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4 Tactics For Becoming an Unconventional Tourist

The following is a guest post. My love of unconventional travel started when I was 12 years old. My dad had decided that, of all the ways to spend Christmas, we should go on a cycling tour around Cuba. And so we did it. We figured out how to...

I Hate Hair: Reasons Why Shaving Your Head Skyrockets Confidence

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world. Enter Aron James: Hair loss is something that happens to our grandfathers. It is the sign of the wisdom that comes with old age; a rite of...

How to Be a Solo-Female Hiker: Put One Foot in Front of the Other

Welcome to #DifferentLifeStories, where Without Boxes shares how people are living differently right now in the real world. Enter Hayley Turner (a.k.a. Little Foot): I can still remember everything about that day, from waking up and walking 12 miles by noon, the dogs...

Do You Really “Find Yourself” When You Travel?

"I know this sounds cliché, but I have to ask—do you really 'find yourself' when you travel?" the girl asked me. Her young friend crouched next to my table, gently stroking the cats as they slept. Café Neko is a small coffee shop in Vienna that allows cats to wander...

When Not Everything Goes as Planned, It Still Goes: A Story About Finding Your Passion

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world. Enter Jen: As a kid, I was told that I was lucky that I already knew what I wanted to do with my life. From age four, I knew I wanted to be...

The Digital Nomad’s Roadmap – A Complete Guide: Successfully Live, Work, and Travel Anywhere

So you wanna be a digital nomad. I’m not surprised: the future is bright for freelancers and location independent workers. Statistics show 40% of Americans will be contingent workers by 2020. That’s a lot of potential for digital nomads! Yet there’s no hands-on guide...

Limitations: Why the 9–5 Job Doesn’t Need To Stop You

Over the years I’ve had a number of conversations with people who talk about cool things they want to do, see, or make. A lot of these conversations end with “Well, I’d love to do it, but unfortunately I have XYZ,” and many times those XYZs are very valid limitations...

Stealing Second Base: From Side Gig to Self Employed Full Time

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world. Enter Katherine Stimson: “You can’t steal second base with one foot still on first.” In the spring of 2010, a Facebook ad posted by a total...

Dreams Are Like Pirate Treasure: Hard to Find, But Worth the Risk

All dreams start somewhere and typically, no matter the size of the overall dream, most dreams start small. Let’s say yours is to feel better at work every day. You focus on sitting up straight in week one. Week two finds you taking a 10-minute walk at lunchtime. Week...

How to Set Goals And Dominate Like Bartholomew Roberts

Setting goals is an art-form that you should always be perfecting, but in the meantime you really need to catch up with the times and learn how to set goals you can actually achieve.

I only tell you this because I love you.

That, and I have spent most of my life setting all sorts of crazy goals. This is partly to remind myself to stick to what I know works.

Pirates are well known for their ability to score ridiculous amounts of booty — and they clearly were living on their own terms, so I think it only makes sense to emulate their tactics. We’re going to be taking a closer look at the tactics and strategies of the most successful pirate of the Golden Age of Piracy: Bartholomew Roberts.

I like to handle things by directly dealing with problem areas, so I’ve picked out 5 major issues I’ve seen people struggle with when setting goals.

Problem #1: You’re not seeing the little picture.

“Wait, what?” you say, frustrated with this problem. “Everyone always told me to look at the big picture.”

Being able to see the big picture is a great start, but when you’re working towards a goal, you already see the end result you’re hoping for in your head. The real reason that you’re having trouble succeeding is because you haven’t figured out how to break your BIG goal into a bunch of SMALL goals.

How Roberts Would Have Done It

Before I can tell you how Roberts would have done it, you need to know a little bit about how Roberts became a pirate.

Roberts started out working in the merchant navy for £3 a month. If I did my research correctly, that translates to approximately $560 USD in today’s terms (calculating for inflation and currency conversion). In other words, he was dirt poor.

Since this was during the Golden Age of Piracy, it wasn’t long before Roberts’ well-to-do ship was taken over by Captain Davis and his pirate crew, and Roberts was forced to put his talents of navigation to work for them. Shortly afterward, the ship he was on was captured by other pirates and Davis was killed. The crew that remained elected Roberts as the new Captain due to his wicked skills and charisma.

So what did Roberts do first? He decided it was in his best interest to avenge the deceased captain. That was his big picture.

Instead of barging in without rhyme or reason, he had to think everything through and create an approach that would bring him to his ultimate goal of revenge.

In order to do that, he broke his overall goal into easily solvable problems that he could manage.

He created a step-by-step plan with a clear end result:

  1. Land on enemy territory at night.
  2. Eliminate most of the men.
  3. Plunder goods.

This allowed him to simultaneously avenge Davis, establish authority, and profit himself and his men. Mission accomplished.

Once he broke his goal down into a step-by-step plan, he likely went into a lot of detail for each step of the way. I wasn’t there, so I can’t say for sure.

The moral of the story is: Breaking down your goals into small steps you can easily accomplish will lead you to success.

Problem #2: You’re taking on too much.

One doesn’t go from being a start-up pirate captain to becoming the most successful pirate in the Golden Age of Piracy all in one day.

Chances are you’re trying to get too far, too fast. You can only handle so much at one time. Your dream may be total domination, but you’re going to have to settle for concentrating on something smaller to get started: Say, dominating your current city.

It’s important to remember that our dreams usually aren’t definable, measurable goals. You may one day attain your dreams, but more often than not you have to get strategic about setting smaller goals in order to reach them.

It’s not always a glorious beginning, unfortunately.

You can’t become a master violinist in a week. You can, however, train to learn correct posture and fingering techniques by practicing every day, instead.

You can’t become a master writer in a week. You can, however, begin learning current writing standards and practices that are directly related to your ultimate writing goal (sales copy, e-books, published books, etc).

