How to Fail in the New Year offered a quick recap of the typical progression of a person with a New Year’s Resolution.  The light at the end of the post is ten questions to create a simple plan to achieve your goal.  You don’t have to answer all the questions.  Answering several of them increases your odds of success.  Use the explanations below to understand the logic and utility of the questions better.
Embrace the pain of thinking ahead to savor succeeding later.

List of 10 Questions

  1. What will I do?
  2. Why will I do it?
  3. When will I do it?
  4. Where will I do it?
  5. What might I enjoy?
  6. Who would encourage me?
  7. How can I view my progress?
  8. What milestones can I celebrate?
  9. What’s an easier way when it gets hard?
  10. What might be next after I knockout this goal?

Questions Explained

Question 1 – What will I do?

Most resolutions are vague.  The first step into failure is vague wishes.  Get specific.  List a SMART goal or system.
Systems are ongoing activities.  Goals are one-time achievements.  Both are good tools but if you stumble aimlessly after completing a goal, create a system,  combine goals and systems, or answer question 10.  Read more on the difference here.
  • Goal – I will lose 10 pounds by March 31st.
  • System – I will eat only whole foods 6 days per week.
  • Goal + System – I will lose 10 pounds by March 31st by eating only whole foods 6 days per week.
Bullsye for goal step 1, Man thinking over question mark for goal step 2, circular cycle for sytem

For a small minority at key moments in their lives, step 2 leads to achieving their wildest dreams. Am I ready for that right now? Systems and question 10 are excellent alternatives.

Question 2 – Why will I do it?

Change is hard.  Knowing what is a good start.  Knowing why increases your odds of continuing when life gets hard.  Life will get hard.  Motivation, discipline, and willpower are overrated.  Create a big-enough WHY lever to catapult you over the hard times.  And answer question 9 to make the hard times a little easier.

Question 3 – When will I do it?

Implementation intentions cement sticking to a new behavior.  To set your intention, list specifically what, when, where, and how you will perform your new behavior.  Maybe you already listed “how” in question 1.  If not answer it here along with question 4.  Keep it simple.  I will perform twenty squats (what) getting my butt below my knees (how) every day after I shower (when) in my bedroom (where). 

Question 4 – Where will I do it?

See question 3.
  • What?
  • How?
  • When?
  • Where?

Question 5 – What might I enjoy?

You might not enjoy anything new.  You are not alone.  Most of us don’t like change.  But what might you enjoy after experimenting for a week to a month?  
A future rock star might not enjoy practicing the guitar on day one.    But playing a few chords of a simple song is a spectacular moment…for some people.  List ideas for what you might like, search for those moments and use them to answer question 8.
If you can’t picture enjoying an activity after a month, do you have a monster WHY driving this change?   A single parent may not like learning programming to pay the bills, but food for a child is a powerful motivator that’s hard to replicate for most goals. 
When in doubt, stick to goals you may eventually enjoy.  Run a two to four-week experiment to find out if you get that rush of pleasure after the pain of starting.

Question 6 – Who would encourage me?

Do you have a spouse, friend, child, co-worker, someone you trust to ask you about your goal, maybe spark a little motivation when you’re struggling or even partner with you to get started?  Maybe you know an expert in this area who might be more than happy to guide you if you ask.  Maybe you want to bet your social network that you’ll post a picture of your heaviest barefoot deadlift wearing a thong in the snow if you don’t meet your goal.  Okay…no one wants that, but one decision to post those words guarantees you’ll get social “encouragement”. 

Question 7 – How can I view my progress?

Everyone wants to win the game of life.  Create a scoreboard.  Gamify your goal.    You can build the most advanced tensorflowin, pythonated, Skynet-inspired artificial intelligence in the world to weigh the significance of your actions or hang a calendar on your bathroom mirror with a thick red marker underneath.  Mark an ‘X’ every day you meet your goal and don’t break the chain.  For digital options, I like Productive and Way of Life.
Don't break the chain calendar with red x marked for first three weeks of January

Post a calendar where you’ll see it every day – bathroom mirror, coffee pot, work desk. Mark a ‘red X’ every day when you meet your goal.

Question 8 – What milestones can I celebrate?

Duhigg explains the habit cycle in The Power of Habit as 1) Trigger 2) Action 3) Reward.  Rewards are best if they’re immediate like that chocolate protein shake after a hard workout.  Milestones are bigger.  The Power of Moments (Ch. 8) compares typical plans versus a “gamified” strategy with milestones.
Typical Plan
  • Level 1: Practice Spanish
  • Level 2: Practice Spanish
  • Level 3: Practice Spanish
  • Level 4: Practice Spanish
  • Level 5: Practice Spanish
  • Goal: Eventually “know” Spanish
Gamified Plan
  • Level 1: Order a meal in Spanish
  • Level 2: Talk to a taxi driver in Spanish
  • Level 3: Understand headline in Spanish newspaper
  • Level 4: Follow a Spanish cartoon
  • Level 5: Read a 1st-grade Spanish book
  • Goal: Talk to coworker fluidly in Spanish
The “gamified” levels are milestones worth celebrating.  If you quit after any level you can be proud of your progress. Use these questions from the authors to create milestones.
  • What’s inherently motivating?
  • What would be worth celebrating that might take a few weeks or months?
  • What’s a “hidden” accomplishment that’s worth surfacing and celebrating?
    • A “hidden” accomplishment is something that normally flies under the radar without anyone noticing like when you fit into an old pair of jeans or solve your tenth client issue of the year. 

Question 9 – What’s an easier way when it gets hard?

Today.  Week one.  The first month.  Now is not the challenge.  Almost half of New Year’s Resolutions die within one month.  Life gets hard.  What’s your backup plan?  
When you create a significantly challenging goal, create an easier option for the dark days.  The easier option is still better than your current pre-goal state.  If you’re not exercising now and your goal is to run a 5K starting with one mile per day, running for just one minute is better than not exercising.  
What’s so easy you can’t say ‘No’? – Leo Babauta 

Question 10 – What might be next after I knockout this goal?

Goals provide purpose and direction.  Achieving a goal creates euphoria often followed by emptiness.  What do I do next?  Remember the man-over-the-question-mark in the image from Question 1.  If you created a system for question 1, you don’t have this problem.  Systems are designed to continue.  If you created a goal, brainstorm one option for what you might tackle after you crush this goal to avoid falling off a cliff afterward.  No commitment.  Just one option.