When I was younger I pulled some ballsy moves, trying to get rich young. My goal was to be rich enough to do whatever I wanted to do by the time I was 25.

Back then I planned to fight my way to the top of the ladder, and sky dive from the ladder’s lofty heights into retirement, riding a golden parachute.

Instead I was left out to dry by the incompetent CEO who hired me then was fired, and I myself was fired shortly after that by the sociopathic founder of the company. It turns out telling your boss he’s full of shit isn’t a smart career move. Who knew?

In the end though, I achieved my goal: I retired at age 25, never having to work again.

The really surprising thing to me is that it was easy.

After Ideal

This is the 80s movie montage segment of today’s entry:

I left Ideal with a few ideas of how to proceed. I knew from my goal map that I needed more time to myself to build a product that had durable value. I found a long term contract (on Craigslist of all places) that allowed me to work from home for less than I made at Ideal, but still more than I had made at Acme. I had several ideas for software products, and kept my ear to the ground for opportunities.

Meanwhile, my lovely wife began writing a blog about a little known ailment called Reactive Hypoglycemia.

She has the illness, which is why she began the research. It was her project, but being the nice hubby that I am, I tweaked the site so it was presentable and accessible, and I typeset a book based on the blog’s content. She released that book onto Amazon last summer.

Her goal for the first month was to make $10. She made $12.77. Eight cents per hour might not sound like a reasonable wage to you, but it was enough. In the months that followed, she grew the number (with a tiny bit of help from me) from lunch, to dinner, and by October 2009, she made enough to pay the utility bill. Something else happened that October too. I’ll get to that in a moment.


The contract I had was cushy. It was a nice job on paper, but I had been hating it for months. It was deadly boring, and going nowhere. Maybe this will seem familiar:

I was staying because I thought I had to. I had followed my own advice to interview with companies regularly, and I could jump ship into a “better” job, but I’d be back at another office, and my goal map had made it clear how dubious that route really was. So I “had” to stay in order to pay the bills. I thought all I needed to do was wait it out, and when the next big, sexy opportunity presented itself, I would jump ship.

That’s that fear trap I’ve talked about. The mud in which we get stuck. The rubber band tethering us in place. But I got lucky.

Getting Lucky

Great news! You're fired!

One Saturday in early October, my client came to my house with his wife. He told me the company was broke, they were losing their house, and he couldn’t pay me anymore.

Bye bye, excuses. Hello, motivation.

I was significantly happier that day than I had been in recent memory. I felt bad for my client, but it turned out that the stress of figuring out how to make ends meet was better than the stress of a dead end contract sapping my life and creativity away.

At first I was still in my old mindset. Which of my various projects could turn a profit quickly? I was caught in this cycle of being a “software developer”, and thinking primarily in those terms.

Then my wife took me out for a drink and proposed a deal.

A Pretty Decent Proposal

She asked me to work with her full time. She had made $246.82 the previous month, and was on track to shatter her goals for October also (the goal was $160, she ended up making $394.01).

She was nearing the threshold she could manage with her organization (or lack thereof), and her technical skills (or lack thereof). She’s a brilliant researcher and writer, and if I could organize, streamline, and optimize the books and blogs, we’d have no trouble meeting the goals for the next few months.

The short version is: **We did that. It worked. **

The longer version is something I’ll flesh out in future entries. If you’re interested in reading about the details of how my wife and I built a mini media empire you can subscribe via Twitter or e-mail.

In the mean time, let me hit the highlights by explaining what I learned in broad strokes:

Lessons for Achieving Financial Freedom

For all the time and energy I spent trying to get rich as a young person, I find it morbidly amusing that my freedom came from some small niche blogs and self-published books. I imagined innovative products and business models, gulping up huge sales wins, before the windfall of a large exit. I imagined blood, sweat, and tears. The reality turned out to be much different, and in many ways better.

Here are the main things I learned:

It didn’t need to be perfect

I have had Creativitis for as long as I can remember. Creativitis is a disease particular to creative people that prevents them from finishing much of anything because they get stuck tweaking it until it’s “perfect”.

Here’s the ontological argument against Creativitis:

That which exists is better than that which does not exist. Therefore an imperfect product that actually exists must be better than endlessly tweaking hypothetical shit to perfection.

If I could offer only one piece of advice, this would be it: it doesn’t need to be perfect. Save perfection for your aimless hobbies. What you need to succeed is “barely passable“.

Our sites started out with terrible looking, free templates. They were unoptimized. They didn’t encourage people to subscribe. The book covers were terrible.

None of that mattered.

There’s time to go back and fix things. StatisticsHowTo.com used to look downright shameful. Now I think it’s one of the best looking math sites around. That’s not saying much though—it’s certainly not going to win any design awards. I only fixed it after I fixed the content, and only after it began making serious money.

Fear held me back

Despite all my admonishments to be bold and take risks, still I was paralyzed by fear. It wasn’t the kind of heart chilling fear you might think of. It was ambient nervousness about an ambiguous future.

My lucky break was a huge lesson to me. Being laid off simulated the courage I should have had to begin with. If I’m ever in a similar situation, it won’t be luck that gets me through, it’ll be the secure knowledge that fear can only hold me back.

My expectations and assumptions clouded my vision

For years I was on the look out for the “big thing”. For the right company, poised to make a killing. For the right business venture with one in a million potential to blow the doors off existing markets.

Of course I didn’t notice the goldmine I was sitting on top of, because it wasn’t big enough. It wasn’t sexy enough. It was only a tangent, marginally related to my skills. It made about $10 a month, while I was making over a thousand times that and thinking that was peanuts.

That’s the magic of exponential growth. You make $10 the first month, and $40,000 the twelfth month. That’s a hell of a raise, if you stop long enough to grab it.

But it’s not quite that easy, because…

Support is essential to ride out the lull

There’s a long time in there—about 10 months—when you don’t make anything. Each month you make as much or more than what you’d made in all your previous months combined, but if that number is still $30, you’re in trouble without a backup.

If you’re going to survive that period, you have to have a nest egg, or a partner who can support you.

It doesn’t have to be hard

Being as hooked into hacker and startup culture as I am, I assumed that success meant pain. Everyone says getting rich is more difficult than you expect when you start. That it changes you. That only the really talented, and truly dedicated “make it”, and only if they get lucky.

That wasn’t my experience. In fact, nothing I did took exceptional skill. I admit I had an advantage over the average person since I have backgrounds in both software development and graphic design, but the work we did isn’t difficult, honestly. The development company I founded when I was 18 was way more work and less money.

I didn’t work insane hours. My wife and I worked pretty much full time (40 hours a week, each) until December when we took a 10 day vacation. Despite our absence, our business grew and exceeded sales goals. In January we took two full weeks off. Sales were even better. In February we worked more or less full time on a couple new projects, but not at any deliberate pace.


Now I am free. Throughout this whole process, moreso than any other time in my working life, I felt a tremendous sense of balance and well being. I tinker around the edges of the business, but I don’t have to. It’s on autopilot, and if I don’t do anything to it at all, it’ll keep earning. It’s as secure as any investment vehicle, and if I want to, I can make it grow at any time.

I did it with a partner, a little luck, a sprinkle of skill, and some patience. I think anyone can do what we did.