Three Questions I Keep Coming Back To

I’ve been journaling for more than forty years, and I have a confession to make.

I was not a "journalist" when I started.

I was a freshman in high school, maybe fourteen or fifteen, and one of my classes required us to keep a journal for the entire year.

Like most teenagers, I wasn’t excited about homework that didn’t have to be turned in every single day.

So when I knew the teacher was about to check our journals, I’d scramble to fill in a bunch of entries. Sometimes the night before. Sometimes right before class. Whatever I could get away with.

Not exactly the picture of a disciplined young philosopher.

But something interesting happened during that year.

Every once in a while, when I actually sat down and wrote about what was happening in my life, I’d discover something.

An idea. A connection. A question I hadn’t thought to ask. An aha moment.

It didn’t happen often. But it happened often enough that I started to recognize something important.

Writing things down helped me see things I couldn’t see while I was busy living them.

That little discovery planted a seed. More than forty years later, I’m still journaling. Not perfectly, not every day. But enough to understand why it matters.

Sunday Mornings on the Promenade

For years, especially before I met Amy, I had a Sunday morning habit.

I’d head down to the Third Street Promenade in Santa Monica, usually around nine, and spend the next few hours doing something that probably looked like absolutely nothing to everybody walking past.

I’d get breakfast. Sit outside, often around one of the big bookstores. Watch people. Enjoy the Southern California sunshine. Watch the morning unfold as the Promenade came alive.

Sometimes I’d write in my journal.

Sometimes I’d read.

Sometimes I’d just sit there thinking.

It wasn’t a rigid weekly obligation, and there were Sundays when I didn’t journal at all. But the important part was that I’d deliberately set aside the time.

Chuck’s time.

Time away from everything demanding my attention. Time to think about my life instead of just living through another week.

And over the years I found myself returning to three questions.

• Where am I?
• How did I get here?
• Where do I want to go?

Simple questions. But not always easy to answer.

And the one that taught me the most was the second.

How did I get here?

The Problem With Problems That Keep Coming Back

Have you ever noticed how certain problems seem to follow you around?

Different job.

Different year.

Different relationship.

Different circumstances.

But somehow, the same damn problem.

Maybe you keep ending up in relationships where you feel unheard.

Maybe every job turns frustrating in the same way.

Maybe you keep making plans to get healthier, only to find yourself starting over three months later.

Maybe you keep putting off the same hard conversation.

And every time it happens, it feels brand new. Another unfortunate situation. Another difficult person. Another unexpected obstacle.

But what if it isn’t entirely new?

What if you’ve been here before, and you just don’t recognize the pattern?

There’s an observation I’ve heard over the years about people repeatedly dating the same kind of person, with different faces and names.

I think there’s something worth considering in it — not as an accusation, but as an invitation.

Not every relationship problem is your fault. Of course not. Other people have their own history and motivations, and sometimes circumstances just deal you a rough hand.

But if a similar difficulty keeps showing up with different people, it might be worth examining what’s repeating. What choices are you making? How are you responding? What are you accepting or avoiding?

Those aren’t comfortable questions. But they’re useful ones.

And that’s where journaling becomes more than writing about your day.

Your Journal Is a Record, Not Just a Diary

I remember reading the book, recommended by a buddy, Stumbling on Happiness, by Daniel Gilbert.

In the book, the author makes a strong case of why we can't trust what we see, what we remember and what we feel.

And he has the research and data to back up the claim.

That rocked my world!

Memory is useful, but how we feel today can influence how we remember yesterday.

When life is going well, we might forget how hard things were six months ago. When life is going badly, we might lose sight of how much we’ve already survived.

That’s part of being human. Feelings can color recollection, and without something to compare it with, we may overlook how much our story has changed.

A journal gives us another kind of evidence: a record to compare against the stories we tell ourselves.

• What was I worried about three months ago?
• What problem was I wrestling with last year?
• What did I promise myself I’d stop doing?
• What did I keep putting off?
• What was working that I’ve somehow stopped?

When you go back and read your own words, the recurring themes start to surface.

Some of journaling’s greatest benefits become visible when we look back over time.

A single entry might give us an insight today. Several entries over weeks or months can reveal a pattern we’d otherwise miss.

A Pattern You Can Actually Watch

Let me give you an example — not something that happened to me, but a picture of how this works.

Imagine you’re exhausted every Sunday night, but by Wednesday you’re dragging again and you can’t quite figure out why. It just feels like you’re always tired.

So you write it down. Nothing fancy. “Drained again. Worked late three nights this week. Skipped the gym twice. Ate whatever was easiest.”

You keep noting it when you remember. Not every day — just often enough.

Then, a month later, you flip back through what you wrote.

And there it is, in your own handwriting: every single week, you commit to too much on Monday, fall behind by Tuesday, and spend the rest of the week chasing your own tail.

What felt like an endless, mysterious tiredness was actually a pattern.

Monday overcommitment, every time. But you couldn’t see it while you were inside it, because each individual week just felt like “being busy.”

Once you’ve seen it in the record, you can respond. Maybe you stop scheduling the hardest work on Monday. Maybe you protect one evening. Maybe you just say no to one thing at the start of the week.

Then you write down what happens. A few weeks later, you look back again — and you can actually see whether the change worked, because you have the before and after in your own words.

