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Welcome to the 22nd issue 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!

After a whirlwind end to January—an eight-day Caribbean cruise and a trip to St. Thomas—I’m ready to dig back into my deadlines. (I had to hop on an American Airlines plane the morning after that horrific mid-air collision in D.C. 🥺 Very. Nervous.)

This week, I want to highlight a subscriber success story. And it all started with a simple, writer-to-writer conversation on a press trip.

Ready to dive in?

Today’s newsletter highlights how a mindset shift makes all the difference.

🔍 Key Takeaways: 

✅ Start at the top.

✅ Challenge comfort zones.

✅ Networking builds opportunities.

Today’s issue is brought to you by Authory. Sponsors help keep the newsletter free, so please click on their link to check out their offer! ⬇️ 

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Freelance Focus: Aiming High: How One Conversation Changed a Freelancer's Trajectory

You know those random conversations that end up being total game-changers? I had one of those last year with Katie Riley, a fellow freelance writer from Maryland.

Let me set the stage: We were on a press trip, squished in a van after an art museum visit. Along with a few other writers, we were chatting about the freelance life, when she asked me how I decide where to pitch my stories.

Without thinking twice, I told her, “Oh, I always start at the top and work my way down from there.” Pretty simple stuff, right? But sometimes the simplest advice hits home the hardest.

Getting Cozy (Maybe Too Cozy?)

Let's be real—we've all been there. You build up some good relationships with certain publications, the editors know your work, and it becomes your comfort zone. I do this myself.

It’s not only easier (less of a sales job to pitch an editor you’ve worked with), it also brings a higher chance of success (the editor knows you can deliver). I’m all about taking the easy path sometimes.

But here's the thing: while those relationships are golden (seriously, keep nurturing them!), they can also become a bit like that comfy old sweatshirt you can't bring yourself to retire. Safe? Yes. Growth-promoting? Maybe not so much.

Comfort zones, while safe, can become invisible cages. They can prevent us from reaching the next level in our businesses, keeping us from the bigger opportunities we secretly dream about.

Why Not Shoot for the Stars?

My pitching strategy isn't rocket science. 🚀 I start with those dream publications—you know, the Travel + Leisures and Condé Nast Travelers of the world. If they pass (or ghost me after a follow-up), I move on to my next tier of media outlets—those that might pay less or have smaller audiences or less prestige. Simple as that.

For me, it’s second nature. I’ve literally used this approach for decades.

For Katie, this was like someone flipping on a light switch. 💡This advice, seemingly simple, challenged her usual approach and opened up new possibilities.

“I hear your voice every time I'm about to pitch now,” she told me later. “It's become my go-to answer whenever I'm wondering where to send something.”

Sidebar: I also once pitched a TV script for Cheers back in the 1980s after taking just one screenwriting class. 🎬 (I was enamored with the show.) Of course, with zero experience in script writing, I got nothing more than a kindly form rejection letter in the mail. But still, even 25-year-old me was all about shooting for the stars. 🌟

From “What If?” to “Why Not!”

The impact of this mindset shift became clear when Katie decided to pitch a hotel review to Condé Nast Traveler—one of her bucket list publications. I gave her some tips and, after some pitch refinement (another benefit of networking with fellow freelancers), she landed the assignment: 🎯 reviewing a property in Provence.

The best part? The editor turned out to be fantastic to work with. Funny how those intimidating dream publications often turn out to be run by, you know, actual humans. This shows that those bucket list publications and clients are more accessible than we often believe.

What's Really Holding Us Back?

Look, I get it. Imposter syndrome whispers “you're not ready” and we fall for it because we all have those little voices in our heads:

• “But I need more experience first.”

• “My bylines aren’t good enough.”

• “The rejection would crush me.”

• “Who am I to pitch them?”

Sound familiar? Yeah, we've all been there.

Breaking Free

Here's the thing about freelancing: your writing chops matter, but your mindset? That's the secret sauce. ✨Being a successful freelancer demands courage to push beyond self-imposed limitations.

The tips below apply to all freelancers, whether you’re pitching media outlets, brands, associations, universities, hospitals, agencies, or any other prospects.

Here's how to start:

✅ Take a hard look at your pitch list. Are you playing it too safe? Make a list of those dream clients that make your heart race a little. They're your new first stops.

✅ Flip the script on rejection. Every “no” from a top outlet is like a free masterclass in what they're looking for. Plus, you're already ahead of everyone too scared to even try. Yay, you! 🎉

✅ Find your people. Connect with other freelancers who are killing it where you want to be. Their insights are pure gold, and their wins will remind you what's possible. I’m a big fan of certain Facebook groups for freelancers and writers, but I know there are a ton of other public and private groups on Slack, LinkedIn, reddit, etc.

Remember, every single freelancer you admire started exactly where you are. The only difference? They decided to take that leap.

While you should continually strive to keep improving and get better at your craft, don’t think you can’t aim for the big leagues.

Your work is good enough for the best. Time to stop keeping it a secret and get out of your comfort zone.

Q1: Ask Me Anything

I received a lot of great questions in this quarters Ask Me Anything email I sent last week! Thanks to all of you who (wisely) submitted a question. (Apologies to those I haven’t yet responded to—I’ve been traveling a lot!)

An AMA is always a great chance to pick my brain and get some free coaching/consulting. I’ll continue to answer some questions individually via email, while others will be featured in upcoming newsletters so our entire Expert•ish Freelancer crew can learn together.

⬆️ High: I asked for—and received—and extra $250 rush fee because a client wanted a quick turnaround on a $3000 project. I should have negotiated an even higher rush fee.

⬇️ Low: I turned down an opportunity to be a guest speaker (even though I know it would be a terrific way to promote my newsletter) because I just don’t have the time, energy, or interest.

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

• Follow me on LinkedIn where I share fresh clips and more freelance tips/insights most weekdays.

• Follow me on Bluesky where I have no idea what I’m doing on this new social platform. 🦋

• Ask Me Anything! Your questions and feedback help shape future newsletter content. You can reach me at [email protected]. 

• Turn to Expert•ish Freelancer’s Tools & Resources page highlighting valuable resources to help you successfully run your freelance business. If you’ve got a resource you love, let me know about it.

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. 😊