UPDATE: The 29 Day Challenge was a smashing success.
Have you heard of the 30 day trial? It’s a personal development thing where you create a positive habit for 30 days. The idea is that we psych ourselves out when considering lifelong changes, but a “no questions asked if you quit after 30 days” trial is doable.
Today I’m proud to announce my own 29 Day Leap Year Challenge. It’s one unit more awesome than the 30 day trial (yes, we’re using golf rules).
Supposedly you shouldn’t tackle more than one habit per month, but I’m not climbing Everest. My goals are manageable and full of slack. For example, “exercise” means whatever I feel like doing. It could be a 15 minute walk or an hour of pumping iron. When you say “I must do 45 squats with 500lbs. daily” you set yourself up for failure, so you bury your sorrows in ice cream and you don’t go to the gym the next day. I’ve found that when you start small with say, five minutes of meditation, you get bored with doing so little and you develop an innate desire to work harder.
To show you what I mean, here are my goals:
- Get up by 9am: If I get up before 9 then yay me.
- Do at least 1 significant task to create passive income: Almost too modest, but the secret is that in my mind I say “yeah, I can handle one task”, and then I end up doing more. Sitting down to work is harder than doing work.
- Exercise daily: Could be as little as a 10 pushups, the key is that once I start I’m unlikely to be satisfied with just 10 pushups.
- Daily drawing or artwork: Could be a simple doodle on a 3×5 card or two hours of intense drawing.
- Blog daily: Sweet! this one’s automatically covered by blogging daily about my progess.
- Eat fewer than 2,500 calories a day: For my height, weight, and activity level - 6’ 2”, 248lbs, mildly active - I need 3,100 calories to maintain (calculate yours here). In the interest of fully going public I’ll say here that I’m technically obese. I need to lose about 60lbs. to be a healthy weight, which is a difficult long term goal, but eating 2,500 calories daily is easy.
- Give up beef this month, except for 2 phở indulgences: Cows are bad for the environment and bad for my blood vessels. Still, I love beef, so I’ve decided to allow myself some wiggle room by allowing myself to enjoy beef in the form I love best: tripe, tendons, and meatballs in phở. Who knows, I might even go to a phở place and order just the fish balls.
- No more than 4 servings of alcohol this month: I have a fun trip this month that involves wearing a suit so I will indulge with some single malt scotch. Drinking tip: never just throw drinks back, drink something good enough to savor.
- Meditate Daily: Believe it or not, doing 10 minutes of Vipassana meditation may be the hardest thing on this list. Why? Because quieting your mind is hard under normal circumstances, and even harder when you’re amped up to achieve a bunch of goals.
Going public with your goals is as crucial as starting small. I’ll be blogging my progress daily and I’ve done one other thing which may shock people who know me in real life…

Dun-Dun-DAH! That’s right, my beloved ‘do is gone. I wanted to get rid of a vain time sink and have an unavoidable reminder of what I’ve committed to do.
You can also view my goals and track my progress (and hey, maybe start your own trial) at Making the Chain, a simple web based goal manager created by my friend and sometime co-conspirator Micah. If you’ve got any goals, even if they’re on the back burner, talk about them in the comments, sign up for Making the Chain, or even better, write about them in that blog you’ve been meaning to start.
As a final bit of encouragement for myself and all of you, here’s a quote I came across in The War of Art:
Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves, too. All sorts of things occur to help one that would never otherwise have occurred. The whole stream of events issues from the decision, raising in one’s favor all manner of unforeseen incidents and meetings and material his way. I have learned a deep respect for one of Goethe’s couplets: ‘Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it.”
- From W.H. Murray, The Scottish Himalayan Expedition
7 Comments ↓
Good one. However how many are ready to follow you is the question? :)
Awesome! I like your idea about leaving some slack in your daily goals. Starting, even with a small action, is definitely the hardest part.
Thanks Micah. Making the Chain is going to be a vital part of my success. I used it on and off before, but now that I’ve made my chains public I’m betting the incentive to stick with it will be irresistible.
Making the Chain is awesome. I just signed up.
Nice! I may just use this as a template for my own 29-day challenge, if for nothing else than an excuse to use Making the Chain.
I have not been able to get this whole challenge out of my head. I feel so inspired that i am going to start my own! I will keep you posted how it goes for me.
YAY Nathan!
That’s great Yuko. I hope your challenge involves lots of artwork :)