That’s the whole mechanism. Nothing mystical. Just a record, a pattern, and a choice you couldn’t have made while you were busy reacting.

How Did I Get Here?

This is why I keep coming back to those three questions.

Where am I? asks me to look at my current reality, not where I wish I were or where I think I should be.

Where do I want to go? asks me to consider direction — what matters, what kind of person I’m trying to become, what I want my life to look like.

But the second question connects the two.

How did I get here?

Because the answer is rarely one dramatic decision.

It’s a collection of decisions. Habits. Actions and inactions.

Things we tolerated, things we practiced, things we kept putting off — and sometimes circumstances entirely beyond our control.

Over time, all of it brought us to where we are now.

If we aren’t willing to examine that process, there’s a good chance we’ll repeat part of it, even when we sincerely want a different result.

That’s one of the most useful things reflection can teach us.

It isn’t enough to know where you want to go. You also have to understand the patterns that brought you where you are.

Otherwise you may be heading toward a different destination using the same habits that got you lost in the first place.

Record, Reflect, Respond

Here’s a distinction worth being honest about, because journaling has a flattering reputation it doesn’t always earn.

Writing about a problem doesn’t, by itself, solve one.

So I think of journaling as three separate moves.

Record. Capture enough of what happened that you can revisit it later without your memory quietly editing it.

Reflect. Look backward and notice the pattern. If the same thing keeps breaking in the same place, that’s information.

Respond. Change one action, then watch what happens.

The first two happen on the page.

The third happens out in the world.

And notice that reflecting already changes something on its own — it changes what you can see.

You can’t respond to a pattern you haven’t recognized, and awareness itself reshapes the situation.

But awareness alone won’t change your circumstances.

Eventually, insight has to become a different choice.

There’s also an easy trap on the other side. Reflection can curdle into rumination if it never leads to anything. You can journal brilliantly about the same pattern for years, growing more articulate about it the whole time, and never change a thing.

The goal isn’t endless self-analysis. It’s a slightly better choice, made once, in the real world.

Sometimes Preparation Looks Like Doing Nothing

There’s an old idea about sharpening your axe before you start chopping wood.

The point isn’t that sharpening matters more than chopping.

It’s that a little preparation can make the actual work far more effective.

I learned a version of that as a Boy Scout, and eventually earned my Eagle Scout rank.

The motto that stayed with me was Be Prepared — practice skills before you need them, and pay attention for chances to help, because even a small good deed can mean a great deal to somebody else.

Journaling and reflection work the same way.

Sometimes the most productive thing you can do isn’t to start another project or work another hour.

It’s to sit down and ask what the hell is actually going on.

Not to avoid the work.

To make sure you’re doing the work that matters.

And if the same problem keeps coming back, maybe the most important move isn’t solving it for the tenth time. It’s asking why it keeps returning.

You Don’t Have to Journal Every Day

Let me make this clear, because I don’t want it to become one more obligation I’ve guilted you into.

I’m not telling you to write three pages every morning.

I’m not telling you to buy a special notebook, though for some people having a special book and pen makes the habit more enjoyable.

And I’m definitely not telling you to become one of those people who never misses a day.

Remember how I started: a teenager filling in entries before the teacher checked my homework. More than forty years later, I’m still not perfectly consistent. That’s okay.

The real value isn’t a perfect streak. It’s giving yourself the chance to think, to record what matters, and to look backward once in a while.

Because sometimes you won’t recognize a pattern while it’s happening. You need distance — and sometimes you need to read your own words from six months earlier to realize you’ve been here before.

Once you’ve spotted the pattern, you can ask a better question.

Not just, “How do I fix this problem?”

But: “What keeps creating this problem?”

And then the question that matters most: “What could I do differently so I don’t end up here again?”

That’s when reflection turns into something more than writing. That’s when it turns into progress.

⚔ The Dojo Drill: Find the Repeating Pattern

Take five minutes today.

If you already keep a journal, look back through some previous entries. If you don’t, grab a piece of paper.

Write down one problem that seems to keep showing up in your life. Then ask yourself three questions.

1. Where am I? What’s happening right now?

2. How did I get here? When has something similar happened before? What keeps repeating?

3. Where do I want to go? What would a better outcome look like — and what’s one thing I could try differently?

Don’t try to solve your entire life in one sitting.

Notice one pattern. Write it down. Choose one small adjustment. Then come back later and see what happened.

Because sometimes the biggest obstacle to solving a recurring problem isn’t a lack of effort.

It’s that we haven’t recognized we’re solving the same problem again.

📚 Leader’s Library

​The Art of Learning — Josh Waitzkin​

Why?

Josh Waitzkin knows something about learning difficult skills.

As a young chess prodigy whose early life helped inspire Searching for Bobby Fischer, he developed an unusually deep understanding of competitive chess.

Later, he turned his attention to martial arts, becoming a world champion in Tai Chi Push Hands competition.

In The Art of Learning, Waitzkin explores what these seemingly different disciplines taught him about developing expertise.

P.S. Know a martial arts gym owner who’s stressed about money or student numbers?

Do them a favor: send them to The Leader's Dōjō, my website where I help owners get more students and keep them longer with simple systems.

One forward from you could change their gym: The Leader's Dōjō​

Chuck