🐧 5 common mistakes when starting a portfolio career

‍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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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.

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💼 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

“I don’t have anything worth offering.”

I’m always surprised when I hear this line.

If you’re a professional with 7+ years of experience in your craft, it’s safe to say you have accumulated valuable skills and network.

No, you may not be an expert in AI, climate tech, or the next hottest technology trend—but you have built unique strengths in your line of work.

Take advantage of this.

With market validation and the right positioning, you can leverage this skillset to get what you want.

My recommendation:

1. Discover your superpowers. You can do this through self-reflection or by asking your colleagues, friends and family, or peers. Take my mini-course to try a strengths exercise.
2. Validate your niche against the market. Peter Park identified his niche of exporting Australian brands to Asia based on his strengths, but it took him 8 months of talking to overseas buyers in Korean & Chinese before making deals with export brands.

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Mistake #4: Spending too much time on your website (and other forms of procrastination)

“I want my website to look good before I talk to potential clients.”

Spending lots of time and money on creating a dazzling website before you even have clients is the 21st century equivalent of burning cash on designing fancy business cards.

Honestly, I get the desire to put your best foot forward.

But the harsh truth is:

Your website is not the reason why you haven’t closed your first clients.

If the client already knows, likes, and trusts you…

… then you don’t need a website to start serving them.

At some point, it’s just procrastination.

My recommendation:

• Sell without a website first. Share your services on socials or in calls and close your first few clients this way. This will save you lots of time. I use this method now and wish I used it when I first started.
• Only build a site AFTER clients request more info. Even then, a 1-pager describing your offer details is typically enough. (I suggest my students to create a free Notion site for this.)

‍

Mistake #5: Starting out with too many offers

“I don’t have enough offers that show what I can do for clients.”

Do you have 12+ offers listed on your website even though you’ve been in business for only 1 month?

Chances are, you’re confusing your clients.

Clear positioning is hard.

If clients cannot understand what you’re offering, they cannot buy from you.

How do you know your offers are what clients want and need?

Without validation, you’re creating more noise than signal.

My recommendation:

• Focus on nailing 1 offer for 1 Ideal Client Profile (ICP). If you can’t do this, don’t let yourself expand to more offers or client segments until you nail it.
• Position your social media and website towards this 1 offer/1 ICP. Align the messaging across all your presences. This will help your offer feel more cohesive and clear to your clients. Goal is creating signal, not noise.

In Summary

Here are 5 common mistakes when starting a portfolio career:

1. Quitting your job too early
2. Working 2+ jobs at once
3. Believing you do not have anything to offer
4. Spending too much time on your website
5. Starting out with too many offers

🌐 Beyond your borders

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💼 The Minimum Investment Amount Where Work Becomes Optional (Financial Samurai)

🗽 You can buy mansions in these Mediterranean countries for the price of a studio in New York (CNBC)

🧠 Social snippets

18 money rules I live my life by.

Sophie Syed went from onboarding hundreds of companies to Hubspot to earning $90k in the first 6 mo. of her side business.

I joined Kevin Prewett on Rising Tide podcast to talk about portfolio careers and startups (Apple, Spotify):

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