🔑 Day in the Life of a Portfolio Careerist

‍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.

But first, a disclaimer:

• These hourly time blocks are for illustration purposes (I don’t explicitly add these time blocks to my Google calendar).
• I do focus on a theme for each day of the week, e.g. MWF are for client-facing and execution work.
• Aside from my client/meeting commitments, most of my schedule stays loose/flexible to adapt to the situation.

Additionally, here’s what I’m actually doing in each work session:

‍

🌅 My Daily Schedule

Let’s take a recent Wednesday for example:

• 7:30am: Roll out of bed, get ready, throw on gym clothes, get out the door, and grab a coffee on my way.
• 8:00am-9:00am: Bouldering Session with friends at a nearby climbing gym (3x a week)
• 9:30-10:30am: Spanish Class. I like taking AM classes with my Preply tutor while my mind is fresh. Also feels motivating to start the day with a quick win.
• 10:30am-11am: Emails/Whatsapp/Slack Comms. I coordinate with our course specialist to prep an upcoming cohort live session. I review content research from our assistant to add to our newsletter.
• 11am-12:30pm: Deep Work Session #1. The projects vary each week. I might be working on a b2b client deliverable, planning a new product launch, coding a lead gen app, setting up an AI automation, preparing slides for a live community call, or writing feedback for cohort/coaching clients.
• 12:30pm-1:30pm: Lunch + Walk. I’ll grab a meal with my wife, then we’ll take a stroll around the park nearby to stretch our legs. If we’re feeling cheeky, we’ll enjoy a pair of fruity paletas (ice pop) on the way back home.
• 1:30pm-3pm: Deep Work Session #2. I keep my deep work sessions flexible in case of any emergent client needs. For example, if a client has an urgent fire, I’ll use this slot to triage the issue.
• 3pm-5:30pm: Clients, Meetings and Business Development. Product advisory call with the innovation team of a large national bank. An intro meeting with a potential partner/sponsor. A couple of rapid-fire 1:1 reader calls. Send BD/outreach messages in between calls.
• 5:30pm-6pm: Emails/Whatsapp/Slack Comms. I try to hit inbox zero.
• 6pm-8pm: Dinner at a casual restaurant with friends or at home. Depending on the day, I’ll do 30 minutes of engaging on social media.
• 8pm-9pm: Cohort Q&A or Fireside Chat. We schedule these at night because we typically juggle members sitting in both Asia and US/Canada time zones. If I don’t have a live event, I’ll start winding down for the night.

So there you have it. That’s my schedule in the nutshell.

Now I’ll share the “why” behind my schedule and a few of my top strategies.

⚡️ How do you juggle a side business with full-time work?

I would start with your desired time allocation to your business. When I was in a full-time role, I tried various approaches to managing a 5 to 10-hour/week side hustle: What worked best for me was carving out 1-2 hours in the morning before the work day on weekdays and Sundays. I noticed I rarely succeeded with my efforts if I left it to after work.

‍

My Favorite Productivity Strategies

1. Prioritize your tasks according to their leverage. I like Stripe’s first PM Shreyas Doshi’s LNO framework which says great work = doing a great job at 10x tasks, good job at 1x tasks, and just getting it done for

2. Write down one big win I want to achieve that day in my journal. This helps me focus. Typically an L task on my TODO list.
3. Start the day with quick wins to spike motivation. By tackling bouldering / Spanish lesson first thing, this helped me kill two birds with one stone: I stay on top of my personal habits and I juice my motivation for the rest of the day.
4. Identify your peak creative/flow state timing. I realized that my mind feels the most creative and productive in the late morning / early afternoon. Hence, given this reason and (1), I tackle my deep work later in the day and leverage the heck out of it.
5. Call it quits early and try again tomorrow. If I’m feeling shitty, I give myself space to rest, go for a walk, and sleep early. My goal becomes recovering energy to spend the next day (instead of trying to brute force it).
6. Carve out a no-meeting writing day (or 2). Content requires focus for me, so I tackle researching, writing, editing, and publishing on dedicated days. This isn’t just the newsletter, but also social media, email sequences, lead magnets—and even course videos/materials. Behind the scenes, I also have an assistant helping me with various research/ops tasks and I’m leveraging AI agents to scale my time.
7. Break outcomes down into weekly work habits. Since it’s difficult to control outcomes like $ revenue, I do an exercise mapping my annual goals to weekly work habits, then track them in Notion. Periodically, I lookback to measure if my actions are generating the desired results and adjust the habits.

Summary

• Time tracking often fails due to energy fluctuation and unpredictable events—especially in an entrepreneurial portfolio career
• Use an energy-first approach instead -
  • Keep calendar flexible except for key commitments
  • Double down when energy is high, rest and recover when energy is low
  • Focus on high-leverage (10x) tasks during peak hours
• My Favorite Productivity Strategies
  • Use the LNO framework for task prioritization (10x, 1x,
  • Establish 1 big win for the day
  • Start days with motivating quick wins
  • Schedule deep work during peak creative hours
  • Maintain a no-meeting day for writing and content
  • Track weekly habits instead of only outcomes

💎 Last Week’s Finds

Just a fun meme for this week - Guy in his 30s trying to ”exit the career rat race.” Accurate or nah?

📚 From Our Archives

The 4 types of portfolio careers. In this previous edition, I deep dived into 4 portfolio career paths—side hustler, expert, freelancer, and polymath.

I also shared 14 real-world examples that illustrate what these paths look like.

Get the case studies:

Read the Deep Dive Here →

✨From Our Community

• I just crunched the data for 537 responses to our newsletter onboarding survey last month. This Income Distribution Chart caught my attention 🕵️
• We hosted our second Community Call last week on offer design! Our attendees included a Google UX researcher, product leader, fractional COO, consulting agency owner, startup founder/CEO, data scientist/ML engineer. Stay tuned for the next one in April.
• Starting soon, we’re going to experiment with featuring reader intros! I’ve been meeting amazing people through my 1:1 reader calls and would love for y’all to meet them too. Reply to this email if you’d like to be featured.