Things That Feel Like Failure but Are Actually Progress
If planning feels discouraging right now, I have a surprise for you.
You’re probably doing better than you think.
A lot of progress doesn’t look impressive. It doesn’t come with checkmarks, before-and-after photos, or that satisfying “I’ve got my life together” feeling.
In real life, progress is quieter. Messier. Often uncomfortable.
In fact, I’m writing this today because I’ve been sick the past three days with a cold. I’ve just been lying around endlessly scrolling on my phone when I’m not sneezing, blowing my nose, coughing, or napping. This made me realize it’s the perfect time to talk about progress (or lack of).
When we set our goals, we are usually feeling our best and are ready to conquer the world…nothing will stop us!
Then life happens.
In my case, I got sick and, of course, all of my beautiful plans for the week took a back seat. That doesn’t mean I didn’t make any progress; progress had just been slower this week, and that’s okay. I’m not going to quit everything I’ve been working towards because I’ve had an off week.
So I want you to keep that in mind when you’re reading this.
Here are some things that feel like failure, but are actually signs that something is working.
1. Starting again (for the third…or tenth time)
It’s easy to believe that restarting means you failed.
It doesn’t.
Restarting means you noticed something wasn’t working and chose to come back instead of quitting. That’s awareness. And awareness is a skill.
People who make progress aren’t the ones who never fall off. They’re the ones who don’t disappear when they do.
Related Post: Never Miss Twice Rule
2. Simplifying your plans
Crossing things off your list because you realized they don’t matter can feel like giving up.
It’s not.
It’s clarity.
Cutting back, choosing fewer priorities, or downsizing a plan usually means you’re learning how much energy you actually have, not how much you wish you had.
That’s not failure. That’s realistic planning.
Related Post: What to Do When Your To-Do List is Too Long
3. Not finishing everything you planned
Life doesn’t care about your planner.
Kids get sick (or you get sick). Work explodes. Energy dips. Days go sideways.
Finishing some things instead of everything still counts. Especially if you finished what mattered most.
Progress isn’t doing it all. It’s knowing what to keep when something has to give.
4. Changing your mind mid-plan
Switching approaches can feel like inconsistency.
In reality, it’s feedback.
You tried something. You learned it didn’t fit. You adjusted.
That’s how systems are built, not by getting it right the first time, but by paying attention and responding.
5. Taking longer than you thought it would
Most timelines are wildly optimistic.
Needing more time doesn’t mean you’re slow or unmotivated. It usually means the task was bigger, harder, or more draining than you expected.
Recognizing that and adjusting your expectations is progress. Beating yourself up for it is not.
6. Choosing rest instead of pushing through
Rest can feel like quitting if you’re used to powering through everything.
But burning out doesn’t make plans stick. It makes them collapse.
Pausing to recharge is often what allows you to keep going at all.
7. Doing the “bare minimum” version
Some days, the minimum is the win.
A short list instead of a full plan.
A five-minute reset instead of an hour.
One priority instead of five.
Showing up imperfectly still builds momentum. Waiting for ideal conditions usually builds nothing.
8. Feeling uncomfortable with your planner
If opening your planner brings up frustration, guilt, or overwhelm, that doesn’t mean you’re bad at planning.
It means something needs to change.
That discomfort is information. It’s telling you the system doesn’t match your life right now.
Listening to that is progress.
Related Post: Why Your Planner Isn’t the Problem (And What Actually Is)
9. Letting go of routines that no longer fit
Outgrowing a routine can feel like regression.
But seasons change. Schedules shift. Energy changes.
Updating how you plan is part of staying functional, not a sign that you “couldn’t stick with it.”
10. Not feeling motivated
Motivation comes and goes. Systems stay.
If you’re still showing up, even without enthusiasm, that’s progress.
Momentum is built by action, not feelings.
11. Needing support or structure
Wanting help doesn’t mean you’re incapable.
It means you’re human.
Using tools, checklists, resets, or guides is not a shortcut. It’s a strategy.
12. Being aware of what drains you
Noticing what exhausts you, frustrates you, or throws off your plans is a big step.
You can’t adjust what you don’t see.
Awareness comes before change.
13. Letting go of “perfect planning”
Perfect plans look good on paper. Flexible plans work in real life.
If you’re learning to plan in a way that supports you instead of judging you, you’re moving forward.
14. Progress that no one sees
Mental clarity.
Less dread.
Faster recovery after setbacks.
Quieter stress.
These things don’t show up in planners, but they matter.
15. Still showing up
Even late.
Even messy.
Even unsure.
Showing up again is the habit that makes everything else possible.
Related Post: What to Do When You’re Feeling Overwhelmed
A gentle reminder
Progress doesn’t always feel good while it’s happening.
Sometimes it feels like uncertainty, adjustment, or letting go of expectations you’ve carried for a long time.
If you recognize yourself in this list, you’re not failing.
You’re learning how to plan in a way that actually fits your life.
And that counts.
