How to Make an If-Then Obstacle Plan for Your 40 Day Challenge

An if-then obstacle plan is a sentence that decides, in advance, what you'll do when a predictable problem shows up: "If [obstacle], then I will [response]." To make one for your 40 day challenge, list the two or three things most likely to stop you, then write a specific, small response for each. At WholeLifeLog we treat this as part of setting up any challenge — because the obstacles are usually easy to predict.

Most challenges don't fail because of surprises. They fail because of the same few things — late nights, travel, a bad mood, a busy Monday — that we could have seen coming.

The research behind if-then plans

If-then plans are based on implementation intentions, a concept developed by psychologist Peter Gollwitzer. Instead of only setting a goal ("I'll exercise more"), you link a specific situation to a specific action ("If it's 7 a.m. on a weekday, then I'll walk for 15 minutes"). Many studies and reviews suggest this kind of planning can improve follow-through compared with goal-setting alone, though results vary by person and situation.

A related method is WOOP — Wish, Outcome, Obstacle, Plan — developed by psychologist Gabriele Oettingen from her research on mental contrasting. The idea: picture what you want, then honestly picture what's likely to get in the way, then make an if-then plan for that obstacle. Imagining only the good outcome, her research suggests, can actually reduce effort; pairing it with the obstacle helps.

Step 1: Find your likely obstacles

Before Day 1, ask yourself:

• When have I given up on similar goals before? What happened?
• Which days or times will be hardest?
• What feelings usually make me skip (tired, stressed, bored, embarrassed)?
• What events in the next 40 days could disrupt my routine (travel, exams, holidays, guests)?

Pick the two or three most likely obstacles. You don't need a plan for everything — just for the predictable ones.

Step 2: Write a specific "then"

A good response is:

• Specific — what exactly will you do?
• Small — often your minimum practice.
• Immediate — something you can do right when the obstacle appears.

Weak: "If I'm tired, I'll try harder." Strong: "If I'm too tired to walk after dinner, then I'll walk to the end of the street and back."

Fill-in template

Copy this into your journal or plan:

My daily action: ______________________

Obstacle 1: If ______________________, then I will ______________________.

Obstacle 2: If ______________________, then I will ______________________.

Obstacle 3: If ______________________, then I will ______________________.

If I miss a day anyway: then I will ______________________ the next day.

The last line matters. Planning your restart in advance removes the "I've already failed" spiral.

10 example if-then plans

#	Obstacle (If…)	Response (then I will…)
1	I get home after 9 p.m.	Do my minimum practice before taking off my shoes
2	It's raining at my walking time	Do 10 minutes of indoor stretching instead
3	I reach for my phone first thing in the morning	Put it back and open my notebook for one line
4	I'm traveling	Do the action in my hotel room right after unpacking
5	I feel too stressed to study	Solve just one practice problem, then decide
6	I forget to read before bed	Read one page right when I notice, even if it's late
7	Friends invite me out on a workout evening	Move the workout to the morning of the same day
8	I want to buy something unplanned	Put it in a wishlist and wait 48 hours
9	I wake up feeling low	Do the minimum and write one honest line about the mood
10	I miss a day	Restart the next morning with the minimum and log why I missed

Step 3: Review and update weekly

Obstacles change. During each weekly review:

• Check your log for "partly done" or "not done" days.
• Ask what caused them. Was it one of your planned obstacles, or a new one?
• Rewrite plans that didn't work, and add a plan for any new obstacle.

Over 40 days, your if-then plans become a personal playbook. (See our guide to the weekly review for a 40 day challenge.)

Common mistakes

• Too many plans. Ten if-then plans are hard to remember. Start with two or three.
• Vague triggers. "If things get busy" is hard to recognize in the moment. "If I have a meeting after 6 p.m." is clear.
• Heroic responses. If the "then" is harder than the original action, it won't happen.
• Not writing them down. Plans in your head are easy to forget.

When you set up a 40 day challenge in WholeLifeLog, writing a couple of if-then plans alongside your daily action gives you a ready answer for the days that usually derail people.

FAQ

What's the difference between an if-then plan and a goal?

A goal describes what you want ("read more"). An if-then plan links a specific situation to a specific action ("If it's 10 p.m., then I'll read one page in bed"), which makes it easier to act without deciding in the moment.

How many if-then plans should I make?

Two or three for your most likely obstacles, plus one for how you'll restart after a missed day. Add more only if a new obstacle keeps showing up.

Is WOOP the same as an if-then plan?

WOOP includes an if-then plan as its final step, but first asks you to picture your wish, its best outcome and your main inner obstacle. Both approaches come from related research and work well together.