The Top 9 Planning Mistakes I See The Most

WHO knew that the most drama would be around planning?! I did not.

We’re talking about time management and productivity in Grow You this month, and alllll the drama is coming up.

It’s hard and amazing at the same time.

It’s hard because it requires looking at the truth of how you’re spending your time versus how you want to. It’s amazing because it’s transformational when you do the work and make the changes.

I’m seeing a common thread come up with all the coaching I’m doing and it’s around the specific mistakes I’m seeing with planning. Hence, this blog post.

I want to share with you the most common planning mistakes I see, so you can avoid them.

There are three categories of planning mistakes:

  1. The technical part of planning
  2. Following through
  3. Your beliefs about planning

Within each category, there are the specific mistakes I want to share to make sure you’re not making them. There are 9 mistakes in the first category, which is the actual technical part of planning. The other two categories are super important, too, but are slightly different, so they’re an added bonus if you make these changes.

Here’s a look at each mistake within each of the three categories…

Planning Mistakes

Here are some of the most common planning mistakes I see…


The first category is “the act of planning” These are the most common mistakes I see with respect to actually planning. It’s the using your calendar, or specific steps that you’re doing that is or isn’t working. The other two categories are about following through and mindset. Here, it’s all about planning the right way.

Here are the biggest planning mistakes I see with respect to the act of planning…

1. Not scheduling time to plan

I’m seeing a lot of people not putting time on their calendar to plan. Or they set it and forget.

You should spend a solid hour every week planning. This is a weekly practice. It’s not a one-time-only thing. You also shouldn’t try to squeeze it in. This should be part of your weekly routine.

I do this every Sunday night for the upcoming week.

You can add “Weekly Planning” to your calendar and block off an hour for this.

2. Not using a digital calendar

Not using a digial calendar is a huge mistake because you always have your phone on you, which means you could also always have your calendar in front of you.

If you only use a physical calendar you increase the friction of the habit. If your calendar is on your phone, then you can make the habit easy.

I use (and am obsessed with) gCalendar. This is free; you just have to sign up with gMail.

I have my gCal on my phone, my laptop, and my desktop. This makes planning super easy and accessible because I always have what I’m supposed to be doing right in front of me. This leads into the next mistake.

3. Not keeping your calendar in front of you

Not keeping your calendar in front of you is a HUGE mistake. I mean it. How can you possibly remember what you’re supposed to be doing all the time? The truth is, you can’t. And you shouldn’t try.

Instead, you should just plan on checking your calendar all.the.time. I’m serious. I look at it before bed. I look at it in the morning. And I have the calendar tab up in my browser 100% of the time while I’m working.

If you do your planning right, then you’ll need to look at your calendar frequently to make sure you know what you’re supposed to do next.

Planning without knowing what’s on your plan is useless. So, make sure you keep your calendar in front of you.


4. Not giving yourself hard deadlines

One of the most common questions I’m asked is “how long should I give myself to do something?” The answer I give is always, “how long do you think?”

The truth is, I don’t know. And you don’t know. But someone needs to decide in order for anything to get done.

What I suggest is for you to decide on a specific amount of time to do something, then do it during that time, then evaluate. Was it too much time? Not enough? You get to decide.

The key is you absolutely must have a hard deadline. If you don’t, you’ll be “working on it” forever.

Think about school. You had a paper due and you got it done by that deadline. That’s how you need to treat your life or you won’t accomplish nearly anything close to what you’re capable of.

Always have a deadline. Period.

5. Not planning for obstacles ahead of time

Many obstacles are going to come up in your life, and it’s not just that they’ll come up, but you know some of them already.

If you have kids, you know they’re an obstacle to you working without interruption ahead of time.

For obstacles you know about ahead of time, you need to turn these obstacles into strategies. 

Solve the problem you have with your kids interrupting when you’re planning. Plan on getting a babysitter or taking them to daycare, etc.

You have to plan for obstacles because they’re not going away. The more proactive you can be about it, the better.

Read my article on 7 Obstacles To Overcome On Your Journey To Weath for some great tips.

6. Saying yes to everyone else before you say yes to yourself

We want to be invited to everything. I get it. I’m the same way. But you know where achieving your goal is? Not in someone else’s mastermind or event or anything else. Your future goal is achieved by you planning and taking action to get it done.

Meaning, you need to learn how to say no with a vengeance.  It’s going to serve you so well. You’ll prioritize your future instead of everyone else’s.

You create your life instead of reacting to it.

7. Not scheduling down time, family time, and rest time

Something I’m seeing a lot of is getting the planning part down, but doing it so intensely that you forget what it’s all about.

Planning isn’t about getting more done. Planning is about intentionally designing your dream life.

This means you MUST plan for down time, family time, rest time, etc.

Now, how much of that is up to you.

You could be in a season where you choose not to have a lot of down time. That’s totally okay. Just don’t make it seem like you’re a victim of that. It’s your choice. You always have a choice.

I chose not to have a lot of down time during law school and also during the first couple of years of building my business. Now, I have a lot of down time. My life is more balanced. But that’s because I wanted to make a bunch of money and build a business first. It was worth it to me. I made that choice and felt good about it.

8. Not evaluating what’s not working

If nothing else, please, please, please evaluate your results.

What I see most people do is the opposite. They do something. It doesn’t work. They do more of it.

