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Are You Unemployable? 5 Reasons Why This is a Good Thing


I’m sitting in a hipster cafe in drizzly Portland Oregon, and I thought it’d be time to reflect with some radical transparency about how the last year of my life has played out.

If you check my story, rife with ups and downs, wins and losses, relationships forged, backstabbing and sometimes shady behavior from collaborators – perhaps you’ll realize a few things.

1) You’re not alone in riding this roller coaster.

2) You’ve likely made more progress than you give yourself credit for.

I’m here to serve as a human guidepost and warning shot on your journey from societal shackles to an ever-expanding sense of autonomy, freedom, and control over the masterpiece of your life.

You’re creating this masterpiece, as unique as your DNA, on a moment-by-moment basis.

Are successful tangible outcomes nice? You bet! But, daily processes and habits built the Great Wall of China and the Pyramids of Egypt – along with some serious sweat equity from the slaves, if we’re calling a spade a spade.

A great wall is built brick by brick.

I’ve shared bits and pieces of my story before, but to give you an idea of where I’m coming from, and the value you’ll get by reading this site, here’s a quick, self-indulgent summary:

  • Reinvented me with an MBA from a prestigious school.
  • I landed a 6-figure corporate job that was driving me insane.
  • I started plotting my escape, by beginning freelance marketing and writing work in my spare time. I was overextended, but the end of corporate shackles was in sight.
  • Turned in the resignation letter, scared shitless but also exhilarated by what was to come.
  • When my final day of corporate employment arrived, a wave of relief, contentment, and excitement to get working on the next phase of my life washed over me.
  • Lots of people close to me disapproved of the new direction I was taking. I didn’t care. I was finally choosing myself.
  • My boss and the HR department casually told me “the door is always open” should I want to come crawling back. This was subtly implying that things would likely not work out for me. Thanks but no thanks, corporate.
  • I left without much of a fail-safe plan, aside from the savings I had managed to accrue, due to living well below my means and aggressively paying down all forms of debt.

The writing was on the wall for me because:

1) I was miserable and running on fumes.

2) There were rumors of a big national competitor coming to town and buying out the company I worked for. I was the canary in the coal mine.

Sure enough, less than a year later, over 1/3 of the company’s entire workforce was laid off – the rumors came true. Now, I didn’t have a crystal ball giving me a perfect glimpse into the future like Biff Tannen in Back to the Future.

No. Rather, I created this certainty within myself first, as the battle is won inside your own mind before you’ll see it in reality. I decided to trust and invest in myself above all else. Burned the ships.

Some of my most trusted advisors and partners in this journey call this decision to on bet on and invest in your new skillset as Job Security 2.0.

Funnily enough, I feel more certain, secure and in control now than I ever did suckling from the corporate teat. I was trading my dwindling hours on planet Earth in exchange for a bi-weekly cash infusion. No mas.

Invest in yourself, ladies and gentlemen.

In the new economy, this no longer looks like long tenure and promotions, 60 hour work weeks impressing an overbearing boss, gold stars on the resume, title bumps and 3% annual raises.

The idea of linear fashion progression towards the corner office, stock options, an ever-growing 401k and keys to the executive washroom has gone the way of the dodo. Seriously, it’s dead.

No., You now must invest in yourself as it’s the only secure bet left to make, in this ever-changing 21st-century economy. The rules, players, skill-sets, technology, markets, and competition are all shifting and evolving faster than ever.

Corporations are not People


When I heard this sound bite a few years ago, I vomited a little in my mouth.

This is no political rant meant to rally the troops.  But I will invite you to notice that corporations have actually never had your best interest at heart. You’ve been handed an illusion of security – as long as the company can leverage your talent to bring in more dollars than they decide to pay you.

If I met a person that had the morality and personality of a corporation, I’d probably punch them square in the mouth and erase their phone number.


You understand where I’m coming from now, right? This is why I type until my fingers go numb that you must get off your ass right now. Double down on investing in yourself, building relationships with others that have seen the writing on the wall and get to work building your 21st-century skillset.

If you’re still working for a company, I encourage you to create your own golden parachute on company time.

Morals, you cry?

Where are the morals when mass layoffs and a crashing economy occur every 10 – 15 years? Besides, how much time do you actually spend doing actual work at your job? How much of it is bullshit, just running out the clock until you can slink out the door at 4:55 pm?

And, if you need even more tangible reasons that it’s time to cut your losses and proudly wear your unemployable status as a badge of 21st-century bravado, here are just a few:

  1. Your intellectual property belongs to the company, not you.
  2. Anything you develop – projects, ideas, clients, patents, etc. – you have to leave behind.
  3. Your best hours, energy and creativity are being sold (for pennies on the dollar) to your employer, each day you shrink away from the challenge of starting your own venture or project tube8.
  4. Job security – where does this exist? Take your head out of the sand and realize it’s a mirage.

The Blank Canvas Awaits

We all start with the same blank canvas and near-infinite possibilities to reinvent ourselves. The playing field has indeed been leveled in recent history.

No longer is the requisite Ivy League (or even state-school 4-year degree) your ticket to the good life – or even any life at all.

I’m not here to debate the merits of taking on massive amounts of debt to kowtow to the existing, and increasingly irrelevant Higher Education, Inc. most of us in the Western World have come to become uncomfortably intertwined with.

I see more and more good, well-meaning, ambitious, free-thinking, self-motivated people get gobbled up and spit out by this machine of institutionalized learning that feeds on souls and % of paychecks for the next 20 years.

So, what should you do instead?

It’s time to stop taking this shit sandwich you’ve been handed lying down, that’s what. It’s time to chart your own course.

Is it scary, painful and overwhelming?


Does it beat languishing in a scenario where your fate is dictated by upper management and shareholders that could give a damn about what you’re good at?


Does your “five-year plan” mean anything to your employer?

Probably not, unless it involves you gaining experience that will make them 10x what they’re paying you.

What about your desire to make a lasting impact on society and those around you via your legacy?

I think the answer is obvious.