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Are Six Figure Freelancers *Actually* Successful?

Lessons on losing a client, being OOO in Japan, and falling deep into the comparison game.

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“You don’t deserve to be here.”

It’s dinnertime in Kyoto, Japan, and my subconscious is being vicious. A platter of gyukatsu — beef cutlet coated in golden breadcrumbs — splays before me, waiting for me to place its marbled flesh on the stone grill. 

Before going to dinner, I’d made the error of perusing Twitter for “just one minute.” As per the usual, my timeline was full of people crushing it – life-changing sums of money being made, deals getting closed, clients getting signed. 

I sighed. 

See, this is an interesting time in my business. For the first time in years, I need to reach out to clients, old and new, after a previous client of mine went in-house (such is freelancing life). 

The dilemma is that I’m OOO in Japan, and don’t want to spend my vacation pitching. But going on Twitter unleashes a flood of shoulds:

“I should be earning more. I should be working. I should not be on vacation.”  

I shot my partner a look across the dinner table. “I’m feeling behind. Like I’m not successful,” I confessed. He stared at me. “How do you define success?” he countered. 

If you’ve had this question thrown at you before, you’ve probably been tempted to respond with the default answer: Money

Success is the freelancer earning $10,000 a month. Success is the agency owner running a seven-figure business. Success is the creator making six-figures.

There’s no denying money is integral to success (you can’t thrive when you’re trying to survive).

But labeling money as success — period — is the easy way out. That answer doesn’t require you to do the inner digging to figure out your values, priorities, and what you want from life.

Instead, you can just point to an arbitrary number — say a $100,000 salary — and get to it. 

But what happens when you hit that number?

You aim for $200,000, of course. 

The result is a never-ending hamster wheel, where “success” is some faraway land whose shores you’ll never reach until you’re a trillionaire. Or as writer Jack Raines puts it:

“In the absence of strong convictions about what you want from life, you will always default to wanting more money.” 

I stared back down at the gyukatsu. Here I was, in freaking Japan. For lunch, I’d had volcanically hot soup dumplings washed down with a glacial Asahi, before meandering through Kyoto’s century-old temples and shrines, laughing with one of my favorite people in the world.  

Success is having the freedom to travel. 

Success is spending time with loved ones. 

Success is not dreading going back to work once vacation is over. 

Money is undeniably important. But what’s just as important is finding your priorities, and using them as your anchor to prevent the comparison game from deluding you into believing that your success (and happiness) is some arbitrary number away. 

I put the gyukatsu on the coal get to grilling. 

Meandering the streets of Osaka, Japan

✍️ Quick Copywriting Tip

Begin with a long sentence. The reader will barrel through it and feel rushed and frantic. Then, use a short sentence to stop them cold — and as they take a breather, your point sinks in. 

This is great for copywriting. For example: 

✖️“Are you tired of being bad at Excel? I can understand. Here’s your solution.” 

✔️ “You’re tired of bothering your co-workers every 34-seconds with an Excel-related question, of wasting hours doing manual tasks, of being too embarrassed to show your boss your spreadsheets. Let’s put an end to this. Today.”

 🥒 Content Diet

The Art Thief by Michael Finkel — Absolutely loved this book. It follows the wild (true!) story of the world’s most prolific art thief, Stephane Brietweiser, who amassed a collection worth $1.4 billion. Fun Fact: The author spent 11 years writing and reporting before publishing. 

The Money Making Expert to 10X Your Income on Diary of a CEO – Every now and then, you stumble on a podcast that’s full of gold. This is one of those. After listening to serial entrepreneur Daniel Priestley, you’ll see the world brimming with opportunities. 

Japan Travel Guide by Me — I spent 12 days and several hours compiling all my recommendations for Japan (Tokyo, Kyoto, Osaka, and Kinosaki Onsen) in Google Maps and Notion. If you’re planning a trip to Japan anytime soon, this is guaranteed to help!

Thanks for being here! 

I hope you have a beautiful week, wherever you are. 

Stay Creative, 

Alice 💌

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