EF#5: 💪 Conquering Imposter Syndrome

Hi Friend!

I hope you had an amazing week as we head into summer. ☀️ It’s only May and it’s already 95 degrees here in Florida, so I’m preparing for a scorcher this year. (Can you say “active hurricane season ahead”? 😳)

My family just returned from an amazing Caribbean cruise to Mexico and the Grand Cayman Islands, which is where I took the beautiful photo above. 🛳 I hope you’ll be creating some wonderful memories with loved ones this summer, whether you’re exploring your community or traveling the globe. That’s part of the freelance lifestyle, remember? Your flexible schedule should allow you to take time off—even if it’s just for a long weekend. Plus, self-care is so important in maintaining balance, avoiding burnout, relieving stress, and improving mental health.

But now, back to reality.

I don’t know what you’ve been hearing lately, but it feels like there’s been a lot of negativity swirling around on social media, especially in freelance circles. From the threat of AI and the tough economy to media layoffs and trouble finding work, many freelancers are panicking as they cling to “the-sky-is-falling” mentality.

While I’m not downplaying some very real concerns, I see no benefit in leaning into pessimism when I can choose to stay positive and proactive.

In this issue, I want to address the 🐘 in the room—self-doubt. I’ll cover:

• How imposter syndrome hurts your freelance business.

• Why common coping mechanisms backfire.

• How action fuels confidence, not certainty.

Ready to dig in?

Freelance Focus: Conquering Imposter Syndrome

Did you ever put your eyes on the prize of landing a big-name client—but you felt “not good enough” to even pitch your services? Or did you ever land a dream project but felt secretly terrified you wouldn't be able to deliver? Or were afraid to even post your perspective on social media, thinking, “Why would anyone care what I have to say?”

Many freelancers, whether new or experienced, struggle with feelings of inadequacy and self-doubt despite their accomplishments, skills, and even years of experience. (🙋‍♀️ Been there, done that.)

Meet, imposter syndrome—your freelancing nemesis. Symptoms include:

• Feeling like a fraud.

• Downplaying your achievements and/or attributing them to luck, timing, or external factors.

• Feeling underqualified.

• Fear of being “exposed” as a fraud.

• Constantly comparing yourself to others and feeling “less than.”

• Doubting your abilities.

• Undervaluing your worth.

Unlock Your Potential

Unfortunately, imposter syndrome can hold you back big time. It can make you undervalue your work, which can lead to charging less than you’re worth. It can cause you to miss opportunities, like when you fail to pitch a top-tier publication because you reject yourself before you give anyone else the chance to even evaluate your skills. And it can negatively impact your mental health, leading to chronic stress, anxiety, and burnout.

But self-belief plays a critical role in your success. Why? Because clients trust freelancers who project confidence. When you truly believe in yourself, it impacts every aspect of your professional life—from pitching, negotiating, and networking to handling criticism, overcoming setbacks, and producing high-quality work. Cultivating self-belief can lead to greater confidence, resilience, and overall success in your freelance writing career.

Easier said than done, right? 

Ditch These Common Confidence Killers

Freelancers often employ strategies like comparing themselves to others and focusing solely on positive feedback to combat imposter syndrome. But, these approaches frequently fail.

Let a Positive Mindset Fuel Your Success

In my yoga class today, my teacher challenged us with a new pose to improve our balance. I’ve struggled with balance lately, so my initial reaction was to do the easier modification.

But then my mantra kicked in: I either can do this or fail trying. Why wouldn’t I at least try?

I did try and successfully held the pose…at least for the first 15 seconds. 😉 Then I got a little shaky and lost my balance. But I readjusted, tried again, and succeeded even longer the second time.

My yoga-infused freelance lesson? I succeeded by tapping my inner strength, focusing, trusting myself, and staying calm under pressure—even when facing challenges. And it all started with my mindset shift from doubting I could do it to at least trying. And that made all the difference. It might take me a long time to master that new pose, but I’m headed in the right direction.

Stop Waiting to Feel 100% Certain

A few days ago, I wrote a LinkedIn post about having a positive mindset and believing in yourself. And it all starts with this premise:

If you think you can't do it, you won't. At least not with that self-limiting mindset.

But if you think you might be able to do it, then you'll at least try. And that's half the battle, right?

As you can imagine, it struck a chord with people.

