How I Jump-Started My Year (And Why I Stopped Planning the Way I Used To)

For a long time, my annual planning looked the same.

I noted how many books I wanted to read.

I identified habits I wanted to create and stick with, and ones I wanted to stop.

I noted which routines were working and which weren't, and which ones were best serving me.

And to be clear, that approach worked. It helped me build momentum. It helped me grow. It helped me create real outcomes.

But eventually, it stopped being the right tool. Not because it failed. Because I evolved.

What gets you to one place is rarely the same thing that gets you to the next. Different destinations require different modes of travel. At this stage of my life, the way I had been planning no longer matched where I was trying to go.

The Problem: I Outgrew My Old Planning System

Tracking books made sense when I was still accumulating foundational knowledge. I’ve read and listened to a lot of books, and I still do. Learning matters.

At some point, though, knowledge stops being the constraint. Most non-fiction books start to sound familiar once you’ve spent enough time in a domain.

I already knew enough to:

• build a meaningful creative project

• earn income outside of an employer

• stay in great physical shape

• build strong relationships

• live a more intentional life

Where there may have been knowledge gaps before, those gaps had largely been filled. What I needed was more doing, more execution, and more experimentation. You can’t read a book about starting a business and expect the business to create itself.

The same was true with habits. I've always had solid habits, especially when my routine is established. Tracking them helped early on. It still works. But habits are no longer the goal; they’re just part of how I operate.

In other words, I wasn't missing discipline. I was missing direction. Well, a focused direction. 

My personal hang-up has been that my brain gets fired up when I explore new domains. But exploring multiple new domains is a quest that will NOT best serve me in my current season.

I wasn’t stuck. I just needed a different way to aim.

The Shift: From Planning Outcomes to Defining How I Operate

This year, instead of starting with goals, I started with something simpler and more foundational:

How do I want to operate, regardless of circumstances?

I defined a small set of baseline operating standards. Not aspirations. Not resolutions. Standards.

Things like:

• how I protect my time

• how I treat my body

• how I show up in relationships

• how consistently I create and ship work

  
  

These aren’t things I “try” to do. They’re how I move through my days when things are working.

Once those were clear, everything else became easier.

Fewer Focus Areas, More Weight Behind Each One

Next, I resisted the urge to plan everything.

Instead, I chose a small number of areas that actually matter to me right now. Not forever. Now.

For me, that meant five big areas:

• creative work

• income independence

• physical health

• relationships

• location and lifestyle

  
  

The test I used was simple:

If only these areas improved this year, would it still be a good year?

If the answer was yes, it stayed. If not, it went.

This alone eliminated much of the noise.

Defining Success at the End of the Year, Not the Start of the Week

Instead of obsessing over daily or weekly tracking, I asked a different question:

What would exist by December 31 if this actually worked?

Not X number of books read. Not X number of trips to the gym. But instead, evidence.

For example:

• How many creative pieces would be published?

• What income would exist outside my job?

• What would my body be capable of?

• What relationships would be stronger?

• Where would I actually be spending my time?

  
  

In some cases, the answers involved numbers. In others, they didn’t. Both were fine.

Just Start. You Can Adjust Later.

This is where most people get stuck. I’m including myself in here, too. I couldn't count how many times I’ve questioned how much time I was investing in this process. But I kept reminding myself that I am doing this once for the entire year, to make this the best year.

We always want the perfect plan. The perfect sequence. The perfect conditions.

You DON'T need them. (noting this here for even my benefit)

One of my podcast guests, Alexander Terry, put it this way:

"At some point you have to jump into the unknown, and that's scary."

That idea stuck with me because it’s true. As humans, we crave certainty. But certainly will keep you in your same small hometown, around the same people, doing the same things with the same people for the rest of your life. The world is a much bigger and more interesting place if you embrace being scared and take the leap.

You don’t need to know how the entire puzzle fits together before you pick up the first piece.

You just need to start working on it.

