Training For the Unknown

★ Or, How to Build and Sustain an Antifragile Career
In: Newsletter

Hi friends,

Welcome to the 21 new readers who subscribed since my last newsletter—thanks for joining!

Today’s newsletter builds on the idea from Intellectual Athleticism from my last newsletter: readying yourself for the complex future that lies ahead in work and life, where flexibility and adaptability are key.

Alright, let’s dive in.

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“I haven’t updated my resume in years.” The number of times I’ve heard friends and colleagues say this is astounding. Not because updating your resume is important, but because it signals a certain level of comfort, or stagnation.

Staying in one place for a long time is certainly not a bad thing. Allowing an employer — or anyone — to dictate your career, growth, and intellectual development — well that, my friend, is a travesty.

As knowledge workers, often with luxurious salaries and compensation packages, we’re prone to believing we’re well-positioned in a growing economy. While this is technically accurate, we are highly susceptible to chaotic events.

Take, for example, if a new manager is brought in to manage your team. If you get along with this manager, they have the power to accelerate your career as they rise through the ranks. Conversely, should you clash with this manager, they have the power to permanently mark your record, possibly holding you back for years to come.

This is not to say that other careers are immune to such situations, but rather to note the false sense of security that exists in most modern careers.

But what can we do? Are we all supposed to just quit our jobs?

Absolutely not. Or at least not right away.

The key here is to take a different approach to your career altogether. To look inside-out, not outside-in. The goal is to become antifragile.

What Does It Mean to Be Antifragile?

Some people benefit from chaotic events. They thrive on them and grow stronger in their pursuits, and are therefore antifragile. Others are utterly incapacitated by these same events, or fragile. It’s critical for us to know and understand how vulnerable we are, especially when it relates to our careers. To better understand this dichotomy, I find it instructive to look toward athletics for inspiration.

Professional athletes spend years developing skills. In many cases, they don’t know exactly what their opponent will throw at them when they’re in the midst of competition. So instead of trying to predict every outcome or potential move, they train for adaptation. They embrace and accept randomness. They make chaos their friend.

Antifragile is a term coined by essayist, and Twitter feud instigator, Nassim Taleb. As Taleb describes it:

"Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better."

The antifragile gets better. I repeat: the antifragile gets better.

So how can we build careers that are antifragile? And what does an antifragile career look like?

Antifragile Career Characteristics. There is no universal definition, but there are characteristics that, when combined, have the potential to deliver antifragility.

  1. Flexibility
  2. Network Strength
  3. Independence
  4. Leverage
  5. Optionality

To become antifragile, we have to train.

Training: The Antidote to Chaos

Recently, I wrote about the idea of intellectual athleticism. The main idea was that, as intellectual athletes, we need to develop ourselves in ways that will allow us to continue growing and learning, without locking us into one particular path. In short, we need to learn to adapt our intellect at a moment’s notice.

As intellectual athletes, we need to think — and train — like world-class athletes. The best athletes sustain high levels of performance over long periods of time. Many people assume that these athletes solely focus on what they’re good at and avoid adversity in training. In reality, they trained for adversity.

In fact, the greatest athletes did some of the weirdest things. They found innovative ways to deal with adversity and prepare themselves for random events. Here are a few examples of elite athletes and their extreme training:

  • Michael Phelps - The highly decorated athlete puts his head in the clouds. It was reported that Phelps sleeps in an altitude chamber at night, which simulates a high-altitude environment, allowing his body to create more red blood cells since the chamber has less oxygen.
  • Michael Jordan - Most people wouldn’t be surprised to know that one of the greatest athletes of all time has a few odd methods, but this one is pretty odd. According to his former trainer, Tim Grover, Jordan used strobe light glasses to mimic the bright flashes of photographers behind the hoop are a major issue in the clutch.
  • Manny Pacquiao - In the ultimate act of training for the unknown, the famed boxer had members of his camp beat him with Thai sticks while training.

These athletes embrace adversity because they know it makes them better. It happens for them, not to them. They don’t view setbacks as a victim. Instead, they focus on what they can control — their training and their response to the situation. In doing so, they develop the mindset that things will continue to happen, setbacks will occur, but they’ll be prepared for them.

