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Welcome to the 17th edition of Expert•ish Freelancer, a newsletter that helps you launch or elevate your freelance business. Every other Friday, get tips, tools, and insights based on my 35⁺ years as a freelance writer.

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Hi Friend!

Well, last week was a struggle. My husband had cancer surgery ON election day here in the U.S. (Cue Chandler Bing voice.) Could this BE any more stressful? Regardless of whom you voted for, this was a stressful time for Americans.

The great news: I’m extremely happy to report that the surgery was successful and my husband is now cancer-free and recovering at home. He won’t need radiation, chemo, or any other treatments. ❤️‍🩹 We’ll have a lot to be grateful for this Thanksgiving.

I took about three weeks off from freelancing to care for my husband, turning down work and putting family first. Plus, I made time for self-care during this stressful period. (Hello, sweet yoga.🧘‍♀️) This freedom and flexibility is why I freelance.

So, I had to feel all the feels this past week or two, dealing with a rollercoaster of emotions.

And now, the reason you’re really here….

Today’s newsletter dives into dealing with failure.

🔍 Key Takeaways: 

✅ Know your limits.
✅ Communicate early.
✅ Learn from failures.

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Freelance Focus: What I Learned From My Biggest Freelance Failure

While we should all focus on our successes, we shouldn’t overlook our failures either. I am not a proponent of dwelling on failures. But I do value the importance of learning from them.

And I’ve got a big one to share.

Early in my freelance career—back in the 1990s—I’d registered with a local service that matches companies with freelancers (think analog version of Contently).

This service had previously matched me with projects for several smaller companies, as I was still building my portfolio as a 👶 baby 🍼 freelancer. I hadn’t yet snagged any bylines in top-tier magazines or worked with any national brands. I was slowly building momentum in my freelance business—but I wanted to vault forward!

Then, I got a project request from a global player in the telecommunications equipment industry. A big-name national brand wanted li’l ol’ me to write some B2B sales and marketing copy—and pay me $10K to do it! I didn’t know all the details yet, just a general overview. But I was all in on this project.

I was thrilled, thinking, “Woohoo! 🎉 This is my big career break.” I. Have. Arrived. 

Keep in mind, the internet was just becoming widely used by the general public in the mid-1990s. A lot of us (especially us non-techies) were still wrapping our heads around what the 🌎 World Wide Web was, how to use it, and what it could even do.

Anyway, I accepted the project and received a very detailed, lengthy creative brief (like, 15-20 pages). The brief outlined the project scope, marketing goals, deliverables, and campaign timeline, and it explained the various components of the client’s very technical products and services.

Immediately, I felt I was in way over my head. 😨 I didn’t understand what the client’s products and services could do for small businesses (their target audience). I barely understood the technical features, and I couldn’t wrap my head around what the benefits were.

But I’d already accepted the project. And it would be for my first national brand. I didn’t want to disappoint this client. Plus—$10,000. 💵

So, instead of seeking clarification from the client or reaching out to my freelance services contact with my concerns, I just forged ahead. (I was in my 20s and had that “I can do anything!” attitude.)

After spending ⏳hours re-reading the client brief and trying to learn how to search (via AltaVista or Ask Jeeves, as Google didn’t exist yet) for the limited information that was currently available online, I was still confused.

By now, a full week had gone by. My deadline for the first deliverable was still a few weeks away. The pressure and stress increased as I realized I was no closer to clarity than when I started. I finally admitted to myself that I simply could not do this project. I didn’t have the technology background or experience to write this copy.

I should have said no from the outset, but I didn’t. 😞

I swallowed my pride, reached out to my contact at the freelance service, and explained the situation. He was…surprised…to put it mildly.

“Why did you accept the project in the first place?”

“Why didn’t you reach out to the client with your questions and concerns?

“Why did you wait so long to tell me this?”

I didn’t have a good answer for any of this. I was mortified.

I’d made him and his freelance service look bad. I made myself look bad. And I left the client scrambling to find another freelancer who was qualified.

I cried. 😭 I felt like such a failure. I thought my freelance career was over.

While this experience did not derail my freelance career, it did sink my confidence for a long time.

