Solo Travel Blog

Fail Now, Ask Questions Later

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“Ready, Fire, Aim” is a brilliant mantra to live by (unless you’re a soldier or BASE jumper…) and has served me well so many times.” Alastair Humphreys


At the beginning of my very first adventure, I contacted a number of people in the adventure travel world for advice on what I was about to do. I am forever grateful I did, for these emails from Adventurers such as Tom Allen or Alastair Humphreys contained the very words which gave me one last nudge toward actually doing it.

I enjoy their blogs posts too and as a result of reading them, combined with my own experience; It’s now clear how these questions were really my fears for everything that might go wrong and the actual result I am hoping for in this type of situation, is for somebody to say “just do it”.

However, although the questions in my emails back then and the search for permission today are still the same, there’s a distinct difference in that I now seem to bulldoze my way into situations and then ask questions later.


Digital Nomad – Part I


“I’ll live in a tent for a couple of Months. That way, I can afford to hang around and spend Christmas with family”

Ireland was too expensive to begin my career as a digital nomad but I came up with a plan to address this by going camping along the Western seaboard and use this time to start developing an online income in my tent every evening.

I say “plan” but really, this just sounded like a reasonably good idea and the only way to avoid spending money to sustain my new lifestyle.

It was a complete disaster.


From Malin Head to Minor Emergency

I had jumped on a bus the previous week to the very North of Ireland (Malin Head) and from there, I began hiking South along the Coastline. My willingness to survive on a diet of baked beans and peanut butter sandwiches was fine, but finding a ditch, a field or a beach to pitch the tent on every evening was not so easy to repeat.

Thing is, there were lots of issues which I hadn’t thought about starting out.

The backpack was so heavy that I couldn’t even get over roadside fences, and there were always fences. This resulted in having to walk along the road for long periods and by mid morning on even just the first day, I was wishing for headphones to escape the noisy traffic.

It also got dark by late afternoon and given that I needed to find a camp spot before then, this required a very long wait for daylight to start hiking again.

Then I was unable to get signal on two of the nights and seeing that I needed to work online, it felt as though I was making life very difficult for myself.

Unfortunately, the beautiful beaches and quaint Country villages were not reason enough to continue and when I found myself naked in the tent one night with an emergency foil blanket wrapped around me, I knew it was time to re-evaluate the logistics for what I was trying to achieve.


No Hanging Around

Despair in Dunree

I had spent the day walking through a small Mountain range toward a place called Mamore gap.

The weather deteriorated as the day went on and mud meant for slow progress. With it being so exposed up on the Mountain, I decided to continue hiking later into the day until I was past Mamore Gap itself.

Rain was pouring down by the time I reached the town of Dunree and once there, I began trudging my way along a narrow dirt track toward the sand dunes on the beach. I was so glad to stop for the day and managed to find some amusement in how difficult the wind was making it to pitch the tent. But then I sat inside, and realized what had happened.

I stood back up in the tent doorway. A million speckled raindrops shot past the head torch, as I looked to the surrounding darkness and then back across a faint light along the shore.

But I was no longer interested in what the scenery might look like the next morning, I was instead thinking how incredibly stupid I had been. Almost everything inside the backpack was soaked through; my clothes, the towel, my sleeping bag.

The waterproof cover had blown away during the excitement of pitching the tent.

It was a disaster, the entire week, a complete disaster. I sat back down, stripped away all the wet clothing and took out the emergency foil blanket.

Dunree tent

End of Digital Nomad – Part I

I shivered beneath the foil blanket with some semi-dry t-shirts and socks wrapped around my legs but amazingly, the blanket generated so much heat that it was actually comfortable right through the night.

It was a lucky escape.

At first light, I woke to the pleasant sound of the ocean and sat outside in the morning drizzle eating breakfast. I was already sick of peanut butter sandwiches but then they always seem to taste better at times like this; when I remember how refreshing it can be to wake up in the outdoors.

But my idea to camp through Winter in Ireland was over. It had been little more than a week of frustration trying to create an online business while living remotely in the tent. A nice lady named Deirdre stopped to offer me a lift when I rejoined the road and from then, it was time to decide on where to go next.

At first I felt trapped by the confines of expensive accommodation but in hindsight not a lot had changed. It had been an awful week but there were lessons learnt and I was still free to continue the life of a digital nomad; I was even so free that I could even take an express bus to the airport the following morning, and so I did.


Permission to Fail & Ask Questions Later

Strangely, it is now me who gets asked for advice often with regard to other people’s adventures or travels but while it’s a great privilege to receive these every time, it also makes me feel uneasy.

Why? Because, aside from “do it”, I have no idea what to say.

The truth is, I’m useless when it comes to preparation and the thought of researching all the possible scenarios for what could happen, bores me. This doesn’t mean I travel into wilderness areas alone with no food or books to read, but rather that I find the process of planning to be one long endless opportunity to procrastinate.

Believe me, if anyone can think up an enormous number of reasons not to do anything in life, it’s me. I just choose not to think this way anymore. The decision to be more proactive in spite of anxiety is a conscious one, as is the decision to do something rather than just talking or thinking about it.

My disastrous hiking trip in Ireland appeared pointless at first but looking back, it was the first opportunity to understand how it’s not important what happened anymore, it’s only important that it happened at all. I did earn a pitiful $15 online which was obviously a major concern, but I was just happy to have started and convinced if I work hard and passionately, I could still make this life on the road work somehow.

Of course I could have planned endlessly and researched all the right ways to go about becoming a travel writer. I could have waited until I was earning enough income online to support the decision to start or even held on until I “knew” it was a viable option to work from out of a tent. I could have done all of these things but I didn’t.

As a result I was travelling and writing, while in the process of just doing this, I was already being what I wanted to be, instead of asking somebody’s permission to do so.

It reminded me that sometimes there really are only two options when making a decision to change something in your lifestyle; You can wait until you have enough money and enough knowledge and enough time and enough permission, or you can eat peanut butter sandwiches and ask questions later.

Dunree BeachSunset DonegalSheep irelandirish cottageMALIN Head

I'm an Outdoor Adventure Blogger from Dublin, Ireland. In late 2013 I began riding a bicycle across Africa and it was during this adventure when I discovered a passion for the great outdoors and the general uncertainty of life on the road. Next April, I am hiking the Pacific Crest Trail.

1 Comment

  1. Psychic Nest

    April 7, 2016 at 1:02 pm

    Hi Derek,

    At least you didn’t get sick after this adventure! The photos are amazing but I don’t know if I would be able to do what you did. Though Ireland sounds like a great place to go on vacation. Thank you for sharing your experience!

    Psychic Nest recently posted…Chakra Balancing Guided MeditationsMy Profile

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