Why I'm Stepping Away from My Dream Job...

After 10 years, I’m choosing to leave something I love. Here’s the “why” behind our family’s next big decision...

⭐️ I serve as the executive director of communications at Singapore American School (SAS)—one of the largest and most respected American schools in the world.

⭐️ I work with an unbelievable team who does award-winning work and who (most importantly) are fun to be around.

⭐️ My kids attend school here.

⭐️ We live on a tropical island with amazing weather and beautifully manicured jungle greenery everywhere you look.

⭐️ I’m paid well, enjoy great benefits, and have more vacation time than ever.

⭐️ My commute to work is less than 10 minutes.

⭐️ We travel around the region experiencing things I used to only see in travel videos.

This is the life I dreamt of—we are literally living the dream.

And, earlier this week, I shared that next academic year will be our final year in Singapore.

(International education has a VERY long lead time for departures in order to allow for optimal overseas recruiting)

I cried when I told my team.

I cried again in our senior leadership meeting.

And, I cried again by myself on my office floor 😭

I love so much about working and living here in Singapore.

As I’ve shared the news over the last few days, the question I’ve gotten more than any other is:

“Why?”

And honestly…

It’s the question we should all ask more often.

“Why” Matters

There are two pivotal times to ask “why.”

Before and after.

I’d argue it’s more important to ask “why” before than it is after. Parents, educators, and anyone who has worked with kids often ask “why” after something has happened.

Why did you…

It’s helpful because it sparks reflection and forces the person to own what drove their behavior and will hopefully improve their decision making in the future.

But the better time to ask “why” is before you act.

That’s what we’ve tried to do. Before we made this decision, we spent a lot of time asking hard questions—individually and as a family.

Asking this before a major decision or action interrupts the autopilot function that many of us rely on.

• Why do you want this?

• Why do you feel this?

• Why do you think this?

Why is uncomfortable—but that’s why we need it.

When you ask “why” enough times, you don’t just make better decisions.
You build a better story.

So, why did our family make this decision?

For values or guiding principles to be truly effective they have to be verbs. It’s not “integrity,” it’s “always do the right thing.” It’s not “innovation,” it’s “look at the problem from a different angle.” Articulating our values as verbs gives us a clear idea - we have a clear idea of how to act in any situation.

(Simon Sinek, Start with Why)

1. Rebalancing Time and Energy

Before I stepped on campus 10 years ago, I told myself I had to at least try to outwork everyone.

I was the youngest leader on the team.
The superintendent had taken a chance on me and I wasn’t going to let him down.

And I didn’t.

I showed up early. Stayed late. Worked weekends. Ate lunch at my desk. Skipped holidays.

Eventually, I built a rhythm. I had a routine that actually worked:

• Up at 3:58 a.m.

• Home for lunch a couple times a week

• One “as-late-as-it-takes” night per week

• Home by 5:30 most other days

It worked.

But… time doesn’t stand still.

My kids got older. I got older.

I’ve clung to the 7:00 p.m. bedtime like a life raft. But we’ve got a sixth grader now. And I think I need more sleep too as I’m no longer in my 30s 😂

Then came a moment I won’t forget.

I was sitting with the superintendent, looking at my leadership scores. They were very high.

As he shared how proud he was and how proud I should be, I could only think:

“The only way to keep getting scores like this… is to keep operating at this same intensity.”

And I knew I didn’t want to do that forever.

But time is only one part of the equation. There’s another factor I’ve learned to pay even more attention to: energy. It’s possible to have a calendar where everything fits perfectly in place and you still feel entirely out of sync.

Energy is everything.

A big part of my role is helping people through tough moments.
Being the person people come to when they’re frustrated, stuck, or just plain upset.

I’m proud of that work and I’ve tried my best to honor the emotions that come through my door, into my inbox, and on WhatsApp.

I’ve learned that emotionally intense work pulls from a different part of me—it’s meaningful, but it can leave me with less to give outside of work.

Often this means that the urgent voices I work with each day get the most energy which leaves my family with the leftovers.

