Question 4: What Is My Plan for Obstacles and Imperfection? (The ‘What If’ Question)
No plan, no matter how perfect, survives contact with reality. Life is messy. You will get sick, your car will break down, a project at work will explode, and your motivation will inevitably dip. A rigid plan that assumes perfect conditions is a brittle one. A resilient plan, however, anticipates imperfection and builds in a strategy for getting back on track. This is perhaps the most overlooked of the questions to ask before goal setting.
Perfectionism is the enemy of progress. The “all-or-nothing” mindset is a common trap. You miss one workout, so you think, “Well, this week is ruined. I’ll start again on Monday.” This is a catastrophic error. One missed workout is a tiny data point. Giving up for the rest of the week is what causes failure. The goal is not to be perfect; the goal is to be consistent and to never miss twice. If you miss one day, make a promise to yourself to get back on track the very next day, even if it’s just a small action.
To prepare for this, you need to engage in what we call constraint-aware planning. Instead of creating a plan for your ideal self who has unlimited time and energy, create a plan for your real self. Be honest about your constraints.
Time Constraints: How much time can you realistically dedicate to this goal each week, even on a bad week?
Energy Constraints: Are you a morning person or a night owl? Schedule your most demanding goal-related tasks during your peak energy hours.
Resource Constraints: Does your goal require money or other resources? Plan for them upfront.
Once you’ve acknowledged your constraints, you can perform a “pre-mortem.” Imagine it’s the end of your goal’s timeframe and you have failed. What went wrong? Brainstorm a list of potential obstacles. For each obstacle, come up with a simple “if-then” plan.
Obstacle: I feel too tired to go to the gym after work.
If-Then Plan: If I feel too tired to go to the gym, then I will do a 15-minute bodyweight workout at home instead of skipping it entirely.
Obstacle: I get discouraged because I’m not seeing results on the scale.
If-Then Plan: If I feel discouraged by the scale, then I will review my input goals (my workout log and food journal) to celebrate my consistency and trust the process.
Finally, establish a review cadence. A plan set in stone is a dead plan. You need to check in regularly to see what’s working and what isn’t. A weekly review, perhaps for 15-30 minutes on a Sunday evening, is perfect. Ask yourself three questions: What went well this week? What was a challenge? What will I adjust for next week? This simple loop of planning, executing, and reviewing allows you to adapt to changing circumstances and ensures your plan remains a living, useful guide rather than a rigid set of rules.
