Today, in 10 minutes or less, you’ll learn:
- 🧑🎓 How a small-town kid's college dream planted the seeds of a happiness trap
- 🔮 The hidden dangers of the "I'll be happy when..." mindset
- ✏️ Practical steps to break free from the Deferred Life Plan
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⏳️ The Deferred Life Plan
“If I just get that promotion, then I’ll be happy.”
I said it at my first job out of school at an edtech startup.
I said it at Dropbox—where I stayed through the IPO.
Replace “promotion” with “new job,” “$X net worth,” or “big client”…
… and you’ll get different flavors of the same thought that has caused me misery throughout my work and life.
Wall Street Journal recently featured a few Americans who decided to “[borrow] years of freedom from their future selves to enjoy some of their retirement while they are still young.“
This runs counter to the ethos of the FIRE movement, which focuses on saving aggressively to achieve early retirement in your 30’s or 40’s.
Is enjoying the present worth the trade-off of slowing the growth of your nest egg?
In this newsletter, I am going to share my own story of the Deferred Life Plan—and how I navigated the tension between delayed gratification and living in the present.
“And then there is the most dangerous risk of all — spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.” — Randy Komisar, advisor at VC firm Kleiner Perkins
Escaping small-town Michigan
In 10th grade, I made a pact with myself:
I’m going to get out of Michigan no matter what.
I was a 15-year old kid with big dreams, but felt isolated in my small suburban town.
Unfortunately, my parents couldn’t afford to send me to a fancy out of state school nor had a network to refer me to for job opportunities in NYC, SF, DC, or other hubs.
So I had to carve out my own path.
How? I decided to apply to need-blind, no-loan US colleges that met the student family’s financial need entirely through grants and scholarships.
No student loans.
I strongly opposed taking on substantial debt due to how I saw people in my life struggle with it. (I paid off my small Stafford loans within a month of graduating college.)
Yet, there were only 12 schools on this elite list.
I realized I would have to work extremely hard for the rest of high school, make sacrifices in my social life, and defer my happiness—all for a shot at attending one of these prestigious institutions.
“If only I could get into one of these colleges, then I’ll be happy.”
Fast forward to 12th grade.
I was running down the stairs of my parent’s house, holding my Dartmouth acceptance letter with a massive grin on my face.
Dartmouth was one of the 12 colleges on the list.
I couldn’t freakin’ believe it.
I felt completely validated.
My hard work paid off.
This moment kicked off my Deferred Life Plan.
A vicious cycle on repeat
Once I was at Dartmouth, I felt like I was back at square one.
Despite experiencing a flash of joy after getting my acceptance letter …
… walking around on campus, I felt like I lacked something.
Like I had a hole to fill.
My new dream was to attend a prestigious law school (this was before I decided to pursue startups in Silicon Valley.)
I felt like this was a respectable goal that was accepted by my ambitious peers.
“If only I could get into a T14 law school, then I’ll be happy.”
Later, my dream shifted to getting a high-paid tech job in Silicon Valley.
“If only I could get into X hot pre-IPO startup, then…”
You get the picture.
This cycle repeated itself for a number of years.
Until my mid-20’s, when I found myself as a workaholic feeling stuck and bordering on burn out.
I was working 60-hour weeks. I wasn’t taking care of my health.
I made lots of excuses and sacrifices for work.
Then, I was rejected for a promotion.
I remember feeling resentful.
The weeks and months afterward sucked.
But that’s when I finally realized:
I had no one else but myself to blame for my own actions.
I was ultimately accountable for my own happiness.
Meet these millionaires
Khe Hy recently shared fascinating survey data from a group of millionaires:
Half of them work in finance.
50% earn more than $250k.
11% more than $750k.
(For context, the average US salary is $54,000.)The survey asked them about their inner lives.
The key question was the following:
If you had no money concerns and purchased all the things you wanted and checked off every place on your travel bucket list (like imagine you won the lotto and several years have elapsed since), what would you do with your time?
What do you think they said?
Keep in mind. These guys (95% men) have by most accounts, already won the game of money.
49% said they’d get a hobby.
27% said they’d teach, mentor, or volunteer.
Only 3% answered “what I’m doing now.”
Yikes.
This is the Deferred Life Plan in full force.
Wait until retirement to do what you enjoy.
But the scary thing is:
None of us know how long we’ll be on this planet for.
Nothing is guaranteed.
Here is what I learned from my own struggles:
There’s two sides to the same coin
Getting into Dartmouth—and achieving my early dream—was a blessing and curse.
Blessing for how it opened up the door to future opportunities.
Curse for how it validated my delayed gratification playbook.
On one hand, I had learned a useful lesson:
Hard work helps you achieve your goals.
On the other hand, I had internalized a false lesson:
You need to work hard and sacrifice happiness now in order to be happy later.
It took me a few years in my 20’s to disentangle the two lessons.
And redefine the second lesson to:
Enjoy the present, while working towards your goals for the future.
I decided to finally pull the trigger on the travel sabbatical I had thought about taking since high school.
I decided to live and work abroad in Southeast Asia.
I decided to quit my job and build my portfolio career.
Now that I’m 33, I feel like I’m finally taking ownership of my own happiness.
I no longer view living in the present in conflict with my future happiness.
I have broken free from my Deferred Life Plan.
How to take control of your own happiness
Feeling trapped in your Deferred Life Plan?
Burned out and not sure what to do?
Here are a few tactics that helped me break the chains:
- Do a Values Audit. Identify your Top 5 Values. Then break down your life into different parts (e.g. Love, Work, Wealth, Health, Play) and evaluate whether you’re living according to your values in each part.
- Work with a coach. When I worked with my career coach in 2017, it was the first time I had spent thousands of dollars on my personal growth in this way. Our sessions were powerful. They helped me disentangle my analytical self and curious self and clarify what I wanted.
- Experiment with small changes. Feeling stuck doesn’t necessarily mean you need to do something drastic like quit your job. Start small. If you value Relationships, this might look like scheduling more lunches with your colleagues, instead of eating by yourself at your desk. Notice how this feels.
- Take a mini-retirement or sabbatical. I suggest taking at least 3 months. Ideally >6 months. For high-achievers, it takes 1 month alone to unplug your mind from the productivity-fueled hamster wheel. Magic happens when you can welcome serendipity into your life.
The key is taking action now.
🌐 Beyond your borders
🇸🇬 Evan Koh Shares His Path To Financial Independence By 40 – A PhD In Japan, A Tech Role At An MNC, Getting Retrenched And Coding StocksCafe, A Portfolio Tracker (D&S)
🏡 The Biggest Risk in Real Estate (AWOCS)
🧑💻 Part-Time Party: Charting the Rise of Part-Time Opportunities (Indeed)
🇪🇺 The European Engineer is the one-stop shop for tech workers based in Europe. Join 5,400+ subscribers getting insights around high-paying companies, remote work, lifestyle, taxes and more. Subscribe here → (Substack)
🧠 Social snippets
I procrastinated on socials due to focusing on our cohort kick-off this week. More social snippets coming soon.
For daily insights, follow me on Linkedin or Threads.
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