Pioneer Nation : The Art of Non-Conformity

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Three Days of Learning & Community: Last Weekend at Pioneer Nation

We did it!

Last weekend I worked with a small and dedicated team to produce our second-ever Pioneer Nation, a gathering of independent entrepreneurs.

For the first time in any big event we’ve done, we took everyone onsite for the entire experience. The event was held at The Resort at the Mountain, a scenic setting near Mount Hood, an hour’s drive from Portland.

Events are a ton of work, but they can also be hugely rewarding. Once again I felt honored and inspired to be surrounded by great people.

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Pioneer Nation Arrives in 23 Days: What’s Your Biggest Business Challenge?

Link: Join Us for Pioneer Nation

At the welcome reception for the inaugural Pioneer Nation, we asked our attendees to write their biggest business challenge on a post-it note and stick it to the wall, then say it out loud in front of their peers.

Here’s what they came up with:

We’re very excited to kick off Pioneer Nation again ... in just 23 days!

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Work

One Log Cabin and 800 Yoga Mats: Some Unconventional Tax Deductions from My Life in 2014

My tax return is complicated for a lot of reasons. First, I run several different businesses which all have their own set of accounting. WDS, our annual gathering, has its own legal structure, including a foundation that is completely separate from all my other projects. Last year we started an all-new event that also has its own legal structure.

So yeah, it’s complicated. It takes about 20 hours just to prepare all the info for my accountant, and as with most tax-prep tasks, it’s not usually a fun process. But I do enjoy seeing some of the charges on my statements from the previous year. They remind me of the crazy life I have, and the many fun experiences that I'm fortunate to participate in.

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The Magic Happens Backstage

Walking into the briefing room for our volunteers, talking with the crew running the stage lights, supervising the branding to make sure everything was consistent—that's when I felt most at home. The rehearsal is the best part. The real magic happens backstage.

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Pioneer Nation: We Did It!

One week ago we kicked off our inaugural event for solopreneurs, Pioneer Nation. Here's a very short recap of how it went.

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Pioneer Nation Begins in Portland

For years I've wanted to produce an event more specifically focused on independent entrepreneurs and people who work for themselves. This is it! Tickets are completely sold out and we're already underway. A few photos from our opening party (last night!) are below, and I'll share more news about the event next week.

Travel

How to Book Airfare on Short Notice

It’s a common myth, yet at first glance it doesn’t make sense: booking plane tickets on short notice should be cheap. If there are empty seats, why wouldn’t the airline discount them as the flight approaches? But as you may have discovered if you’ve ever tried to jet off on a whim somewhere, you’re inclined…

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The Big Trip (AKA “One Small Thing Can Change Your Life”)

In 2006 I was living abroad in my final year on the hospital ship. I’d been moonlighting by building a new business, and later that year I’d move back to the U.S. and relocate to Seattle. There was a marketing conference being held in Chicago, and it caught my attention. I was all the way…