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Greg Isenberg Shares His 2024 Annual Planning Guide

Greg Isenberg
Last updated: February 12, 2024 1:43 pm
Greg Isenberg
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4 Min Read
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Greg Isenberg is a multi-exit Silicon Valley entrepreneur and owner of Late Checkout product studio. He has:
- Headed Product Strategy at WeWork
- Been an advisor to Reddit
- Founded a startup, Islands, which was sold to WeWork
- Founded 5by, which was sold to StumbleUpon
Guest Author: Greg Isenberg

This is my 2024 annual planning guide for entrepreneurs, multipreneurs and creators. I put this thread together to help you make the most of your year.

It’s 8 questions to ask yourself, with a system to hold you accountable. Grab a coffee or drink and let’s dive in:

1. What are 2 ridiculous goals for the year?

Set 2 goals for 2024 so big it’ll make you laugh. So big at first blush it feels unrealistic.

But if you slow down, and put pen to paper, maybe it’s more realistic than you think.

Turning your big ridiculous goals into just audacious goals by outlining the mini-steps to get there. Audacious goals are just ridiculous goals with steps to get there.

System for you:

– Prerequisite is the 2024 mentality: anything is possible.

Remind yourself of that. Write it everywhere.

– Break your goals into 5-10 mini goals

– Review your 2 ridiculous goals quarterly.

– If it feels less audacious after a quarter, you’re on the right track.

If it feels more audacious after a quarter, you’re off-track.

– Adjust mini goals as you learn

2. What do “style points” look like for you?

Winning your year isn’t just about hitting a dollar number, selling your company or going IPO. It’s about how you do it.

Maybe it’s 100% creative freedom to build whatever you want. Maybe it’s working with your brother to build a family business.

Maybe it’s working everyday in your underwear.

I don’t know but writing it out helps.

How you earn your money (style points) is just as if not more important than earning your money. I’m pretty surprised how little attention people give to style points. Well, that changes today.

Let’s get it.

System for you:

– At the end of every month, rate your month on style points from 1-10 (no sevens, because that’s a cop out answer).

– If you’re 6 or below, what can you do to make it a 8 or above?

– Write out 2-3 ways.

– By regularly assessing and adjusting how you approach your work, you can change course pretty easily.

3. What are the “uncool” opportunities that everyone is ignoring?

The uncool opportunities are often the most interesting ones. In 2021, everyone was focused on crypto, very little on AI.

Today, the opposite is true. In 2021, everyone was focused on VC-backed businesses, very little on cash-flowing businesses. Today, the opposite is true.

A steady stream of uncool opportunities coming your way is critical. Be an opportunity miner in 2024. I call these opportunities “silent giants”

System for you:

– Use software spy tools like GummySearch, Etsyhunt, Jungle Scout etc to find up and coming opportunities

– Twitter DM one new interesting person every week in your industry or adjacent industry. You learn something when you’re not a silo.

– Refine your content diet. Listen to podcasts that give you an edge.

Listen to them while you workout (health + wealth). Remove content creators that don’t add to your edge. Unfollow old people, follow new people. Spend 10-15 minutes a month refining.

More 2024 questions continued in the next tweet (you got this):

Check out the original tweet here

TAGGED:div5

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