q Keil Hubert: Read Nails - Business Reporter

Keil Hubert: Read Nails

The best-laid plans of new uni grads often implode on first contact with the working world. Business Technology’s resident U.S. blogger Keil Hubert looks back at history, literature and storytelling techniques to explore why young workers mistakenly think that they can accurately plan out their careers.

During a recent family dinner, my father asked my oldest son what classes he’s taking at university in order to get a competitive edge in the job market. My son thoughtfully explained that he’s focusing on cultural anthropology and psychology classes with an organizational behaviour focus so that he can better understand personnel dynamics in pretty much any type of company. He’s guessing that the US job market for new graduates won’t improve significantly by the time he gets his degree (despite some recent positive trends) so he should therefore enter the market with as broad a skillset as possible. My father and I both agreed that his plan is appropriately pragmatic; it’s darned hard to predict what the job market will be like in three years.

During the discussion, my father asked me what I’d done to ‘optimize’ my courses for maximum employability back when I was an undergrad. I laughed and admitted that I’d never put any planning into how my courses might help me in the future because – as far as I’d been concerned at the time – there wasn’t going to be a ‘future’.  It was the late 1980s, and I’d grown up with the absolute certainty that we were all going to die once World War III inevitably broke out. The only ‘options’ we had were to sit around at home waiting for the Soviet nuclear missiles to incinerate us all [1], or to enlist so that we could die fighting when the Warsaw Pact horde came thundering through the Fulda Gap. That was why I’d enlisted in the Army when I turned seventeen.

It’s hard to express to millennials just how unsettling the ’70s and ’80s were. When the Berlin Wall suddenly fell in 1989, I spent days wandering aimlessly around my university campus, utterly confused about what was happening in the world and unable to get a handle on what it meant for the future we were never supposed to have. Then the Soviet Union went and dissolved in December 1991 – the same month that I graduated and got commissioned as an Army officer. I hit 1992 with absolutely no plan at all for my future – I’d never given any thought at all about what to ‘do’ for work. I had a bachelor’s degree that I didn’t know how to leverage, no real personal direction, and no inkling of how to translate my skills into a means of earning a living. It’s funny now; it was terrifying back then.

Pretty much this, all the time, but much less attractive.
Pretty much this, all the time, but much less attractive.

There are two key takeaways from my experience that I try to share as often as I can with teenagers and young adults when we discuss career planning and job hunting techniques: first, whatever plans you make for your future are only useful so long as the future unfolds exactly according to your assumptions. Second, swift improvisation is a more consistently successful tactic than rigid adherence to detailed life plans. Most of life for most people, I argue, is spent making *#&$ up in response to unexpected and nonsensical plot twists. Perfect plans are appropriate for people wealthy enough to warp the world to their will; the rest of us have to improvise.

I’ve done a lot of career training for Boy Scouts and Venture Crew members over the years. I’ve also done a ton of coaching for young professionals, both in the public and private sectors. I do what I can to teach people how to understand the working world in such a way that they gain an advantage over their competitors in a corporate environment. One consistent misconception that I’ve found in over 15 years of lecturing, mentoring and counseling is that a lot of young adults assume that their path through their working like will unfold largely like a classic literary or video game quest:

  • First, you identify the minimum prerequisites required to start your chosen adventure
  • Then, you follow a series of well-defined ‘waypoints’ that are fixed and pre-ordained between your starting location and your end goal
  • You’ll defeat a series of level-appropriate incremental challenges at each waypoint thereby unlocking access to the next segment of your epic journey
  • Finally, after you’d defeated the big End Boss challenge, the universe rewards you with a new accomplishment and you ‘win’ the game that you were playing

During one evaluation board for a prospective Eagle Scout candidate, the young man earnestly explained to us that he was going to attend a prestigious national university after he graduated from high school, then would become a doctor, and thereafter would be a complete success in life. Curious, I asked if he’d submitted his application to the uni of his choice… He admitted that he hadn’t, but couldn’t see why that would be a problem because that was instrumental to his life plan. I asked what his backup plan was in case he didn’t get into that specific school. Glowing with unwarranted confidence, the lad said that he’d have no problems getting into a school… that boasted a six per cent acceptance rate. He also said that he’d have no difficulty getting enough scholarships to afford the fifty thousand quid a year in tuition. Rather than call the young man out on his staggeringly unlikely long-shot, I advised him to focus on his ultimate goal (becoming an MD) and to be prepared to improvise on his way there, because life rarely works out the way you need it to. He didn’t listen; he couldn’t imagine why things weren’t going to work out for him exactly as he’d planned it.

‘I don’t understand how you could be depressed. All you have to do is choose a personal quest, and then everything will automatically work out in your favour.’