How Roberts Would Have Done It

Once Roberts accepted his new role as a pirate captain, he knew he was signed up for a whole new life. That meant new priorities and new goals.

Instead of immediately setting out for worldwide pirate plunder unprepared, his first step was to build up his resources. How did he do that? He started by adding 2 ships to his fleet.

If he were you, he would make sure he prepared himself the same way, no matter what your goals are. That said, sometimes the answer isn’t as simple as needing a bigger fleet.

Resources can be anything from literal tools, to education, to teachers, to a group of individuals who will help you hone your skills. Which resources you need will change depending on the nature of your ultimate goal.

The moral of the story is: You need to spend some time identifying the resources you need before taking your first steps forward.

Problem #3: You’re not structuring your life.

Most of us go through our daily lives without thinking too hard about why we do what we do. We do it out of necessity to protect our sanity.

The problem with this is that you’ll never achieve anything that takes effort that way. How does the saying go? Nothing worth doing is easy.

When you’re striving towards a goal, it’s time to really analyze why you spend time on the things you spend time on. When you’re working towards a personal goal (and not one with a team) …you are your own crew.

Crews need direction to succeed. More importantly, you need a direction to succeed.

How Roberts Would Have Done It

It wasn’t long after Roberts career got started that they attacked and looted their first real bounty. Before things got out of hand, he decided it was time to provide his crew with a code.

That Code would provide them with the structure they needed to keep themselves focused and successful. Each and every member of the crew swore to uphold it on the Bible.

Roberts had his own code, too.

He was known not to bother with things if they didn’t need to be done — good, or bad. While he didn’t care for his prisoners as well as some pirates did, he never treated them worse than he felt the crew demanded it. Well behaved passengers often received gifts. He was precise and specific with his actions. He did not hesitate when it was time to get a job done.

The moral of the story is: You need to create a code of conduct for yourself. By establishing rules that are designed for your success, you’ll find yourself naturally moving towards your goals even on autopilot.

(Automating success… now that is something else, isn’t it?)

Problem #4: You’re not being specific enough.

We began to uncover this problem in #1 on the list, but even when you break your big goals into smaller goals, it isn’t always enough. If you’re making general goals like “get in better shape” or “become a guitarist”, you will never reach them because that is not a measurable result.

Those aren’t goals at all… those are generalizations.

Instead of saying “Get in better shape”, you should be defining what “better shape” means to you. For example, I want to have a visible six pack at least for one day of my life, before my next birthday. By creating a specific goal, I’ve been able to find a lot of small but effective ways to work towards getting in shape.

Instead of saying “Become a guitarist”, you should be defining what “guitarist” means to you. For example, maybe you want to be able to play a specific song, or record at least 6 of your own tracks. By creating a measurable goal, the next steps will become abundantly clear to you.

Your goals need to be measurable.

How Roberts Would Have Done It

It’s very unlikely Roberts ever thought in terms of wanting to become one of the most successful pirates in history.

Roberts was a highly focused man, with great charisma and the knowledge of how to get what he wanted. He became so successful because he stuck to specific and simple goals.

Roberts’ pirate career lasted for a very short four years, but he looted well over 400 ships in his time. His boldness came from a knowledge that in order to succeed unfailingly as a pirate, he needed to lay waste to anyone and everyone in his path. With that as his directive, it became a simple matter of planning how to tackle each encounter that came his way.

The moment you can stop second-guessing your directives and specifically outline your goals, figuring out what to do will stop being so difficult.

The moral of the story is: If you are having a hard time figuring out your next step, you haven’t gotten specific enough.

Problem #5: You think life is predictable.

More often than not, once we’ve set out on a goal it feels as though every life event that could possibly interrupt it gets in the way.

The odds are stacked against you. Your brain will find every distraction, every excuse, and every reason you should stop working so hard at something. Once the euphoric feeling of beginning a new journey is over, the gloves come off.

That’s because you went into this thinking that your willpower would carry you through the fight. Guess what — your raw willpower is almost never going to be enough to see you through. You have to put yourself in a situation where you can’t fail for fear of drastic consequences, or set yourself up for success by anticipating failure with a plan to fight it, and create yourself a net of accountability.

One way or another, you have to be ready for life’s changes. You have to know when it’s time to give up goals, or modify them for your new situation.

How Roberts Would Have Done It

Think way back to the beginning of our story with Roberts. Roberts was probably just hoping to become a great navigator working in the merchant navy when he first started working on the merchant navy ships.

Life changed. Pirates captured him and put him to work.

Roberts didn’t give up his dreams as a navigator. He rolled with the punches, stepped up to the plate and decided he would take advantage of his new situation by owning up to his true potential.

His whole philosophy changed, he decided that being a commander was better than being a common man, since by then he had dipped his hands in muddy water (a.k.a. performed dirty deeds) and was already a pirate.

He was able to fulfill his dreams of becoming a master navigator, but not in a way he ever would have imagined to begin with.

It’s time to set a goal.

Once you’ve taken a moment to think about what your dreams have always been, you have to start thinking about what that means for your life in the upcoming days, weeks and months.

You need to pick some goals that you can break down into step-by-step plans, and get yourself an accountability team.

In fact, you should consider participating in the Life On My Terms challenge, which is launching right now. 

All you have to do is pick 2 goals, get a video camera, and take 1 minute to talk about what you did yesterday about it, and 1 minute to talk about what your mini-goals are that will bring you closer to them today. As a community, we are all going to be each other’s accountability partners through the month of November, and you can change your life by being a part of it.

Upload it to YouTube and tag it as a video reply to the video I just posted this morning, and you’ll be ready to go.

Anne Dorko
Live streaming musician. Risk taker. Mindful queer. Digital media producer. World traveler.

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