6 Questions to Ask When You Fall Off Your Plan (and Get Back On Track)

Ever feel like you're constantly making plans that just… evaporate? 

You're not alone. 

As a planning and behavior change coach, one of the most common questions I get is, "What do I do when I don't stick to my plan?" It's frustrating, right? You map out your week with the best intentions, full of productive time management strategies, only to find yourself veering off course by Tuesday.

The first thing I want to remind you is: plans are MEANT to be flexible.

Good planning is not rigid. Things change, a good plan helps you change with them without disrupting your whole vibe.

And here’s another thing: planning is a skill, not something you're born with. And like any skill, whether it's goal setting, improving work-life balance, or boosting productivity, it takes practice. So, if you're struggling with planning and personal organization, don't beat yourself up, do some reflection (with these 6 handy questions) and keep going, keep practicing, you will get better at it.

Now, as promised, here’s six powerful questions to ask when you don’t stick to the plan. They can help you get back on track and develop more effective planning habits.

“Good planning is not rigid. Things change, a good plan helps you change with them without disrupting your whole vibe.”

1. Did the Plan Just Need to Change?

Life throws curveballs. Sometimes, despite your best efforts at personal organization, your carefully crafted plan simply needs to be adjusted. 

Maybe your appointment runs late, an unexpected errand pops up, or your kids' schedules change. This doesn't mean you're a planning failure. It just means you're human, and life happens. 

P.S My family physician is chronically running an hour late - so, I leave “white space” or something very flexible after my appointment. And I bring a book to the office 🙂

2. Did I Make My Plan with Compassion for Future Me?

Be honest: did you create a realistic plan that allows for rest, relaxation, and the simple joys of life? 

Or did you pack your schedule so tightly that even a superhero would struggle to keep up? 

We often expect ourselves to be machines, capable of doing all the things, all the time. But that's a recipe for burnout and poor personal organization. Compassion for your future self is crucial for plan adherence and long-term success.

Think about it: would you tell a friend to follow such a packed and demanding schedule? Probably not! Treat yourself with the same kindness and understanding.

It can be hard to start paring down your schedule, especially if you've been operating at a frenetic pace for a while. Making intentional choices about what to keep and what to let go of is key. If a super-packed schedule keeps making you fall off track, here's a tip:

Look at the things that get missed when you've fallen off track. Assess the consequences of postponing each one, and find the thing that has the most minimal consequences. Then, deliberately plan not to do it this week. Yes, you will have to do it at some point, but this will help your brain see that you can intentionally defer things without life falling apart. You're creating proof that you don't have to do all the things all of the time. Bonus: This tip also helps with Radical Prioritization!

3. Did I Radically Prioritize My Goals?

We all have a million things we want to do. But successful planning and effective goal setting require tough choices. 

It's not just about what you want to do, it's about what you're willing to not do. Want to finally paint your master bedroom? Great! But what are you willing to let go of to make that happen? Maybe it's skipping a few episodes of your favorite show, delegating a task at work, or saying no to reorganizing the family Google Drive right now. Radical prioritization is about aligning your actions with your true priorities and making conscious decisions about how you spend your limited time and energy. It's a core component of effective self-management.

What you’re willing to give up to make time for your current goals is the hard part of prioritization. There’s about one million frameworks about how to pick what you want but very few on how to let go of other stuff so you can finally make that career jump, DIY your whole house remodel, or learn to dance hip hop in your 40’s. Support and objective insight is crucial, and coaching is the perfect opportunity to get both.

4. Did I Plan Something Fun and Restorative?

All work and no play makes for a very stressed-out you. Effective planning is for more than productivity, it’s for better well-being. 

Did you schedule time for activities you genuinely enjoy? Did you prioritize getting enough sleep? 

If your plan is all about obligations and zero fun, you're setting yourself up for failure and burnout. Remember, restoration is not a luxury; it's a necessity for maintaining motivation and achieving your goals. Schedule in that yoga class, that coffee date with a friend, or simply some quiet time to read a book.

If you're internally scoffing because there’s no way you can make time for that crap. I’ll give you a bonus question to chew on. How much time do your burnout phases eat up? How many hours, days, or weeks go by where you do the bare minimum to keep yourself, and maybe a couple of kids alive? Is there a chance that a week of burnout takes up more of your time than some intentionally scheduled rest ever could?

5. Did I Anticipate and Leave White Space for Unforeseen Obstacles?

The key to effective planning is to build in some "calendar white space" – think of it as an emergency fund for your time – to accommodate those inevitable surprises. This buffer time allows you to adjust without feeling completely overwhelmed or running out of time for important things.

Life is unpredictable. Kids get sick, errands pop up, and unexpected delays happen. By building in buffer time, you can handle these curveballs without derailing your entire week and impacting your overall efficiency.

6. Did I Go Back to My Plan?

Planning isn't a "set it and forget it" activity. It's an ongoing process. Did you review your plan throughout the week?

Often, we create a plan, full of good intentions and time management strategies, and then promptly forget about it. Regularly revisiting your plan is essential for staying aligned with your goals, adapting to changes, and ensuring your plan remains a useful tool for productivity and success. Set aside a few minutes each day to review your schedule and make any necessary adjustments.

So, next time you find yourself veering off course, don't panic. 

Ask yourself these questions. Chances are, your plan simply needed a tweak. And if it didn't? That's okay too. Plans are meant to be flexible. They're tools to guide us, not rigid rules we must follow blindly. They're part of a larger self-management and productivity system.