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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
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