Why? Because believing you “might” be able to do something (even if you’re doubting your ability to pull it off) fuels action to at least try. But believing you can’t do something stops you in your tracks.

If I relied on feeling 100% sure of something before I tried it, I’d have missed out on a ton of opportunities. In fact, over my entire 35⁺ years as a freelancer, I’ve said “yes” to thousands of things that made me uncomfortable, scared me, made me question my capabilities, and triggered fear of failure (or humiliation).

What happened when I tried even though self-doubt crept in?

Sometimes I failed. (But I learned how to improve for next time.)

But most of the time, I succeeded.

Ignoring My Inner Critic

Here are a few real-world examples of times when self-doubt knocked on my door, and I ignored it and succeeded anyway.

• Pitched a top-tier magazine and landed an assignment.

• Asked an editor for more money.

•  Wrote about a topic I had zero knowledge of.

• Asked for a referral from clients.

• Set a higher fee than I thought I'd be able to get for a copywriting project.

• Launched a humor blog. (Yep, really. 😂)

• Signed a year-long contract with a national brand.

• Been invited on a press trip.

• Interviewed VIPs like CEOs, physicians, government officials, scientists, and industry leaders.

• Wrote a deliverable (like a case study or video script) that I had never written before.

• Asked for a testimonial from clients.

• Pivoted my business.

• Tried a new marketing strategy.

• Launched a newsletter.

Taking that first step, even with a “maybe,” is half the battle. What are you ready to “try” with your freelance business—even if you’re not sure you’ll succeed?

⬇️ THIS is what it looks like when you believe in yourself. (Watch until the end for some feel-good happy tears! 🥹)

I’d love to hear your take on this! Send me an email to let me know. I’m at [email protected].

Mindset Matters

From Katie, a subscriber and freelance writer:

“Whenever I go to pitch something lately, I hear your voice answering my question, 'I just start at the top and work my way down from there.' That was the first time I've experienced such a direct answer when I think, 'Where should I pitch this?' So, thanks for being a big motivator for me lately as a writer.”

The backstory: Katie and I had traveled together recently and we got to talking about pitching editors and landing big bylines. I shared my pitching process, where I start with the top-tier media outlet that I think my pitch would be a good fit for. If I get a rejection (or more likely, hear crickets), then I move on to the next big outlet. So, for travel, I target my bucket-list publications first (like Travel + Leisure and Conde Nast Traveler) when the story idea would be a good fit. Then I move down my list of other big-name, reputable publications that pay well, but they’re not at the very top. If I’ve exhausted those outlets, then I send the pitch to smaller or less prestigious publications. Sometimes my pitch finds a home, and sometimes, I never land an assignment. But, when the pitch is a good fit, I always start at the top. Why wouldn’t I?

Tools & Resources

Need a shot of confidence? Watch these videos and listen to these podcasts to learn solid strategies for believing in yourself and overcoming imposter syndrome:

• The Futur by Chris Do: How To Build Self Confidence & Overcome Imposter Syndrome

• Marie Forleo: Feeling Self-Doubt? How to Believe in Yourself Anyway

• Marketing Mentor by Ilise Benun: What You Can Do About "Impostor Syndrome"

• Dare to Lead by Brené Brown: Jodi-Ann Burey and Ruchika Tulshyan on Imposter Syndrome

Build your own freelance toolkit by exploring the Resources page on the Expert•ish Freelancer website. I’ll be regularly adding a variety of resources that I use or have heard good things about, such as tools/services, podcasts, books, websites, etc.

As a newsletter subscriber, you’ll be the first to know about these resources—many of which won’t be publicly available on this Resource page!

 High/Low

High: I had three articles published in the same print issue of one magazine: the May/June 2024 issue of SUCCESS magazine. That’s a career first for me! 😊 Plus, this follows a digital article published on their website during the same month, titled “As I Enter My 60s, Here’s the Advice I Would Give to My Younger Self.”

Low: My income was down the last two months due to too much travel and working on Expert•ish Freelancer. Fortunately, I’d expected this and already planned for it, knowing I’d be back to normal in the coming months. But it illustrates the ups and downs of freelance life—even after all these years.

Up Next

Stay tuned! I’ll be addressing these thorny issues in the next few newsletters:

• Dealing with money issues

• Choosing or changing niches

• Finding clients

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.

 In the meantime….

Be kind. Do good. Give thanks. 😊

With gratitude,
Lisa

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