The TL;DR, The EOY Fear Edition


A bi-weekly roundup of EOY fears
December 14 - December 27

Wrap Up The Old Year With Your Fears

In the last TL;DR, I asked whether you set New Years Resolutions and got an amazing 50/50 split:

I'm fascinated by the intersection of goals and fears and not many people do fear better than Tim Ferriss. You may know him from his "4-hour Workweek/Body/Chef/etc." empire of self-help content. If you're in the entrepreneurial world, it's hard to miss him: he's got his marketing and branding on lock which tends to be a turnoff for me (like how I hate your favorite sales guru).

However, in my reflect-and-plan stage of my year, I put pride aside and started to nibble at his stuff.

Every Friday, Tim sends out an exclusive email with the five coolest things he’s found (or explored) that week.

It could include exclusive giveaways or chances to interact with Tim, books, gadgets, albums, articles, new hacks/tricks, and — of course — all sorts of weird stuff he digs up around the world.

Click below to sign up for free.

But let's get back to that ye-olde mind-killer: fear.

Tim has a popular TED talk (linked at the end of this email in the PS.) about "fear-setting," an exercise around defining, visualizing, and then averting your deepest darkest.

In this TL;DR, I'm going to give you the short version of Tim's quarterly recommended exercise so you can wrap up 2024 and harness all the fresh-start energy coming next week.

Step 1: Define your fear

Take your fears and write them down. The writing is key: it forces you to put words on a feeling.

Hot Tip: It's probably not a decision or an action that scares you, but all the negative outcomes that could happen after the decision.

Step 2: Embrace the Suck

Detail out all the gory negative worst-case scenarios. Be sadistic and push the limit. Write it down.

Step 3: Dissect With Logic

Tim talks about making two columns to analyze your fears. The first is a list of Prevention strategies, either to completely dodge a negative outcome or just mitigating 10% of the worst case scenario. They might be preventative (practice your public speech 20 times) or a contingency plan (have your notes handy in case you forget your speech).

The second is a Repair: if the worst-case scenario happens, what are the consequences and how could you recover from them? Who/what could support you when you're living your worst nightmare? Will you survive utter failure, and if so, would you be that bad off?

Step 4: The Upside

If you took the risk you just detailed, what possible benefits could come from it? Might you achieve a long-held dream, gain new skills, or improve your life in some way?

Step 4: The Cost of Analysis Paralysis

What happens if you did nothing? Will you regret it? Will you miss out on opportunities? Often, the cost of inaction is greater than the cost of action.

Step 5: Assess and Decide

You just spent time putting words to your fears, looking at them critically, coming up with all sorts of contingency plans, recognizing the benefits and downsides: now what? Do you pat yourself on the back for doing a great analysis, or do you make the choice?

Something to think about: Freakonomics suggests that you quit and Angela Duckworth suggests that you grit. Decisions decisions...


📈 While you're stewing in your fears, if your worst case scenario involves "my small marketing agency" then you can de-risk whatever you're deciding with the Small Agency Assessment, with only a few days left of our Black Friday Deal.


A TL;DR from the CRO

While going outside in a snowstorm may be uncomfortable, the possible upside is that you can experience the pure joy of romping in fresh snow.

-Roman Noodles, Chief Ruff Officer

PS. Roman turned five years old this past week! Happy birthday, CRO Noodles!


I've been reviewing feedback on this newsletter (thank you everyone who contributed!) and for 2025, I'm acting on it. The most requested change was "More Practical Guides or Resources," which is why Tim's fear-setting got the feature today.

The second most-requested change: reviews of new technologies. For that, I'll be rolling out nuggets in the next few TL;DRs but if you have some downtime during your holiday break, take a venture into AI image generation with Automatic1111.

You too can make an alter ego for your dog:

To a fuzzier 2025,

Dan from Learn to Scale


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PS. Avoid self-destruction in 2025 and bring your fears into the light. Happy new year!

Dan Newman

Entrepreneur, Professional Learner, & Proud Failure. Writes about sales, marketing, and entrepreneurship from the eyes of a learning and development nerd. Lead teams, manage people, scale a business, and learn better through the biweekly irreverent newsletter, the TL;DR.

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