Image: Unpoint Culture

We’re already one month into 2017, but in the spirit of finishing, I needed to get this post out.

If years had mythical personalities, 2016 would be the gorgon Medusa — a slithering, monstrous head of year that you never want to meet, and heaven forbid if you do, should never look directly in the stone cold eye.

We collectively beat up 2016 to a bloody pulp already — that poor, poor number — so that’s not my intent here. Personally speaking, 2016 wasn’t my finest hour either. I set myself big, bold goals…and then promptly accomplished hardly any of them. Heaven knows I also spend enough time beating myself for things not done, so that isn’t my intent here either.

Instead, I’ll try to harness my inner Perseus and approach 2016 like he did Medusa: with a sharp indifferent sword and a shiny reflective shield.

After all, 2016 was just a year and I’m just a human. Here’s how this human lived their life last year.

Highlights of 2016

Five of my most popular articles on traveling, living and working deliberately. Free download here.


1. Writing

While I fell short on most of my writing goals (more in lowlights below), I managed to mine a few highlights I’m proud of:

  • Wrote 30,000 words in mini guides for our Escape Tribe program, in an effort to improve and bolster up our curriculum.
  • This is how you write hit Top 10 on Medium.
  • Start Before You’re Ready was picked up by Quartz and received generous love from Reddit founder Alexis Ohanian, which was fun.
  • Writing “I went to the woods because I wished to live deliberately” partly led to me speaking at Creative Mornings London.
  • Challenged myself with paid travel writing gigs for places like Mr. Hudson (a writing challenge in itself since the site is for sophisticated and gay men, of which I’m neither.)
  • Continued with my morning pages ritual, with 60-70% success rate.
  • Interviewed one of my heroes — adventurer, writer, filmmaker Alastair Humphreys.
  • Explored thoughts, opinions and emotions about the U.S. election and aftermath, which felt out of character for me.
  • Produced an ebook of 5 of my most popular articles on traveling, working and living deliberately. (Which you can download for free here.)

2. Travel

Exploration of our Earth remains a top priority for me. Living in London made it easy to explore more of the beautiful UK, mainland Europe and parts of the world I’d never seen. I kept exploring in 2016.

Visited Africa for the first time. Spent about 9 days in Uganda, all thanks to Uganda Marathon. Went on a safari, helped with local community projects, helped raise a bunch of money for the country, and ran a half marathon there to boot.

“The Hill” — Masaka, Uganda (Uganda Marathon)
Murchison Falls National Park, Uganda


More European trips.
Athens. Madrid. Munich. A week in Croatia (Dubrovnik and Korčula). Chamonix, France. Ran a retreat in Umbria, Italy. Slovenia for Christmas markets.

“Escape to Umbria” Tribewanted Umbria, Italy
Lake Bled, Slovenia


Spent more time in the US this year.
San Francisco to see my sister. Northern California for a weekend retreat. Southwest Colorado for vision quest with Bill Plotkin and Animas Valley. Chicago to see my brother. San Diego and Joshua Tree with Dom. Los Angeles to see Steve. Big Bear with Zach. Florida with my dad. Ohio for Christmas with the whole family.

San Juan mountains, Colorado. Photo: Joshua Gorman.
Joshua Tree National Park 


Explored more of the UK.
Mini adventures and day walks in Kent, Sussex, New Forest, Epping Forest, Glastonbury, Cornwall, and Isle of Skye in Scotland and a bunch more places. My two favorites:

  1. A two-day trek along Pilgrim’s Way from Wye to Canterbury
  2. Isle of Skye
Pilgrim’s Way, Kent, UK
The magical of Isle of Skye, Scotland
Stumbled upon a pile of rocks. Seemed important. Other people thought so too.


3. Work

Most of my 2016 working hours were spent in London with Escape the City. It was a challenging year at Escape. We saw the team almost double, one of our co-founders burn out, and all of us feel the uncomfortable growing pains of transitioning from a startup into a small business.