To be clear, this kid wasn’t daft. He also wasn’t overtly arrogant; he’d demonstrated that he possessed a sound and admirable moral centre. The board recommended him for advancement to Eagle Scout because of his demonstrated potential to serve the community. I’m confident that he’ll be a Good Man when he grows up, and I unreservedly wish him good fortune. The trouble is, I really doubt that the dominoes are going to fall exactly as he needs them to in order to execute his plan as-written. Things will go wrong, and he’s going to have to adapt. Realizing that is going to be… traumatic.

I suspect that a lot of kids get this misguided view of a mechanistically-unfolding future from pop culture. Video games and adventure movies slavishly cleave to this trope: the protagonist is offered a quest to complete by a secondary character. The hero receives a notional or literal map showing them their path. Their adventure then unfolds along the route to the goal. The hero encounters many strange people and places, overcomes obstacles, prevails over danger, and eventually reaches his or her destination. The hero’s journey prepares him or her to overcome their final challenge, thereby concluding the plot. Picture Gandalf the Gray telling Frodo Baggins to take the One Ring to Mount Doom in Lord of the Rings, or Doc Mitchell telling your character about the man who shot you and left you for dead in the desert wastes outside Goodsprings at the start of Fallout: New Vegas.

We understand these stories and we embrace them because we’ve been telling each other stories like this for at least four millennia. Writers have been employing this literary tactic since the Epic of Gilgamesh. We respond to it because it makes sense to us: Joseph Campbell argued that all of us (as a species) resonate with variations on a common, universal ‘monomyth.’ The story structure is so familiar that it only makes sense that people would superimpose the structure of the common ‘hero’s quest’ concept to their everyday life. Everyone is necessarily the hero of his own life story, after all.

The thing is… the classic linear quest mechanic doesn’t often play out reliably in real life. Getting from point A to point B is usually a lot more like Star Wars; a story that started as one quest [2] and then went in a completely unexpected direction [3] when the quest became impossible to resolve. [4] For people, we aim for point B from A, find that it’s impossible to reach B, and then shift instead to point Q – often because it’s the only point reachable from wherever we are when B loses viability. Most people go through their lives pursuing and discarding goals that seemed reasonable at first, but couldn’t actually be completed due to unfolding circumstances.

Along those lines, I personally never had any sort of a plan for my life when I was a lad; I didn’t map out how to progress from a gormless civilian to a junior squaddie, and then to a senior squaddie, and finally to a dead squaddie; that was more like choosing which side of a runaway train to jump off of before it derailed. It was more of a ‘lesser of two evils’ scenario than any sort of a logical quest.

‘When the interviewer asked me where I saw myself in five years, I probably should’t have said "Same as everyone else — as radioactive ashes in a barren nuclear hell-scape."'
‘When the interviewer asked me where I saw myself in five years, I probably should’t have said, “Same as everyone else — as radioactive ashes in a barren nuclear hellscape.”‘

Still, the lack of a coherent plan didn’t leave me foundering when my whole ‘World War III ends the world’ plot was unexpectedly cancelled. I suspect that this is partially because I’d gone a different route with my leisure reading than many of my peers when I was a lad, and I’d internalized different lessons from the stories. Yes, I’d read the LotR books as a kid but I didn’t much enjoy them. [5] After finishing those, I borrowed a tattered copy of an old Conan story from one of my friends and gleefully took to the overall flavor of Robert Howard’s pulp-era sword-and-sorcery world.

I found Howard’s Conan of Cimmeria to be a much more approachable and reasonable character than any of Tolkein’s hobbits, elves, or rangers: Conan didn’t have any long-term plans. He stumbled through a bunch of different short-term jobs, and wasn’t always successful at them. He was highly proficient in a bunch of related skills but he gained that ability on-the-job rather than through formal study. He frequently found himself in over his head due to circumstances beyond his control, and he frequently had to adapt quickly to confusing circumstances in order to survive. He relied on his wits and sudden bursts of aggression to get out of trouble. Planning was never high on his agenda.

That first story that I read – Red Nails, printed by Weird Tales in 1936 – told the story of a very different Conan than the movie versions have portrayed. I couldn’t relate to the protagonist’s exceptional physical prowess, propensity for violence, or smouldering intensity. I could, however, relate to the character irate frustration at being caught up in other people’s problems – drama that he didn’t understand and didn’t want to be involved in. The protagonist wasn’t even important to the antagonists’ quests; he just happened to be caught in the wrong place at the wrong time. In order to survive, he had to improvise quickly and make the best of an awful, unwanted situation. That resonated. Still does.

When I found myself suddenly bereft of purpose and direction after the Soviets decided to take their metaphorical ball and go home in 1991, I didn’t try and plan out some sort of epic career path. Instead, I took advantage of a random encounter with a temp agency and picked up a minimum wage gig typing form letters in the basement of a downtown bank. I knew how to use a PC, and the agency was willing to pay me to type – done! That led to winning a gig writing emergency checklists for an airline pilot training school in Texas. They needed someone who could make WordPerfect for DOS dance, and I’d used WP at the aforementioned bank – I’m your guy! That gig led to a sysadmin’s billet, and so on, job after job, until I found myself working full time leading people in the tech sector. Nothing had ever been planned; everything came about thanks to swift and aggressive pursuit of unexpected opportunities, Conan-style.

