Lifehacking – Pre-empting Life’s ‘Compelling Events’ to Live Without Regrets

Have you ever heard this narrative?

  • Person lives 'normal' life
  • Is struck by tragedy (divorce, redundancy, terminal illness, etc.)
  • Suddenly decides 'what's really important'
  • Changes their life disruptively to maximise the rest of their days
  • Tells you (and everyone) that this is the best thing that ever happened to them

Yeah, me too.

If you read Eric Ries' “The Lean Startup” (by the way you should) he talks about 'Pivot or Persist' meetings. In short, rather than waiting for a compelling event, like running out of runway, or a sudden revenue spike, you hold regular 'Pivot or Persist' meetings. So rather than making decisions when you're under pressure, with volatile emotions, you pre-empt a given event and make (somewhat more) rational decisions. You choose the path of the organisation rather than having it chosen for you.

My philosophy is to do this with (my) life.

Why wait until you're made redundant before starting a new venture? Why wait for terminal illness before spending time with friends and family, travelling and knocking off the 'bucket list?'

In fact, all of the disruptive compelling events, the bad ones actually constrain your ability to fully live life. Despite Jack Nicholson and Morgan Freeman, jaunting around the world in “The Bucket List” it's pretty unlikely you're going to be up to getting on a longhaul flight when on chemo. Even if you were allowed, you'll probably not have the energy or motivation.

At the end of the day you haven't been given tomorrow, and your 'wealth' is a mental construct. In the scheme of the universe your 70 years and material wealth are infinitessimal.

At the end of your life you regret the things you didn't do, the chances you didn't take, the people you didn't love, the places you didn't see. Not the things you did.

You have so much to give, so much to experience, so much to see, and do, so many to help, and such a short time to Love and be Loved.

So don't wait for the universe to throw something in your path, rather sit down on a regular basis, figure out what you want to do, and…

…just do it.

Getting Close Now

Project 2012: Day 227

Update 1 – Planning


The planning phase for my Bucket List Ride, the Topdown Tour of the US 2012 is really starting to ramp up now. I’ve booked and paid for most of the bike rental. I pick up the bike in Seattle on 9th September from Motoquest. My flight is booked, as is the Vancouver to Seattle bus.

I’ve also paid for a return flight from Long Beach to Seattle for the 19th September, when Lucy and the girls fly in to the US.

Safety Gear

Because I’m riding alone, I wanted to ensure that people could track my progress, and that I have a way to call for help, or alert Emergency Authorities even if there is no cell signal. To this end I ordered a SPOT GPS Messenger, which does exactly that.

You can follow my progress on the page on this blog. I’ll also be testing it on my Black Dog Ride week-end that you can check out at Feel free to sponsor me 🙂

The one frustration is that a device that costs just $99 in the USA (which is about AU$93) is charged at $200 here in Australia. “On Sale”

I also ordered a UTAG ICE Dog Tag. This is a USB device that carries all of my personal, identification, medical and emergency contact information. Along with insurance details. If I’m unconscious, I want to ensure that people can rapidly get the information they need to treat me. Especially insurance in the USA, not to mention my rare blood type.

This is a cool device that hangs around your neck, just like a dog tag, but plugs into any USB drive.

Home from Home


I’m planning to get off the beaten track, and at least half of my nights will be camping. Partly to minimise cost, but mostly because I actually enjoy getting out into nature, and the ride from Top to Bottom on this continent’s coast has some of the most spectacular nature in the world.

Now Air Canada is quite strict on their “1 bag 23kg” policy, so I’ve been researching light, strong, weather proof, compact, yet large enough, inexpensive tents. 🙂 No mean feat. Especially when this has to include my Helmet, and Riding gear.

After weeks of research, including building an Excel model, looking at tents both locally (more expensive, have to include in flight weight) and in the USA (less expensive, have to bring it back, potential warranty issues) I ended up finding a tent left over from the Aldi “Extreme Hiking and Mountaineering Sale”

Alloy poles, gear loft, alloy pegs, taped seams, bathtub groundsheet, 2 entrances, 2 vestibules, in a compression dry bag, at only 2.5kgs and just AU$70 – bargain. 🙂

Especially when you have 60 days to return it if not satisfied.

Now I’m doing the same with both sleeping bags, and hiking self inflating mattresses. I’m also looking at a dry bag for the camping gear on the back of the bike.

At the moment I’m unsure about cooking equipment, as I may just eat out all the time. I’d rather not spend too much time shopping at supermarkets.


Another big issue is what to take in the way of electronics. On the one hand I don’t want to spend all my time editing, and posting etc. On the other this is a “once in a lifetime” opportunity and I don’t want to leave the SLR at home and then get to experience a shot that I’ll never get the chance to see again.

Of course all of you get to live life vicariously through my lenses as well.


Suffice to say I’ll have:

  • Contour GPS Helmet Cam
  • iPhone 4S for most Instagram and Candid Shots
  • Canon 550D with twin lens for serious photography
  • All three of the above devices take HD video – but I may try and reclaim my Flip Camera from the friend I lent it to a year ago
  • For editing and Internet, I’m tossed between the iPad and the MacBookPro. I’m erring toward the iPad at the moment because of battery life, ease of charging, limited replacement cost should something happen to it, weight, and the limited functionality will minimise the time I’m messing around with electronics. Mostly this trip is about disconnecting.

To that end, I’ll be testing the iPad this week-end as well. If it works, I’ll leave the MacBook at home. I can pretty much do everything on the iPad and iPhone.

That’s it – I’m getting the riding gear together as well, but I’ll leave that for another update.