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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...

What Happens When Pirates Lose Their Gold?

Have you ever seen someone lose track of their thoughts halfway through a sentence?

Have you ever been that person?

The feeling is amplified about ten times over when you lose track of your goal halfway. Maybe life got in your way. Maybe you weren’t specific enough about what you needed to do.

Maybe you just plain forgot. (Some of us are like squirrels: easily distracted by shiny objects.)

How do you get back in the game when you forgot you were playing one to begin with?

Reevaluate the treasure at stake.

If you forgot your goal halfway through, there’s a decent chance it wasn’t a goal that really matters to you.

If you don’t care about your goals, you’re not getting to the heart of your real passions and dreams.

Ask yourself: Is this actually treasure I care about? Do I really want this for myself?

Here’s a cheat sheet of questions to answer:

  1. How does this goal bring me closer to my real passions?
  2. How does working towards this goal make me happy?
  3. Where will I find myself in life if I quit this goal?

Maybe it’s still worth it.

Sometimes life is truly overwhelming. In fact, it’s healthy if you can completely block out the stressors in your life every once in a while.

…but as a pirate ninja, you have to be able to learn to tune back into your motivators. Motivation is a positive stress. (Yes, there is a difference between negative and positive stressors.)

You need to determine whether you were escaping your goal as a healthy tactic to recharge, or whether your goal is just something that simply isn’t important to chase.

Think like a Captain.

In the Golden Age of Piracy, the decision to continue working towards a lost treasure was a matter of life or death. A good captain knew when it was time to call it a day. He knew when it was time find a new treasure to chase. On the other hand, the captain also had to make the call when they should keep pursuing that same treasure.

You’re the captain of your own life. Is this treasure worth it?

Still in? Rethink your strategy.

While some strategies require time and persistence to prove valuable, you still have to follow that strategy in the first place. You would rather follow a less effective strategy (that still works) than only pretend to follow a much better strategy.

If you’re not sticking to your strategy (or you have been, but it’s not working) it may be time to change things up a bit.

The very act of reevaluating whether you care about this treasure may have stirred up enough motivation that you don’t need to rethink your strategy. On the other hand, you may be inspired with a new approach.

Here’s a cheat sheet to think through whether you need a new strategy:

  1. If I’m being honest with myself, am I sticking to my original strategy?
  2. Is that strategy showing progress, even if only a little bit?
  3. If I create a new strategy, will I be able to commit to it?

Maybe you need a new mental approach.

If it turns out that you just need that kick in the butt, start thinking about when you get your best work done.

For example: I’ve noticed that my friend Loren and blogger at Unlifer does his best writing on the days he doesn’t overcommit to work.

He might want to shoot for smaller daily goals to avoid unnecessary stress. That stress seems to stop him from succeeding – and makes the pressure worse every following day when he remembers how he failed the day before.

Think like a Captain.

If you constantly ask your crew (your brain) to work at 100% performance all the time, you’ll have a mutiny on your hands before you know it.

Find the balance of hard work and encouragement. You have to stay energized and excited. Stick to bite-sized goals, small wins, and an keep your eye on the prize.

Evaluate whether you need a break, or a harder push. Everyone operates best in different conditions. You have to experiment and see what keeps you on track over a sustained period of time.

Is your strategy working or do you just need to experiment with the way you put effort in?

Go for the small win.

Staying inspired is hard when you feel like your entire ship has been sunk. It’s not easy to keep sailing forward when the sky is stormy and the future looks bleak.

That’s when you need to go for the small win.

Lost your ship? Get on dry shore and begin looking for your next one. Find that strategy that works. Planning a strategy is a win all by itself.

Need a more effective approach? Pump up the crew with a brainstorming session on what keeps energy high and motivation strong. The act of gathering your thoughts and ideas is a win.

Each and every baby step that relates to your goal is a win. You’re reading this, aren’t you? That’s a win. Count it. Keep it. Hold it up as a prize.

This is your win. Own it.

Here’s your cheat sheet for recognizing wins:

  1. Does what you’re doing relate to the overall goal?

If you can answer “Yes” once per day, you’re winning.

Maybe you’re not after a measurable goal.

How will you know when you’ve achieved the treasure? If you’re going for a lifestyle change, that’s great, but using life as a measuring stick can be overwhelming (and depressing, when you get sidetracked).

Keep track of the small wins. Every win is progress.

Gather your lessons from the fails, then throw the rest out.

Then, make sure that your overall goal can be measured. You won’t recognize the wins if you don’t know how to measure them. Pirates have the upper hand here: gold is easy to count. How do you count yours?

Think like a Captain.

The captain of the ship is in charge of doling out rewards, payments, and punishments. A good captain knows that if he only hands out punishments, he’ll lose his crew. To keep everyone in line and the ship in tip-top shape, he’ll keep the crew well paid and constantly remind them of how they’re getting closer and closer to the next payout.

Keep the goal in mind, and remind yourself of the payouts you’ll receive by taking each step close to your treasure.

Stop making excuses.

You’re the only one who really controls your life.

The things you believe, your hopes and dreams, your passions, your goals… those are in your control. No one is going to hand those to you. They are yours.

The problem is that there are a lot of excuses that are handed to us. Some of them are pretty solid, too. There’s a lot of predetermined things in our lives we have little-to-no say in: The family we’re born into, the schooling we received as children, the neighborhood we grew up in, the beliefs we were taught by our parents. The economy we live in. The government we’re under. The bureaucracy of typical corporate life.

How much of that do you use as an excuse to not change your life?

Maybe you need to open your eyes.

Living differently is hard.

We are fighting the norm. We’re proving that you can live on your own terms, regardless of the circumstances around your birth or the things your teachers told you about your IQ scores. We’re proving that you can live out-of-the-box. We’re proving that you don’t have to follow the recipe taught to us our whole lives.

If you’re satisfied to use your circumstances as an excuse, you’re in the wrong place. Your feelings of failure are a self-fulfilling prophesy, because when you accept excuses – no matter how legitimate they feel – you’ve quit. The only person you’re fooling is yourself.

Anything worth doing isn’t easy.

Think like a Captain.

When you’re the captain of the ship, there’s a lot out to get you. No government is OK with you existing in the first place. Every single ship in the ocean is your enemy. Chances are you didn’t exactly grow up in a nurturing childhood.

In other words, a pirate captain is fighting every situation life ever handed them.

You’re the captain of your own life. The waters are dangerous. If you want to be in charge, you’ll have to actually take the helm and guide your ship wherever it is you want to go. Nobody else will do it for you.

– Anne
Captain of the Pirate Ninjas

P.S. I wrote this article from my personal experience. Over the years, I’ve struggled with working towards goals and how to get back on track when I get derailed. This weekend was a huge distraction for me – from my health & fitness goals, to my writing goals, to just about everything I’m working on right now. I hope that these tips help you as much as they help me when this happens.

We’re all human and get off track at one point or another, but we have to remember the bigger picture and get right back on board.





  1. Avatar

    I think i’m a squirrel cus i get so easily distracted by shiny things and unusual things and everything else it seems. I still don’t know what i want to be when i grow up.

    • Anne Dorko

      Haha!! I am the same way 🙂 And honestly, I think that a lot of people feel that way – not knowing what they want to be when they grow up (no matter how old they are). Age is just a number, right?


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