Ciao from Italy. 👋 

I’m not typically a pasta guy, but got hooked on the fresh Amatriciana here.

This week, our cohort enrollment opens (and closes), so you’ll receive a couple of emails sharing details about how to enroll.

Now, let’s dive into today’s edition.

Today, in 10 minutes or less, you’ll learn:

• 🤑 The critical financial milestone to hit before leaving your full-time job for a portfolio career

• 💻️ Why perfecting your website might be the biggest waste of time when starting out

• 🎯 The counterintuitive reason why having fewer service offerings can lead to more clients

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FROM OUR CLASSROOM

🚀 Enrollment opens for waitlisters on Tuesday!

515 students have already joined the waitlist. 🤯

I have earned 6-figures from my side hustles taking 10 hrs/wk, traveled to 10+ countries while doing it, and used my extra time to build businesses and see loved ones.

But here’s the reality:

This took me years of trial and error and making costly mistakes.

That’s why I have taken everything I have learned and boiled it down into a simple system that others can use—while avoiding the mistakes I made.

Starting on October 1st, you can have this system.

That’s when I launch Remote Side Hustle Launchpad, my 6-week cohort program to help you go from zero to launching your consulting or coaching side hustle—without sacrificing your mental health.

This is the playbook that I wish I had when I first started.

I’ll show you exactly how to use my playbook to launch your side hustle through weekly live office hours, actionable lessons, and a supportive peer community.

Interested? Click the button below to get priority access to enrollment:

💼 5 common mistakes when starting a portfolio career

Recently, readers have asked me about starting a portfolio career.

Whether it’s because they feel stuck in their job, lack of control over their time, or face burn out—many are curious about this path.

Over the last year, I have featured thriving portfolio careerists, including:

• Eric Sims - Ex-UBS Managing Director with 2+ million Linkedin followers

• Karina Mikhli - Former Publishing Executive, now Fractional COO

• Fayzan Rab - Ex-Product Manager turned into Psychedelics Researcher and Executive Coach

• Aki Taha - Ex-Netflix, Google, and Uber Recruiter starting the TalentStories Newsletter

I have also written about my own decision to leave my last full-time role to start a portfolio career. 

But as you and I know… this path is hard. Success is far from a given.

In this newsletter, I’m going to walk through 5 common mistakes I have seen people make when starting a portfolio career (and what to do instead).

Let’s start with the first mistake:

Mistake #1: Quitting your job too early

“Should I quit my job?”

The reality is that many people vastly underestimate the amount of time it takes to build new income streams.

For example, Tiago Forte is now one of the top online educators, but he didn’t make more than $81,009/year until his 5th year in business.

I have seen portfolio careerists hit a wall about 9 months into going full-time.

For some, their engines are purring. They have 2-3 income sources generating 6-figures of cashflow. Sustainability is within sight.

But for many people I know, they find themselves racked with anxiety, staring at a dwindling bank account balance. Signaling only 2 months of runway left.

Do you trudge onwards or start job hunting?

Ideally, you can avoid needing to make this decision.

My recommendation:

1. Build a margin of safety first. I wrote about my decision to quit my job. I had 12+ mo runway, side income, supportive partner, and geoarbitrage giving me a strong buffer before I left.

2. Achieve 3+ months of consistent income from your side hustle. Don’t quit after only 1 month of income. This could just be a one-time spike. I had 3+ years of career coaching income before I left. I knew I could consistently generate more if needed.

Mistake #2: Working 2+ jobs at once

“Should I just grind as hard as possible on my side hustle?”

I have seen other people lean to the other extreme and punish themselves with 80 hours/week of work on their main hustle + side hustle.

For most people, this is a recipe for burn out.

Yes, this arrangement may be born out of economic necessity. But if you have the luxury of time to read this newsletter, this is unlikely your case.

Instead, I would question what’s compelling you to do this?

Is it a genuine pursuit of curiosity and excitement?

Or is it your inner saboteur telling you to work harder to prove that you’re enough to yourself or others?

Whichever it is, the crux is you’re unlikely getting leverage out of your time.

My recommendation:

1. Limit yourself to a 10 hours/week side hustle. The marginal hour spent is not worth the marginal mental health impact. Unless if you truly feel joy from the incremental time spent.

2. Learn to leverage the value of your time spent. Most Americans can make $1,000 in 100 hours. But can do you it in 1 hour? Or 10 minutes? Parkinson’s Law. You’ll get more done with a time constraint. Utilize your strengths.

Mistake #3: Believing you do not have anything worth sharing