With great challenge comes great opportunity, and despite the pain (or maybe because of it), the business continued to be successful in 2016. We continued to bring hundreds of people together to make positive and meaningful changes in their careers, in London, New York, and elsewhere. Through it all, no matter the stress or challenges, I get to call this my day job. And for that I’m endlessly grateful. Here were some personal highlights:

  • From January to March I worked closely with our Escape Tribe program to build upon and strengthen our curriculum. It was good work, including lots of research and writing and workshop design, and largely I felt good doing it.
  • Led an Escape To Umbria retreat with Mel in enchanting Monestevole, Umbria, Italy.
  • Launched, sold, ran a high-end online course called Kickstart Your Career Change. Ended up with 24 people from around the world. It was challenging work, tried to do too much of it by myself, and ended up burning myself out by the end. But I was proud to have done it.
  • As part of the online course, I also tested private 1-on-1 coaching with four people. Lots to learn here, but the fact that I did it and hopefully helped some people in the process felt like a win.
  • Ironically, a big highlight was actually a break from work: I took a 7 week sabbatical from August to September to spend more time in the U.S. with family, and create space for a 11-day vision quest.
  • Continued to give talks and workshops in London and abroad: 3 talks at Shoreditch House; one talk at UCL; spoke to a group of MBA students at IE business school in Madrid; met Escape communities in Madrid and Munich; a small workshop at Uganda Marathon; Education First in Manchester; Creative Mornings London; plus talks and workshops at Escape in London.
  • As a team we explored moving to a Teal organizational structure, based on Frederick LaRoux’s book Reinventing Organizations. It was fascinating to be a part of it and as a team explore unconventional conversations around individual wholeness, self-management, and evolutionary purpose.
  • Outside of the Escape bucket of work, Tales of Iceland continued to sell fairly well in 2016, considering it was published over three years ago.

4. Film/TV/Acting

In 2015 I checked off a fun bucket list item: act in a feature film. Calling it acting miiiight be stretch, but I did spend two days as an extra (or “supporting artist” as they call it in the biz) in the latest Bond film Spectre.

Scene from Spectre. Image: James Bond Wiki

Watching actors Ralph Fiennes, Naomi Harris, Andrew Scott and director Sam Mendez all work their craft, I was a kid in a candy shop. It was one of my most thrilling experiences of 2015. From a storytelling perspective, I soaked it up like sponge: so this is how a complex story is told visually!

I had to keep the magic going in 2016.

It turns out London mayor Sadiq Khan is on a mission to “catch up with New York and take over LA”, and I’ve been impressed how much work I’ve managed to keep getting in films and TV. Here’s what I did in 2016:

  • One day on Rogue One, on set with writer/director Tony Gilroy (although still haven’t seen the film to know if I made the cut).
  • One week in Wonder Woman as a “Turkish Soldier”.
  • One day each on The Royals, The Crown, and two other TV shows I can’t mention yet.
  • Auditioned for two commercials — one whiskey, one cider — but was selected for neither. The experience was funny though.
  • Two days on a huge upcoming 2018 film with an iconic director — wish I could talk about but can’t yet!
  • Was also in talks with two production companies host and/or participate in two TV shows in the U.S., neither of which materialized, but were fun to explore.

5. Personal Development

Creative Mornings talk

2016 saw me continuing the deep internal work I began with my wandering five years ago. Part of that was continuing a curious fascination and communion with the natural world that’s been growing over time. I went deeper in 2016:

  • Vision Quest. After gobbling up two of Bill Plotkin’s books (Nature and the Human Soul and Soulcraft), I reached out to the man and signed up for two workshops with him and his guides — a Soulcraft Intensive and a Vision Quest.
  • Worked with coaches for the first time. I’ve been reluctant to do this (ironic given the work I do at Escape), but one of my big realizations in 2016 was my need/want for help and guidance from mentors, elders, and coaches. Between Bill Plotkin and his fellow vision quest guides, coaches we work with at Escape in London, and even my dad as a helpful sounding board and coach for my career, I’m becoming more comfortable asking for help.
  • Creative Mornings London. In October I was invited to speak at Creative Mornings London. While I don’t think it was my best talk, I stick it here in Personal Development because I stretched myself to explore and speak to 100 people about my growing relationship with nature, musing on what it means to be human, and my struggle to own the title “writer.” All of which felt edgy. I’m proud I put some of those ideas into the world. You can watch the video here.
  • Read 16 books last year. Short of my goal of 25, but still a good number. Here were my favorite 10:
Follow the books I’m reading at Goodreads.
  1. Sapiens: A Brief History of Humankind by Yuval Noah Harari
  2. The Power of Myth by Joseph Campbell (reread from 2014)
  3. Reinventing Organizations by Frederic Laloux (the illustrated version)
  4. Daily Rituals: How Artists Work by Mason Currey
  5. Working Identity: Unconventional Strategies for Reinventing Your Career by Hermina Ibarra
  6. Wild Mind: A Field Guide to the Human Psyche by Bill Plotkin
  7. Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days by Jake Knapp (via learnings at Google Ventures)
  8. Nobody Wants to Read Your Sh*t by Steven Pressfield
  9. Crossing the Unknown Sea: Work as a Pilgrimage of Identity
    by David Whyte
  10. The Symposium by Plato

Lowlights of 2016

Clearly there’s much to celebrate in 2016. How could I call 2016 Medusa?

