Yesterday, with 361 days remaining before my deadline, I hit a very important milestone on whatever this path turns out to be: the first instance of…


A friend pointed out that if I am to chronicle my experiences in pursuit of a meaningful livelihood, then it will be less interesting if not outright insincere for me to leave out the parts where I’m less sure of what I’m doing or whether I’m going to get to where I want to go. After all, if you were only interested in “Hey look at me! Everything is awesome and I’m having more fun than you!”, then you would never leave Facebook. Since you’re here, I’ll do my best to try to paint a realistic picture of the experience associated with this project that I’ve undertaken.

(Critics are calling ‘White-Collar Nirvana’ a “gritty”, “no-nonsense” look at what it means to pursue a dream and an ideal in the face of so many reasons to do otherwise. Terrence Howard turns in a stellar performance as the moody protagonist, simultaneously capturing the character’s hardened exterior to the world and his simmering struggle within. In so many pivotal scenes throughout the movie, Howard’s actions and body language tell of a dogged determination that is betrayed only by his seemingly wistful eyes – revealing of the fact that the story runs much deeper than the immediately obvious.)

It’s probably worth noting that the decision to jump off the Purgatory mothership when I did was made rather abruptly. To be clear, I’ve aspired for some time to eventually step out into the world on my own. (I know – big shocker. Believe it or not, I came to a point where I didn’t particularly enjoy being employed by a faceless corporation…) But the game plan for the last half-year or so had been to bide my time at the most recent gig and use the excess mental energy to plot my next move. I had some thoughts on the matter but nothing fully formed. What I was certain of, though, was that I wouldn’t make a move until sometime in 2017.

It was only in the week or so leading up to my departure that I began to reconsider that timing. This change was brought on by a series of events that I’ll detail another day; for now, I will summarize them as basically boiling down to two things. One was that I began to consider what would happen if I didn’t stick it out for another six-months-plus, as I had been planning up until that point. (The answer, as it turns out, was far short of the catastrophe that I might have been previously afraid of.) The other was that The Big Idea hit me.

The Big Idea was, to be sure, the culmination of a whole bunch of events and personal evolution dating back arguably to the day I was born but, more saliently, to the last few years. However – I will admit this at the risk of conceding my insanity – this idea, that brought together everything I’d been feeling and thinking about, only hit me approximately 48 hours before I ultimately tendered my resignation.

You might correctly suspect that the idea (to start a non-profit business in a for-profit environment) must have been pretty compelling to me if it led to my deciding within two days to quit my job in order to pursue it. And how. I obsessed over it for those 48 hours, becoming more certain with each passing minute that not only did I want to do it, I had to do it. As someone who prides himself on careful employment of verbalized certainties, I don’t say this lightly: I genuinely believe that I didn’t have a flicker of doubt in those 48 hours.

But it was bound to happen sooner or later.

So there I was yesterday, just shy of the one-week mark since being struck with the idea that led to me quitting my job, and four days after actually doing so, feeling the first hint of doubt.

It’s okay. I knew this was going to happen. I’m no psychologist, but it seems to me that a dramatic change of course with never any doubt is more likely a sign of clinical insanity than it is of appropriately unmitigated inspiration.

(Consider the guy who one day decides that his diet will consist solely of eating the stuffing out of his couch cushions. I’m pretty sure that guy isn’t stopping every so often to conduct a measured analysis of his nutritional choices… You know, I’m not entirely certain that I should be eating these cushions, but I think I’m on the right track so I’m gonna go for it.)

So after I absorbed the initial impact of the onsetting doubt, I took a breath and considered that it’s probably okay for me to feel some apprehension. If I didn’t, I’d be running the risk of waking up one day and realizing that I’ve been eating couch cushions this whole time.

For what it’s worth, the doubt was brought on by the realization that I probably have a realistic shot at only very modest amounts of external funding for my Idea. I had been doing some research regarding the availability of grants for small-business and/or non-profit startups. And whereas I believe strongly enough in my goal that I would defend my ability to put large sums of grant money to good use (were it available), it turns out that the real world will probably only make relatively nickel-&-dime amounts available to me.

Which means that I will be hampered in my ability to immediately recruit a team to join me in this pursuit.

Which means that – unless I want to borrow a bunch of money that I’ll need to repay – I will, as they say, need to ‘bootstrap‘ this thing.

Which means that I’ll need to get out there and pound pavement, being my own sales force at the outset.

Which means that it’ll be really slow going until I can generate enough cash flow to be able to start building a team.

Which means that my vision (of, among other things, making a materially positive impact on the world around me) will be slow to develop. And wouldn’t I be better off just clipping six-figure coupons working for The Man and just giving to charity out of that? And who the hell walks away from that sort of income and security anyway? And on and on…

With the benefit of a little bit of hindsight (and a good night’s sleep), I can confirm that part of what I was feeling was attributable to exhaustion. I can safely say that I’ve never applied myself to a job the way I’ve applied myself to this new venture over the past five days. (To say that I’ve thought about the business for every waking moment would actually be an understatement, because I’ve also had some pretty fitful sleeps on account of unconscious preoccupation with it.) I’m not worried about this exhaustion, by the way. I think the first week was bound to be pretty chock-full of nervous energy, so I’m sure things will level out as I go. Plus, I’m loving essentially every minute of it so far (doubt notwithstanding). I wouldn’t have it any other way.

Beyond the exhaustion, the other thing I’ve considered is – if I am to be responsibly open-minded and alert about this whole thing – that some of this trepidation is warranted. The sort of hubris that would be required to conveniently ignore all of the questions that were nagging at me yesterday is probably the very same hubris that could end up representing the express train to Failuretown. (I’m tempted to write an extended aside about who might live in Failuretown and what life would be like there. Instead, I’ll give you the gift of picturing that however you want to. You can imagine all of your least favorite people living there, maybe even on the same street, leading a life of non-stop falls up the stairs and grocery bags breaking on the way to the car. You’re welcome.)

So, yeah. There are gonna be some things that I have to figure out along the way. And I have to accept the fact that those things may result in this project working out a little differently than I’ve been envisioning.

(This seems like a good time to mention that, as much as I’ve been vocally allowing for the possibility of my failure in this pursuit, I have not once internally conceded the same possibility. The honest truth is: in order to not come across as deluded, I will tell people and write about the fact that failure is not impossible…but – shhhhh – I don’t actually believe that. (And yes, I just employed the seldom-seen triple-negative: I don’t believe that failure is not impossible. Whatever. By this point, you know what you’re getting here.))

I’ve decided that a little doubt ain’t gonna stop me. If I thought I was going to fix the world in five years, I have to be okay with the chance that it might take six instead…

If you need me, I’ll be over here chowing down on this couch.


4 thoughts on “D-Day

  1. Of course you’re right. Instead of chewing on the couch, write. Write the outline and fill in the blanks. Make a presentation, send it to everyone you know, and tell them to pass it on. Then, forget the number of days, weeks. Just go on.

    Liked by 1 person

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