10 Things I Learned At The World Domination Summit

This past weekend, 1000 travelers, hustlers and entrepreneurs descended upon Portland, Oregon for the World Domination Summit, a gathering about living an unconventional life in a conventional world, hosted by Chris Guillebeau.

Somehow I managed to weasel my way in by signing up extremely early (as tickets sold out in 2 waves after about 10 minutes each wave, this involved sitting by my computer and hitting “refresh” repeatedly until tickets went on sale).

It was two and a half whirlwind days filled with keynote speakers, workshops, happy hours, exploring downtown Portland, and amazing conversations with all sorts of interesting people.

It was such an awesome experience and there’s no way a single 1600 word post will do it justice. But I wanted to give a taste of some of the cool things I learned and people I met.

So without further ado, in no particular order, here are 10 things I learned at WDS:

1. It’s never a great time to create, but you do it anyway.

At her Fire Starter Session, Danielle LaPorte told a story of how she kept working on her business in the midst of a separation with her husband. She would come home after tearful conversations and still have work she needed to do – so she would buckle down and write.

There is no great time to create, so you learn to keep creating, even if you don’t feel like it. If you wait around for the creative well to flow before you start doing anything, you might be waiting for a long time. People who learn to put in the work even when they don’t feel like it are able to chip away at their goals, one small step at a time.

2. When choosing business projects, first choose the one that will make you money the fastest, and then choose the one that will make you the most money.

This is another salient point from Danielle. Starting a business or changing the direction of your business is tough, and in the beginning the most important things is to get money in the door quickly. This means the first project you choose should have a low barrier to entry, such as offering a service.

After 18-24 months, once your business is rolling, the next step is to choose projects that will make you the most money, and that are the most meaningful for you. These may have a much larger investment in time or energy up front, but will be the most rewarding – such as creating a product or writing a book.

3. When doing an interview, prepare much more than you think you need to.

In his workshop on podcasting, Gregory Berg, who has been working in radio for almost a decade, described that preparation is the single most important thing that will lead to a successful interview.

For an hour long interview, he will often prepare 5+ hours of material to talk about. This gives him the ability to follow the interviewee if they go on an interesting tangent, and the flexibility to change the course of the interview based on how it’s going.

4. Being vulnerable means that you might be rejected – but that’s okay.

Brené Brown is a researcher studying vulnerability and shame, and the speaker of this beautiful and highly-viewed TED talk. We were lucky to have her as one of the keynote speakers for the weekend.

During her speech Brene talked about the “conference anxiety” that comes with an event like WDS – you want to take advantage of the chance to meet so many other like-minded people, but at the same time you have a hard time building up the nerve to make the approach and say hello.

She said the key is to approach people with the perspective of being open-minded to the new experience, while not tied up in the outcome if it doesn’t work out. Rejection is okay, and it doesn’t need to make you feel guilty or ashamed.

I can’t say I got full-on rejected at any point during the weekend (everyone, including the well-known/famous people, was really nice), but I did get a couple of facial expressions that seemed to communicate “I like you, but I’m tired of talking to you.” Oh well, that’s okay, and it won’t stop my from trying more next year :-).

5. Untangle from both criticism and praise.

One of my favorite speakers for the weekend was Chris Brogan – his talk about courage and bravery involved handing out superhero trading cards (mine was Firestar, by the way), multiple comic book references, and telling us to embrace the persona of our inner superhero when putting ourselves out there.

One of my favorite quotes of his talk was the above statement about untangling from both criticism and praise. The first part is more obvious – we need to be open to constructive criticism but can’t be bogged down by negativity, especially when starting a new project.

He added that we also need to untangle from praise, to avoid becoming “that person” who gets cocky when they start succeeding, only to the detriment of their career and personal relationships.

6. You can’t figure out what you’re passionate about in the abstract – it takes action and skill to discover passion.

Perhaps one of the more against-the-grain speakers of the weekend was Cal Newport, an author and professor of computer science at Georgetown, who argued that the advice “follow your passion” is flawed.

He pointed out the discrepancy between Steve Job’s advice during his famous Stanford commencement address to “never settle,” versus what Steve Jobs actually did when he started Apple Computers, which was not to follow his passion at the time (Zen Buddhism), but to pursue an intersection of a valuable skill and market need and start building computers.

Cal’s point is that skill comes first and passion comes later (as it did for Steve Jobs). Instead of flitting from passion to passion, focus on getting good at something that is rare and valuable, and use this skill as leverage to create the kind of life you will be passionate about.

7. Who you surround yourself with is everything.

One of the workshops I went to that was particularly on point with the theme of the weekend was Scott Dinsmore’s talk on how to connect with anyone.

Early on Scott quoted Jim Rohn – “You are the average of the five people you spend the most time with.” This idea has been especially relevant for his business; it wasn’t until started spending time with other people making a living through doing work they were excited about online that he realized his dream was possible.

These same people also supported and guided him as he revamped his blog, and multiplied his readership over 160x. He credits these relationships as one of the most important factors in his success.

8. If you’re not sure what you can give a person you want to connect with, be genuine and offer them a unique experience.

So if relationships are key to succeeding with your work, how do you form these relationships, especially if the people you want to talk to are much “bigger” or farther along on their career trajectory than you?

Scott offered a few good pieces of advice: 1) Be genuine and treat the person like a friend, rather than someone you’re trying to get something from, and 2) offer them a unique experience by connecting about something other people don’t.

When Scott contacted Warren Buffet, he didn’t talk about investment strategy like most people do, but instead wrote a sincere letter about how he was about to propose to his now wife, and was following Buffet’s advice to “marry up” (great marriage is a topic near and dear to Buffet’s heart).

Within a few days Buffet had written back inviting Scott to visit him in Omaha to look at rings. Yes, really. He spent a few days over there, bought a ring and proposed to his wife. This amazing meeting happened because Scott made the connection in a unique way.

9. Twice as many people say they live in “utter chaos” as people who describe themselves as “highly organized.”

Just a little factoid from Scott Belsky, author of Making Ideas Happen, who gave a keynote speech on how creative types can be better at executing their ideas.

In one of the studies he quoted, 7% of people said they were highly organized, while 14% said their level of organization amounted to “utter chaos” (most people self-described somewhere in the middle).

I just liked this because I’m actually one of those people who would put myself in the “highly organized” category. Yeah! Any other extremely organized (anal retentive) types out there too??

10. The best part of WDS isn’t what you learn, but the people you meet.

Don’t get me wrong – I learned a ton of cool stuff and was introduced to a lot of new ideas (my scrawled notebook is proof). But I didn’t really learn anything I couldn’t have picked up staying in Los Angeles reading a couple books and watching some TED talks.

What made it worth leaving my comfort zone and flying out to Portland for the weekend was all the awesome people I met. Seriously – people who founded amazing charities, traveled the world for years, started hundreds (!) of businesses. People who gave me a lot of ideas an inspiration for where I want to take my writing and my business in the near future. And hopefully I offered them some unique perspectives or experiences that added to their lives, too.

What an awesome weekend! I’m already signed up for next year, and can’t wait to see what everyone does (including me!) from now until then.