When we think about our work as training, we change our mindset and, therefore, our relationship with it. Instead of thinking about a continuous flow of work, we can break it up into different sessions, where we focus on one particular area. For example, writing this newsletter takes time and energy, which uses different “muscles” than other work tasks. To train for it, I write every morning, study great writers, and read content (articles, books) on how to be a better writer. This is a method I designed to help me train to be a better writer, but the same principles can be applied to anything.

Training Principles and Practices

The lessons of athletics are timeliness and should be consistently reevaluated, especially now that we treat work as a sport.

Like becoming a professional athlete, becoming an intellectual athlete is a lifelong pursuit. It requires discipline, focus, and consistency. If you want to become an intellectual athlete, you need to take steps to make it a reality. Here’s the method and approach I use to develop the mindset and training program.

Set Goals and Train with Intention.

Whether we consciously recognize it or not, we’re already training ourselves for something. The question is: for what?

The day slips by — you’ve done stuff, but not really. Maybe you checked some boxes, but did you really accomplish anything? This is the equivalent of showing up to the gym in jeans, aimlessly wandering around for an hour, then eating a burrito to celebrate.

Know that what we’re trying to accomplish is critical, otherwise, it’s not training. Don’t try to tackle it all at once, though. Instead, aim to get 1% better at something every day. Progress is (almost) always better than perfection. Approach training with intention and you’ll see progress. Don’t, and you won’t.

Find a Training Partner.

It’s easy to set goals, it’s difficult to stick to them. Finding a training partner will keep you accountable for your goals and help you stay focused on consistency.

I have people that continue to push me in healthy, personal and professional competition. They help me train for a career with antifragile characteristics (e.g. flexibility, independence) by forcing me to examine weaknesses in the categories listed above.

Get Coaching.

Coaches are ruthless. Anyone who played sports as a kid likely recalls a time when you thought “they’re trying to kill me.” While some coaches are truly sadistic, most coaches — or at least the good ones — are good at identifying weaknesses and using the tools at their disposal to reshape you.

Athletes have a coach for a reason — it’s difficult to accurately assess our performance without feedback. Coaches, mentors, and advisors help us see ourselves in new ways and continuously develop.

Pursue Practicality and Passion.

This sounds like a no-brainer, but you’d be surprised by how many people jump into something they’re not actually passionate about simply to get fame, notoriety, or money. If your athletic abilities are not directed towards your passion, you’re starting an uphill battle. But that doesn’t mean it should be your only pursuit. Sometimes, you need to pay the bills — which is a component of antifragility.

Taleb specifically advocates bimodal strategies in work:

Have one very stable gig and one volatile vocation by moonlight.


Who are the people that you admire most? Make a list of people who inspire you and make you work hard. Setting your sights high will keep you focused and remind you what you’re aiming for in your future pursuits. Learn from their habits, skills, and techniques. And then make them your own.

Inject Randomness.

If you want to be prepared for randomness, you have to experience randomness. Setting goals and tracking progress are two key elements of the process, but testing is an entirely different beast.

It’s easy to check off our goals and our progress, but proving ourselves is much harder. Athletes have big tests — games, events, etc. — that not only focus their efforts, but allow them to gauge their abilities.

Design your own or find ways to inject them into your life. Randomly apply for that job you’ve been eyeing. Live for a month without income. Try a skill you’ve never tried before and see how you fare.

Rest and Retest.

Athletes can feel when their body needs a break. It’s not so easy with intellectual work. Instead of waiting for your body to tell you, block off time during your week to ensure you’re properly rested.

Science writer Ferris Jabr summarizes the benefits of downtime in this Scientific American article:

“Downtime replenishes the brain’s stores of attention and motivation, encourages productivity and creativity, and is essential to both achieve our highest levels of performance and simply form stable memories in everyday life … moments of respite may even be necessary to keep one’s moral compass in working order and maintain a sense of self.”

Training every day isn’t good for anyone, so don’t be shy about taking a calculated rest period.

Take Control.

Jobs are replaceable, and most people are not well-positioned to define their own destiny if someone decides the job isn’t for them. To take control of your future and career, antifragility is the key that unlocks that door. But antifragility doesn’t just happen.

Want to get a promotion? Want to get a job offer? Want to start a business? These things come through focused, intentional effort.

Building an antifragile career takes time, so don’t wait. Get to work.

Enjoying Path Nine?

If you liked this post, I’d really appreciate it if you share the post!

Thanks for reading, and see you next week,

— Kevin K. (@kkirkpatrick)

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