Like this … but without the machismo, brawn, sex appeal, historically-innaccurate helmet, or giant axe.
Like this… but without the machismo, brawn, sex appeal, historically-innaccurate helmet, or giant axe.

To be absolutely clear, I’m not suggesting that I have anything in common with a hulking barbarian from the mists of fictional pre-history. For me, it wasn’t about the character, but rather about the tactics employed by the character in order to resolve the plot: Be the best you can be at whatever you’re doing right now. Keep your eyes open for disruptive changes in the environment. When things start to go bad, take immediate action to get out of the way. If something potentially beneficial appears, take a shot at it. No matter what, recognize that pretty much everything going on around you is mired in confusion; do the best that you can with the resources that you have at hand. Don’t waste time complaining that things ‘aren’t fair’. Think strategically, but act tactically – you can’t secure your long-term objective if you fail to win the immediate fight. And when things go to crap – which they will – abandon your old plan for a new one that has a better chance of success.

I try like hell to teach this concept to the young adults that drift into my orbit. I want them to be successful. That’s why I cringe every time I hear a well-meaning lad or lass tell me that they’ve got their future all figured out. It’ll be this school, then this degree, and then that job, like clockwork. Their quest-structure worldview makes it all seem so logical and inevitable. Just follow the quest arrow from one waypoint in the plot to the next until final victory is assured. I do my best to convey the idea that their plans are a great way to get what they want… but only if they work out exactly as scheduled. If (when!) those plans get crushed under the weight of an indifferent future, they need to adapt. To make it up as they go along. To act in the heat of the moment, like a man fleeing a burning building.

My military science professors used to admonish us cadets: the best plan that takes too long to execute is useless, whereas an adequate plan executed immediately will often save your life. Their Conan-esque approach to battle planning is (I believe) just as applicable to corporate life. Plans are great fun, but they’re really only statements of intent. The further into the future you plan, the less likely it is that things will unfold the way you’d predicted. Life is lived largely in the heat of the moment, changing direction and adjusting fire as-needed in order to survive the moment. Therefore, logically, every skill that that optimizes your ability to assess what’s unfolding in front of you and facilitates your reaction time is a darned good investment.

Based on that premise, my father and I agreed that my kid probably has a much better ‘plan’ for his post-uni future than either of us ever did. It’ll be interesting to see how things play out for him.


[1] The town I grew up in was ringed with 18 Titan II nuclear ICBMs. I remember being told when I was ten that this weaponeering meant that we’d be among the first round of targets for a Soviet nuclear first strike – the Russians would want to cripple our missiles so we couldn’t shoot back.

[2] To get Leia’s droids to the rebels on Alderran.

[3] To stop the Death Star from crushing the last rebel base.

[4] Because the Death Star destroyed Alderran and everyone on it.

[5] Heresy, I know; if Peter Jackson wants to punch me for saying that, I’ll make time in my schedule to accommodate him.

POC is Keil Hubert, keil.hubert@gmail.com
Follow him on twitter at @keilhubert.
You can buy his books on IT leadership and IT interviewing at the Amazon Kindle Store.

Keil-Hubert-featuredKeil Hubert is a retired U.S. Air Force ‘Cyberspace Operations’ officer, with over ten years of military command experience. He currently consults on business, security and technology issues in Texas. He’s built dot-com start-ups for KPMG Consulting, created an in-house consulting practice for Yahoo!, and helped to launch four small businesses (including his own).

Keil’s experience creating and leading IT teams in the defense, healthcare, media, government and non-profit sectors has afforded him an eclectic perspective on the integration of business needs, technical services and creative employee development… This serves him well as Business Technology’s resident U.S. blogger.


Keil Hubert

Keil Hubert

POC is Keil Hubert, keil.hubert@gmail.com Follow him on Twitter at @keilhubert. You can buy his books on IT leadership, IT interviewing, horrible bosses and understanding workplace culture at the Amazon Kindle Store. Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant. Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.

© Business Reporter 2021

Top Articles

Reforming upskilling strategies for the changing work landscape

Leaders across industries must upskill the workforce to deliver new business models in the post-pandemic era

Green or greenwashing?

Procurement must stamp out greenwashing from supply chains, to ensure that organisations’ products and goals are not just a “green…

American View: Why Do Cultural Taboos Frustrate New Technology Implementation?

Businesspeople seldom evaluate new technologies on capabilities alone; why do peoples irrational beliefs impede attempts to discuss worthwhile innovations?

Related Articles

Register for our newsletter

[ajax_load_more loading_style="infinite classic" single_post="true" single_post_order="previous" post_type="post" elementor="true"]