Fear is not a stop sign

_{Day 180/100}

Hey—It's Tim. 

I woke up at 3am last night.

I think the realisation of what’s about to happen finally hit me.

I’m making the biggest jump of my life without a safety net.

I’ve been pushed before - by bosses, friends, circumstance.
This time? No shove. Just me, the ledge, and the air.

Big goal, bigger doubt

If you’re reading this with a goal bigger than your stomach and a doubt bigger than your goal - you’re my person. The “what ifs” sound smart, but they’re cowards in tuxedos. They want you stuck in research. They want you “optimizing” the plan you still haven’t lived.

Living with “what if” hurts.

Fear is a compass

I used to treat fear like a stop sign. Turns out it’s a streetlight: yellow means “on it,” not “go home.”

In work, the idea that scares you is usually the one that opens a new room. New room = new outcomes. Your career is just a series of rooms you learn to enter faster.

Do it scared

Courage isn’t the absence of fear; it’s the choreography. Hands shaking? Good - hit publish with both.

Here’s the choreography I’m using right now:

• Name the monster in seven words. “Pitch the CMO about a revenue share.” “Ship v1 with an ugly dashboard.” If it takes a paragraph, you’re hiding.

• Shrink the monster to a brick. One email, one mock, one 20-minute call. You don’t build the wall—you place the next brick on Sunday night.

• Put a timer on the brick. 20 minutes. Not “until it’s perfect.” When the timer dies, you ship the brick.

• Invite consequence. Text a friend: “If I don’t send proof by 9:00am, I owe you $100 and a public apology haiku.”

• Press the scary button while scared. Don’t wait to feel ready. Ready is a rumor.

The marketer’s scary ladder

• Soft scare: DM three customers and ask one blunt question.

• Medium scare: Publish an “opinion with receipts” post that could be wrong.

• Hard scare: Propose the campaign you’ve been avoiding because it might define you.

If you can’t decide which rung to step on, pick the one you’ll still be thinking about in bed.

Your Sunday prompt

Fill this in. Just getting it out of your head and on to paper is half the battle:

The scary thing is: _____

My first brick is: _____

I will do it at: _____

Proof I did it: _____ (screenshot, link, sent email)

Reply with your four blanks if you want accountability. I’ll read every one.

This week, don’t negotiate with fear - schedule it. Put the brick on your calendar. Set a 20-minute timer. Ship while shaking.

✌️ Tim "Press send to continue" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. I had a folder of things I wanted to talk about, but thought people wouldn’t want to hear them.

Then figured, f*ck it. And that’s what you get on a Sunday.
It’s the more personal stuff.

I’ll be honest, most of these emails are for me. It’s just a bonus if you read them.

Penfriend.ai
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