Location Independence: Location Indie's Side Hustle Success Challenge

Happy Travels, my friends!

I’m really excited to dig into today’s topic, which is all about side hustles. First off, what is a side hustle? Well…if you type “side hustle” into Google, you’ll get somewhere around 76,100,000 results in a blistering 0.69 seconds. At least, that is what I got.

Now I’m wondering just how fast 0.69 seconds is. Ok, I just spent about 3 minutes tapping at my phone trying to get my stopwatch to stop at 0.69 seconds and I failed. I got 0.65 about 20 times, 0.68 maybe 8 times, and 0.70 twice. My range started stretching as my eyes blurred and my thumb got tired.

Ok…aside over.

I changed my search query to “what is a side hustle” and found results better suited for where we are going. On Wonolo, Christine Hanks gave the best definition of a side hustle on her post aptly titled “What is a Side Hustle? Definition of Side Hustle, Examples, Benefits of Side Hustles, and More”:

“A side hustle is any type of employment undertaken in addition to one’s full-time job. A side hustle is generally freelance or piecework in nature, providing a supplemental income. Side hustles are often things a person is passionate about, rather than a typical day job worked in order to make ends meet.”

What makes a side hustle different than any other part-time job is how much agency you have in the decision-making. In a part-time job, you are typically still working for someone who makes those decisions for you. On the other hand, side hustles tend to offer you more freedom. You are the primary decision-maker and you determine the time you spend working, where you work, and how much money you spend or earn.

When I left the military in 2019, I had a plan to take over my father’s musical instrument repair business, Camarillo Music Services (formerly, South Texas Music Works), and write fiction novels full time until I could learn how to write a travel blog and start a podcast. The blog and the podcast were like the light at the end of the tunnel. Gatsby’s green light beckoning me to something better. But like Gatsby’s light, those were elusive dreams that existed in some distant, surreal future.

Enter COVID-19.

Like many others around the world, we were hit hard as schools closed and music programs shut their doors. As people began to emerge and kids returned to school, funding was diverted and constraints upon constraints have prevented us from establishing a steady flow of business and revenue. The worst part is that no one really knows when things will get back to normal.

Suddenly, I found myself pit between a rock and a hard place, so it is said. Those elusive pipe dreams were now at my doorstep. In the blink of an eye, I was in the deep end of the pool hoping I could swim.

Now, how do I turn my side hustles into sustainable endeavors?

One step is learning from those who do it. Enter, Location Indie’s Side Hustle Success Challenge.

The Challenge

I stumbled on Jason Moore’s Zero to Travel podcast sometime in October 2020. At that time, I was focusing on putting the final touches on my first fiction novel. I had stopped working on my recently founded travel agency and had made no headway in building a blog or website.

Frankly, I was overwhelmed and found solace in writing, so I hid in my book. Each morning on my run or cycle, I started listening to Jason’s episodes rather than Randy Ellefson’s “The Art of World Building” or Mike Duncan’s “The History of Rome” or the Green Brothers’ “Dear Hank & John."

Side note: All three of those podcasts are absolutely phenomenal! If you haven’t listened to them, I’d strongly advise that you do, along with John Green’s “The Antrhopocene Reviewed” and Travis Sherry’s “Extra Pack of Peanuts Travel Podcast”.

AND…we’re back!

Listening to Jason’s podcast inspired me to face my fears and start putting in the work toward my goals. Amanda and I latched on HARD to the idea of being location independent and having the freedom to travel the world with our kids while sustaining our livelihood. I simply couldn’t get enough. And, what seemed like every night, I was telling Amanda a different story about these amazing people who achieved success in what really amounts to entrepreneurship.

Then, I heard about the Side Hustle Challenge. I hear one of my favorite quotes in Pirates of the Caribbean at this very moment. “Who is she?!” Ha!

Seriously, though, what is the Side Hustle Challenge?

In a nutshell, it is a 7-day virtual event where Travis Sherry, one of the co-founders of Location Indie, gives live lessons on how to build a successful side hustle around skills you already possess in order to help you gain financial, time, and location freedom.

