WDS 2016: The experience of a lifetime

Jas Hothi
8 min readAug 26, 2016
WDS closing party (Credit: Armosa Studios)

Short intro

(skip this bit if you just want the juicy stuff…)

I can’t remember exactly when I first heard about WDS, but it was sometime in late 2015 — early 2016, when my general dissatisfaction with life came to a head. This was to be the start of a transformational journey (one that continues) which saw me get hooked on the science of happiness, initially as it really honed in on some of the things which weren’t being met in my own life and was helping to tangibly identify exactly why I was feeling like I was, and what I could better do to improve my situation, my wellbeing and my life as a whole.

One of the major factors playing a part in my “quarter life crisis” (yep, so “millennial” of me) was the dissatisfaction I had in the job I was doing at the time and the accompanying work-life balance (or lack of) that accompanied it.

In no particular structured order, my spiritual awakening gained momentum and I started delving into more and more books and blogs; from lifestyle design (Tim Ferriss), new ways of working (freelancing/solopreneurship, entrepreneurship, portfolio careers) through to happier living in general (from the concepts of mindfulness and flow through to minimalistic living), I was reading it all. There was also a big movement I was seeing in individuals who apparently felt the same, with job dissatisfaction often being the thread which tied us all together. “Doing work you care about” must have always existed as a concept, but it is in these last 2–3 years that this movement really seems to be gaining momentum. I became aware of the Live Your Legend movement, immersing myself in their blog posts and resources (this was before “Live Your Legend local” started, with dozens and dozens of in-person meetups in cities all over the world, including London), before I found “Escape the City” closer to home and was immediately hooked. It was a step into a whole new world of work, good living, focusing on what’s important, self improvement…the list goes on.

Credit: AnousLaCalifornie

Main bit

(the “juicy stuff”)

In this last year alone, I consider myself so fortunate to have found myself in so many amazing communities of like-minded people. And I’d clearly been going through this career change/happier living stuff for a long time — did I really need more inspiration, did I really need to be part of yet another group?

I had booked my WDS ticket several months before, at a time during my “Escape the City” course and perhaps getting carried away in the moment. (Through Chris Guillebeau’s books, Live Your Legend, Leo Babauta/Zen Habits, and more — both WDS and Portland kept cropping up and calling out to me, so I knew I had to experience it at some point). As the August “WDS week” approached, With my attention on my Masters course and making the pilot for my education programme happen, I hadn’t had so much time to dwell on WDS and, though looking forward to it, I couldn’t help wondering whether the investment (time and money) had been a sensible decision.

How wrong I was to have even doubted it. For, whilst I remained to be a community member of the groups I’ve mentioned (e.g. Escape the City, my Masters Group), interactions with these groups had for the last number of weeks and months primarily been online, with courses at both ending earlier in the year. Those other groups I was a part of had physical meets once a month as a minimum, if that. And if there’s one thing I know, despite my introvert-appeasing tendencies to delve into things online and quench my thirst, there is simply no replacement for that real-life, physical human connection. There just isn’t, and there never will be. Human connection can’t ever be scale; in-person is always where the magic is, tech is merely an enabler to keep it going and carry it forward in between the bouts of non-in-person-ness (my word). Digital connections/apps are far more transient than real-life.

WDS proved to be a week-long real-life warmth-fest of positive, inspiring, unconventionality-embracing folks from all over the US and beyond (Canada, Europe, Australia, Asia) with meetups, academies, talks and tons and tons of serendipitous interactions.

Impossible to sum up in words to someone who has’t attended, here’s my best shot of what made WDS the best conference I’ve ever been to:

  1. I got to meet some of my heroes…
    I got to see, in-person, some of the folks whose blogs I’d been reading and podcasts I’d been listening to over the last couple of years, and gaining inspiration from. To name a few, Chris Guillebeau (the WDS orchestrator himself), Chelsea Dinsmore, Leah & Naz (of The Connection Effect), and Jonathan Fields.
LYL Meetup — my head is small, but my smile is wide… (credit: LYL)

2. … and see that they were just “regular” people, like me!
Throughout the week, the WDS speakers, team, and whole community would get together and mingle, let our hair down. There was no hierarchy, no “us and you”, no ego’s. And the fact that these were people, just like us, who — yes — had worked hard and down impressive things. But that could be us. (I was reminded of the “You are the average of the 5 people you hang around with” quote, and the mindset shift that Scott Dinsmore describes during his interview with Jonathan Fields when he was plugging away for 3–4 years on his blog with no luck, before he moved to San Francisco and found a real-life community of real people doing extraordinary things — one of my favourite interviews ever).

