What 18 Years of Annual Reviews Taught Me: A Live Q&A

I’ve done an annual review for 18 years straight.

There’s almost nothing else in my life I’ve been this consistent with. Every part of my life has changed in that time. I’m a completely different person.

But every year I ask myself whether I should do a review, and every year I find a reason. The return on that time is too clear to skip.

A review gives me perspective. It puts things in proportion: what’s important, what isn’t, and what deserves more of my time and attention.

It also gives me clarity on the big decisions we all face as adults. Where to take my career. What to do about a relationship, my health, my finances, or where I live.

That’s why I wrote Life in Perspective: The Art and Power of the Annual Life Review. It’s a hands-on field guide, with a full checklist at the end of each major part, so you don’t have to invent the process yourself.

To celebrate the launch, I went live to answer your questions about the book. Here’s the replay, and below are my best answers in writing.

Why the book exists

Why write a whole book about one practice?

I don’t write books casually. Each one takes me three or four years of active work, plus the years before and after. So before I start, I ask myself: what’s worth that much of my life?

The answer is always a system.

A random collection of tips isn’t worth your time. You can find good advice anywhere. Building a Second Brain was a complete system for managing knowledge. The PARA Method was a complete system for organizing your digital life. A system compounds. It’s more than the sum of its parts.

After my first two books, I took a year and a half off. Then I looked at my life and asked what had made the biggest difference. The answer was the annual life review.

I call it a practice, a ritual, or a tool. Underneath, it’s a system for uncovering insights about your life and work, on purpose instead of by accident. I don’t know of anything else that touches so many areas at once: your health, your finances, your career, your business, and your relationships with your kids, your partner, and yourself.

I’ve never done any kind of formal reflection. Is this for me?

Yes. You’re the person I had in mind.

The only reason to write a book is to reach people who wouldn’t otherwise find this. People who won’t come across my YouTube channel or take my course will still pick up a book.

So my main principle while writing was to remove friction. Where I could have given you ten options, I gave you fewer. Sometimes just one recommendation.

I know how it feels to start something new and have no idea where to grab on. You’re floating in space, not sure which way is up. This book is a map through that space. You can trust that the time you put in will be worth it.

What did your annual review look like at the start, and how long should it take?

My first review was in 2008. I was 23. I sat down with a tiny pocket notebook and wrote three goals and one intention for the year.

That took about an hour, and it felt like a big investment. It also felt scary. Writing my dreams down, even in a private notebook, felt like setting myself up to fail.

Each year, I spent a bit more time. Ninety minutes, then two hours, then three, then four. Eventually eight. Today my ideal is a whole weekend.

Here’s my recommendation for you: eight hours.

That’s the threshold where the review becomes transformative. You can do one full day, two half days, or an hour a day for a week. Somewhere around eight hours, you start to see connections and parallels. You get epiphanies, where you look at your life almost from the outside and see something you never saw before.

I know eight hours is a big ask with everything on your plate. I’m still asking, because I’ve made the process as practical as I can. You won’t spend those hours lost in the weeds.

If you only have one hour, use it. Write down your top three goals, or one person you want to get closer to. Whatever time you give this will be some of the best time you spend all year.

Perspective comes first

You say the biggest changes start with a new point of view, not a new plan. What does that look like?

This is where I differ most from other advice on planning your year.

Everything is downstream of your perception. Every plan, habit, metric, or goal you come up with depends on what you see and understand about your life. And the pattern I notice again and again is that people jump into action too fast. They reach for a solution before they’ve understood half the problem.

That’s why the book is built on the ARC Method:

1. Appreciate the past
2. Reflect on the present
3. Create the future

Two of those three stages are about perception. You spend most of your review seeing your life clearly before you decide what to create next. What happened this year? Why? What influences could you amplify, and which could you reduce? What has worked for you before?

It amazes me how rarely people look at the evidence of their own life. We’ll listen to an outside expert, a podcast, or a book (including mine) before we listen to ourselves.

Here’s an example from my own review.

Overwork has been one of the most consistent themes in my reviews. It isn’t a leak in the roof that I can just fix. It has deep roots. I can trace it back to my father and my grandfather. And I don’t want to get rid of it completely, because work plays an important role in my life.

At the end of 2025, I asked myself whether I had good work-life balance. On the surface, the answer was yes. I’m usually done by 2 or 3 p.m. I spend a lot of time with my kids. I’m present all weekend. I gave myself green check marks.

Then I asked my wife what she thought. She didn’t say it accusingly. It was a simple observation:

“Your work gets the best of you, and we’re left with what’s left over.”

Ten months later, I can still hear that sentence. It was true. Work gets the best of my time, attention, energy, and enthusiasm. My family gets what remains.

Notice that I haven’t made a grand plan. I haven’t set a goal. What matters is that moment of letting the truth hit me. There was grief in it, and also recognition and gratitude. That moment is the change in perspective, and everything else unfolds from it.

By the way, talking with your partner, kids, parents, or close friends about what comes up in your review is one of the best sources of feedback you’ll get.

You can’t predict what your shift in perspective will be. It always comes out of left field. That’s exactly why it’s so valuable.

What’s the most common thing people discover?

Every discovery is different, because it’s based on each person’s life. But at a general level, most people are surprised that they’re surprised.

If you’re drawn to a practice like this, you’re probably already introspective. You read about psychology, maybe you meditate, you’ve done some inner work. That experience can become a trap. I fall into it myself. I read a psychology book and think, “Oh, I know that bias. I’ve heard it all.” I’m not open anymore.

