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“Taking Risks” Is Not the Same as “Doing Hard Things”

Recently I’ve been noticing that I haven’t been taking enough risks. I don’t want to be complacent! And I always want to be challenging myself.

I’ve also been saying that I don’t feel like I have a big idea or am doing something hard. For a long time, I could immediately identify a major goal I was pursuing that required a lot of attention, investment, and sacrifice.

But in trying to move forward and make some changes, I think I’ve been making a mistake: taking risks and doing hard things are not necessarily the same.

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If You Lost Everything, Would You Look Back or Look Forward?

I went to the hotel gym one morning while I was traveling. When I finished on the treadmill, I went back to the elevator to head down to my room... except there was just one problem. Yep, once again I’d forgotten my room number.

I spend 100+ nights a year in hotels and still haven’t perfected a system for remembering where I “live” on any given night. Sometimes I carry the little check-in envelope around in my pocket, and sometimes I take a photo of the door, but at least once every dozen nights, I start to walk back toward my room before realizing I have no idea where it is.

This time, I tried to retrace the steps that took me out of the room and to the gym. Was it 1406? I thought it was. It sounded like the right number.

I went back to floor 14 and everything felt familiar. I turned down the hall and came to the room, which looked like the right one. The door was slightly ajar, and I assumed I’d mistakenly forgotten to close it all the way when I left. Not ideal, I thought, but it happens.

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“I Can’t Be Jealous of the Past. I Can Only be Jealous of the Future.”

I recently went to see Peggy Guggenheim: Art Addict, a curious film in the sense that it focuses much more on the subject’s love life than it does her love of art. Still, it was good overall and I’m glad I went.

The film showcases the development of several abstract and other non-traditional artists, including Jackson Pollack. I've always liked Pollack’s work, but I don’t think I understood the audacity of it until seeing this new film.

I often feel inspired when I hear about larger-than-life figures who pursued big ambitions. People like Pollack, and Peggy Guggenheim, did big things.

Then I went home and I thought: “What big thing am I doing?”

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Adventure Is Worthwhile In Itself

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"The most difficult thing is the decision to act, the rest is merely tenacity. The fears are paper tigers. You can do anything you decide to do. You can act to change and control your life; and the procedure, the process is its own reward. Adventure is worthwhile in itself."
-Amelia Earhart

You often hear about how we regret the things we don’t do more than the things we do. Looking back at the experience of traveling the world, this belief shines through whatever hardship I encountered.

Sure, I can remember the struggles. I can remember sleeping on the ground, running out of money, missing my flights. I remember not being sure if I’d make it, if I’d have to give up somewhere.

If I think about it, I can remember sweating it out in Eritrea, detained by the police overnight before I was put on a plane to Cairo. I remember flying to Angola and Pakistan without the required visa, wondering what would happen on the other side.

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A New Year’s Wish for the Wanderer

Every evening the sun sets, then rises again a few hours later.

Yet something feels different about this particular sunset and sunrise. Oh, that’s right ... it only happens once a year.

Yep. It's time to stop writing the old year’s name whenever you fill out the date for something. For the next 365 days, the world has a new number.

If you wander out and about today, you may receive wishes of happiness from your barista or whoever else you encounter. You may notice the gym is especially full today. A new crop of well-meaning people with good-intentioned “resolutions” are off to the races.

Online, people are talking about “new year, new you” and you’re like … okay. How does this new year somehow make a "new me"?

And yet. It is a New Year, after all. Something is different. So why not use it as a catalyst for something positive?

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2015 Annual Review: Looking Forward to 2016 (Ready or Not!)

LookingForward1 And…. once more, with feeling! Today’s post is all about the future.

In keeping with this unusual year, the format for this post is a bit different than I’ve done before. I noticed that I was feeling some resistance in writing it, so I finally decided to just sit down and start, without worrying about trying to adhere to a specific style.

Previous Posts

Much of the year feels like it's been spent in a time vortex of some kind. If I could, I’d put the whole year on rewind and go back to January.

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2015 Annual Review: Lessons in Life, Success, and Loss

363846688_2270694504_z Every year I set aside a long block of time, typically the better part of a week, to look back at the year that’s ending and look ahead to the next.

And so we begin the 2015 Annual Review.

I try to live an active life and pursue a lot of different challenges and adventures. Pretty much every time I begin the review, I think, “What a crazy year it’s been!"

In the case of 2015, I began the year fairly well, had the worst thing imaginable happen in the middle, and then managed to close out on a relative high note.

As I sat down to write these notes, I have to confess that I wasn’t feeling super excited. My mind continued to drift toward the negative emotions, revisiting the things that have made me sad. As usual, though, I discovered that there were several good things from the year that I’d completely forgotten about.

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2015 Annual Review Is Here! This Updated Free Tool Will Help You Plan Your Entire Next Year

Over the past eight nine years, nothing has helped me to accomplish big goals and stay on track more than a single exercise I complete each December: the Annual Review.

Tomorrow I’ll publish a long post with my successes, failures (which are always more interesting), and lessons learned from 2015. This will probably be my most personal review year ever, for a variety of reasons, and I promise to share much of it with you through the blog.

But Wait, You Too!

My favorite part about the review is that it brings a degree of order to my multi-faceted life and career, which consists of many different projects and roles. My second favorite part is seeing what everyone else comes up with. Over the years, many of our readers have conducted their own Annual Reviews, frequently sharing their lessons with others on their blogs or in the comments or just with friends and families.

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Visiting My Brother at Quantico National Cemetery

It’s been five months since my brother’s death, and I’ve been back to his former city of Washington, DC several times since then. Until last weekend, though, I hadn’t visited his gravesite.

Quantico National Cemetery is about an hour or so from my usual hotel in Arlington, and once you get off the freeway, the drive isn’t unpleasant. I visited on a Saturday when the offices are closed and there are no services, just a few other people coming to say hi to their loved ones.

I arrived on a bright day, thankfully not a very cold one even though it was November, and I parked at the entrance where a computer is set up to help visitors find the location of a specific gravesite.

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“Don’t Pursue Something that Someone Said You Should Want”: Derek Sivers at WDS

19482941249_1d60667f8b_z In early spring 2016 we’ll release the last (small and final) round of tickets for WDS 2016, a global gathering like no other! If you'd like to join us, be sure you're on the waiting list for first notice.

But first, we’re rolling out speaker videos from the 2015 event. Derek Sivers, founder of CD Baby, author of Anything You Want: 40 Lessons for a New Kind of Entrepreneur, and all around non-conformist shared with us his secrets of success.

Check out the video!

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It’s Not How Much Email You Get, It’s the Lack of Purpose in Your Life

1194826111_0ecb951c52_b If you misidentify a problem, your proposed solution probably won’t work.

Let’s say you have a headache, so you decide to amputate your leg. You’ll probably still have the headache, and then you’ll be missing a leg as well. For more effective treatment of headaches, consider a glass of water and perhaps an aspirin.

Many other treatment plans fail for the same reason. Something is wrong, and you think you know what it is, but that’s just because you’re looking at the obvious.

You may feel, for example, that you’re “overwhelmed.” And perhaps you are. Or you may feel generally anxious, and perhaps you are—or maybe it’s something else entirely. But before you dash off to treat the symptoms, declaring email bankruptcy or a digital sabbatical, promising to return with a 28-day series of themed Instagram photos, take a look at the bigger picture of your life.

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