After giving myself time to lick my ❤️‍🩹wounds, gather what was left of my pride, and reflect on this experience, I learned some valuable lessons that I’m sharing here.

1. Know your limits and capabilities. As a freelancer, it's important to be honest with yourself about your capabilities. Rather than accepting a project you're unqualified for—even if it seems like a huge opportunity—it's better to turn it down upfront if it’s not a good fit. This preserves your reputation and avoids disappointing the client.

2. Communicate proactively with clients. When you're unsure about project requirements or feel in over your head, reach out to the client immediately with your questions and concerns. Do not let an entire week or two go by feeling confused. Asking clarifying questions shows the client you're diligent and committed to doing great work.

3. Acknowledge mistakes and take responsibility. Rather than keeping my concerns to myself, I should have been upfront much sooner about my limitations and my inability to complete the project. But, when I finally did, I totally owned up to my mistake. I didn’t make any excuse. This, in turn, builds trust and credibility.

4. Learn from mistakes—but don't let them define you. Failures are inevitable, especially early in a freelance career. Use your mistakes as learning opportunities. How? Reflect on what went wrong, extract the lessons, and apply them going forward. But don't let one mistake derail your entire freelance journey.

5. Build a strong professional network. Having good relationships with other freelancers could have helped me mitigate the damage and find a solution. (At the time, I didn’t know even one other freelancer. 😢) Cultivating these connections can provide valuable advice and support when challenges arise.

6. Manage your mindset and emotions. My feelings of 🫢 embarrassment, disappointment, and worry felt insurmountable. How could I ever come back from this? Embrace failure, knowing that one setback doesn’t ruin your entire career. Pick yourself up and keep moving forward—even in the face of setbacks. This is how you develop resilience and a positive mindset.

7. Extend yourself some grace. Practice self-compassion, especially in the early stages of your business. You’re on a huge learning curve as you navigate project challenges, work processes, and client relationships. Cut yourself some slack and be kind to yourself. Don’t 😵‍💫 spiral into imposter syndrome. Instead, learn from your mistakes and move on.

8. Build self-confidence. It took a while to feel confident again. Believe in yourself and don't be afraid to take on new challenges. But know the difference between stepping outside your comfort zone and leaping outside your comfort zone into another universe you’re not equipped for.

Bottom line: Failures, while painful and embarrassing, can be powerful learning experiences that shape your future success—if you approach them with the right mindset. I’m hoping you can gain some insights from my biggest failure to help you navigate similar challenges.

When You’re Ready Here’s How I Can Help:

• Follow me on LinkedIn. I share more freelance tips/insights most weekdays.

• Share Your Success Story. I would LOVE to hear how you’ve implemented any of the ideas in Expert•ish Freelancer and found success. I might even include your win in a future newsletter. You can reach me at [email protected]. 

• Want to learn more about me? Hop over to my (needs to be refreshed) website: www.LisaBeachWrites.com.

• Turn to Expert•ish Freelancer’s Tools & Resources page highlighting valuable resources to help you successfully run your freelance business. You’ll find recommendations for apps, tools, training, services, websites, blogs, podcasts, books, videos, and more! If you’ve got a resource you love, let me know about it.

• Ask Me Anything! Your questions and feedback help shape future newsletter content. (I’ve already answered a few subscribers’ questions in past issues.) You can reach me at [email protected]. 

Thanks for allowing me into your inbox!

I look forward to sharing my freelance journey with you, and I look forward to hearing about yours. I’m just here as your guide. Take what works for you, and tweak it to your needs. Rinse. Repeat.

I’ll be back in two Fridays with another edition of Expert•ish Freelancer.

In the meantime….

Be kind. Do good. Give thanks. 😊

With gratitude,
Lisa Beach

FYI: In yoga, the instructor often closes the session by saying “namaste” as a way of acknowledging and honoring the light, spirit, or goodness within each person in the class. 🧘‍♀️ It’s often used as a closing to convey unity (we’re all interconnected), gratitude (thank you for this shared experience), respect (I respect you and your journey), and peace (may you find peace within yourself). Essentially, it's a way to acknowledge the shared experience and to leave with a sense of peace and connection. 😊