You can revise the direction later. You can recalibrate. You can change your mind. But nothing happens until you move. (If this resonates, I highly recommend listening to the full podcast conversation with Alexander Terry.)

A Note on Using ChatGPT

One thing I'll share openly: I used ChatGPT as part of this process.

Not to outsource thinking, but to pressure-test it. As a working partner.

I used it to:

• ask better questions

• reflect my own thinking back to me

• tighten language

• spot inconsistencies

  
  

It helped me get about 90 percent of the way there on my own time, without scheduling a meeting or involving anyone else.

That said, it doesn't replace a human pressure check or accountability partner. It doesn't know your life the way you or someone close to you does. It only knows what you tell it, and you can only tell it things from your own biased position.

But as a thinking partner? It's been incredibly useful.

The Point of All This

This wasn’t about building the perfect plan. However, I did create a pretty dope-looking PowerPoint presentation for myself.

It was about choosing a new way to move that actually fits the person that I have become. Not the person I was in 2016-ish, when I first started taking annual planning and goal-setting seriously.

If you’re feeling stuck, overwhelmed, or oddly uninspired by the planning methods that used to work for you, it might not mean you’re failing.

It might mean you've outgrown them.

And if that’s the case, you don’t need a brand-new identity or a 40-page plan.

You just need to start operating differently.

The following is a consolidated path I took to reflect on past years and plan for 2026. You don’t need perfect answers to all of these. You just need answers that are honest enough to act on.

1. How I Operate (Baseline Operating Standards)

These questions are about how you move through your days, not what you want to achieve.

• When my life is working, how do I actually operate day to day?

• What behaviors are non-negotiable for me now, regardless of circumstances?

• What am I no longer willing to tolerate in my own behavior?

• What do I consistently do when I feel grounded, healthy, and effective?

• Where do I tend to create unnecessary friction or complexity?

2. What Actually Matters This Year (Focus Areas)

This is about choosing fewer things and giving them real weight.

• If only a few areas of my life improved this year, which ones would matter most?

• What areas have an outsized impact on everything else?

• Which areas am I tired of deferring or putting “after” something else?

• What would make this year feel meaningfully different from the last one?

3. Creative Work and Output

This is about production, not identity.

• What would make me proud of what I created this year?

• What does “consistent” actually mean for me in terms of output?

• What would exist at the end of the year if I followed through?

• How do I want my creative work to expand my network or opportunities?

4. Income and Independence

This is about structure, not hustle.

• What would meaningfully reduce my dependence on a single employer?

• What level of independent income would change how I make decisions?

• What single source of income, built by me, would meaningfully change my leverage if it became reliable?

• What am I building that could grow without requiring more of my time every month?

5. Body, Health, and Physical Presence

This is about capability and confidence, not optimization.

• When do I feel most like myself physically?

• What kind of shape allows me to move confidently through the world?

• What does “being in shape” actually mean to me, not abstractly?

• What would my body need to be capable of a year from now for me to feel proud?

6. Relationships (Romantic and Otherwise)

This is about intention and selectivity.

• What does it look like for me to invest time and energy with intention?

• How quickly do I recognize when something isn’t a fit?

• Where am I spreading myself thin instead of going deeper?

• Which relationships would I regret neglecting another year?

• What would stronger, fewer relationships look like in practice?

7. Location, Lifestyle, and Forward Motion

Determining what forward motion looks like now

• Where do I feel most aligned with how I want to live?

• What does a less deferred life look like for me right now?

• What experiences am I postponing unnecessarily?

• What would it look like to move forward without having everything figured out?

8. Defining Success at Year End

This ties it all together.

• If this year went well, what would be true by December 31?

• What evidence would exist that I actually followed through?

• What would I want to be able to say I built, experienced, or changed?

• What would make the effort of this year feel justified?

You don’t need perfect answers to all of these. You just need honest ones that are good enough to act on. Good luck and Godspeed.