How A Week Long Workcation Changed My Life (And Business)

Note from Sean:

 A couple months ago Noah Kagan wrote a guest post here about the concept of a workcation – something very near and dear to my heart 🙂

In the process, he gave away a trip down to Austin where one lucky Location 180 reader would join him and his team at AppSumo on a workcation of their very own.

Stephanie Halligan of the Empowered Dollar was the recipient, and I asked her to do a recap post talking about her experience and the impact it had on her business.

This is the result 🙂

Take it away Steph!

“Prepare yourself ☺”

That was the last email I got from Noah Kagan of AppSumo as I headed off for my workcation in Austin. I had the chance to meet with an incredibly successful online entrepreneur like Noah and spend an entire week away from distractions to focus on growing my own business.

So yeah, I definitely had to prepare.

A month before, I’d won Sean and Noah’s workcation contest to take a trip to Austin and hang out with the AppSumo team for a day. When I found out that Noah had picked me, I literally jumped out of my chair. This opportunity couldn’t have come at a better time in my business.

Since quitting my job in October to start my own freelancing/consulting work and live the “location independent” lifestyle, I’d had never travelled anywhere special and taken my work to a new city (a real workcation). I’d also been so laser-focused on my client work that I’d neglected my own money-making projects for my website, The Empowered Dollar. I had begun drawing comics on my website, and the response had been great, but I wasn’t quite sure how to turn my cartoons into income.

Enter the workcation: a perfect opportunity to spend a week focused on my own work and a chance to chat one-on-one with the chief sumo of online money-making, Noah Kagan.

Lessons from Noah: Test, test, test… and test some more

My week-long workaction in Austin was one of the most rejuvenating experiences I’ve ever had for my business. I kicked off the trip with Noah and his team at AppSumo HQ for a day of work, hanging out, and talking business. After a chatting over lunch about everything from relationships to the challenges of eating low-carb while travelling (I definitely fell off the wagon in Austin), Noah pulled me aside to dive into my business.

After just a half hour with Noah, he had blown up how I thought about my business. Here’s some of the most powerful advice I got from Noah:

 “If you had to make $100 in a week from your business, how would you do it?” That was the most thought-provoking question I’d gotten about my business. I told him I would probably put together the best content from old blog posts, package it into an ebook and sell it. He looked at me like I was crazy. “Does that sound fun?” he asked. No, I admitted. It didn’t sound fun at all. And it certainly didn’t use my natural skillset or passion. Which led him to his second piece of advice…

“Do what you’re good at.” If I was really talented at making ebooks, if I was an amazing online marketer, or I was really passionate about product creation, an ebook might be perfect for me. But I wanted to make comics. My ideal day would be drawing comics for my website and drawing comics for other people – and getting paid for that. So that meant focusing on money-making strategy where people could pay me directly for what I’m good at: cartoons.

The Empowered Dollar

Test and experiment first. Worry about scale later. Noah reminded me that I couldn’t worry about scale (like a product) until I saw patterns in the market. My job was to see where my comics stuck and test, test and test some more until those patterns emerged.

So with the challenge of making $100 before leaving Austin and figuring out a way to selling my comics directly, Noah suggested I send out an email to my newsletter letting my readers know I had three comics prints for sale. Even if no one bought a print, I could reach out to the people who clicked on the PayPal link to ask them why they were interested in the print and what kinds of comics they’d like to see in the future. I got some incredible feedback about my cartoons. And a day after sending out the email, I sold my first print. I was now officially a paid cartoonist 🙂

Making the Most of a Workcation

My time with Noah changed my entire business strategy, and I spent the rest of my time in Austin testing and drawing comics. I realized a lot of what made my workcation such an incredible trip was the work I’d done to prepare for it. I’d put a lot of intention into what I’d wanted out of my trip and creating time to focus just on my own work. Here’s what helped make the rest of my workcation a success:

Clear the calendar: The best thing I did for myself was remove all meetings and outside obligations from the calendar for a week. I wanted to keep my time in Austin focused on me and my business, not anyone else’s. This meant doing a lot of extra client work before my trip, but it was worth it to have a week to just think about my own work.

Know your WiFi situation: I booked a very relaxing, peaceful AirBnB studio for the rest of my time in Austin – the perfect environment to dive into my work. But relaxing and peaceful doesn’t necessarily equate to “high-performing internet.” Luckily for me, it worked out in my favor: the lack of consistent WiFi made sure that I was focused on my writing and comic-creating. But if I had needed consistent WiFi the entire time, I might have been in trouble.

Take a day or two off for just vacation: I made the mistake of trying to pack every single day full of work and vacation. After a few days of working in a row, I recognized I needed a day of just exploring and adventure. I was in an exciting new city, after all!

Come with a plan…and be open to ditching that plan. I’d come into my trip planning to spend a week working on an ebook or an online course about getting out of debt… a plan that obviously blew up after my conversation with Noah. I’m glad I came prepared with an idea and a project to work on, but I’m also glad I was open to changing things up when I realized that I needed to go in a new.

After my time in Austin, I’m planning to take a workcation every three months. Even if I only get to travel a few hours away, there’s something incredible about creating the time and space to work on my own projects and focus on growing my business.

If you’re location independent, think about stepping out of your routine to explore a new place and focus on you and your business.

And it certainly doesn’t hurt to check in with an awesome mentor like Noah before or during a workcation to make sure your business on track.

Stephanie Halligan draws cartoons about money at The Empowered Dollar, a personal finance web comic about crushing debt and creating financial freedom. When she’s not doodling or blogging, she’s helping startups and nonprofits design financial education apps and programs.

Stephanie @ Empowered Dollar June 23, 2014 at 9:07 am

Thanks again for the workcation of a lifetime! If anyone wants to hear more about my experience, feel free to reach out to me directly.

Also, this is a pretty hilarious photo to see first-thing when clicking on your blog, Sean 🙂


noah kagan June 23, 2014 at 9:33 am


This was an AMAZING article to read first thing Monday morning.

So glad you were able to grow a lot through being out in Austin.

It seems that 99% of your growth really came from all the great tacos we ate 🙂

Keep kicking ass!


Stephanie @ Empowered Dollar June 23, 2014 at 11:57 am

It was totally all taco-fueled inspiration 🙂


kathleen June 23, 2014 at 11:56 am

WOW this is cool, Stephanie. I love seeing how you think, and I can’t wait to see where you go. Did you make $100 before leaving Austin?


Stephanie @ Empowered Dollar June 23, 2014 at 8:02 pm

I did! Well, $90 🙂 It’s so simple but so awesomely crazy what happens when you put out a service or product and see what happens.


Anne @ Unique Gifter June 23, 2014 at 2:02 pm

What an awesome experience! I’m glad to see that you liked it so much you’re going to do it every three months! A girl can dream…


The Wallet Doctor June 25, 2014 at 12:36 pm

Way to follow your passion! Glad to hear things went well. I may just have to try this out for myself.


Chas June 26, 2014 at 10:51 pm

Thanks for sharing ‘Workcation’ story, Stephanie. As one of your subscribers, I get a kick out of your comics. Keep them coming!


Stephanie @ Empowered Dollar June 29, 2014 at 5:54 pm

Thanks everyone!


Martin June 30, 2014 at 12:11 am

Testing is key! I got to spend some time in Austin a few years ago, isn’t it awesome?


Stephanie @ Empowered Dollar July 7, 2014 at 5:19 pm

Totally. I love that city.


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