△ | MMD | The Planning Fallacy: Why Your Goals Take Longer Than Expected


This week's edition is brought to you by Realizations.
Self-Mastery Journal: A Better You, One Page At A Time.

6/9/2025

I used to have a horrible taste in my mouth about sales.

Not sure why, just despised it and was committed to never being a salesman.

So, like anyone trying to avoid going down the sales route... I got a Master's Degree.

But that didn't work out and years later I found myself looking for a new gig.

You're probably thinking I went and got a sales job but boyyyy let me tell you... that's exactly what I did (shameful face)

But I embraced it. I had to.

And now I'm a believer that anyone who doesn't know what they want to do for work should get into sales.

Here's What I Learned & Why It's Important

Sales is personal development disguised as a job.

That is, if you do it right.

It teaches you:

  • The importance of communication & relationships.
  • It's not about how much you know, but how you deliver the message.
  • Setting proper expectations matters more than the expectation itself.

Learn these skillset's and you'll have no problem succeeding in any department.

But let's focus on setting proper expectations...

Under Promise, Over Deliver

Imagine this, you place an order on Amazon that says 1-day delivery. Yet it takes 5 days to arrive.

You're frustrated. Of course you are, they didn't meet expectations.

Now imagine you place an order that says 14-day delivery and it arrives in 5 days.

Would you look at that?! Check out that service. You're pumped and might even feel a little special.

They were both delivered in 5 days, yet your reaction to it is completely different.

The expectation is that it will be delivered.

The expectation they set is when.

For some reason, when it comes to personal development, we struggle with setting proper expectations.

You set an expectation with 1-day delivery when in reality it might take 100 days to arrive on your doorstep (metaphorically speaking).

The Planning Fallacy

There's this thing called the Planning Fallacy.

It states that we tend to:

  • Underestimate unforeseen obstacles.
  • Overestimate our capabilities.
  • Align the timeframe with the best-case scenario.

Usually when you are setting goals, you're in a motivational mindframe.

Think about it.

Your excited about these goals. So you write them down. You're in a headspace ready to go to battle.

And as you set these goals, naturally you assume that every day moving forward you will feel this exact same way.

You fail to realize that obstacles will come out of nowhere.

Maybe you:

  • Slept like shit.
  • Get sick.
  • Are frustrated.

Hell, maybe you just have some days mixed in where you're not on your A-game.

And it is starting to frustrate you because you expected 1-day delivery but now you're on day 27.

You don't realize it, but you are on the right path.

You just set the wrong expectation.

Rule of Thumb

According the the Planning Fallacy, the rule of thumb is to 2x or 3x the time you think it takes to achieve a goal.

This doesn't mean you can slack off.

Work as if it needs to be done at 1x, but set expectations that it could take 2x.

That's the difference between shocking yourself with what you're capable of doing and feeling frustrated.

AKA Patiently persistent.

So next time you find yourself frustrated with where you are at, ask yourself these 2 questions:

  1. Am I putting in the work?
  2. Am I on the right path?

Chances are you are on the right path, you just need to recalibrate your expectations and keep going.

Stay the course.

Until next time,

Dallen "Big Sales Guy" Reber

Last week we talked about how true experts are constant beginners.
If you missed it you can check it out
here.



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