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.

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.

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