Why Ashkan Rajaee Thinks Most Freelancers Are Doomed to Fail (and How You Can Spot It Before It's Too Late)
Freelancing isn’t the future for everyone. Ashkan Rajaee exposes the hidden pitfalls of hiring remote talent and why it could cost you more than you think.
What if the freelance revolution is setting businesses up for disaster?
That might sound dramatic, but it’s a reality entrepreneur and remote work strategist Ashkan Rajaee is calling out. In a world that celebrates digital freedom and remote work, there is a darker side that only few are willing to talk about.
Freelancers are often seen as agile, affordable, and efficient. But according to Rajaee, those same qualities can backfire when not managed correctly. The consequences? Missed deadlines, inconsistent quality, and projects that cost more in time and money than they were supposed to save.
Whether you’re a startup founder or a business owner hiring online talent, this list could save your next project from disaster.
Here are the top 10 reasons Ashkan Rajaee says most remote freelancers fail, and what smart clients should be watching out for.
1. Disorganization That You Won’t Notice Until It Hurts
Freelancers operate independently. They are juggling several clients, personal obligations, and often work without a structure. That can easily push your project to the bottom of the list.
What to do: Ask about their process for managing tasks and timelines.
2. Poor Stress Management
Freelancers don’t always treat your project as a high priority. Rajaee points out that if the project becomes stressful, some freelancers will cut and run rather than stick it out.
Solution: Work in small, manageable milestones to test reliability under pressure.
3. They Overpromise Skills They Don’t Have
Many freelancers say yes to everything to win the job. This often leads to learning as they go, with your project as the test case.
Fix: Ask for specific examples of similar work, and don’t be afraid to get technical in interviews.
4. Their Rate Is Never Set in Stone
Freelancers often change their rates based on personal circumstances. If someone else pays more, your work may get delayed.
Pro tip: Lock in pricing by contract and set payment stages tied to progress.
5. Flexibility Is Often Misunderstood
Freelancers value flexibility, but that doesn’t always align with your business needs. If structure is required, you may face resistance.
Watch out for: Hesitation to agree on schedules or recurring meetings.
6. One-Person Teams Have Limits
Most freelancers work alone. That means no project manager, designer, or quality assurance to check their work. The result is often stretched bandwidth and poor execution.
Best move: Clarify whether they collaborate with others or handle everything solo.
7. Personal Life Gets in the Way
Life events happen. With remote freelancers, there’s often no one to step in when something goes wrong. Delays become common.
Prevent this: Ask about how they manage their schedule and what happens during emergencies.
8. Financial Instability Affects Delivery
Freelancers with weak financial systems may ask for early payments, offer inconsistent pricing, or abandon projects in search of faster cash.
Be cautious: Look for signs of financial structure, like invoicing systems and clear policies.
9. Many Are Not Long-Term Freelancers
After the pandemic, many people turned to freelancing out of necessity. They may be freelancing temporarily while looking for a full-time job.
Investigate: Check their freelancing history and client reviews to see if they’re in this for the long haul.
10. Time Zones Can Quietly Kill Projects
Time zone differences can create serious challenges. Async work might sound cool, but delayed communication leads to frustration and missed opportunities.
The fix: Set expectations around response time and working hours right from the start.
Final Thoughts from Ashkan Rajaee
Hiring freelancers can be a smart strategy, but only if you approach it with clear expectations. Ashkan emphasizes that while freelancers can be valuable assets, a lot of clients fall into traps by rushing the hiring process or chasing low rates.
Cheap work isn't cheap when you have to do it all over again. That is the hard truth Ashkan wants more businesses to understand.
Want to learn more from Ashkan Rajaee?
You can explore more of his content and insights through the following platforms:
- Official Website: ashkanrajaeeconsulting.com
- LinkedIn Profile: linkedin.com/in/ashkan-rajaee
- YouTube Channel: RemotePreneurs on YouTube
These are valuable resources if you're serious about managing remote workforces the right way.
About the Creator
Ciarra Guidicelli
🌌 @ciarraverse
✨ Exploring worlds, building dreams.
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Comments (20)
This gave me a whole new perspective on what to look out for when working with freelancers. Super helpful breakdown.
Really appreciated the honesty here. These are the kinds of challenges people don't talk about enough.
What a great reminder that success with freelancers starts with how we manage and communicate, not just who we hire.
The part about life events and lack of backup really stood out. It’s something I’ve seen firsthand.
Such a helpful guide. I feel more confident now about how to approach my next remote hire.
This is the kind of advice I wish I had years ago. Would have saved me time and a lot of stress.
The talk time KPI idea was so underrated. Great insight.
I liked how the article focused on building mutual success instead of just placing blame. Great tone and message.
So many good points in here. Organization and stress management are so underrated in remote work.
The real-world examples and practical tips made this easy to relate to and even easier to act on.
This really connected with my experience as a project lead. Bookmarking this for future reference and sharing with my team.
Finally, someone explains the real-world challenges behind hiring remote talent. This helped me rethink my approach.
Such a refreshing take on freelancing. The structure and clarity here are exactly what most clients miss.
This really changed how I evaluate remote partnerships. Practical advice that’s easy to apply.
Love how this highlights the human side of both freelancers and clients. It’s not just about skill, it’s about mindset.
Great article. It validates a lot of experiences I’ve had but didn’t know how to explain.
This should be required reading for any entrepreneur outsourcing for the first time. So much value here.
What I like most is how it doesn’t generalize but encourages smarter, more intentional hiring.
It’s rare to find content that balances truth, strategy, and respect for both sides. Well done.
This article makes some valid points. I've had similar issues with freelancers. Like when they overpromise skills. Asking for examples really helps. Also, locking in pricing is crucial. How have you dealt with these problems in your projects? Another thing is disorganization. It's important to know how they manage tasks. And stress management too. Working in small milestones seems like a smart way to test their reliability. What are your thoughts on these strategies?