Your Annual ‘What Was I Thinking?’ Review.

Warren Buffett said that in the world of business the people who are most successful are those doing what they love.

Steve Jobs believed that doing great work requires loving what you do.

Bill Gates said, “A lot has changed, but I remember how excited I felt for the next chapter.”

You get my point…

It’s that time of year again. The moment when the court calendars are quiet, the inbox slows (a little), and you finally have 10 seconds to look up from your laptop long enough to ask the annual, highly technical professional question:

“What was I thinking?”

Welcome to your 2025 ‘What Was I Thinking?’ Review.

This is the unofficial, un-billable assessment lawyers everywhere should be doing but rarely do.

Let’s start with the basics:

Ask yourself, honestly…

1. What made me choose this as a profession?
Think back - when was the last time you were doing what you loved? What do you still love about what you do? Or…What changed? How do I get that love back?

2. What did I say yes to this year that I absolutely shouldn’t have?
If the list is long, that’s normal. No one teaches boundary-setting at law school. See my email from 2 weeks ago.

3. Which moments made me think, “Never again”?
This is important data - hang on to it.

4. What did I keep doing out of habit rather than purpose?
Every professional has at least one legacy behaviour still hanging around from 2017.

5. Which successes did I barely acknowledge because I was already onto the next thing?
A classic lawyer move. Let’s stop that, please.

6. And the big one…what do I want to do and think about differently in 2026?
Because your mindset is the real strategy. Everything else is very complicated admin.

Why this matters

It’s year-end and you’re tired, depleted, still performing, but disconnected from what you actually want. (Here, you may need to think about what it is you actually want).

This review is your chance to pause, reset and step into 2026 with clarity rather than obligation.

No resolutions you won’t stick to. No holding hands around the feelings circle. Just clarity.

It makes you purposeful. It makes you confident. And it makes saying “no” a million times easier (and we all need that skill).

One more question…

What version of you do you want showing up in January?

The exhausted one?
The stressed one?
The quietly resentful one trying to hold everything together? You know who you are!

Or the grounded, intentional, “I remember why I chose this profession and what I’m doing this for” version?

You get to choose.

If you’d like support resetting, refocusing, or designing a year that actually suits the lawyer (and human) you’ve become, let’s talk.

Here’s to a 2026 with fewer fires, more wins, and much better boundaries 🥂

You’re doing great!