One of my favorite quotes…

“Experience teaches you nothing. Evaluated experience teaches you something.” – Andy Stanley

Meaning, you need to evaluate what you did. You need to see what didn’t work and why. Without any judgment (see #9 below on that). Then, try something else. Do what works.

9. Beating yourself up

If something isn’t working, the worst thing you can do is beat yourself up about it. It’s not nice, but more importantly, it’s just not useful. It doesn’t help you out at all. It changes nothing. You only hurt yourself when you beat yourself up.

As a follow up, I highly recommend reading How To Stop Beating Yourself Up (podcast is here, too).

Instead, approach what you’re doing with curiosity and compassion. Have an openness (judgment free zone) when you look at what’s not working. From there, you can seek to understand. And from understanding, you can change.


The 9 mistakes above are the most common I see when it comes to the technical planning side of things.

Now, I want to shift gears and talk about the other half of planning, which is the follow through.

1. Not following through

Not following through is a huge problem. Half of planning is actually planning. The other half of planning is following through.

If you’re not following through, then planning is useless.

Follow through is all about your mindset. It’s not about your circumstances or anything outside of you. It’s you and your thinking.

If you don’t follow through, you need to work on the relationship you have with yourself (self-love and commitment). (This is what I can help you with in Grow You.)

2. Misunderstanding why planning is important

Part of not following through is misunderstanding why planning is important.

Planning reduces the need for willpower and reduces decision fatigue.

When you decide at least 24 hours in advance, you’re clear-minded, using your prefrontal cortex. In the moment, it’s your primitive brain at work and it will always choose what is most pleasurable and least painful.

When you understand this, you get it. You stop thinking there’s something wrong when you don’t feel like doing the thing you planned to do. Nothing has gone wrong. You have a human brain that wants to stay comfortable. That’s it.

I always expect and plan for resistance. My relationship and commitment to myself is so strong that I do things I don’t feel like doing all the time if I’ve planned them ahead of time.

3. Believing your own excuses

What I see happening more and more is that we’re lying to ourselves and believing our own excuses.

Examples: “Life is hard; I just got busy; other things are a priority.”

If you believe your excuses, you will give yourself a break.

Instead, come from a place of love and follow through no matter what. Like you would if you were disciplining your child. You wouldn’t let the 2 year old stay up all night. You would put him to bed even if he didn’t want to. Your primitive brain is the 2 year old. Your prefrontal cortex is the parent. Follow the rules set from your prefrontal cortex (i.e.: the plans you make for yourself at least 24 hours ahead of time).


4. Thinking it’s going to feel good when it’s time to do the thing

The biggest point that I can’t stress enough is that you’re never going to feel good doing difficult things that you’ve planned to do if  it’s causing you to grow.

By definition, growing means doing something new and different. Your primitive brain hates this. It wants to recycle the old. It wants pleasure. And it wants to avoid pain.

The biggest favor you can do for yourself is to tell yourself you’re going to do it anyway, from love.

It’s like when you have to fast because of a blood test versus fasting because you’re dieting. When you’re fasting because of a blood test, you tell yourself things like, “It’s going to be fine. This is temporary. I’ll be able to eat soon. This is helping me.” Contrast that when you fast for dieting (intermittent fasting) and you may come from negative self talk like, “this is stupid, I hate this, I just want to eat, I don’t see any real difference.”

When you can learn to love yourself through the discomfort of doing something you don’t want to do, you’ll follow through with your best laid plans.

And this is how you achieve your impossible goals. You have integrity with yourself. You do what you say you’re going to do.

More Resources On Discomfort:


The final category of mistakes that I see with planning is in the beliefs category.

If you don’t understand why planning is important and how it provides you with the ultimate long term care and freedom, you’re unlikely to do it (it is tedious after all).

1. Believing that planning is limiting and rigid

Planning is not rigid or limiting. It’s the opposite. Planning is your ticket to freedom.

It doesn’t mean overwork. And it doesn’t mean do too much.

It means making decisions ahead of time

When you plan, you decide with the most rational part of your brain. You design your life with the clearest vision possible. It’s the best way to guarantee your future.

This means you make space for what’s most important, including your family, down time, learning time, life events, life insurance, real estate planning, etc.

Your future is in your best laid plans.

2. Believing that you’ll always be behind

If you have negative beliefs about your life, like “I’ll always be behind,” then no matter what plans you make, you’ll sabotage them.

Your thoughts ultimately create your results. So what you have in your life right now is a result of your prior thinking.

If you think you’re behind, then you will stay behind.

I highly recommend jumping in this free training for the life coaching tools that can help you the most with this: 9 Tools To Up Level Your Life.

3. Believing that you don’t have enough time

Just like I mentioned above, if you believe it, you’ll find it a way to be your reality.

If you think you don’t have enough time, then you won’t have enough time.

We all have the same amount of time. You have a choice how to think about time. You can choose to think you have enough time.

Other Time Management Resources:

A Final Note

We started with the top 9 biggest planning mistakes I see coaching high achieving women on time management and planning. We rounded it out with the remaining planning mistakes with respect to following through and mindset.

My best advice for you is to turn each mistake into a new habit.

This process is like sharpening your ax before cutting down the tree, as the saying goes. The sharper your ax (the better your plans), the easier and more likely it will be for you to cut down the tree (or to accomplish your goals).

Planning might not be the most fun for you, but it will give you the freedom to design your dream life, and for that reason, it’s 100% worth it.