I need your help: challenge me something!

Find a horizon
Find a horizon

In three months, I want to have completed 7 personal challenges.

I’m not too bothered about where the achievements weigh in on a global scale – I’m not trying to set a world record – just a “Tim record”.

I need your help to help me work out what to do. I’ve had a few ideas, some of them are ok, some of them aren’t so great. What do you think I’d find challenging?

A note: challenges have to be vaguely appealing to me – it doesn’t matter whether playing golf or BASE jumping are challenging, I don’t want to do either.


Other suggestions welcome

  • Complete a street marathon
  • Swim over 100m across open, cold water without assistance
  • Swim 30 consecutive lengths in a 50 metre pool
  • Drop a stone in weight and maintain it for at least 30 days.
  • Be able to do 50 sit ups in 5 minutes
  • Be able to do 10 consecutive pull ups
  • Run 70km over 7 consecutive days
  • Run 10km in under an hour
  • Climb up and down x000 metres in xxhours (how many?!)
  • Do a 20 mile hill walk
  • Do a 30 mile hill walk


Other suggestions welcome

  • Get baseline climbing qualifications
  • Get baseline kayaking qualifications
  • Get baseline windsurfing qualifications
  • Get surfing lessons
  • Go paragliding
  • Bake something new
  • Make a short film (must not be a documentary, music video or advert)


Other suggestions welcome

  • Throw two, 3 course, dinner parties
  • Perform two open mic nights
  • Prepare an entertaining 30 minute talk on notechnical subject and give it at two barcamps
  • Learn the Melbourne Shuffle
  • Write a song for Youtube


If anyone can suggest technical challenges that are actual challenges, that’d be good.

  • Be able to deploy a 4 machine Magento cluster from a script (or systems provisioning system) with mysql master-master replication, Varnish ESI, local CDN, SSL, sane firewalls and low impact scheduled backups.


I’d quite like to have a travel section here, but I can’t think of anything that sounds appealing that’s a challenge. (I’m not a fan of “x countries in x hours” because it seems rather shortsighted, and liable to make sure you only see a bunch of airport lounges, in addition most “visit this country” challenges seem to essentially be “spend some money”, which isn’t really a challenge – the challenge was getting the money or being a creative routefinder.)

  • Travel by as many different modes of transport as possible from A to B

So yeah, which 7 of these should I do? What should I do that’s not on this list?

You tell me.

14 thoughts on “I need your help: challenge me something!

  1. Bucket lists I love bucket lists! Choose the ones which are different from things you do regularly.. as opposed to building on skills you’re already comfortable with– because it’s FUN. Saying that, if I were to pick 7 things for myself from this list I’d choose everything (except the running flavored ones) under fitness, paragliding, then throw a dinner party to celebrate. Oh and I’d definitely put BASE jumping on the top of your list *nods*

    1. It’s funny. I’m not keen the term “bucketlist” because it’s defined a list of stuff to do “before you die”.
      I guess you could either assume that I’m not going to speculate when I’m going to die and take a very pessimistic view ‘to be safe’, or, more optimistically, I don’t really think “a lifetime” into the future and would prefer to try something today, so if I liked it, I can do it again tomorrow. :)

      BASE jumping clearly goes right at the bottom of any list, specifically, “after completing basic skydiving training”, and “after completing every other list, ever”.
      It’s so cool… yet so something I think I have to stand back and let other people do it. There’s plenty of dangerous adrenaline sports that don’t involved 180’s into cliffs… err… like speedflying.. erk. no, not that!!

      Hmmm, you’re right that most of those skills are fun, but they open new doors and aren’t really that much less fun than most of the fitness ones (just probably a bit less tiring!) :D

      I’m nervous about doing too many things that are the same, partly because I get bored easily, and partly because when combined, they don’t seem all that challenging and varied – just ” a fitness program” or “Tim picking up badges at snail herding” etc. ;)

  2. My suggestions:

    Learn to contact juggle
    Hold an unsupported handstand for 10 seconds
    Learn to tightrope walk

    If you pick any of those, you can join me doing the same challenge at Circus House :)

    That and finding out if it’s physically possible for me to do the splits, which you’re also welcome to join me on trying, but for some reason most guys don’t seem to see the appeal.

    As for your existing suggestions, definitely the Melbourne Shuffle!