3. There were lots of introverts! (Impressive, given the 1,000 “main-stage” attendees — reduced from 3,000 last year)
I decided to test my theory (of there being lots of introverts there and also trends in the Myers-Briggs profiles of attendees; I take all this stuff with a pinch of salt, but I also love to spot a trend) by asking various people where they sat on the introvert-extrovert continuum; there seemed to be a whole lot of mid-scale “ambiverts”, many of whom favoured the introvert side, and some of whom identified as being extroverts. But it was a big conference and there were lots of introverts, just like me! Interestingly, there were Myers-Briggs trends too… in particular, I recall speaking to a number of INFP/ENFPs.

4. It felt like a family
Outside of the various meetups and events, us WDS-ers were recognisable by the smart tags we proudly wore around our necks as we wandered around Portland. This led to lots of warm smiles and serendipitous interactions.

5. Portland is just a really, really cool place
Living in SW London, I have often though that if I ever moved to London (especially the City), I would find it quite a lonely place to settle and establish solid social relationships. (My friend, Amy, who I actually met on the first night at WDS — thanks to the WDS app which helped link the “early arrivals” — lives in LA, and admitted that it took a while there to find “the good ones”. I imagine it’s a similar story in any large city, and especially so in those where average earnings are higher (simplified explanation: more competition/keeping-up-with-the-Joneses effect, less togetherness/community). Portlanders are so cool and so friendly. On the street, at the Windows store (I bumped into it looking for the Apple store!), and at bars and restaurants. (This made the WDS Hero’s Journey a lot more fun and friendly too — a Friday morning series of group tasks we had to complete, many of which involved engaging the friendly folks of Portland).

6. There were lots and lots of warm, supportive, helpful, loving people
who were just like me! Different ages, from different walks of life, doing different things, at different points in their life, having had different stories, and inevitably on different journeys. And yet we were pretty similar. That alone was pretty magical.

WDS 2016 closing party — MJ + jellyfish (Credit: Armosa Studios)

I could go on and on.

Though it was such a powerful experience is so many ways, the 2 biggest takeaways for me:

  1. When you surround yourself with amazing people, it makes the “amazing” seem more normal, more possible. Do that!
  2. Being PHYSICALLY around “your” people is so important. There is no replacement for it, even if you’re very active and connected on groups/blogs/podcasts online. Perhaps monthly meets aren’t enough… if we all procrastinated less online each day, though committed to a weekly meet, wouldn’t that be better for us all?! We’re always “so busy”, yet this business is often unproductive and the multitasking-form of business, which just isn’t good at all.

Some other notable highlights for me
- On arriving for Registration, I found myself sandwiched in between Chelsea Dinsmore and Corbett Barr. #starstruck
- After Registration, Chelsea & Steve (another LYL team hero) invited me to the LYL Local Meetup in Portland later that day!!
- I told Chelsea how incredible she was and what an amazing job she has done with Live Your Legend (I even bought her a drink at the closing party and 100% agreed that the DJ needed to play some Pitbull & Kesha) #wow
- Mr. Money Mustache inadvertently knocked my drink out of my hand and insisted on buying me another — until he realised he only had 3dollars in his pocked! #walkingthetalk
- I was lucky to have spent time with Leah Hynes & her awesome husband — Leah even invited me to join The Connection Effect’s amazing community! (It felt like an invitation to attend Hogwarts) #badasscouple

Note: I had an extra day in Portland after WDS had ended* — and even got to experience some of its beautiful nature. Aside from waterfalls, Portland has beaches and mountains too. Definitely need to make time for all of that next time! Some light waterfall hiking was the perfect mind re-energizer after the summit*

*(bar an Academy or two on Monday — but my schedule was free)

View from Wahkeena Falls trail, Portland, OR (credit: Lauren Roerick — WDS friend + hiking buddy)

Personal takings from WDS2016

I am blessed to know a number of inspiring individuals, mainly through the groups and communities I am a part of. But it’s left me wondering - ought I concentrate on cultivating a handful of these interactions, making more of an effort in real life, rather than aim to “keep in touch” with lots of individuals — no matter how positive and inspiring they are? I feel this is something I need to act on right away.

This was the 6th year of WDS, and I met equal numbers of previous and new attendees at WDS2016. WDS keeps getting better and better it seems, and in 2017 they are hiring a whole “WDS lodge” for the community, with rooms for WDS attendees to stay :)

I’d encourage you to take a look at World Domination Summit; if anything you have read in this piece has resonated, it might well be for you.

And if in doubt — do it. Take it from me, it’s well worth it.

Jas Hothi

i like to write things · INFP