📖 Read Time: 3 minutes
📩 What you’ll get out of this newsletter: a practical system for making decisions quickly (without spiraling into analysis paralysis).
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No big pitch here, but y’all filled our calendar in August for sprints so we hired a new team member (Welcome, Lauren!) and are opening a few more slots for brand audits and ghostwriting in September.
If you are a founder, coach, or VC and want clarity + speed in building your brand online and offline, let’s chat!
Let’s get into this weeks newsletter…
Ever notice how the most successful people you know… aren’t the ones who always make the perfect call?
They’re the ones who make calls, period.
Meanwhile, you’re stuck weighing pros and cons, reading another book, asking five more people what they think. By the time you’re “ready,” the opportunity’s gone, or it feels too late.
Decisiveness isn’t about being right. It’s about trusting yourself to handle being wrong.
Why This Has Been on My Mind
I recently started re-reading Decisive by Chip and Dan Heath. I’ve struggled with making quick decisions. From ordering ice cream as a kid, to picking my favorite font as an entrepreneur.
My mind would get wrapped up in the optionality, and worrying what if I make a wrong choice and regret it?
About 8 years ago my friend Naz (shoutout, Naz—you’re probably reading this!) invited me a lecture where Chip Heath was speaking.
After enjoying his other book The Power Of Moments, I started reading Decisive and one line stopped me cold: “Prepare to be wrong.”
It hit because I realized how much of my indecision wasn’t about choosing… it was about wanting guarantees.
But life doesn’t hand out guarantees and the people who win big don’t wait for them.
The Heath brothers call out four villains that stall decisions:
Narrow framing (thinking it’s “this or that”)
Confirmation bias (seeking proof you’re right instead of testing assumptions)
Short-term emotion (letting temporary feelings sway the call)
Overconfidence (believing you can predict the future too well)
Their antidote is the WRAP framework:
Widen your options
Reality-test assumptions
Attain distance before deciding
Prepare to be wrong
The Core Reframe
We think indecision protects us from mistakes.
Really, it just delays progress.
Jeff Bezos used to say: if you’ve got 70% of the information you wish you had, that’s enough. Make the call. Waiting for 90% is usually waiting too long.
Here’s where Bezos and the Heath brothers overlap beautifully:
Bezos gives you speed (act at 70%).
The Heaths give you safeguards (WRAP to avoid obvious traps).
Put together, you get a system that’s both fast and resilient. Bezos ensures you move, the Heaths ensure you don’t move blind.
5 Moves to Build Decisiveness Immediately
Here are some simple guidelines to consider when turning you’re expertise Into a service.
1. Apply the 70% Rule
If you’ve got most of the data, stop waiting. Bezos used this to scale Amazon. It forced momentum and left room for course correction.
2. Put a Timer on Decisions
Give yourself 24 hours (or less) for most choices. Time limits force clarity.
3. Flip the Script: “What’s the Cost of Waiting?”
We obsess over the risk of the wrong move… but rarely calculate the hidden cost of delay.
4. Practice Micro-Decisions
Order the first thing on the menu. Take the first flight option. Send the first draft. For once, don’t overthink it. Small calls stack into instinct.
5. Audit Who You Ask for Advice
Every extra opinion adds friction. Pick 1–2 trusted filters, not a committee.
Genius Tips: Decisiveness Reframes
Perfect timing is a myth.
Waiting is a decision—usually the worst one.
Speed compounds. A decent decision now beats a perfect one later.
Progress loves momentum more than accuracy.
Confidence doesn’t come from being right. It comes from moving forward anyway.
If You Take Nothing Else From This
Decisiveness isn’t about knowing the future.
It’s about stacking evidence that you’ll survive mistakes AND adjust as you go.
That one shift flips the script: from paralysis over being wrong → to proof that you can handle being wrong.
And if you want a deeper dive, Decisive by Chip and Dan Heath is the best breakdown I’ve read on how to escape the mental traps that keep us stuck.
thoughtfully, yet quickly
— alex 💭 (@heyalexfriedman)
P.S. Forward this to a friend who’s stuck “thinking it over” for the 10th time.
P.P.S. if you missed it at the top… Y’all we are opening just a few more slots for September. If you are a founder, coach, or VC and want clarity + speed in building your brand online and offline, let’s chat!
