You might be an exception, but at least 97 percent of the rest of my audience are sea anemones: If I poke at them, they retract into self-protective balls.
Also, neither you, I, nor anyone else reading this likes being told what to do. I’ve learned the hard way that examples and stories motivate better than facts and tips.
So here’s my plan:
Rather than poke at you push yourself harder, I’m going to pick on a single person as an example—a guy whose too-soft tushy is ripe for a swift kick:
Myself.
I hope this kick reverberates so hard that you feel it vicariously and decide to push yourself, too.

Free Wake-Up Call
Take the 20-question “Comfort Zone Assessment” to find out in just 3.5 minutes:
Where are you complacent?
Which area of your life most needs a push?
How to get started?
It’s gimmicky and unscientific, but also quick, fun, and revealing.
PS: Surprise personalized accountability challenge afterward.

Dear Chris,
Suck it up, buttercup.
Quit finding ways to weasel out of pushing yourself.
You made your plan to pump your life up in 2023. Now it’s time to sweat through it.
Push yourself or get pushed around.
Life’s a bully. If you don’t push back, it’ll make you miserable.
Push yourself:
- Professionally or your audience will stop caring about what you say and competition will make you obsolete.
- Physically or the decay of age will catch up to you fast.
- Psychologically or your mental callouses will fade and you’ll become fragile and sensitive.
- Romantically or your bond with Kim will weaken and she will push you away.
- Personally or Zac will learn from your loserish example.
- Adventurously or boring people and boring activities will engulf your life.
Keep expanding your comfort zone like you wrote about but aren’t doing well enough.
Push yourself for your enjoyment and gratitude.
Who says you can’t push yourself, “enjoy the moment,” and be grateful for what you have at the same time?
You can. Activities like playing intense sports and writing are examples. Think of your perpetually perfect day.
One thing’s for sure:
You’ll have less and less to enjoy and be grateful for if you don’t push yourself to make more.
Push yourself to spark chain reactions.
Whenever you’ve pushed yourself toward a concrete goal—visiting a hundred countries, becoming a world-denting start-up CEO, monetizing your YouTube channel—you crashed. Even then, you kept spinning your wheels like one of Zac’s wind-up cars against the wall.
At least you pushed yourself!
But you also burned out.
So push yourself toward only one goal: growth.
That comes from activities like talking with people who challenge you, experimenting with new ways to grow your business, and being a leader. They’re like nuclear fission: They take a lot of your energy up front but release even more. That way, instead of burning out, you burn brighter and brighter.
Push yourself to chisel your identity.
“Loving yourself for who you are” is a recipe for hating yourself and going nowhere in life.
As the world’s most famous self-pusher, David Goggins, wrote, “If you don’t challenge yourself, you don’t know yourself.” And if you don’t know yourself, how the heck are you going to love yourself? It’s fake.
So start by challenging yourself to tear away frivolous identities that make pushing yourself harder than it needs to be.
For instance:
- You think you’re clever, but the masses don’t seem to be crowding to hear your ideas. So drop that charade. Show them you’re a good learner instead.
- You think you’re easy-going, but that’s not going the way you want it, is it? So forget about that identity and focus on another, being proactive, instead.
Push yourself even when you’re not sure which way to push.
Quit wasting your time trying to find the most energy-efficient ways to push yourself.
Whenever you think, “Maybe I should…,” dump the “maybe” and swap “should” with “will.”
You’ll make mistakes you’ll regret in the short term, but that’s the best way to minimize long-term regret. You know this! You dicked around researching, writing, and making videos about regret for over a month last year…
…But you’ve done regretfully little to put that knowledge into action.
Even if the only action you can come up with is some cliché way to push yourself like a 30-day challenge, jumping in freezing water, making a public commitment, or doing a long-term fast, do it.
Pushing yourself will give you momentum.
Push yourself where it hurts.
You know how Oliver Burkeman wrote, “The advice you don’t want to hear is usually the advice you need”?
Well, something similar applies to pushing yourself:
The actions you don’t want to take are usually the actions you need to take.
Think back to the fake pushers who joined you for 24 daily mini-challenges in December:
- The outgoing people who proudly shared their experiences completing the social challenges but went suspiciously quiet about the introspective ones.
- The lonely, self-involved people who loooved the journaling challenges but found convenient excuses to not go out and do favors for strangers.
You’re just as guilty!
You often “push yourself” to write more blog posts, which ducks the real challenges of either A) Doing things worth writing about, or B) Connecting with people to figure out what they’re interested reading about from you.
If it doesn’t make you uncomfortable, you’re not pushing yourself.
Push yourself harder with the help of others.
The right people will call you out on your BS excuses, help you see in your blind spots, and give you a push when you’re running on fumes. But you’ve got to find those people and listen to them.
Return the favor, too. You get fulfillment by helping others push themselves.
Speaking of which…
Dear Reader,
Are you ready to push yourself?
Actually push yourself.
Don’t just say you will later, pull out your phone to check your emails, and get back to letting life push you around.
Push yourself in an energy-generating, not willpower-depleting, way that shows you what you’re made of.
Thought Starters
- 👷♂️ Learn hard. Something I had to learn the hard way: By far the best way to learn is to learn the hard way. [Update: I changed my mind.]
- ↔️ Decide hard. “If you don’t know what to do, do the hardest thing possible.” – Alex Hutchinson on this podcast.
- 🧗♀️ Easy doesn’t do it. “Self-esteem comes from achieving something important when it’s hard to do.” – Clayton Christensen.
- 💉 Strengthen your “psychological immune system.” That’s what Dan Gilbert calls our brain’s ability to rationalize decisions in this podcast episode. The more you use it by making and acting upon decisions, the stronger it gets. And the more you experience how your psychological immune system protects you when things don’t go as planned, the braver you become.

Free Wake-Up Call
Take the 20-question "Comfort Zone Assessment" to find out in just 3.5 minutes:
Where are you complacent?
Which area of your life most needs a push?
How to get started?
It's gimmicky and unscientific, but also quick, fun, and revealing.
PS: Surprise personalized accountability challenge afterward.

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