Spoiler alert: I will not be giving out trade secrets. Instead, I’m going to approach things generally day-by-day and focus on how it impacted me. It is a paid service, after all (only $27 for the week). Part of the marketing noted that if you are not willing/able to spend $27 to learn how to build your side hustle, then you are not ready to embark on the journey.

“If you can’t afford to buck up $27 and spend one week to change your life and finally get a side business rolling then this challenge is most definitely NOT for you.”

I wholeheartedly agree! I’m on a very tight budget right now. I picked up extra Uber deliveries to cover the cost but, let me tell you, it was 100% worth the price of admission!

Let’s get going!

Day 1: Why Location Independent

We started bright and early Monday morning at 1 p.m. CST. Wait, what?

Yes, I said 1 p.m. You may be asking yourself “What kind of ‘professional’ service is this?” And that is the very point of the Challenge. Enter scene Travis Sherry, co-founder of Location Indie, in his Sunday best…a blue tee shirt with yellow words that said “Side Hustlin’’”…sporting a solid 5-o’clock shadow, an unkept hairstyle, and a nifty black earpiece. Now, you must be scratching your head thinking, “What have I gotten myself into?”

One of the first things Travis touched on was the fact that he is literally living what he is trying to give us. Why are we starting a 7-day lifestyle coaching event halfway through your typical workday? Well, because he is time independent. He hates mornings and, since he makes his own business decisions, he chooses to work in the afternoon. Therefore, we, as the consumers, shift to his schedule.

As for the shirt, I commented on it and one of the team members (either Stephanie Lay or Kaycee Bowen) responded that I should keep an eye out each day on his shirt choice. Suddenly, it was clear to me that any preconceived notion of business and developmental coaching/mentorship should be thrown out the window.

This is what it means to live the Location Independent (LI) lifestyle!

Oh, and did I mention the entire challenge was run via Zoom and Facebook Live out of Costa Rica? Pretty cool, huh?

Alright, so Day 1 was all about getting us to buy in to the LI philosophy. I must admit, I had a little trouble keeping up with everything as I was on the road after a day of Uber & Doordash food deliveries. The irony was not lost on me. I was learning how to build a LI lifestyle while I was, in fact, doing one of the multiple projects I use to fund my entrepreneurial spirit.

Everything got off without a hitch and the live cast was running simultaneously on Facebook and Zoom for the scheduled hour. The attendance was definitely booming, a fact readily apparent by the constant stream of chats on both platforms. I thought Travis did a good job balancing his teaching with monitoring the chats. He periodically called out people by name and consistently asked questions that drove direct engagement.

The LI team worked well together, as other members like Stephanie, Kaycee, Jason, and Mitko Karshovski continually responded to the chats while Travis presented the lesson. These guys were on it and really kept everyone engaged the entire time.

Overall, Day 1 did well to spur enthusiasm, giving everyone (presumptive, I know) that jolt of motivation and assurance that success outside the conventional 9 to 5 job is attainable and sustainable. We were challenged to throw caution to the wind and articulate what our dreams to the group. I felt like Travis was speaking directly to me when he said we needed to ignore the inclination to plan all the what-ifs and just throw it out there.

I said: “personal: visit every country in the world with my wife. business: build a nonprofit from scratch geared toward connecting impoverished towns from across the world through education.”

Yup…now how on Earth am I going to do that?! That was the point. Throw it out there and see if it sticks, then shape your life so you can get there.

It was fascinating reading everyone else’s responses, as well. I loved that a community quickly grew out of nothing and all of a sudden we were all supporting each other and sending reassuring responses.

The best part, for me, was the hard truths. We were given a shiny success model good enough to make anyone’s mouth water, only to be told that most of us will not be able to achieve all three of those right now, or for quite some time. This wasn’t a get-rich-quick scheme. This was a training for a marathon.

Time to get to work!

Day 2: Types of People Who Try to Go LI

Sadly, Travis wore the same shirt today. But that’s ok, it was the first chance to win a prize!

