Succeeding against the odds: finding ways to seize opportunities with inspiration from role-playing games, movies, memoirs, and Linkedin

Ole Wilken
16 min readApr 22, 2022

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The only thing I hear is my heart — I’m inspired By the challenge that I find myself standing eye to eye with The Roots, The Fire 🔥(2010)

My ADHD probably had a negative effect on my ability to stay focused in school, which in turn led me to spend 8th through 10th grade in a school for children with learning disabilities or other challenges. Most people with this kind of background turn away from studies that require a lot of reading and writing and find a different path in life. Initially, I did too. I could hardly sit still and do traditional school work, so I turned my attention to skating, graffiti, video games, graphic design, and theatre. But I also found the challenge of higher education compelling and firmly believed that it could improve my ability to pursue my passions in life. I was able to find the resilience I needed to overcome challenges, and the risk of not succeeding due to my disability, perceived, and rather robust limitations.

Indeed, the risk of not succeeding academically was high for me and others with ADHD (studies suggest that only a small percentage of university students with ADHD actually graduate. See also DuPaul et. al. 2021). However, we can succeed against the odds, especially if we share our journeys and allow others to see that it can be done (you can read more about my take on ADHD here: Embracing neurodiveristy: beginning with my ADHD 🧠). As Fiona Hill writes in her book, There is Nothing for You Here, about unequal access to education and today’s “infrastructure of opportunity”; it is not easy to believe that you have an equal and fair chance to achieve success if there’s no one like you at the “top” or in the position you hope to be in one day. It’s not impossible to believe, or hope, as we know from the example of every celebrated and revered trailblazer who was “the first to____________” (fill in the blank). They’ve shown us what’s possible, and they make the journey less fraught for those who can follow in their footsteps and stand on their shoulders.

However, absent those trailblazers and good examples, we are more likely to be ridiculed for sharing or discouraged from acting on the belief that we can do something out of the ordinary. It will be easier for school teachers, friends or family members to label our hopes and dreams unrealistic.

For example, when I asked a student councillor at the University of Copenhagen about the requirements for studying at places like London School of Economics, the councillor said — looking at a 29 year old sociology student without any obvious special credentials: “are you sure you want to do that? That’s quite difficult”. Or three years later (in 2013), when I told my dad, that I had been accepted into a graduate programme at the University of Oxford and intended to accept the offer, he looked at me with a grim expression and said, “why Ole? Why put yourself through that?”. He had seen me struggle in school — like he had struggled, and he was worried about me. But he also understood that I was not looking for the path of least resistance, and this probably made him even more worried. In fact, it worried most of my friends and family who knew about my battle with depression, which at one point had morphed into severe suicidal ideation. In the words of David Goggins (whose autobiography aptly captures many of my own feelings and inner dialogue), I emerged from severe depression in 2005 and found a way to transform self-doubt and perceived limitations into a kind of fuel and drive for personal development or — in the words of Goggins — my “metamorphosis”.

Steeling myself for the journey ahead, I held on to a thin veneer of belief emblazoned on three letters of recommendation from university professors, and key standard words in the informal offer from Oxford, which were seared into my memory: my application was of “a commendable standard”. I read the email over and over again — the dog had caught the car. I was staring at an unbelievable opportunity, and I was not sure that I could seize it. Again, as Fiona Hill writes in her enlightening book about her improbable career trajectory and today’s barriers to opportunity, even when opportunity presents itself, it takes resources to seize it, and I barely had enough. Economically it would require more than I or my family could afford, and I wondered whether I was at all intellectually or mentally fit for graduate studies at Oxford University.

But I was not about to stop my metamorphosis — I was actually beginning to live my dream of following my curiosity and working on issues and opportunities that I was passionate about. Moreover, I felt a sense of moral obligation to take seriously the extraordinary and privileged position I suddenly found myself in. For me, it was an easy decision: if you can, you don’t pass up an opportunity like this. At the time, I was 32, living with my partner, Tina, our two daughters — Mira (4) and Asta (6), and my bonus daughter Karla (11) in Copenhagen. With a combination of loans and student grants, I raised GBP 12,000 for tuition fees and moved to Oxford, alone. We could not afford an apartment in Oxford for all five of us. So, Tina and the kids stayed in Copenhagen, and they had to share our home with a sociology student, since we had to rent out a room in our apartment to make ends meet. This situation was of course challenging for all of us, but it felt doable, and necessary. Luckily, I think Karla, Mira, and Asta enjoyed the company of their new flatmate.

From left: Broad Street Oxford; top, Ursula Hicks House, where I lived (part of Linacre College); bottom, one rare mandatory selfie during a morning run in front my graduate school department (School of Geography and the Environment); Asta and Mira playing on the Linacre College lawn, one day before my graduation in 2014.
From left: walking to Linacre college with Tina, Karla, Asta, and Mira (picture taken by my aunt. My mother and her sister came to my graduation ceremony); With my fantastic classmates after our final exam; Mira, me, Karla, Asta (in the airport, on our way home from Oxford), and my Oxford University degree certificate (for Karla, Asta, and Mira).

