And managed to buy a house at the same time

Photo: Ales Nesetril/Unsplash

While most people awoke the morning of January 1st, 2020 — blissfully unaware of the dumpster fire ahead — I awoke in a panic.

No, I was not some psychic capable of predicting the horrible events of 2020, I awoke in a panic because of another number.

$14,383.15

After a major repair on our aging car, moving to a new city, going a month without a paycheck, and two years of poor spending habits, our credit card debt had ballooned out of control.

On January 1, 2021, exactly 366 days later (2020 was a leap year) that number was $0.


How to find the time you supposedly don’t have for your side gig

Photo: Andrea Piacquadio/Pexels

I get it.

You hate your job. You wish you could do something more meaningful with your life. You want more freedom, blah, blah, blah.

If it were 2015, I’d probably say something like “Quit your job! Follow your dreams! Who wants to die shackled to their cubicle?”

When I left my full-time job to do God-knows-what, I even low-key bragged about it.

Many of my projects don’t yield positive financial returns. But the growth I experience and the knowledge I collect by challenging myself with new projects is an investment in myself.

Yikes.

Do you know what happens when…


No need to audit your local college’s business class

Photo by Fabian Blank on Unsplash

A wise oracle once said:

I got the dough, got the flow down pizat
Platinum plus like thizat
Dangerous on trizacks leave your a flizat
I don’t know what they want from me
It’s like the more money we come across
The more problems we see

We’ve heard it all before, mo money, mo problems. But that doesn’t apply to us entrepreneurs and freelancers, right? I mean, mo money means we’re doing something good. Besides, who has time to review financial documents? That’s why we have accountants.

Well, I hate to break it to you, having a foundational grasp on…


No off-shore bank account required

Photo by StellrWeb on Unsplash

When I left my comfy full-time job back in 2017, I coincidentally landed my first freelancing client that very same day. I named a price, they said yes, and 24 hours later, a cool stack of cash was digitally piled in my PayPal account.

At first, I was annoyed by the pesky PayPal fees — but the thought of making money on my own, without a big corporate employer, excited me too much to care otherwise. Plus, I was an entrepreneur now, you gotta spend money to make money, right?

I relayed the good news to my three other entrepreneur…


Life has options now

Photo: Ehud Neuhaus/Unsplash

In January, I wrote an in-depth article outlining how my wife and I managed to pay off $14,383.15 of credit card debt in 366 days. While I am extremely proud of that accomplishment, I wasn’t entirely truthful in my telling.

Nothing I originally wrote was false, everything I said was true. I did, however, leave out one crucial detail: we had more debt besides the credit card.

There was the personal loan we took out in 2019 to cover moving expenses that was still a hair over $10,000. There was our new iPhone 11s that we finally upgraded after three…


Why LLCs simply aren’t enough

Photo by Christina @ wocintechchat.com on Unsplash

You have courses to conduct, content to create, and clients to consult, the last thing on your mind as a Digital Entrepreneur is your tax burden.

When I left my full-time job in 2017 to venture out into the world of digital entrepreneurship, I was — how do I say this gently? — naive. I had a vague idea of how to make money but what I was supposed to do after I earned it, I had no idea.

My friend Alex suggested I file for an S-Corp election.

“An escort election?”


Aldous Huxley predicted it all.

Photo by Hybrid on Unsplash

I’ve never read a book before that made me instantly double-check the often ignored first few pages with all the publication and copyright information. As soon as I finished reading Aldous Huxley’s Brave New World, I had to flip to the front of the book.

1932, this book was published in Nineteen Thirty-Two. That can’t be right, I thought to myself. Books that are nearly 100 years old are about whales or parries or the French Revolution. Was Huxley a prophet among mortals?

Brave New World is a work of speculative fiction about a future World State whose main purpose…


My wife adores old musicals.

I’m more or a Hamilton and Les Mis kind of guy.

So when she begged me to watch a sequence in Hello, Dolly! that she claimed made her extremely happy, I was a bit hesitant.

“Come on, it’s the opening song in Wall-E,” she said with a little pouty face.

“Fine, press play.”

I say this with all earnestness, I have not been able to get the song out of my head since.

I’m singing it around the house.

I’m blasting it on the way to the grocery store.

I’m whistling it under my…


It’s time I took my work seriously

Photo: Carlos Arthur M.R/Unsplash

I guess it started when they demoted me to customer service.

It wasn’t exactly the career trajectory I envisioned for myself. Fresh out of college, an industrial engineering degree in tow, I landed a job at a pretty well-known company. Let’s call them The Big Ketchup Company.

A few weeks into the job, a couple of billionaires bought The Big Ketchup Company and completely gutted the business, inside and out.

I was young and cheap, so instead of firing me, they sent me to the customer service department.

Again, I had a degree in industrial engineering. …


What I’ve learned after 4 years of self-employment

Photo: Andrea Piacquadio/Pexels

I quit my job in June of 2017. No, I didn’t have a plan. No, I didn’t have enough savings. No, I wasn’t entirely prepared for reality on the other side.

Because of my — let’s call it hastily and ill-advised departure — I put myself and my family $26,000 in debt, I had a complete breakdown, I tried making it as a YouTuber by daily vlogging for 40 straight weeks, and I still don’t know what I’m doing with my life.

And yet, leaving my job was also the best decision I’ve ever made.

So, what’s the point of…

Declan Wilson

Stay-at-home dad. 9-to-5 escapee. Aldi aficionado. Me in a nutshell→ declanwilson.co/start-here

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