I’m not going to go in depth about the homework to save you some additional reading time. I will say, however, we were assigned homework each day. We posted photos of our work in our private Facebook group where we received feedback from team members and peers. The networking aspect of the Challenge was worth the initial price, alone! Engagement was encouraged and we were incentivized with the chance to win a prize if we actively participated and posted our homework.

It was pretty cool when a lady I had been speaking to most of Monday evening was announced as one of the winners. Sure, I was a little bummed not to win but that just inspired me to keep engaging.

The raw honesty was a refreshing component. Travis shared his personal experiences which added a level of authenticity to the material. Honestly, I found the subject matter a bit dry and zoned out a couple times. I wouldn’t say that was the fault of the LI team, rather I just didn’t care too much about it because a lot of it did not apply to me due to my unique circumstances.

If you hadn’t bought in by now, being “sent home” to take a hard look at our expenditures certainly did the trick. That was fun!

Day 3: Types of Jobs

This was when I really started feeling the excitement. And, it was not just because I won the prize today! In case you are wondering, it was “Limitless” by Jim Kwik.

Anyways, that exhilarating rush was a result of Day 3’s topic. It was time to start figuring out what job we wanted to do. Judging by the chat, I wasn’t the only one feeling the heat pick up. That was to be expected when Travis started off the day asking us who was in need of tough love.

Well, he gave it on Day 3!

I wish I would have counted how many people responded with utter disappointment and devastation when he laid out the reality of content creation pursuits. Deep down, I felt that metaphorical kick in the gut and sat back thinking, “Well, now what?”

While it was difficult at the time, in hindsight, it was much needed and I am extremely grateful for the bluntness. I’m not saying the LI team are a bunch of dream-squashing monsters. Each harsh truth was followed with a tactic geared toward success.

The “Aha” moment for me came when we talked about perfection. To keep this family friendly, I will refrain from using the expletive which preceded perfection but will note the hilarious face Amanda gave me when I said those two words aloud while we were sitting in my parents’ kitchen. It’s ok, we were alone. :)

The sentiment was exactly what I needed to hear. As one diagnosed with OCD, my paralyzing anxiety seemed to fade into oblivion as I read the two-word phrase pop up in the chat, one person after another. Then, to see others expressing their struggle with forgetting perfection and stating their own tribulations, I felt an overwhelming sense of belonging with all of these strangers.

“Comparison is the thief of joy.” -Theodore Roosevelt

Day 4: Make an Offer

Lights, Camera, Action!

Nothing sums up Day 4 better than those three words. Today was all about action, putting our product or service out into the world. Ready or not, face your fear and go!

By this point, many people began forging bonds through networking and budding partnerships thanks to the open and honest dialogue.

I was personally inspired by Blake & Margaret Boyd’s Incite Coffee Company. Keep an eye out for a coming social media post on January 27th featuring them. I am planning on featuring their company along with select others that truly inspire people to make a difference in the world in a blog post later this year, so subscribe for that. :)

Another fantastic thing occurring by Day 4 was a meteoric rise in my confidence. I’m not the most social person. I often prefer living by Mark Twain’s words, “it is better to remain silent and be thought a fool than to talk and remove all doubt.” So, who was this Challenge Michael? Challenge Michael was outgoing and vocal. Challenge Michael chimed in with recommendations.

Still, the moment of truth was stirring. I had promoted my services before but really remained noncommittal. Noncommittal was no longer an option. I crafted my offer at long last, realizing that I needed to shift my value proposition a bit, and clicked “Post.”

Guess what? The feedback was phenomenal! I even piqued the interest of a handful of fellow Challengers with my new “Route Novel” idea, one of which received a free version in exchange for feedback and review.

Side Note: Travis wore a hilarious shirt that read “I tackled the buffalo.”

Day 5: Finding Your People

I started off Day 5 lending my two cents to someone who was struggling putting together her varied interests into a singular model. Afterwards, I sent a number of messages to my first client about her San Diego “Route Novel.”

