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Dear 20 | Intentional Living

@dear20journal

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Intentional life design 101; lessons I wish I had at 20. Started at 37, 10+ years journaling. I help people design their life through journaling.

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Eileen Gu and Alysa Liu won gold the same year doing the exact opposite thing under pressure.

As I reread my journal entries, I constantly ask myself what I could have done, what I should have done.

There's no absolute answer sitting at the bottom of any of them. And I'm ok with that.

In April 2020, I was asked to give a professional opinion on someone I didn't think was getting a fair shake. I weighed everything and landed on an answer. There were more perspectives in play than I gave room for, and I was the one with the deciding say. That's still true today — and it was still the right call for who I was in that moment.

Break the thought down. Analyze it. Land somewhere defensible.

Today's journal entry was different. Pages of something I'm still working through, where the roles are reversed and I have less leverage than I did back then.

I gave myself grace today. I let it go.

I used both. Both were right when I used them.

✅ Dear 20: you'll use both. Stop looking for the one that means you've got it figured out.

✅ Journal Prompt: Think of something you're weighing right now. What would it look like to stop weighing it and just let it go instead? taken in Tysons Corner, Virginia by @dear20journal

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2 days ago

November 12, 2020. I finished my first Hemingway story and wrote one question in red ink:

Am I Francis Macomber, or am I Robert Wilson?

Macomber spends most of the story afraid: of the lion, of his wife's contempt, of being seen. Then, for a few minutes, he isn't. That's the short happy life in the title. A few minutes.

Wilson never needed the moment. He'd already made his peace with fear.

Six years later, I think the question was wrong. Nobody is one or the other. Some days you're climbing and sweating. Some days you sit at the top and think you've arrived. Some days you walk like you have nothing to prove. Then the stairs loop back around.

The goal was never to become Wilson. It was to stop letting fear, or anyone else, decide when my life starts.

✅ Dear 20: Don't wait to become fearless before you start living. Macomber did, and it lasted minutes.

✅ Journal Prompt: Where are you still waiting to stop being afraid before you let your life begin? taken in Washington D. C. by @dear20journal

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9 days ago

Every goal has a sequel. I never wrote mine.

May 26, 2016. My journal reads: "I hit my goal of 170." That year, I stepped on the scale 175 times. By 2024: 33.

That's the whole story in two numbers.

Rumi, in Coleman Barks' rendering: "I should be suspicious of what I want." I should have been suspicious of how finished 170 felt. It was chapter one, and I stopped reading, one skipped weigh-in at a time.

A decade later, the sequel comes first: hold 200 for two years. Weigh in on a schedule, whether I want the number or not. Because the heaviest stretch of my life was also the stretch I looked the least.

A scale you step on is an early warning system. A scale you avoid is furniture.

Why two years? Research on long-term weight loss is blunt: on average, more than half the weight comes back within two years, and about 80% by year five. Two years is where most sequels quietly fail.

Mine did.

✅ Dear 20: Be suspicious of your goals. 170 was never the goal. It was a number standing in for one: a life I could keep.

✅ Journal Prompt: Write down a goal you're focused on. Now ask: if I hit it tomorrow, what would I still want? taken in Washington D. C. by @dear20journal

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12 days ago

Today my journal entry was all about how grateful I am for being a part of a community that has given so much to me and the people I know today. I watched a dear friend tie the knot and marry his dream woman. I cried, and it felt so good to see him and her happy.

Building community has always been a part of my DNA. I love the social cohesion of bringing people together. Being from Hawaii, a cultural melting pot, I wouldn't have it any other way.

I hope one day people will know me as someone who reaches out, builds community, and brings people together.

✅ Dear 20: Build community now, because you have no idea what life stages are coming — and the people who show up for you then will be the ones you invested in today.

✅ Journal Prompt: Who in your community right now would still show up for you in a life stage you can't even picture yet — and are you investing in that relationship like you know it? taken in Warrenton, Virginia by @dear20journal

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21 days ago

Six habits. One blank. Nobody fills in #5 — not because they don't want to, but because of a real psychological loop.

1. Smoking
2. Drinking
3. Weight
4. Exercise
5.
6. Education
7. Relationships

Swipe through for what goes there, and why it's not a discipline problem. (Receipt: this is basically what carried me through Saturday 9 of rebuilding my w̶a̶l̶k̶i̶n̶g̶ running habit — full story in an earlier post.)

✅ Dear 20: The wall that’s supposed to hold you up is already cracking. You’re just too close to it to see the damage.

