Hey readers,

I’ve been enjoying meeting many of you in 1:1 reader calls and our Community Calls. 🤩

I realized we have an incredibly fascinating bunch on this list—and I’m excited to start highlighting some of your stories here soon.

Today, in 5 minutes or less, you’ll learn:

• ⚡ Why time-tracking actually killed my productivity (and what works for me instead)

• 📅 A behind-the-scenes peek at a portfolio careerist's exact daily schedule (from 7:30 AM to 9 PM)

• 💪 7 unconventional strategies to get more done while working less

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📆 Day in the Life of a Portfolio Careerist

"I don't have enough time."

That’s what readers reported as their #2 obstacle for building a portfolio career (#1 is not knowing how to start.)

I get it. For much of my 12-year career, I used to drown in time management pain.

What was I doing wrong?

I was blindly following conventional advice. Use tactics like time tracking. Batching tasks. Pomodoro technique.

But they felt like putting bandaids on a gaping wound.

The irony was that it wasn’t until I let go of controlling every minute of the day—that I ended up feeling more in control of my time than I ever did.

WTF. How is that possible?

In this edition, I break down my exact weekly and daily schedule—plus the unconventional productivity strategies that worked for me.

But first let me share what I meant by “letting go”:

💥Why I Stopped Time Tracking

Do you plan out every hour of the day? That used to be me not too long ago.

If you looked at 29-year-old Dexter’s schedule, pretty much every hour was rigidly planned out on my Google Calendar—even explicit time slots for “relaxing.”

This never worked because things didn’t go according to plan 50% of the time.

And even if I stuck to the schedule, ~25% of the time, I also just wasn’t feeling super productivity. I was in a crappy mood, didn’t sleep well, or felt stressed out.

Yet I’d pressure myself to sticking to my plan (“are you even disciplined?” - my negative self-talk).

Then I would stress myself out to finish tasks, miss a commitment, and make myself miserable the next day— starting a vicious negative cycle.

Until I realized something HAD to change.

I forget who inspired me —but I started talking to friends about this topic. Somewhere along the way, I got motivated to try focusing on ENERGY instead of TIME.

This was the mental shift I sorely needed.

Fast forward to today:

I take an adaptive approach.

I keep a relatively open calendar with a theme for each day.

If I’m feeling energized, awesome. I double down—heck, triple down on knocking out my TODO list.

If I’m feeling down, it’s cool. I go for a walk. I take it easy. I hit the bed early.

Now that you get my mentality around managing time, let me show you my actual calendar:

📆 My Week at a Glance

Here’s an example of what my week looks like as a self-employed portfolio careerist.