Sep 25, 2026 · 18 min · 8 segments
Can't picture where you'll be in five years? Same here. In episode 70, I break down what a 5-year plan really is, including the pros, the cons, and the honest truth that it's not for everyone. You'll…
Let's start with the good stuff.
Here are five pros of doing a five-year plan.
The first one gives you some degree of direction.
Without one, it's easy to stay busy for years and never actually arrive anywhere or arrive where you want to go.
A plan keeps you off the hamster wheel.
Number two, it gives you a clearer yeses and nos.
When you know where you're headed, it's easier to turn things down that you know are going to pull you sideways.
If you're someone who says yes to everything, this one could be a game changer and it can help you stay on track because you know where you want to go.
Number three, small choices that add up.
This gives you those small choices like a 20-minute walk, a monthly deposit into a savings account, at class on Tuesday nights.
Stretch those across five years and they become a completely different life.
Number four, you'll gain proof of progress.
On the days you feel stuck, like you haven't completed much, you know, I'm sure some of you guys have felt those days.
I know I have.
You can look back and see how far you've come.
Number five, you can make wishes turn into actions.
Some days become, by this year, I'll have this done.
And here are the five cons that I've come up with.
First one, life happens.
A job loss, a move, a baby, a health scare.
Some plans feel out of date in six months.
And some of these things can just throw a plan completely off track into a different direction, right? Number two, it creates pressure and perfectionism.
A plan can become a stick to beat yourself with, like get those feelings on behind schedule is a rough thing to tell yourself.
Number three, you're guessing at a future you.
The you of five years from now will want things today that you can't imagine quite yet.
Let's start with the good stuff.
Here are five pros of doing a five-year plan.
The first one gives you some degree of direction.
Without one, it's easy to stay busy for years and never actually arrive anywhere or arrive where you want to go.
A plan keeps you off the hamster wheel.
Number two, it gives you a clearer yeses and nos.
When you know where you're headed, it's easier to turn things down that you know are going to pull you sideways.
If you're someone who says yes to everything, this one could be a game changer and it can help you stay on track because you know where you want to go.
Number three, small choices that add up.
This gives you those small choices like a 20-minute walk, a monthly deposit into a savings account, at class on Tuesday nights.
Stretch those across five years and they become a completely different life.
Number four, you'll gain proof of progress.
On the days you feel stuck, like you haven't completed much, you know, I'm sure some of you guys have felt those days.
I know I have.
You can look back and see how far you've come.
Number five, you can make wishes turn into actions.
Some days become, by this year, I'll have this done.
And here are the five cons that I've come up with.
First one, life happens.
A job loss, a move, a baby, a health scare.
Some plans feel out of date in six months.
And some of these things can just throw a plan completely off track into a different direction, right? Number two, it creates pressure and perfectionism.
A plan can become a stick to beat yourself with, like get those feelings on behind schedule is a rough thing to tell yourself.
Number three, you're guessing at a future you.
The you of five years from now will want things today that you can't imagine quite yet.
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