I had a great time at Oxford. However, throughout my time there, I did worry about my mental health and learning difficulties, and I actually chose (wrongly in my opinion) what seemed like the path of least resistance (which turned out to be the opposite): I masked, suppressed and tried to ignore my darkest demon — that paralysing self-doubt. I had mastered this strategy since 2005, so it felt reasonable to continue, although I could feel my mask and armour starting to crack. Feeling more vulnerable than ever, I tried to keep it together — why stop now at this critical juncture and risk falling apart? I felt tremendous internal resistance at the mere thought of approaching supportive services and opening up about my challenges with paralysing self-doubt or hyper work attitude which could result in burn-out.

Going it alone, so to speak, acting as if everything was fine, I suffered during exams. Instead of using two full weeks to research and write an exam paper, I could spend up to 10 days procrastinating at the library — reading too much and writing too little — , or at a pub with friends in the evening. Then I would spend 2 days curled up in my bed, depressed, disappointed while my heart was racing. I was a mess. Then, fear of failure and severe and potentially deadly depression lurking on the other side of that failure would flood my system with adrenaline. As Phil Knight, the creator of Nike, wrote in his autobiography — which I would not read until years later — the idea of stopping scared me to death. Chasing a “crazy idea” and running from the spectre of depression — a great dark Nothing — I would complete an exam paper nearly from scratch in less than 48 hours. I did this twice — getting distinction on one of the papers. As fate would have it, this paper spelled out my crazy idea, about digitally enabled material participation or an object-oriented social network, which is also the subject of my PhD project.

I wondered how I had survived this process without a heart attack. I also learned that I was intellectually fit and I could perform well under pressure, which gave me a confidence boost. Notwithstanding, I wish I would have taken better care of myself and used supportive services — they were certainly visible and accessible, but I was afraid to engage them and open up.

I have since discovered various supportive services, medicine and workout routines (especially crossfit and open water swimming) which enable me to function at a higher level than I have in the past.

From left: Summer 2021 in Norway. Me and Tina; Asta, Karla, Mira and me; Me after a mountain lake swim.

In an uncertain world

As I found some level of success, despite the bad odds, I constantly searched for inspiration and self-help lessons in an eclectic collection of books, podcasts, movies and video games. I especially gravitate towards science fiction, role playing games and memoirs by leaders in business and politics. Mary Shelly’s Frankenstein is one of my favourite books. I identify with the passion of Dr. Frankenstein and the pain of his monster — the ultimate outsider — which is so human that all it craves is love, companionship and acceptance, which the monster fails to receive and Frankenstein fails to provide. From a formative sci-fi classic to a formative memoir, former US. Secretary of the Treasury, Robert E. Rubin’s memoir, In an Uncertain World, is an early example of a book that shaped my thinking. Rubin recounts a key moment in his young adult life when he became certain that “the only certainty is that there is no certainty”. If you accept the premise, then one’s approach in life easily tends towards weighing probabilities and tradeoffs and taking steps to optimise the likelihood of producing the outcomes you want. I’ve found Rubin’s approach to dealing with uncertainty very inspiring and his book paved the way for my general interest in decision making theory, which include other great books like the classic Thinking Fast and Slow by Daniel Kahneman, and Superforecasting: The Art and Science of Prediction by Philip Tetlock and Dan Gardner.

Four books that shaped and inspired how I approach life and work: Frankenstein by Mary Shelley In an Uncertain World by Robert E. Rubin, The Start-up of You by Reid Hoffman and Ben Casnocha, and The Hard Thing About Hard Things by Ben Horowitz.

Similarly I read Reid Hoffman and Ben Casnocha’s book, the Startup of You to glean insights on how to plan one’s life and career so as to avoid bouncing around too much or missing opportunities by being too focused on a single objective. In reading it, I realised how Rubin had already inspired me to apply many of the tactics Hoffman recommends to increase the likelihood of succeeding academically and professionally. Hoffman, however, had helped me in a different way before I read his book.

LinkedIn itself, which Hoffman had founded, was key for me as I was looking for guidance on how to succeed in higher education and after. Initially, my parents — who had never pursued a university education — did not encourage me to go to university and it had felt like an unattainable place. Once I got there, I was struck by a combination of intense imposter syndrome and a great sense of opportunity.

Had I, a pupil once deemed unfit for most schooling, slipped through some crack in the system? In the back of my mind, I was constantly prepared to be expunged, like an artificial transplant rejected by the host’s (social) tissue. I felt like a transplant, or alien on the verge of alienation. In addition, I would shift between feeling utterly defeated and gloriously inspired by my studies. But all the while I wanted to understand where and what this new unfamiliar path could lead to.

