Some Questions to Kickstart the Year
I’ve had a few rough annual “check-in” templates I’ve tried over the years, and like everything in the reflection world consistency and frequency are way more important than the actual questions you reflect on.
But, never miss an opportunity to reflect.
So, here are some I like, leaning on the Tacklebox core frameworks.
Sell the Position (more on it).
Most people mess up resolutions or goals by adding tasks without removing any. We’re goldfish and we grow to the size of the bowl - you don’t have extra time lying around to learn to code or add an extra hour a day on your startup. Step one is always removing, not adding.
So, let's remove the bad stuff. Start with a big piece of paper (that you’ll use a few times today), and write down everything you do. It’s usually easiest to look at a calendar or your photos from the last couple of weeks, as well as text chains, Netflix queue, etc. The hobbies/activities you do, the friends you keep up with or think about, family relationships, other relationships, social media, text groups, tv time, etc.
Now, make a second list of things you'd love to do. Could be relationships you’d like to strengthen, time spent on a startup, time spent learning about generative AI, learning to cook, taking up piano, whatever — the stuff that’d make you more like the person you’d like to be.
Finally, the third list. The stuff from the first two that'll make it into your life. Pick the stuff that aligns with the type of person you'd like to be. Drop the stuff that doesn't build you up.
The Not Fun Part: You'll need to create plans to drop the stuff that doesn't serve you any more. Draft how. Example — a text group that sucks your time all day. Mute it, timebox 8-8:15pm each night to catch up and respond. Set aside 30 minutes each week to talk to each member on the phone. For bad habits — two hours a day on Tik Tok, say — remove a piece of the habit. That's usually enough. Delete your password and give it to your mom, so every time you want to sign in you need to text her and you feel like a jackass. Or, work with your phone in another room under the mattress. Whatever.
CEO
Easier one. Someone super competent stepped into your life and took it over. It's now their life. What’s the first thing they’d do?(Now, do that thing).
Put Your Ass Where Your Heart Wants To Be (book)
I loved this book. The message is, whatever you want, make sure you’re there. If you want to write movies, move to LA and your success rate will 10x. It’s more about buy-in. How can you physically show that you are bought into whatever is in your heart? If your goal is to raise money from VCs this year, how can you be around them constantly? If it's to sell to colleges, how can you be around colleges constantly? How can you make sure your ass is where your heart wants to be this year?
System Improvements
A really useful question to ask - How can you create five hours of lazy time for yourself each day? If you’re in email 3 hours a day, how can we make that 15 minutes? VA? Better filtering system? If you need to answer emails for your day job, how can we automate those? Templates? Text Expander? How can you build playbooks that allow you to do things that are amplified and used 1000x?
Fun
What do you do that makes you laugh and giggle and feel like a kid? What’s actually fun? How can you make sure you do it more?
Example — my answer to this was "I love playing sports, that's the most fun I have." Then, I looked at my time, and I … never play sports. Ever. I go on the peloton. I go for runs. But…no sports. So, yesterday I joined a pickle ball league, a basketball league, and a bowling league. Fun is good.All this stuff relies on you knocking #1 out of the ballpark. The most important thing you can do is drop the stuff that isn’t serving you any more.