🐧 Your side hustle roadmap

INSIDE: Ideal Client Profile, Growth Channels, Pains and Dreams, Your First Experiments
January 21, 2024

Google just laid off another 1,000 employees. Unity cut 1,700 staff.

Will the tech job market recover in 2024? 😨

It's hard to say. But many high-performers I know have full-time jobs while diversifying their income streams.

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

  • 1/ Who Are Your Clients
  • 2/ Where to Find Them
  • 3/ What Pains They Face
  • 4/ How You’ll Solve Them
  • 5/ Your First Experiments


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🗺️ Your side hustle roadmap

You might have a side hustle idea, but feel confused on how to turn this idea into reality.

And you’re not alone.

Recently, I surveyed students in my remote side hustle beta program.

31% said they find “crafting a roadmap” to be the most daunting part of starting a side hustle.

In this guide, we’re going to break down how to build a side hustle roadmap:

1/ Who Are Your Clients 👯

After choosing your niche, it’s critical to define who your customers are.

Think of at least 3 attributes that define them.

Here’s a couple examples:

Example #1: B2B Consulting

If you offer biz dev consulting services to scaling startups, you may pick attributes like:

  • B2B SaaS startup founder
  • Series A or B
  • Trying to expand into a new geographic market (e.g. Southeast Asia)

Example #2: Dexter’s Career Coaching

Let’s take the career coaching side hustle I started in 2019.

I defined my ideal clients as:

  • In their late 20’s / early 30’s
  • Worked as tech professionals
  • Felt stuck in their current job, wanted to change roles or companies

Action Items

  • Write down 3 attributes that describe your ideal client profile
  • Don’t get too hung up on your choices. Later, you can iterate.

2/ Where to Find Them 🔭

Now that you’ve decided on “who” you’re helping, let’s discuss how to reach them.

According to Lenny Rachitvsky, today’s top B2B startups reached their first 10 customers using these channels:

Similarly, when you’re building a side hustle you can leverage a set a similar channels:


  • Your immediate network
  • Linkedin
  • Twitter
  • Tiktok/Youtube
  • Email (Newsletter, etc.)
  • SEO/Organic Search
  • Cold Outreach
  • Communities (Reddit, Slack groups, etc.)

Example: Dexter’s Career Coaching

  • I found my first clients on coaching marketplaces and Facebook groups.
  • Later, I started reaching clients through Linkedin and referrals.
  • I skipped my immediate network because I wanted un-biased feedback on my solution.

Action Items

  • List at least 3-5 places where you can find these potential clients.

3/ What Pains They Face 🤕

Now we’re getting to the good stuff.

Have a casual conversation with a few people who fit the attributes you wrote down for (1).

If you’ve never done customer interviews before, use The Mom Test to help guide you.

Questions you can ask:

  • Have you thought about doing this before?
  • Where are you getting stuck? Why?
  • What else did you try?

Pay attention to the specific words and phrases they use to describe their pains.

Example: Dexter’s Career Coaching

  • One pain that I identified with my clients was they felt stuck in their career transition.
  • Here’s the actual words and phrases they used:
  • “The past 3-4 years, I feel like been wasting it. No idea what I’ve been doing”
  • “Started feeling overwhelmed”
  • “I’m in transition — not lost, but unprepared”
  • “I’m transitioning from my current field. It’s very challenging and scary.”
  • This helped me understand their struggles more deeply. Later, you can use your clients’ language to better position your offer.

Action Items

  • Write down at least 3 pain points your potential clients are facing.
  • Include the actual words and phrases they say to describe this pain.

4/ How You’ll Solve Them 🫶

Finally, now that you’ve uncovered your clients’ pains, craft tailored offers that solve them.

Brainstorm solutions to the problem statements that you heard from your clients.

Example #1: B2B Consulting

If you’re helping a B2B SaaS startup founder with entering the US market, you may offer a service where you handle strategy and execution for their US go-to-market.

Example #2: Job Search Coaching

If you’re coaching product or engineering professionals in their job search, you may offer product case or technical interview prep services.

Action Items

  • Write down at least 3 potential offers that you can create to solve the pain points you identified in (4)

5/ Your First Experiments 🧪

Now to tie everything together, plan out how you’re going to test your hypotheses and validate each of the previous points.

Remember, this is an iterative process.

Your experiments will evolve as you validate more and more of your roadmap.

Hypothesis Template

  • If [I take x action],
  • Then [I can get attention/interest/desire/action from y customer for z offer]

Next Steps Template

  • If this hypothesis is true, then [I will take x action]
  • If not true, then [I will take y action]

Example: B2B Consulting

  • Hypothesis: If I can meet fintech startup founders through my immediate network, then I can convince them to schedule a discovery call with me for my go-to-market services.
  • Next Steps:
  • If this is true, then I will validate whether or not this founder has the pain point I’m solving (step 3) and if they’re willing to pay for my solution (step 4).
  • If not, I’ll go back to iterating my channel or client definition.

Now you’re ready to put your experiment to the test. 💪

Action Item

  • Plan your hypothesis and what actions you’ll take from your experiment
  • Run your experiment in the real world!

🌐 Beyond your borders

🏋️ Two unexpected in-demand side hustles: tour guides and athletic instructors for seniors. Post-covid revenge travel is still a thing. And growing senior populations means more demand for activities to stay fit & social (link)

🇸🇬 80% of Singapore professionals are considering a new job in 2024, according to Linkedin. Main motivations: higher pay, better work-life balance. This is up 15% from 2023. I’d love to see data on side hustles :) (link)

💼 Should your job determine how you invest? I’ve always wondered: if you work for a tech company and get loads of equity, should you shift your asset allocation away from tech? Now I know the research on this topic (link)

💌 Reddit: Is it harder for single expats? Comments were fascinating. Lots of opinions on both sides. Personally, while I can’t A/B test my life choices, I feel very happy to be abroad with my wife (link)

📆 How I can help

That’s all for today!

Whenever you’re ready, here’s how I can help you:

1. Work with my tax team - Get personalized guidance from a US expat tax professional.

2. Sponsor this newsletter - Get in front of over 5,000 professionals and business owners in the US and Singapore.

For daily insights, follow me on X (@dexteryz) or Linkedin.

Join my Free 5-Day Side Hustle Crash Course

In this free course, I'll help you step-by-step to setup your side hustle for success.

Get the lessons that helped me quit my 9-to-5, travel the world for one year, and diversify my income streams.

Dexter Zhuang

Dexter is the founder of Money Abroad, a website focused on financial independence for professionals abroad. He has 10+ years of experience building products and teams at companies like Dropbox, Xendit, and startups. He's lived and worked across the US, Asia Pacific, and Latin America. His work has been featured in global publications like Business Insider, CBS, US News & World Report, and Tech in Asia. He graduated from Dartmouth College.

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