you can to skip ahead. Skipper, the odds are against you. JQA’s quote offers some refreshing perspective. Instead of pushing on to do well in all you do, push on to do right in all you do. Success must follow some objective standard, and if you’re pushing towards that objective, your powerful moves will come as de facto decisions.

Asking for help doesn’t mean you’re weak; it means you’re trying to get things done right. Those who do things the right way are not helpless; they’re powerful.

Theodore Roosevelt: You can’t help others if you’re just scraping by.

Roosevelt was a weak child, prone to sickness and generally living as an invalid. Had it not been for his father’s help, he might have stayed that way all his life. Instead, his father charged young Teddy to take up regular exercise, a practice that would become central to his idea of manliness. Ignoring doctors’ worries, TR climbed the Matterhorn at age 22.

His story, of course, doesn’t end there. He went on to lead a life of public service, family devotion, and general gain. He couldn’t have done any of it without his father’s help. He’d have been stuck.

The same is true for any skipper today. Your life is mostly ahead of you. Will you leave it average because you’re too arrogant to see that others can and will help you?

When you ask for help, remember these four thoughts:

  1. You are already dependent.
  2. You can’t stall in your ventures.
  3. A powerful move is good, but the right stand is better.
  4. You can’t help others if you’re just scraping by.

How have others helped you in your skipping endeavors?