    1. I’d like to be able to do an unsupported handstand, but I think more upper body strength (and possibly weight loss!) lies between me and there and should probably come first… then hah, yeah, making myself a bit more flexible. Splits? Hah, I’ll leave you to it! :)

      I’m going to Shuffle at some point, I suspect developing my foot muscles will make T-boning and Running man easier. Hmmm..

      Thanks! :D

  3. Tim! I’d happily accompany you on any/all of the following, if you wanted awesome support :D

    Climb up and down x000 metres in xxhours (how many?!)
    Do a 20 mile hill walk
    Do a 30 mile hill walk
    Get baseline climbing qualifications
    Get baseline kayaking qualifications
    Get baseline windsurfing qualifications
    Get surfing lessons
    Go paragliding
    Make a short film (must not be a documentary, music video or advert)

    What about Caving? I’m planning to do that soon with a friend.

    I also challenge you to eat…meat! bwhaha :D

  4. Cycle ~40 miles to Liverpool in under 5 hours.
    Cycle ~60 miles to Blackpool in under 6 hours.
    Cycle 10 miles a week outside of commuting!

    1. $DayJob contract doesn’t allow me to paid IT side projects. I’ve no real desire to test patience for £365/year – if I wanted to be a consultant sysadmin (the easiest, least stressful route) I wouldn’t work for these guys. I suspect if I wanted many many many headaches I could start advertising myself as desktop support but I will never do that and I will never let anyone use me as Windows End User support.

      In terms of hypothetically creating a product – yup that’s a good challenge – but I’d prefer the end game wasn’t money – otherwise half the work will be about working out which dodgy ad networks offer the best PPC and how many users I can pile onto a site.

      On the other hand, if you’d like to buy a groundbreaking, new social network, that’s revolutionized the lives of its users, do give me a shout! ;)

  5. Fitness: Take up a totally new sport (such as handball, extreme ironing, thai kick boxing… )
    Skills: Make a chair from scratch (doesn’t have to be this one, though it’s quite cool http://hartzivmoebel.blogspot.de/ )
    Culture: Learn a musical instrument or dance from another culture (Samba… bongo drums…. bagpipes… no hang on, not bagpipes….let’s have some compassion on your fellow citizens here….)
    Technology: Create a projection TV using an old beamer and a laptop
    Travel: Go somewhere that’s hard to get to, like the Faroe Islands, Greenland or Mongolia

    1. Hi Cath! Thanks for the suggestions!

      I read Falkland Islands not Faroe Islands but all the same, neither are actually *that* hard to get access to:

      Difficulty = time + money

      Difficulty = [not that much] money

      Difficulty = money

      Difficulty = time + some visa bother forms + money

      I mean, it’s actually completely possible to visit the South Pole for $:

      I mean if you want to *work* on the Antarctic Amundsen-Scott station, and can somehow persuade Raython that they want you, even though you’re not a US citizen, it’s not impossible:

      Or if you’re something I’m not:

      As it is, I’m quite happy working in locations without internet via satellite. ;)

      What’s a beamer? Some kind of projector? Projectors are frustrating devices (generally replacement bulbs are worth more than the projector), but projector + media centre really is just about making the laptop aware of the projector. Converting display formats can usually be solved with ebay + an adapter. :) You should have a go! :)

  6. Oh, I’d quite like to do the swimming ones myself! Do either of those!
    I reckon the weight loss one is (relatively) easy if you do any of the other fittness ones properly (=with training) …
    Can I be invited to the dinner parties please? :P
    The make a film one sounds quite cool as well.

    1. Mmm, yeah. Some of them aren’t *that* difficult I don’t think. I’m slightly wary of setting the bar too high for swimming ones given that I’ve not done serious swimming for a few years. I’d prefer to complete it in just a few weeks and be able to get a new one, than face with myself with something that I can’t see as realistic. To be honest, the cold water one, I’d be surprised if I couldn’t do that now, but setting it up in a semi-safe way requires a little more thought.
      I guess, actually, the best way to do it would be down a slow flowing section of fairly deep river where I was still in my depth and not, out-currented. :S
      OR actually, a lot of lakes and tarns are actually relatively shallow.
      Probably not something I should attempt on my own perhaps…. or maybe I should just go for it and stop scaring myself.
      You’re right about the weightloss one – I suspect that’s mainly about eating correctly which might take some resolve/getting used to.
      Hmm. I’ll keep thinking..
      Thanks! :D

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