I signed up to LinkedIn in March 2010, one year after I had begun studies at the University of Copenhagen, and the platform immediately appealed to my inner video and role-playing game enthusiast. I saw my new public professional profile as a main character I had to develop and I browsed through more advanced profiles to map the kind of “quests” I had to complete to advance from level to level. From my perspective, Linkedin’s network and reservoir of public professional profiles provided key insights about the road I could travel in this “infrastructure of opportunity”. Linkedin literally expanded my horizon and the future I could imagine for myself. I still wonder whether Hoffman also thought of Linkedin this way — as a real life analogue to Dungeons and Dragons character sheets.

Still, I found it difficult to deal with the uncertainty. Would my actions actually lead to the outcome I was aiming for, and what was I aiming for?

In hindsight, I can see that in moments of doubt, I tend to lean towards the mindset of Yoda’s famous imperative: “Do. Or do not. There is no try”. Although, to add some nuance, I think the ‘trying’, is in the ‘doing’, and we’re probably more likely to try something, if we set out to just do it — like Phil Knight did with Nike, in pursuit of some “crazy idea”.

Jedi Master Yoda teaching Luke to wield ‘the force’ in Star Wars: Episode V — The Empire Strikes Back.

Or, in the words of Andreessen Horowitz cofounder and general partner, Ben Horowitz: “When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same.” (2014). Truth be told, the words of wisdom that echo most often in my head when I face a challenge are: “No retreat, No surrender” from the movie of the same name (which I must have watched at least a dozen times). But it’s not just the words of the title which bubble to the surface of my consciousness and then petering out in some uninspiring way. No. I hear the voice of a friend yelling at me, telling me to ‘not give up, and not give in’ (as Eminem says in Lose yourself). I imagine the voice of R.J. yelling to Jason, who is getting elbowed in the face by Ivan “the Russian” (Jean-Claude Van Damme):

NO RETREAT! NO SURRENDER!

No Retreat, No Surrender (1985). See Youtube clip of R.J. here (2:59)

In building the “startup of myself”, I got distracted and unfocussed when I started to pay attention to my odds of success — which didn’t look great. “After all”, I would often think to myself that “I’m a stranger in strange land. I went to a school for ‘misfits’ and children with learning disabilities”. So I had more than an inkling that I was doomed to fail, like when I was curled up on my bed in Oxford, wondering wether a heart attack was imminent. These thick rough patches seemed nearly impossible to get out of — yes, sort of like lifting an X-wing Starfighter from a swamp with the power of some esoteric ‘force’ or willpower that I felt unable to wield or conjure, until I suddenly did. That is, when I decided to fight and ignore the bad odds.

For me, the bad odds seemed tied to paralysing self-doubt, which seems rooted both in ADHD and some childhood trauma associated with feelings of being unable and unwelcome, and school teachers telling me that I would not amount to anything. Or when councillors and my parents told me — directly or indirectly, the opposite of what Fiona Hill’s father told her: “there’s nothing for you there, Ole”. On the other hand, when I was in my mid-twenties and decided to pursue a university education, I was propelled by a relentless drive, and I gained momentum when my grandfather and new teachers encouraged me. As I write about in another essay, my maternal grandfather was an especially important mentor and supportive voice. Then, being one of those educationally late bloomers, I could suddenly perform at the top of my class, as I started to chip away at two years of preparatory education to meet the entry requirements for the University of Copenhagen. During this time, I also felt like a transplant. Like the underdog, fighting for a place in the world — a place outside the boxes the world (and I) had readily available for me, and I found an infrastructure of opportunity in government sponsored education, and new friendships.

Ralph McQuarrie illustration of Deak Starkiller/Luke Skywalker versus Darth Vader: To me, Deak’s/Luke’s posture in this image perfectly captures the energy and spirit of a fierce underdog fighting against totalitarianism, dark times, and that dark corner of the mind where joy, hope, and vigour fades away.

Tell me the odds (but I might ignore them)

Continuing on the tangent related to the inspiration I’ve found in the Star Wars universe and how it relates to the inspiration I have found in the writings of Hoffman and Horowitz: Horowitz’s advice reminds me of the mindset of Han Solo (you know, our iconic Star Wars anti-hero). Solo’s approach to decision-making is aptly illustrated in the scene where he steers the Millennium Falcon (his spaceship and another iconic non-human Star Wars character) into an astroid field to evade his enemies. C-3PO (the robot side-kick/companion) tells Solo that the possibility of successfully navigating an asteroid field is approximately 3,720 to 1. Knowing that he needs to take immediate action to avoid certain death, Solo replies: “Never tell me the odds”. He then enters the astroid field and escapes despite the odds. Similarly, Horowitz recounts his trials and tribulations as the CEO of Loudcloud and Opsware and the hard choices that enabled him to steer his company clear of bankruptcy and soldier on, despite the odds.

