When Dylan was kind enough to allow me to be a guest on his website, he asked that I write “Something along the lines of going out on your own, hustling, and then where you’re at.” Instead of being clever with this, I’m going to just go straight through his request, exactly as he laid it out.

Going Out On My Own

There is a thin line between remarkable and stupid. I walk this line like a tightrope. I broke every rule when I quit my job. Anything that would make common sense to a regular person, I said to hell with.

I stood up from my desk, which overlooked Charlotte from like the 20th floor of a tall building uptown, and I went to lunch with no intention of coming back. I text my team leader that he was great but I wasn’t returning to work.

So what are the rules I broke? They’re so common. I’ll pull them straight from the webmaster’s mouth, Dylan Madden himself. You can find this quote on his recent post, Young Man Part 3.

Dylan says: “Don’t EVER just quit your job without any idea of what to do. Only take calculated risks. This is how you will get to where you want in your life.”

Well, I quit my job without any idea of what I was going to do. I actually only had that job a couple months. I found that even a new job with a great team and better pay could not shake the restlessness I struggled with. So I left.

As far as calculated risks go…I had about a grand in the bank but I figured if I sold everything I owned and cashed in my retirement I could survive about a year if I lived like a monk and FIGURED OUT how to create side hustles. That’s right, I quit with no “side hustles.”

This is where I will differ from EVERYBODY IN THE WORLD who quit their job for internet riches. Well, pretty much.

I had no side hustles. No income. No successful blog. No fallback. I actually had about $50,000 in debt. I was working on a novel, maybe I could sell it. My first ever.

Soooo, what an idiot, right? Why would Dylan ask me to guest post? I guess for the same reasons everyone else seems to enjoy my story.

Despite all these “fatal mistakes” I made, I’m still here. Still jobless. But still alive. Still writing stuff. Hooray, Kyle.


Like I said, I had no idea how to make money online. I had no online products. I didn’t understand niches or how they worked. How to target them. I didn’t know online marketing, giving value, SEO, etc etc.

I just sold all my stuff. Everything. It all went on Craigslist.

Once everything was gone I paid my half of the rent for the remainder of the lease to my roommate. That money had to leave my hands so I wouldn’t spend it and put my roomie in a tight spot.

Then I made a little “bed” out of the throw pillows left behind on accident by the guy who bought my couch.

My only option was the book I was working on. I poured a couple grand into editing and publishing my novel. I bought into the idea that if I paid fat cash, I would get a fat return. Dramatic laughter.

I had no idea I could basically do it all myself. Maybe pay someone on Upwork to edit it for $100. Someone else to make a cover for $25. I didn’t even know sites like Upwork existed.

I published the novel. But I hadn’t built an audience and my book didn’t solve a problem. I didn’t know those were important. So, you can imagine what my sales line looked like, right? Yeah, it was pretty flat…

So what did I do?

I wrote another novel. Even FEWER sales. I also wrote a free novella to promote my novels. All this time I was reading like crazy. Grabbing everything I could to figure out how to sell a goddamn book online.

It was through all of these attempts, these “failures,” I got one clue. One, single, (metaphorical) clue for how to make money online. That’s all I had. Today I have maybe two or three clues. But I’m just over a year in. I quit my job February 16, 2016 and I started from scratch.

Where I’m At

So now that I have a couple clues I’m turning my attention to niches. My author page realkylemilligan.com is now a dating advice page.

The site I started about quitting my job all99life.com now offers fitness content. I’m going to start dripping more of my personal story into it again. It’s a weird site. And hideous. I love it.

I have learned over the last couple months that these (fitness and dating) are broad assed niches. I am working on new sites and niches that are more targeted.

I am figuring out how to get regular jobs for about $100 a pop on Upwork. I sleep where I can. Luckily, my car is paid off. Sounds awesome, right?

Look, my path is not for everyone. Every blogger I’ve ever read says don’t do exactly all the things I did.

You can appreciate or scoff at my decisions, and I won’t change. The thing is, as much as I love you and want your everlasting happiness, I equally don’t give a shit about you. But that is to your benefit. I won’t bullshit you!

I don’t have a lifestyle product or blog to sell you. I’m not here to tell you I figured it all out in 30 days and YOU CAN TOO! Or that entrepreneurship is all rainbows and sunshine!

Hell, if it was they would call it “jogging,” not “hustling.” Or something like that…

Where am I now? Well, I’m doing NOW what you should do 24 months BEFORE quitting your job. But so what?

Let me stop right here for a second, because I think this is important…

I want to refer back to another quote from Dylan Madden in the Young Man Part 3 Article: “I’ve been so broke that I couldn’t afford a sandwich from Subway. So broke that spending money on a bottle of water meant financial ruin.”

This is the same guy that said never quit your job without knowing what you’re doing and only take calculated risks. A lot of wildly successful people have a similar story. So my question is…what difference does it make? Just start.

I didn’t have to know what I was doing and take calculated risks to be broke! Nobody does!

But it does take a phenomenal level of willpower to voluntarily sacrifice the luxuries of not being broke. To willingly subject yourself to poverty and keep pushing anyway.

That’s where I’m at. Tons of work. Tons of experiments that yield no payout. Tons of “side hustles.”

But guess what? I have a new niche I’m launching soon and I’m super stoked. And here’s why I’m insane: I have no proof that this one will work.

All my experience tells me I will fail. Everything up to this point says this endeavor will result in tons of time in, a couple pennies out.

But every time I try something new I get the sense I am THAT MUCH closer to “figuring it out.” I think this one could make a couple bucks!

That’s the secret. Insanity.

That’s what drives me. I could make six figures, easy, at a job. My resume is stacked.

But I still get more excited about the 38 cent payout on amazon when someone buys a book through one of my affiliate links. Or when someone drops five bucks on one of my novels.

This might frustrate you. You might have all sorts of guidance on what I “should do,” but I don’t answer to you. I don’t do it for you. I understand what I could have and what I could do and I still choose what I choose.

I guess that’s why some people think I’m stupid. But I’ll never be unremarkable.

Kyle Milligan is a fiction author. His novels focus on the challenges of modern dating in the prominent hookup culture. Kyle’s books and dating advice can be found at realkylemilligan.com or on Twitter @realkmilli. Kyle also blogs on the topics of entrepreneurship and fitness at all99life.com.

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