At 10:30 a.m., I jumped on a one-on-one Zoom meeting with Lynne Nieman, the owner of Wander Your Way. Talk about good fortune! Lynne has established herself in virtually every professional aspect that I am an aspiring toward. We spent just shy of an hour talking about everything under the sun, and I learned things I could implement immediately to help my business grow.

Challenge Day 7 was about building an audience. Did you know that it takes, on average, 7 views of something for someone to purchase it? Travis related his personal experience with a Facebook ad to drill home how difficult it is to convert sales.

How do we beat the odds?

Well, for one, you need an audience. The LI team seemed to operate in lock-step during the ensuing discussion, Kaycee talking about the “Todd Cloud,” Mitko dropping metrics and equations for success, Stephanie and Jason fielding questions about offers, and Travis, front and center (wearing a shirt picturing a person with the words “*expletive* awesome”), singing about raining referrals. Ok, Travis wasn’t really singing.

After class, Kaycee stayed on for another hour-long session to advise us on the world of Virtual Assistants. This was a totally impromptu addition, not included in the price of the Challenge, which speaks volumes to the kind of people you will be learning from.

Day 6: Sustainable LI

“Time you enjoy wasting is not wasted time.” - Bertrand Russell

Even in the waning days of the Challenge, our first weekend session did not disappoint. Day 6 focused on forward motion. How many times have you made a plan to do something but didn’t follow through? I don’t think I have enough fingers to count mine. Something I learned in the Army was accountability. Accountability is everything. If you are not accountable to your actions, you will not be taken seriously and people will be unlikely to trust you.

That is the same in every aspect of life, professional and personal.

How do you ensure you implement your grand ideas? How do you avoid “entrepreneurs guilt?” The answer is the same. Accountability.

Again, I will avoid sharing the tactics Travis scribbled out on his dry-erase board. You can join the next Challenge to learn more. I would like to say that his willingness to open himself up to the group and share deeply personal anecdotes adds a truly unique dynamic to the class. Day 6, like the previous five, definitely put on display Travis’ mastery as an educator. While his transition to the LI lifestyle is particularly fortuitous for me, I certainly feel remorse for the youth who lost someone with a true gift for teaching.

I stayed on for another extra session with Mitko after Travis’ session wrapped up. His stair-step approach to success in a service-related field was yet another impressive presentation. Mitko went above and beyond, building out a PowerPoint presentation to reference during the call. Immediately after the call, I implemented the “elevator pitch” format he shared, which really helped me narrow my value proposition.

Side Note: Location Indie offers a more intensive class, called the Lifestyle Launch Academy. They just added one-on-one mentor sessions to the package starting January 2021. In these sessions, you get to pick between Kaycee and Mitko. Let me just say, you cannot go wrong with either of them. I’ll add the link to sign up when it is available. Currently, it is only open to those in the Challenge.

Final Thoughts

I decided, given the length of this post already (I promised I get you some shorter posts soon), that I will forgo review of Day 7 and our extra Day 8. Let’s leave something to be imagined. Plus, when you embark on your NExT step and sign up for the Challenge, I want you to enjoy some of the surprises as well. Suspense is moving!

I started out debating whether $27 was worth spending for 7-days of information I was fairly certain I already knew. The first few days I held fast to my skepticism, certain my confirmation bias would be affirmed and I’d be kicking myself for wasting money. Well, I doubt I could have been more wrong.

The Side Hustle Success Challenge served many more purposes than simply building a side hustle. If you recall the definition of “side hustle” from the beginning of this post, my pursuits do not really qualify as “side hustles.” That doesn’t matter when it comes to the applicability of what I learned over the past week.

I am renewed, motivated, and confident. The feeling that is bursting from my chest is truly priceless. I have had so many epiphanies this week and my idea book is full of things I want to try, things I never even considered, much less thought I could ever do. For example, I am now learning how to build an App!

None of that would have been possible without the Side Hustle Success Challenge, in my humble opinion.

The two best components were: Action and Network.

The true value of this service is that it brought like-minded people together and challenged us to be bold. Something much easier done in the company of others like us.

Think Big, Act Small.

- Michael

~ Change the world one nameless stranger at a time.~

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