I sat down at 39 and asked a question that scared me. Here’s what I found on the other side of it.
What You’ll Learn
- How a retirement simulation can send you spiraling (and how to recover)
- Why comparison is costing you more than you realize
- What actually happened when I stopped looking at others and looked at myself
- How your past doesn’t define your next decade
Let me tell you about the question that sent me into a bit of a spiral.
I had just turned 39. Nothing dramatic happened that day — no big event, no crisis. I just sat with my thoughts longer than usual and asked myself something I had been avoiding for a while.
What if I had done things differently? Where would I be right now?
That question hit harder than I expected. And for a little while, it took me to a pretty dark place.
The Fidelity Simulation That Started It All
It started the way a lot of these stories start — with a retirement planning tool.
I opened Fidelity, ran the simulation, and what I saw genuinely scared me. Not a little behind. Not slightly off track. Way behind. The kind of result that makes you sit back in your chair and stare at the screen for a minute before doing anything else.
My first thought was: I’m going to have to work until I’m 65. Maybe longer.
And that thought did not sit well with me at all.
Twenty-five more years of work. What if I get sick before then? What if I don’t make it that far? I’m out here enjoying my life, but I want something more than just getting through the week. I want freedom — real freedom. The kind where you wake up and decide what the day looks like. Not the kind where your alarm decides for you.
Growing up, I absorbed a certain kind of mindset around work. I spent years living in South Korea, and if you know anything about Korean work culture, you know it runs deep. Working hard, logging long hours, pushing through — that was just normal. That was what you did. You didn’t question it. The rat race wasn’t a trap, it was just life.
So when the Fidelity simulation told me I was behind, part of me thought — okay. This is just my life. Work, sleep, repeat. Maybe that’s all it was ever going to be.
That’s a heavy feeling to sit with.
Then Social Media Made It Worse
Living in the Bay Area does something to your sense of normal.
I started spending time in personal finance communities — Reddit, Facebook groups focused on FIRE and financial independence — and what I found there was equal parts inspiring and demoralizing. There were 25-year-olds announcing they had hit $500,000. People in their early thirties crossing a million. Posts about retiring at 34 getting thousands of likes and hundreds of congratulations.
And then there was the other side of it — the influencer side. People my age or younger showing off luxury apartments in San Francisco, nice cars, weekend trips to Cabo, and then casually mentioning in the caption that they were planning to retire soon. All of it perfectly lit, perfectly edited, perfectly designed to make you feel like everyone else had figured something out that you hadn’t.
I was envious and worried at the same time. Which is a really uncomfortable combination of feelings to sit with.
But what really got to me wasn’t just the money. It was the age gap. It was watching people younger than me — sometimes significantly younger — already at a finish line I hadn’t even properly started running toward. And I started to second-guess everything.
Did I waste my 20s and 30s?
Was my MBA worth it? Was my career path worth it? Should I have studied something different, gone into tech, gotten a job at Google, and been one of those people posting success stories that would have changed everything?
Those are uncomfortable questions. And I didn’t have clean answers to any of them.
The Turning Point at 39
Here’s what I’ve learned about spiraling — at some point you either stay in it or you decide to climb out.
At 39, something shifted. Maybe it was the birthday. Maybe it was just exhaustion from feeling bad about a situation I hadn’t actually tried to change yet. But I made a decision.
My 40s were going to be different.
Not in a vague, motivational-poster kind of way. In a specific, roll-up-your-sleeves, actually-do-the-work kind of way. I did a full review of my finances — assets, accounts, everything. I stopped looking at where I was compared to some 28-year-old tech worker in Palo Alto and started looking at where I was compared to where I needed to be.
And I decided I was going to take it year by year. At 40, I wanted to be able to say I used that year as a real stepping stone. Not a year that just happened to me — a year I actually built something in.
This year alone I’ve saved more money than I have in previous years. I’ve also challenged myself to visit 24 places — international trips, domestic trips, places right here in California I’d never been. Because freedom isn’t just a retirement goal. It’s something you can practice now, even while you’re still building toward it.
The Philippines Was Always Part of the Picture
Here’s the thing though — I wasn’t starting completely from zero. Not really.
Back in 2017, when I was living in Korea, I bought a condo in Manila. My thinking at the time was practical — I was planning to stay in Korea long-term, and I wanted a place in the Philippines I could visit every few months without having to stay with family. I didn’t have a car payment at the time, so I treated the condo payment almost like one. It just made sense.
I wasn’t thinking about retirement then. I was just thinking about having a base.
But then in 2024, I became a dual citizen — Filipino and American. And something about holding that citizenship made the question feel more real. Could I actually retire there? Could the Philippines be home?
The more I thought about it, the more it made sense. I already own property there. I know the country. I have family there. And the cost of living — especially compared to the Bay Area — is a completely different world. What felt like a question mark slowly turned into a plan.
That condo I bought in 2017 thinking I’d crash there between flights? It might end up being the foundation of the retirement I’m building right now.
What I Want You to Take Away
If you’ve ever looked at a retirement simulation and felt your stomach drop — I’ve been there.
If you’ve ever scrolled through social media and felt that mix of envy and worry watching people younger than you announce their financial wins — I’ve been there too.
And if you’ve ever asked yourself whether you wasted your 20s and 30s, whether your choices were the right ones, whether it’s too late to change the trajectory — that one I’ve been through as well.
Here’s what I found on the other side of all of it.
The comparison was never real. The influencers were selling a version of their life, not the whole thing. The social media posts were the highlight reel. And the Fidelity simulation — as uncomfortable as it was — wasn’t a verdict. It was a starting point.
I didn’t waste my 20s and 30s. I lived them. I worked hard, I moved to another country, I got my MBA, I built a career, I bought property in another country on instinct, and I became a dual citizen. None of that was wasted.
It just wasn’t optimized yet.
That’s what my 40s are for.
What’s Next
This is where the real work starts. In the next post, I’m breaking down the actual numbers — not the scary simulation, but the full picture of where I actually stand. Because understanding your real financial position changes everything.
If you’re in your 30s right now and worried you’ve fallen behind — read the next post first. If you’re in your 40s and feeling the same way I did at 39 — this journey is just getting started.
Have you had your own version of this moment? That birthday or milestone where you realized something had to change? Drop a comment — I’d love to hear your story. Sometimes knowing you’re not alone is the first step.
Posted on: June 16, 2026
Reading time: 6 minutes
Word count: 1,350
Written by: Ono
Categories: My Journey
Tags: comparison trap, early retirement, FIRE, retirement planning, personal growth
About the Author
Ono is a banking professional documenting his journey toward early retirement. What started as a personal question at 39 turned into a real plan backed by numbers, intentionality, and the willingness to do things differently. He’s sharing CraftYourExit because the path he’s building didn’t have a blueprint—and he thinks you might be building something similar.
Learn more about Ono’s story →