Reworking my calendar allowed me to be present physically but without the energy I wanted to offer.

That’s not the rhythm I want anymore—I want the most important people in my life to get the best of me.

2. Fueling My Entrepreneurial Curiosity

If you ask my wife about my dream project she’ll roll her eyes and ask, “which one?”

She’s right—she’s had to listen to me pitch her on way too many ideas over the years. Here’s a few from the highlight reel:

City Edition Ties - imagine color blocked ties using the exact color palette of your favorite sports teams. I even sourced samples at one point but couldn’t ever get the material right. It’s too bad because I wear ties every. single. day.

Draft App - an app that would allow me and my brothers to do a snake-style draft at the start of each season and then track the winners each week. (still need this one because we do this manually each season)

Frameworthy - I began handlettering custom frame mattes years ago for each of the vacations we took as a way to preserve the details of the trip. Eventually I began doing them as moving gifts for people who left Singapore. I wanted to do this at scale to help others commemorate the most meaningful moments (frameworthy moments) in their lives with a custom frame they could proudly hang in their home.

Children’s Books - I’ve got two manuscripts I’ve run through multiple writing groups and editors and began shopping them around for an agent but haven’t found someone willing to take a chance on them yet.

Keep Asking - I mean, you’re here reading this so you’re familiar with this project. I’ve been here writing for over 4 years and now have over 5,000 people who show up each week. I wonder what is possible if I spent more than a couple hours a week on this project. I’ve got a completed manuscript for a book that I’m shopping around to agents. I’ve almost completed the one-semester course I’m working on and I’ve been testing out videos on YouTube.

So, what’s next?

When I wrap up here in June 2026 I want to jump deeper into Keep Asking. I keep thinking about how valuable this idea is for high school seniors and recent graduates as they prepare for a decade filled with some of the biggest decisions of their lives. I want to create something that gives them a framework for using questions to create the life they really want.

Ultimately though, I could totally see myself back in education. It’s just such a special place to be.

So, if you happen to know a book agent, an app developer, a clothing manufacturer, or a printer, let me know because I’ve got some ideas 😂

3. Modeling Risk and Discomfort

This one’s the scariest.

But also the most important.

We want our kids to experience discomfort and thoughtful risk taking.

“We are living progressively sheltered, sterile, temperature-controlled, overfed, underchallenged, safety-netted lives.”
― Michael Easter, The Comfort Crisis

This is especially true in an incredibly developed nation like Singapore. We are so fortunate to enjoy the comforts of life here.

It’s not lost on me—we are in a very privileged position to be asking these kinds of questions. And that’s exactly why it matters.

We want our kids to see that they can adjust to new settings and situations. We want our kids to see us take calculated risks as a family so they know they have the capacity to do that too (now and in the future).

We want them to know that dreams can evolve. That comfort can’t be your only compass.

That sometimes, the bravest thing you can do is leave something great to pursue new growth and new dreams.

Even if you don’t know exactly what that is yet.

We want to model that.

Because if we’re going to tell them to be brave in their lives, we have to be brave in ours.

So That’s My Why.

We’re not leaving because something is wrong.

We’re leaving because something is shifting.

Because life has seasons and a new one is on the horizon.

I’m proud of the growth I’ve experienced here—professionally, personally, and as a parent. I’m incredibly grateful for the people I’ve worked alongside, the mission I’ve been part of, and the opportunity to serve a school I deeply love 🦅 ❤️

And I’m also excited—for the unknown, for the experiments ahead, and for a chance to build something new.

If you’re sitting on the edge of a decision right now—big or small—I hope you’ll take the time to ask:

Why?

Because clarity rarely comes from outside.

It comes from the questions we ask ourselves—in those small pauses between the noise.

And If You’re Still Reading…

Good for you—that was a journey 😂

Thanks for being here.

For letting me be honest.

And for asking the kind of questions that matter.

(And if you’re curious what comes next for us… I’ll share more in the months ahead)

Keep Asking,

Kyle