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Create Contradiction & Reskill Gracefully

Updated: Apr 17, 2021

We create opportunity not by our excellence in one single thing. There is always someone more proficient in a particular skill. Whatever I know now, someone else will know more tomorrow. Business and technology evolve, re-framing the debate on familiar challenges.

Our social media and film tend to magnify, celebrate and drive viral those singular outliers who sacrificed everything, did it the hard way and achieved virtuous redemption happily ever after. We all know the corollary of this is to feel 'I'm not good enough', make resolutions we don't keep, and count the days we missed our commitment each week rather than the days we kept it.

There might be a more efficient, consistent approach to creating our next opportunity. We could reflect on the unique combination of skills and breadth of experiences that make us who we are (Chris Guillebeau, The $100 Startup). For example, I'm not the greatest sales person on earth, or the most proficient technical user of AWS. My German grammar could use some serious work! Yet I am good enough at all three of these things, have sector-specific e-commerce experience and enjoy learning about computers. This made my last role managing e-com startups for AWS Berlin feel like home. When I arrived in that role, I thought to myself: why wasn't I more courageous about this years ago?

When I arrived in that role, I thought to myself: why wasn't I more courageous about this years ago?

When we patiently assess our bouquet of skills, nurture our passions, and embrace our contradictions, our personal development path lights up. Milestones are more realistic and achievable. Doors fly open and it feels we have always been destined for what comes next.

If you are only aware of your one skill, you only have one card to play. If you haven't linked your passions and contradictions into how you present, you might be underselling yourself. This trend puts you further at risk: 43% of employers expect to decrease their workforce due to technology integration, and 41% "plan to expand their use of contractors for task-specialized work". Translation: you not only need to beat the fastest, smartest machine at your task. You also have to be that many salary multiples better than not just everyone in your city or country - but everyone within working hours of your timezone.

Whether that seems credible to you or not, 94% of employers expect employees to gain new skills on the job (up from 65% on the same survey in 2018). On average, employers expect returns on workforce skills investment within one year (!). (World Economic Forum, 2020).

These factors, combined with an accelerate pace of change, pressure existing workforce security, especially in jobs, companies and sectors that might not prove resilient:

For those workers set to remain in their roles, the share of core skills that will change in the next five years is 40%, and 50% of all employees will need reskilling (up 4%).

World Economic Forum, Future of Jobs Report - Digest (October 2020)

I have three suggestions in mind for thriving in this environment, and I welcome your feedback:

1. Create contradiction.

How often have you heard someone say, "I'm not happy with this. It's not what I want any more. I'm going to give myself two years to stick it out, then I'll do something about it."

"I know I want to do something else. I just think I should get promoted first, right?"

We invested ourselves in a path (to promotion, the next bonus), but we know we should start something new. Why fight it? Why not be patient and 'tough it out'?

How did we get here in the first place? Perhaps others reminded us this was the safe choice. We have insight now that we didn't have when we signed up. If we continue to make a series of 'just two more years' decisions, what will things look like in 4 years? In 10?

I'm not necessarily encouraging you to tell off your boss (sounds fun) or make bad long term decisions. I'm encouraging you to stop obsessing over tactical turns, and start steamrolling your own path guided by your unique contradictions and exactly what matters to you. Once you harmonize the contradicting strengths, passions and experiences you bring to the table, you will start falling into success every day.


Why take an individual role, once you have management experience? Why move to the city or country that suits you, when you might have a higher salary staying put? Today's growth industries eventually slow down and calcify as they become mature. The candidates hired for this role 5 years ago might not make it through a phone screen today. When you take a risk or present a contradiction, it challenges everyone else who isn't taking the same risk.

In my experience, our contradictions potentiate one another. They are greater than the sum of their parts. It is never enough to have one good skill. Rather than have opportunities in one field OR another, why not have opportunities in both? Aren't there unique combinations that relatively few people in the world could compete with you for, if you did the work to identify them?

My contradiction involves languages, countries and industries (retail and cloud computing). When was the last time you got a pen and paper and thought differently about harmonizing yours?

I believe I can work for American companies in Germany or UK and provide value by integrating both cultures and sharing perspective. I can work for European companies expanding to the US, because I understand the concerns of EU businesses about the US market, while being an authority on my home country consumer behaviors, regulatory trends, etc. I could also look at Chinese companies in Europe like Alibaba, where I would share a language with the senior management chain and understand the peculiarities of the office culture, while still spending my personal life in Europe. Each of these options also feature unique business travel opportunities to reconnect and keep the cultural connections I care about alive.

2. Re-embrace what you loved as a child. When you do, you are unstoppable.

If you enjoyed the privilege of play in your childhood, what did you like most? What could you easily focus on, for hours, day and night? For me, it was probably my first MS-DOS operating system. My first CD-ROM drive was exciting, but nothing compared to the 14.4kbps modem my dad brought home one day, in dark green anti-static wrapping. BBS boards offered an uncharted land of unusual discoveries. I remember the day we drilled holes in the wall between my play room and my dad's home workspace. We ran yellow, plaster-dusted ethernet cable between our two computers to play the first network multiplayer computer game I ever experienced (Warcraft 2).

I enjoy a lot of privilege, and I have still been nudged, encouraged, and told to 'stay in my lane'. I didn't join AWS until 2019, but I started covering cloud computing as a research analyst in 2009. I had a technical mentor testing me on AWS white papers in 2014. I never followed through and tried to interview because people in my network encouraged me to stay in my industry. I was told that it was so hopelessly complex I could never expect to catch up, and I should do the smart thing and 'play to my strengths'. When I saw AWS people around campus, I was intimidated by their bravado and self-confidence. While I still felt successful doing something else, I regret listening to this advice for so long and believing it myself.

When I finally took baby steps on this, the next thing I knew I was supporting a senior data scientist to build a predictive model for fashion. I started preparing for an AWS certification exam and passed well above the minimum bar, because I enjoyed the work. I attended events and started networking, and the next summer I was flying in to interview.

3. Create a secret initiative.

When you have a secret initiative, known only to you and close friends outside work, you would think this makes it easy to procrastinate on. After all, who will see you pushing it back, saying one thing and doing another? Instead, it has the opposite effect. Satisfaction at work depends less on the work assigned to you, and more on your weekly progress toward your own initiative (holding two networking coffees with a department you like, completing a few modules in a certification course, etc.). Even in a frustrating job, you can transcend a difficult manager or distracting office politics. You can then build out public projects on top that benefit your department (for example, a new digital transformation initiative) and make your manager look good. This snowballs, buying you more space and resource to operate in the open with your new skillset and create the achievements you need to present when you interview for a better role.

These are three ideas I've used to reignite my motivation and achieve my #1, must-have 5 year goal (move to Berlin with a job). Identifying and harnessing your contradiction, rekindling your fundamental passion and creating a secret initiative to explore it will orient you and create upskill/reskill opportunities that feel natural and authentically you. You can create five and ten year goals (if you like) knowing that you can adapt and flex certain variables while being stubborn about what matters most.


Have you found creative ways to harness your contradictions? Or a way to bring your childhood passion back into your working life? How about a secret project that sent you over the moon? I would love to hear from you:

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