✅ Journal prompt: Write 3–4 sentences to the future you who inherits what you’re avoiding today. What is it, and what will it cost them? taken in Washington D. C. by @dear20journal

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22 days ago

I used to jog 7-8 miles every Saturday for weeks on end — until I didn’t. This time I built it back with walking first, and it wasn’t caution, it was math. Willpower drains every time you force yourself through something hard; habit doesn’t cost you anything once it’s automatic. Walking was how I paid from the account that doesn’t run out, cheap enough to repeat without fail while the habit did the harder work of becoming automatic, which takes closer to 66 days than the popular 21. Nine Saturdays, no exceptions, wasn’t just consistency — it was the mechanism. Every time I journal I write out three goals, and somewhere in those nine weeks I watched one of them shift — which is the only reason a 5k is even on my mind now.

✅ Dear 20: you don’t start with the big goal. You start with the Saturday, and let the big goal show up once showing up stops costing you anything.

✅ Journal prompt: what’s something you started small on purpose — and where is it trying to grow now? taken in Washington D. C. by @dear20journal

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24 days ago

October 9, 2020: four things going well.
October 10: five things.
October 11: five more.

October 12: two full pages. Not gratitude. A problem at work I couldn't shake.

Some days I open the journal and go looking for what's good. Other days I go straight at whatever's bothering me. Some days it's both, and some days it's neither in any clean way — just whatever comes out. There's no format I'm following. No rule that says today is a gratitude day or a problem day. It's inconsistent, it's incongruent, and honestly it should be — real life doesn't alternate between "grateful" and "struggling" on a schedule either.

The two-page days — the ones where I actually sit with a real problem instead of skimming past it — are the entries that count most. But even that isn't a rule I follow every time. What actually matters isn't whether any single entry looks a certain way. It's the trend across all of them — that I keep coming back to the page, in whatever shape that day needs.

✅ Dear 20: don't judge the journal by any one entry. It's not supposed to be clean or consistent. Judge it by the trend — whether you keep showing up, messy or not.

✅ Journal Prompt: Looking back at your last few journal entries, what's the trend — not any single day, but the direction they're pointing? taken in Washington, DC by @dear20journal

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24 days ago

Merriam-Webster made "gaslighting" Word of the Year in 2022. The first real theory of how it works — from researchers Klein, Wood, and Bartz — wasn't published until 2025. Their model says it works by hijacking something basic: how much we depend on trusted people to help confirm what's real. It's not one denial that does the damage. It's repetition, until you stop trusting your own read altogether.

July 2, 2019 — after real frustration working with someone, not a first impression — I wrote one line, often credited to Lincoln though I couldn't verify it: "I don't like that man. I must get to know him better."

At the time, that felt like wisdom — applying what Olympic skier Eileen Gu calls an "analytical lens" to my own thinking. But I had no way to tell correcting a bias from erasing an accurate read. That framework didn't exist yet to warn me.

This shows up in at least 5 separate 2019 entries. Rereading them now: parts of my own account lean toward his version, not just mine. I was applying the lens. I just didn't know what I was defending against.

He left the company not long after. Maybe I wouldn't have written that line if I'd had the framework. I don't know.

A separate 2025 study, by Darke, Paterson, and van Golde, tested something people assume works: pushing back in the moment. It doesn't reliably protect you against someone close to you. What held up instead — writing it down, before repetition gets the chance to work on you.

Writing this is the strategy. Not the topic — the practice. But the practice needs a compass, not just discipline.

✅ Dear 20: Write the raw account first. Don’t re-question what happened. Calibrate the lens second.

✅ Journal prompt: Write something that's bothered you — raw, exactly as it happened. Then ask: was any of it shaped by someone else's version before you started writing? taken in Washington, DC by @dear20journal

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25 days ago

Identity diversification isn’t supposed to fail like this — and it didn’t.

Raygun probably never called it that. PhD in cultural studies, competitive breaking career — two real identities running side by side for years, not engineered, just two things she actually cared about.

I watched the new Netflix documentary on her this week, and a few things surprised me. Making the Olympics wasn’t a long shot — she won her qualifier outright. Losing badly wasn’t a surprise either, she said so herself. Before Paris, her therapist asked the classic worst-case question. Her answer: “the whole world could laugh at me.” Nobody thought that was realistic.

That’s the part that broke the model — not the Olympics, not the loss. One clip going global. Years later, budget cuts cost her the university job too, and she’s said the scrutiny played a part.

She didn’t stay down. A third identity, public speaking, built after the first two took hits.