For one, I can’t help but look at the goals I set for myself at the beginning of last year and feel disappointed I didn’t make much progress. You could chalk it up to negativity bias: “things of a more negative nature have a greater effect on one’s psychological state and processes than do neutral or positive things.” Either way, even with the highlights, 2016 hurt a lot too.

Here are the 2016 lowlights — the true Medusas I dread to stare in the face:

1. Writing

My goal for 2016 was to write daily and ship weekly. That didn’t happen. Why not? In general, I’m still playing small potatoes with this writing stuff. I can announce myself as a “writer” on stage at Creative Mornings, but a few blogs posts here won’t cut it. I’ve still yet to become a professional. I’m still sitting on stories I’ve told myself for four years I need to get out of me. I did have a few big hits I’m proud of, but the giant gap in my writing between March and September was disheartening as well.

2. Work

I often floundered in my work at Escape and struggled to find my place in an ever evolving business. Coupled with one of our founders burning out and removing himself from the day-to-day operations, I often felt lost. Sometimes I’d wonder: Have I overstayed my welcome here? Has the business outgrown me? Have I outgrown the business? I took a 7 week break to regroup and reconsider my direction, which felt great. But soon after I returned, and especially in November and December, I got swept into challenging team conversations that left me feeling negative and drained. I was doing ‘the work around the work’ as we often say. At the expense of work I enjoy and feel I can excel at.

3. GiveLiveExplore Publishing

After publishing Tales of Iceland in 2013, my friend Steve and I dreamt up a whole Tales Of series — entertaining and informative anti-guidebooks to unique places around the world. We headed to Ecuador to live out what would become Tales of Ecuador and had an epic adventure. In 2014, Steve followed through on his end of the bargain — he wrote the book. And I moved forward with my end to publish and launch it. I hired a cover designer, editor, got test readers, and took it close to the finish line of publishing it…and then stalled. I never published it.

It corresponded to my move to London and working with Escape 150% full time. Simultaneously Steve started his MFA at Iowa. Both of us became consumed with other projects and directions. 2014 passed. 2015 crept by. So did 2016. Steve confronted me about it and we had some difficult conversations. All in all we got to a good place and ended up having a fun reunion in LA this year, but I still felt a tremendous amount of guilt and shame for failing to take this across the finish line. Good news is our friendship is still in tact. Disappointing news is that Tales of Ecuador is indefinitely on hold as Steve explores selling a novel.

4. Getting too comfortable / drifting / falling asleep

I’ve become comfortable in my life in London — maybe too comfortable. This isn’t a problem necessarily, except that I notice it as a recognizable story playing out in my life. When I’m too comfortable, I risk losing the fire in my belly. I begin drifting. Drifting toward the easy, the predictable, the known.

Of course, there’s a lightness and freedom in going with the flow of life. We like to think we’re in total control of our lives, but it’s mostly the facade of control. There seems to be a paper thin line between drifting and flowing; between flowing with life and falling asleep in life.

You notice it when you catch yourself living life with no agency, no sense of urgency, the loss of Thoreau’s drive “to live deep and suck out all the marrow of life.” It’s one reason why I needed to “enter the woods” once again. To recenter myself. To wake myself back up. To avoid falling back asleep. I have a feeling this is a lifelong pursuit, one that I’ll continue to struggle with.

5. Grief

Lots of grief. Between the US election, my sister’s boyfriend Max’s head trauma (fortunately he’s much better now), and other difficult situations I don’t want to talk about here, I felt a lot of grief in 2016. I’ve struggled, like many people, how to reconcile the people I love so dearly in my life, with an ideology and outlook on the world that feels at odds.

This feeling of grief oddly ties into one of my most positive experiences: the vision quest. Apparently the more accurate translation of vision quest from Native American cultures is To Lament — a passionate expression of grief or sorrow. Or rather, to cry out for a vision. So maybe it’s fitting that 2016 was the year of my vision quest.

*Why We Review

Here’s why this type of reflection and celebration is important, even one month late: 2016 was actually an incredible year. But I needed to take the time to deliberately look back and remind myself of the highlights, not just my shortcomings. Humans are funny like that.

What’s in store for 2017? Time will tell, but I’m optimistic.

Mainly because I’m not focusing on goals, but instead on intentions.


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