Freelance Friday: The Top 5 Challenges Freelancers Face

(And How to Solve Them)

Hey Freelancer 👋

Freelancing gives you freedom, flexibility, and fulfillment… but let’s be honest—it also comes with some real challenges.

This week, we’re breaking down the top 5 most common struggles freelancers face—and more importantly, how to overcome them.

Whether you’re just getting started or years into your journey, you’ve probably faced one (or all) of these.

Let’s fix them.

1. Finding Consistent Clients

Feast or famine is real—and it’s draining.

How to fix it:

  • Build a weekly outreach habit (DMs, email, or LinkedIn comments)

  • Set up a simple inbound system: landing page, lead magnet, basic funnel

  • Ask for referrals after every successful project

👉 Clients should come from multiple sources, not just hope.

2. Raising Your Rates

Undercharging keeps you stuck. But raising rates feels scary.

How to fix it:

  • Increase rates for new clients first

  • Package your services so the value is obvious

  • Practice saying your price without flinching

👉 If you want to earn more, you have to charge more—and own your worth.

3. Staying Focused and Productive

When you’re your own boss, distractions are everywhere.

How to fix it:

  • Start each day with ONE clear priority

  • Time block your most productive hours

  • Use tools like Notion, Trello, or Google Calendar to keep yourself honest

👉 Focus isn’t natural. It’s built.

4. Setting Boundaries with Clients

You’re not on-call. You’re a professional.

How to fix it:

  • Communicate availability clearly

  • Use contracts (always!) with scope and turnaround timelines

  • Politely push back when scope creep starts creeping in

👉 Boundaries don’t make you difficult. They make you effective.

5. Getting Paid on Time

Chasing invoices? You’re not alone.

How to fix it:

  • Always use written agreements with payment terms

  • Require a deposit before starting work

  • Set up auto-reminders or use platforms like HoneyBook, FreshBooks, or Wave

👉 You’re a business. Get paid like one.

"Obstacles don’t block the path—they are the path." — Zen Proverb

This Week’s Challenge

Pick one challenge you’re facing right now.
Use the action steps above—or tweak them—to move it forward this week.

The path to a thriving freelance business isn’t about avoiding problems.
It’s about solving them smarter, faster, and with more confidence.

📩 Want Freelance Friday in your inbox every week?
Subscribe here → https://freelancefridaynewsletter.com

Talk to you next Friday,
Michael Fleischner

Download The Solopreneur’s Guide: Structuring Your Solo Business

Many solopreneurs unknowingly lose thousands annually due to incorrect business structuring. Our comprehensive guide—LLC vs. S Corp vs. Sole Proprietorship—helps you confidently pick the right setup, optimize your tax savings, and protect your profits. Besolo has helped hundreds of solopreneurs like you to navigate the challenges of running your own business and get your questions answered.

Get FREE Stuff!

📩 Help us reach our goal of 10,000 subscribers! Refer 3 friends → Get our exclusive “Freelancer Pitch Guide”

  • Refer 10 → Free 30-min freelancer coaching session

  • Refer 25 → Featured in Freelance Friday + shoutout on LinkedIn

 

Reply

or to participate.