One day when I was about 20 I was talking with an old school friend who’d recently returned from several months of traveling round Africa. It was amazing hearing about his experiences, but one of the things that really stuck with me was his comments on luggage, he said,

“the only way to travel is to travel light – just take a small shoulder bag and nothing else”.

And now over a decade later, after having been through many moves and several rounds of getting rid of all my possessions and buying them all again afresh, I’ve pretty much distilled my life in to a standard cabin luggage suitcase.

The current hobo CEO suitcase

Hobo CEO suitcase as of Feb 2012

So let’s have a look inside, what does the hobo CEO carry and why:

The essentials

1. A rather feminine bright pink cabin sized suitcase
   Unless I’m staying longer than a month, or want to bring a lot of gifts, always hand luggage only. Suitcase on wheels preferred to rucksack – easy to pack efficiently, and if I want a bag to carry stuff around during the day, I’ll stick it in the suitcase.Bonus points for durability and eccentric (gay?) colours.
2. Smartphone
   I have an unlocked iPhone, this is perhaps more useful than a star trek communicator/tricoder/phaser thing. I buy a data pay as you go sim for each new country I visit, and voila I don’t have to worry about maps, info, communication, advice, killer hamsters etc. I can use the internet sharing feature and tether my laptop to get online wherever I am.In fact a more minimal hobo CEO suitcase would be just my pocket with my wallet, passport and iPhone.
3. Sim cards
   
   I’ve got a fair few of these now – I like to keep the same local phone number if I can.
4. Laptop (mac book pro)
   The mobile office
5. Internet Banking Keys
   As a fallback I can still use telephone banking, but these little chaps are pretty small and it doesn’t matter if I lose them abroad (they are generic devices)
6. Current books I’m reading
   My preference is to read novels on the ‘old school’ paper format – I read before bed and just find paper more relaxing than electronic ink/pixels. I like to recycle books, so always pick them up second-hand or best get them off friends who’ve already read them so I get a little pre-selection thrown in free. I give them away (or send back to the owner) when I’ve finished.
7. Passport(s)

Optional Items

1. Lightweight Goretex Jacket
   Fashion and style is of little importance to the (this) hobo CEO, for clothing the criteria is “practical and durable”. A Goretex jacket is lightweight and covers a wide range of climates and uses – from a basic waterproof in tropical storms, down to a great top layer over some woolens for zero and (just) subzero temperatures.
   A note on fashion and style If you believe you need to wear clothes that look a certain way (stylish, formal etc) then I perhaps I could entice you to reset your beliefs – I’ve pretty much never worn a suit (unless for fun); wearing stylish clothes pales in comparison to the impact of PERSONALITY; weddings, funerals, no special effort on clothing for them either, I turn up and give my heart to the occasion; attracting women? wearing a pair of Armani jeans isn’t suddenly going to make you interesting, fun to be with and confident. Pay attention to what is underneath the clothes, otherwise it’s like a dusting of icing sugar over a turd.And for Women The female sex perhaps, has a slightly different agenda. But hey I’m a man and this is my suitcase so I wouldn’t for one minute imagine any women would pay the slightest attention to my recommendations for garments :).
2. One (or so) change of clothes
   I find it optimal to have not much more than one change of clothes, it’s easy enough to buy new clothes most places in the world if anything wears out.Also I do have some clothes left with friends/relatives in a few different countries so I get the double bonus of a change of out fit plus the novelty of being several years behind (ahead?) current trends when I return.
3. Walking boots
   I like the outdoors, and really I struggle to fill the cabin sized suitcase anyway, so there’s usually enough room left for some bulky boots.Again, girls – yes, take only one pair of extra shoes, then you can have the fun of shopping for new shoes when you reach your destination, win-win situation!
4. Swimming shorts
   Similar level of versatility to the Goretex jacket – swimming pool, beachwear, everyday shorts and the gym.
5. Gym kit
   I could easily pick this up in a shop wherever I am, but I like to exercise everyday so I find it’s convenient to have appropriate clothes at all times.And the practical minded among you will also have realised that gym kit can double up as another change of clothes!
6. Brightly coloured Underwear
   I Change underwear everyday (unlike my jeans), or go commando. Again bonus points for feminine/eccentric colours.
7. Quartz Crystal
   Apparently this counters some of the ill effects of electromagnetic radiation from computers. I received one as a gift recently, it’s small and lightweight, so I’m currently trying it out.
8. Silicone ear plugs
   High quality ear plugs are very useful for varied sleeping conditions and I’m not always guaranteed of easily finding them in some of the countries I visit.
9. Travel Adapter(s)
   
   Again I could pick these up at the airport when I arrive, but they’re pretty small.
10. Earphones
11. Currency
    
    I don’t usually bother getting currency in advance – I’ve never been to an airport that didn’t have a VISA ATM, but it’s quite Jason Bourne to have a suitcase full of different currencies (left over from previous trips).

A word on posessions

Remember the fight club IKEA scene? an excellent work of cinema and great comment on identification with/attachment to possessions:

[youtube http://www.youtube.com/watch?v=dN8vyO8ILD8&w=560&h=315]

I’m not the first person to dramatically shed all my possessions so no doubt you’ve heard of the concept of a minimalist lifestyle. Anyway I don’t think I’m so extreme, simply I’m just not that attached to stuff anymore – I enjoy having nice things but can easily let them go if I need to.

(Protip: If I do acquire things, I like to recycle/re-use. Generally I look for high quality furniture/kitchen items etc. second hand rather than some brand new IKEA made in china plastic/MDF crap)

Besides most of the places I’ve stayed in over the last 5 years were kitted out with top quality furnishings anyway:

Flat in Mitte, Berlin

Heritage Accomodation – Penang, Malaysia

Bathroom, flat in Shoreditch, London

What would be in your hobo CEO suitcase?