✅ Dear 20: diversification protects you from a bad year — not a one-in-a-million outcome nobody saw coming. Build it anyway.

✅ Journal prompt: the identity you’d protect hardest — how big would a realistic hit actually be? taken in Washington D. C. by @dear20journal

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a month ago

Watched Eileen Gu’s @eileengu episode on Jay Shetty’s @jayshetty On Purpose Podcast @jayshettypodcast recently, and one part stopped me.

She talked about journaling since she was around four years old — describing herself as deeply introspective, someone who breaks down her own thought process and applies what she calls an analytical lens to her thinking. Then came the line that’s been circulating since the Olympics: “You can control what you think, you can control how you think” — and she named the mechanism behind it as neuroplasticity.

I didn’t have that language for it when I started. But it’s the same mechanism I’ve been running through journaling for over 10 years — starting messy, working to find the half-full, letting the reflection turn into goals I didn’t plan in advance.

Swipe for the full process, step by step now. taken in Washington D. C. by @dear20journal

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a month ago

The instinct when you’re scared of losing your job is to work harder. That’s not what actually worked at Facebook.

March 21st, 2019, I got the offer. Over the months that followed I wrote plenty of goals — workouts, meditation streaks, running 8-10 miles weekly. It wasn’t until December 7th, almost nine months in, that I noticed every one of them was still centered on keeping up with Facebook’s pace. That was the day I stopped writing goals about the job and wrote one for myself instead.

It was real progress — that tracking genuinely got me far. But reading those journal entries back that week, I could see what it wasn’t: separate. Every number I was tracking existed to help me match the pace of a place built on hard, fast, constant results. Getting good at keeping pace with your job isn’t nothing. It’s just not the same thing as having a life outside of it.

Facebook doesn’t take people who can’t operate at that pace — that was never the issue. The issue was that I’d let the goals centered around the pace become the only thing measuring me.

What I wrote on the 7th was different. A real goal, aggressive, with nothing riding on the job’s calendar or its metrics. The first thing in almost a year that had no relationship to Facebook at all.

Tim Ferriss has a name for what that gap was — identity diversification, areas of growth that don’t report back to the job. I’d had areas. They just weren’t independent ones. Getting better at matching a company’s pace will take you far. It won’t give you separation. Only a goal with nothing riding on the job does that.

It worked. That goal is what carried me through the rest of my time at Facebook and into the move back to government that followed.

✅ Dear 20: goals that live outside your job but still answer to its pace will get you far. They won’t give you a second identity. Only a goal with nothing riding on the job does that.

Swipe for why this matters more than ever right now → taken in Washington D. C. by @dear20journal

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a month ago

Some kids who watch a parent die become Batman. Some become prisoners. Fiction only tells you about one of them.

Batman's my favorite character. Decades of comics, and I couldn't find one page where he processes what happened — an 8-year-old who watched his parents get shot. Not one. UCLA psychologist Drea Letamendi told MEL Magazine this is interpersonal trauma: human-driven, intentional, dangerous, harder to recover from. Recovery needs to start right away — not decades later, alone in a cave.

Malcolm Gladwell calls kids like him "eminent orphans" in David and Goliath. A quarter of history's most documented high-achievers lost a parent before 10. Some get catapulted forward. Some don't — the same research shows they're 2-3x more likely to end up in prison. Same wound, opposite outcomes.

I almost said journaling is the difference. Not that simple. Researcher Willoughby Britton set out to prove meditation only helps — found it can worsen sleep, cause dissociation, worsen anxiety for many. Journaling has the same risk: pain without shape becomes rumination with better handwriting.

Nietzsche: "One must still have chaos in oneself to be able to give birth to a dancing star." Chaos isn't the problem — it's raw material. Tope Awotona watched his father killed in a carjacking at 12, built a billion-dollar company to finish what his father started. But chaos alone doesn't become a dancing star — not without shape. Batman spent 22 years shaping everyone else's story. Never his own.

Even Letamendi's drawn to him for it. "I don't have the same connection to someone like Superman," she told MEL Magazine. "Batman is a work in progress." Maybe that's why the page stays closed. Finished stories don't sell 87 years of comics.

November 2016. I wrote about a childhood memory — helping a bully who'd tormented me for years, right after he threw my bike in the trash. Didn't know what to call that yet. By the end I wasn't even writing about him anymore — I was questioning whether truth was too relative to regulate change at all. That's the shape I mean.

Same wound, two endings. One becomes a hero. One becomes a headline for the wrong reasons. Fiction only shows you the first. taken in Arkham Asylum by @dear20journal

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a month ago