C-3PO and Han Solo: The origin of Solo as the Idealised entrepreneurial leader and trailblazer who defies and succeeds against the odds. Star Wars: Episode V — The Empire Strikes Back.
Stereotypical “think-inside-the-box” analyst who is nearly incapable of thinking on his feet, i.e. improvising and not following protocol, although 3PO has been know to take initiative and do something unexpected. Star Wars: Episode IV — A New Hope.

Han Solo has become the archetype of the entrepreneurial trail blazer who relies on cunning and a predominance of courage over timidity to defy overwhelming odds of failure. On the other hand, C-3PO is timid and tends to suffer from “paralysis by analysis” by over-analysing every situation — which appears to be the opposite of a good entrepreneur according to contemporary discourse and start-up zeitgeist.

Ultimately, these two characters are diametrical opposites on a personality spectrum that I think most people can identify with. I imagine that even Michael Jordan sometimes had an inner dialogue that went like: “Yes, I can. Oh no, I can’t. Yes, I can.” Obviously, the important thing is to stop the dialogue at “Yes I can” and get on with it, which is easier said than done.

To me, these two stereotypical mindsets exemplify two key features of my own personality: C-3PO’s preference for going through extensive scenario analysis and doing things by the book — following etiquette and protocol — and Solo’s willingness to see odds as a function of contingent past events and find the under-appreciated potential for beating those odds. C-3PO speaks to my belief in the utility of conventional wisdom, but I also have a history of following a more Soloesque mindset and thriving when I am the underdog on a mission that seems destined to fail from the perspective of conventional wisdom.

Being conventionally unconventional

Maybe all the hours I’ve spent watching Star Wars and playing video games instead of reading and doing any conventional work have led me to appreciate how films — and pop culture in general — provide an epic fictional analogue to my own pursuits in life, without this being a necessary prerequisite for this kind of mindset. Nevertheless, this seems like a valid and obvious conclusion, especially do to my seeming inability to harbour an intellectual thought without triggering some part of my brain to go: “oh. that’s like [insert conventional reference] from [insert movie or song title]”. It also works the other way around. For instance, when I hear a song like “Run” by Snow Patrol, or many other love songs, I think of the lyrics as a way of calling out to objects, that — if we indulge in a bit of object-oriented animism with philosophers like Ian Bogost, Graham Harman and Tristan Garcia — might ‘feel’ abandoned and left without the same socio-digital illumination that humans enjoy on social media platforms.

From the left: Ian Bogost, Graham Harman and Tristan Garcia. Wiki-snippet about object-oriented ontology and speculative realism: these strands of philosophy reject “the privileging of human existence over the existence of nonhuman objects”.

Things are lit up with pixels via online marketplaces, inventory and supply chain management systems. But how do they light up digitally in everyday life once we have acquired them and they accompany us to work, to the gym, on a long hike, on a first date, or to a job interview? What if things were ‘lit up’ digitally and recognised — with a greater degree of care — for their central role in our lives and the mess we’re making with them as we turn things into waste and send them off to landfill or waste incineration plants? That’s what I think about when I hear Run by Snow Patrol:

Have heart, my dear
We’re bound to be afraid
Even if it’s just for a few days
Making up for all this mess
Light up, light up
As if you have a choice
Even if you cannot hear my voice
I’ll be right beside you dear
“Run” by Snow Patrol

How would a thing represent itself online? How would it choose to engage with its human companions on social media? How can we translate the speculative will of objects into a new kind of social media presence for things? When we care about the things we buy and live with, will we also want to see ourselves beside them in the virtual mirror of ourselves, and when we see ourselves next to our dear companion objects, will we be moved to care for them even more? Like infant subjectivity understood through the lens of Lacan’s psychoanalytic ‘mirror stage’, we might find a new sense of material self when we look into a digital mirror of ourselves and our nonhuman companions and thereby begin to identify with a new-found material self image. Somehow, for a million reasons, this is what I think when I listen to Run by Snow Patrol and read object-oriented ontology and speculative realism.

So, building on my gaming experience I think it makes sense to view a personal virtual profile as analogous to building a character and inventory in a role-playing game (RPG). And I view Hoffman as a role model and inspiration. Not only for his qualities as a thinker and entrepreneur, but also for his candidness about applying what he learned from playing Dungeons and Dragons and studying philosophy to his business ventures. Developing from this perspective and personal history, it’s not surprising to me that I’m fascinated by the idea of merging features from expansive virtual worlds in RPGs (like character inventory management systems) and insights from social science to build a virtual social network of human-product relations and reshape the way people connect with products they need and appreciate in life (as I write more about here).

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