In two week’s time the second World Domination Summit is taking place in Portland, Oregon. The event is organised by Chris Guillebeau and the speakers at the event include some of my favourite bloggers/authors, including Jonathan Fields, Pam Slim, Scott Belksy and Danielle La Porte.

Here’s a video from the last event:

When tickets went on sale at the beginning of the year I took a chance and bought myself one, as I knew they would sell out fast. I was still not even sure if I was going to leave my job at that point, though deep down I must have known I would.

I still can’t quite believe I’m going! According to the WDS site’s calculations, I’m making an 8400 kilometre journey, and I’m not the only one coming from far and wide, with people coming from all over the globe.

I’ve been preparing by watching the daft comedy series Portlandia on Netflix, which has made me wonder what I’m letting myself in for. The series stars Kyle MacLachlan, aka Agent Dale Cooper from Twin Peaks as the Mayor of Portland, as well as various other guest stars.

According to the above video, “Portland is the city where young people go to retire!” so it’s no surprise that a lot of bloggers with unconventional businesses and lifestyles would end up living there, as well as Chris himself – for example Charlie Gilkey of Productive Flourishing, Jonathan Mead of Illuminated Mind and his wife Ev`Yan of Sex Love Liberation, Emilie Wapnick of Puttylike, Tyler Tervooren of Advanced Riskology, and Tammy Strobel of Rowdy Kittens (thanks to another Portland resident, Janet of Purple Pandy for compiling this handy list!).

This trip is going to take me way out of my comfort zone. I’ve never taken such a long flight anywhere on my own before, in fact I haven’t really travelled anywhere on my own properly before at all (apart from going from Scotland to Ireland which hardly counts). Add to that the fact I know hardly anyone (though I’ve had brief contact online with a few other people attending, including CMC type Melissa Dinwiddie who’s featured in the above video from last year with her ukulele!).

So I am very nervous about the experience but it seems appropriate to do it in the year that I’m testing the waters of being freelance/building a creative business, and while I’ve still got a few months of funds left. I’m expecting to meet quite a few inspiring people and possibly learn a few things about myself in the process. So.. here goes!

If you’ve taken a step outside your comfort zone recently or in the past, tell me about it in the comments. And if you’re also going to WDS I’d love it if you introduced yourself!

p.s. I’ll be sending out the latest update to the Ditch the Day Job Diaries on either Sunday or Monday * which will include a sneak preview of my new micro-manifesto which will be released at the beginning of July.  *Correction – the video and email now won’t be sent until next week at the same time as the manifesto will be released.

You can subscribe here to catch up with all 14 episodes, including the most recent, which ended on something of a cliffhanger as I considered the possibility of going back to full-time work…

17 Comments

  1. Hi there! I’ve been subscribing to your blog for awhile, but have yet to comment, even though I’ve enjoyed many of your articles. :) I’ll be at WDS, and I live in Portland, so I’d be happy to share some must-visit restaurants and such!

    Safe travels!
    Hannah recently posted..How to be a karaoke rockstar

    • Hi Hannah, that would be fantastic. Judging by your blog you’re a good person to know (I love karaoke!). Thanks for getting in touch :)

  2. Milo I went out of my comfortzone last year by electing to go to Galway in Ireland by train and boat a 12 hour journey with innumerable changes. I freaked out a little on the first leg – and then calmed down – I actually wrote a whole newsletter about it boils down to fear of change – email me and I can send you a copy. I have been to the US twice by the way the first time in great trepidation to see one of my films screened in NY and I had a awesome time.
    m recently posted..moving on

    • Hi Mary, that journey definitely sounds like a test of character – would love to read your newsletter. It must have been amazing to go to a screening of your film in NYC also! Thanks for stopping by :)

  3. Hi Milo,
    I was at WDS last year (and immediately put my hand up for repeat tix this year!) and can say that this trip will undoubtedly be worth it! It is INTENSE but unbelievably amazing. Enjoy – and say hi if we bump into each other!
    Gillian @OneGiantStep recently posted..Saving For Travel

    • Hi Gillian, that’s great to hear and I’m glad you had such a good experience last year. I’ll definitely keep an eye out for you!

  4. Milo, have a good trip. Too bad I won’t be in the States to catch up. World domination starts with this conference it looks like. Expecting to read a full report on your blog.

    Time to check out your video too – why am I not getting your stuff via email? I paid my subscription twice last month!?!
    Vishnu recently posted..How to embrace change by shaking up your life like a martini.

    • Cheers Vishnu. Knowing my past form at conferences it will be more like ‘sitting sheepishly in the corner’ but you’ve got to try right?

      Haven’t recorded the video yet, nor sent out an email. Probably should get on with that.

  5. I’ll be at WDS too!I’m also nervous, but beyond excited to be around so many amazing people. :)

    • Hope to see you Erin – and sorry for delay in responding, I missed the notification somehow.

  6. Milo. I’m so happy for you that you are going to WDS. Enjoy every moment. Portland is a great city and you will fit right in, mad genius that you are. Can’t wait to hear about it. Say hi to Melissa for me.

    • Thanks very much Kim, I’m really excited, and currently running round frantically trying to get myself organised! Pretty sure there will be people there who are both madder and much closer to genius than me ;) and of course I will say hi to Melissa!

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