In 2014, I published a post entitled “Line in the Sand“, lamenting the fact that following the prescribed model for the American Dream left me frustrated and restless. I ended the post stating:

We live in an age of opportunity, those willing to fight for dreams can have them. I will not be corporate America’s debtor for long. My family will have their Dad home each day. We will explore, create, take risks and challenge ourselves. We will live.

Looking back on the post, there’s a bit of the entitled Millennial tone executives love to hate, but there’s also a decision to actually do something about the frustration. Complaining is no solution.

I started that job thinking managers would want to hear about complaints so they could fix the problems and oil the machine better. I ended the job bringing solution ideas and solutions instead of complaints. After all, no one was forcing me to work there — I signed the contract (see MJ DeMarco for a kick in the pants on this topic).

Interestingly enough, dumping the complaining victim mindset and adopting the problem-solving entrepreneur’s mind is what allowed me to leave the job on my own accord and successfully transition to self-employment.

Idealist or Realist?

It’s popular sport to point out how clueless Millennials are (I’m half Gen-X and thus, only half clueless). They don’t realize how good they have it, how promotion takes hard work, and how life isn’t all about having a good time.

What’s the model? Work hard in school, go to college, get a job, save, climb the ladder, retire, and then start living.

I can’t speak for others, but I can speak for me. The trouble isn’t with working hard, or not appreciating having food and shelter. The trouble is the model — it devours humans.

What’s the model? Work hard in school, go to college, get a job, save, climb the ladder, retire, and then start living. Presumably, this used to be a fair deal because employees would sacrifice 30 or 40 years of strength and personal time in exchange for pensions and easy latter years.

With pensions a relic for all but the most fortunate souls, the math becomes fuzzy quickly. Is it really worth giving the majority of each week to a company whose true love is shareholders and only retirement obligation is 401k accounts?

There’s no guarantee any of us will even make it to retirement age in the first place. So it’s hard to stay angry at the 22-year-old who is unable to find a job, is saddled with college debt, and faces flipping burgers as the most viable near-term employment. It’s not living.

Freedom is a Fight

Breaking free from the corporate machine has been hard, and I’m not all of the way out — yet. I may never be all the way out of dependency, I may die trying.

Some people may be able and interested in dirt-bagging for the short or even long-term. For many of us, this wouldn’t be feasible, appealing, or responsible. So simply walking away is often unrealistic or just plain foolish. Read Quitter by Jon Acuff for some thoughts along these lines.

Since writing Line in the Sand in 2014, and even before then, I’ve been working to extricate myself from the corporate world, spend more time around my family and get outdoors more.

For me, this has looked like using my day job skills (web design, strategy and marketing) to pursue avenues of income which allow online or remote income generation. Getting unchained from the cube was the big first step for me.

Bailing on the cube may not be a priority for others, but it was mandatory for me because it represented a dead end which wasn’t life giving.

The Side Hustle Is Hard

Seeking alternate avenues of income has been very difficult. I’ve started my own business, built experimental test projects (including Ruin Your Knees), forced myself to network, taken on contracts with other groups, spoken at conferences, and done whatever it takes to stay independent. Much of this had to be kickstarted deep into the night while still working the day job, all of this while raising small children and trying not to be a pathetic husband.

In the short-term, this has hardly looked like the working from a hammock lifestyle we see on social media. It’s been long, frenetic days taking care of clients while attempting to construct systems and processes which can turn the hustle into a real business and lifestyle.

Still, I’ve spent astronomically more time with my wife and children than when I was in the office. My home office has an open door for daily wrestling matches and hugs, we drop the kids off at school in the morning and are waiting for them at the bus stop everyday.

I get to run at lunch with Eric multiple times a week, something I never did at the day job. We trained for and ran around multiple wilderness areas, circumnavigated Mt. Hood and ran across the Grand Canyon twice in one day. So, there’s progress though it isn’t easy. The end result is autonomy, which is worth the sweat and stress. The only failure would be not trying.

Eric running around Mt. Hood — somebody sponsor this guy or at least offer him a remote mechanical engineering job. Download this photo for free like 10,000+ others have on Unsplash.

I ain’t trading my youth for no suit and jacket
I ain’t giving my freedom for your money and status
So don’t say I’m getting older
Cause I’ll say it when I do

Cause everybody I know, everybody I know
Is growing old, is growing old too quickly
And I don’t wanna go
So how am I supposed to slow it down so I can figure out who I am?

And I ain’t trading my dreams for no 401k
And I ain’t giving this fire for a cold, cold heart
So don’t say I’m getting colder
Cause I’ll say it when I do

Cause everybody I know, everybody I know
Is growing old, is growing old too quickly
And I don’t wanna go
So how am I supposed to slow it down so I can figure out who I am?

Some of us surviving
Some of us just roaming
Some of us just hoping the world will move more slowly
And some of us alive
We’re all gonna die one day

— Judah and the Lion