We’ve had so much exposure to therapy-speak that it glances right off us.

The review gets around that. You answer a standard set of questions about the main areas of your life: health, finances, mental health, relationships, home, work, and income. And reliably, you see something you’ve never seen before.

It’s like realizing there’s been a pink elephant in the corner of your bedroom the whole time. It’s very familiar and completely new at once.

I don’t spend much of the book describing that moment. I lead you to it, so you can have your own epiphany and know exactly what it feels like.

Doing the review

Is this a goal-setting book?

You could put it in that category, but that irks me a little. Much of the book addresses the biggest pitfalls I’ve seen in goal setting over years of teaching and coaching.

Take New Year’s resolutions. Someone decides in the first week of January, with no forethought, to lose 10 pounds. I honor the optimism behind that. But a goal you thought of a minute ago has no momentum behind it. It isn’t rooted in your experience. It’s threadbare.

The deeper questions are where your time should go. Who have you become this year? How are your values changing? What changed your outlook on life? What matters most to you now?

I do cover goal setting toward the end of the book. But a goal is an output of the process, an implementation detail. A goal that comes from self-knowledge is richer and more meaningful. You’ll be more committed to it, and it’s far more likely to succeed.

Does this work if my year was a complete disaster?

This question matters a lot to me, because I’ve had plenty of low years.

For many years, I struggled with a chronic illness that kept me from living the life I wanted. Facing that, and admitting that my body was holding me back, was hard to see.

In the book, I also share the story of 2024. It was the first year our business lost money. As the owner, I covered that loss out of my personal accounts to keep the business afloat.

Looking at those numbers in my review, I had to face that I hadn’t done my job as founder and CEO that year. It was painful. It was also healthy and healing. Without that ritual to sit with the emotions, I don’t think I could have done what came next: change our business model, the size of our team, and our strategy.

When you push a feeling down, the lesson inside it gets pushed down too.

That’s one of the main themes of the book. Smart, analytical people tend to lead with analysis. That’s not bad. But we need to balance it with feelings, intuition, and the desires that emerge without explanation.

The review is mostly about appreciating your life. In fact, appreciation is the very first step. There are practical ways to get into that state, using music, writing, art, and your body. When you start from gratitude, you stop planning from a place of scarcity, trying to fix or erase the past.

So yes. I’d say this book is more valuable after a disappointing or painful year than after a year when you won.

Are there lessons for working parents?

Yes. I’ve been a working parent for six years, and my reviews took on a different flavor once I had kids.

The side effects of my blind spots got amplified. Without kids, overwork might burn me out, but it doesn’t affect anyone else much. With kids, it changes everything.

So I now spend more time on a new category of questions, many of which are in the book. How am I affecting the people around me? What values am I embodying? Which lessons from my parents am I passing on to my kids, and which do I want to stop?

You don’t need to be a parent for this, though. One prompt I love: who are the five most influential people in your life? That one’s easy. Then flip it. Who are the five people you influenced most this year? I rarely think about that during the year. The review is my safety net for asking it.

Did you use AI to write the book?

Definitely not.

The only reason to write a book is that you want to do the hard thinking yourself. That’s why it took three years. AI could have produced something in a few days.

The book also benefits from a lot of people. More than 1,000 people have gone through our Annual Review course since 2019, and that course is the main source of what’s in the book. Then I invited everyone who’d taken it to read an early manuscript. Around 400 said yes. Their feedback on what worked, what didn’t, and what was confusing led me to rework the manuscript extensively.

When should I do my review, and how should I use the book?

Put it on your calendar now. Treat it like a meeting with your accountant or your annual checkup with your doctor. It’s just as important, because it’s with the most important person in your life: you.

Timing matters more than you’d think. Time of year, weekend versus weekday, morning versus evening, high energy versus low. I cover all of this in one of the early chapters.

This is also why we’re publishing on November 3. Most people don’t think about this until December or January. That early date might even hurt sales. But I wanted you to have the book in hand before you sit down.

Here’s how I’d use it:

1. Before your review, read the prologue and the first four chapters. That’s about the first third of the book, and it covers the whole method.
2. During your review, use the next three parts (past, present, and future) as a real-time playbook, step by step.

Now it’s your turn: pre-order your copy

Thank you to everyone who joined live and asked such perceptive questions. I could tell you’d already been thinking hard about this.

After all these years, it still feels a little surreal that this book exists. Decades of experience, every mistake I made, and everything I learned teaching this practice are now in one book. I’m proud to be the one to introduce you to it.

Life in Perspective comes out November 3, 2026. If you pre-order now, you’ll get a set of bonuses to help you do your best review yet. Any format counts (hardcover, ebook, audiobook, or the UK paperback), from any retailer in any country, including independent bookstores.

Pre-order 1 copy and you’ll get:

• The first two chapters, emailed as soon as you claim
• The recording of the Annual Review Summit, our virtual event on November 4
• The Annual Review Compendium guide
• An invitation to our private Circle community

Pre-order 2 to 4 copies and you’ll also get one Essential seat in The Annual Review 2027, my live program, for every copy (up to 4). Each seat is a $249 value. Give the extra copies and seats to a partner, a friend, or a colleague, and do your reviews together. Essential seats are limited to the first 1,000.

Pre-order 5 or more copies and you’ll get everything above, including 4 Essential seats, plus one Premium seat ($997 value) with three small-group coaching calls with me. Premium seats are limited to the first 50.

If you already pre-ordered, your order still counts. Claim your bonuses by November 8.

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