In 2021 I ditched the 9-to-5 grind, started my own business, and traveled the world.

Two years later, it all worked out wonderfully and I’m happier, healthier and freer than ever before.

I ran a Q&A recently on X and got a few questions that I thought I’d elaborate more on. Wondering what it’s like to take a leap so you can do the same (but with a plan and confidence)?

Here’s the backstory:

How did you find the courage to quit your 9-5 job without a backup plan?

It all started with a simple exercise – writing my own obituary. Morbid, right? 😅 But it made me realize that sticking to my 9-to-5 was a waste of my potential.

Sure, quitting without a backup plan was scary, but I had my family and friends as my safety net. They love me and I knew that if everything didn’t go the way I planned, I always had a place to sleep at night.

I didn’t really have anything to lose.

What were your initial steps in starting your own company?

My entrepreneurial journey began like a scene from a movie.

I wrote my obituary and realized my free life didn’t include working for someone else and lining their pockets.

I wanted to uncap my salary.
I wanted to decouple my living location from my work.
I wanted to control my own destiny.

So I quit my job and just started – with zero plans. (I don’t recommend this.)

Initially, I reached out to personal contacts, then to strangers on the internet. No website, no LLC, no formal business account – I just went for it.

I’m fortunate to have grown that business to multiple six figures now.

How did you manage to hit $10k/month 30 days after starting your business?

This milestone came quickly, and here’s why: I said no to short-term projects and focused on securing monthly retainers instead.

Short-term projects will place you back in the seat of an employee. You charge hourly and you trade time for money. Ew.

Monthly retainers turn your services into a subscription product. Then you can work on optimizing your that product to save you time and money. That’s the freedom I’d imagined when I quit my job in 2021.

What were the biggest challenges you faced in the early days of your business?

Two major challenges were 1) my lack of confidence in selling myself and my services and 2) my lack of social proof.

I’m my biggest critic. It was tough at the onset to sell myself because I didn’t know if I could actually follow through on my promise. Once I had a few clients under my belt (and a LOT of mistakes), I started to gain confidence.

Starting from scratch also meant I had no track record to show my clients. I just had a few testimonials from former bosses. Any social proof you can scrape together in the early days is SO helpful. Here are a few examples:

• Client logos
• Testimonials
• Awards
• Certifications
• Statistics

Can you share strategies that helped you reach six figures in revenue within a year?

First, as a business owner, you must do outreach.

You can’t wait and expect people to come to you. Once you deliver results for a few clients, you may have the luxury of referrals (the best marketing is no marketing at all). But not at first.

Outreach is all about pattern interruption. Your targets likely get hundreds of social and email messages a day. How are you going to stand out and show you can provide major value – no matter your services?

Second, I placed immense value on customer service. Open, consistent and honest communication probably being the most important element of the customer experience.

Third and most importantly, results trump everything else. If you have shitty customer service, if you can’t communicate worth crap… BUT you deliver the value your promised to your clients, that’s gold!

Why did you choose Colombia as your first destination? How did it impact your business?

Colombia was a random choice actually.

Previously, I was living in the Midwest USA. A friend raved about Medellín’s beauty and Midwest values. I can confirm both after living here for two years.

Plus when I left the country, I wanted to learn Spanish. So there’s no better way than diving headfirst into full immersion.

Monk mode in those initial months was a catalyst for huge growth in my business. Because I arrived with no friends or social life in Colombia, I had no choice but to grind.

Now two years later, I own real estate in Colombia and am on my way to permanent residency.

How do you handle business operations while constantly moving between countries?

My business is entirely online, so with just my laptop and internet, I’m all set.

Interestingly, I find planes to be my most productive workspace. Probably because of the lack of internet connection (generally unavailable intra-continental in Latin American flights).

What tools & systems do you use to manage your business remotely?

Notion is the center of my business (and many others’). Almost all of my daily work is inside that platform.

Apart from Notion, I rely on the basics: Google Suite and structured work cycles. Nothing too fancy, but they get the job done.

Because I made the shift from freelancer to business owner with multiple employees, systems were really important. The more we could optimize them to save time, energy and costs, the better.

How do you maintain work-life balance while traveling & running a business?

Admittedly, 2022 was a tough year for me. I got lonely. I underestimated the importance of relationships to my health.

That experience of living in 7 countries in the span of a year and a half taught me a lot about work-life balance.

Since then, I’ve done three things that have made the world of difference for my relationships and health:

• Built a strong online community
• Turned virtual connections into real-life friendships
• Established a home base (gave up constant nomadism)

When I am traveling though, my routine is sacred. That’s the only consistency you can possibly have when uprooting yourself every few weeks or months.

But even so, I make sure to shake things up once a month. There’s a fine line between sticking to a routine and becoming too programmed. You have to leave room for some spontaneity.

What inspired you to start Freedom Files? What’s your mission with it?

Inspired by Nathan Barry and Jay Clouse, I started Freedom Files. Through all their content and experience, they’ve taught me that “teaching what you know” can be a viable (and noble) internet business.

The mission? To help young people like you realize their full potential and live freer through online business and location independence. I’m documenting my journey and others’ so you can live your free life faster.

That’s my journey in a nutshell. It’s been full of uncertainty and difficulty – but absolutely rewarding.

If you’re dreaming of a similar path, I want you to know it’s possible with a bit of determination and support. Let me know if you have any questions. Email or DM me on X. I respond to every message.