Building an anti-fragile career (& life!)

With the recent layoffs at Twitter, Stripe & Meta, alongside the implosion of FTX, this appears to be the decisive starting point of the tech downcycle in the US. While market leaders & institutional investors have adequate resources to ride this impending downturn, the real impact is going to be felt by tech workers, who designed their lives around the prevailing system of high cash comp, RSUs whose value kept going up (courtesy of a low interest rate fueled bull market over the last decade), fielding multiple job offers largely driven by their employer’s brand and work-from-home flexibility.

This downturn will shift the power back into the hands of employers. Many in their 20s & early-30s will discover that they are ill-equipped to operationally, financially & emotionally deal with this drastic reset in the tech job market. In most cases, the hardship they will go through will have nothing to do with their capabilities or contributions.

As we all prepare to face this downturn with little personal control over many externalities, I believe this is the right time to ask a really important question – “how do we build an anti-fragile career (& life!)?”. For those not familiar with this concept, it was coined by one of my favorite modern thinkers – Nassim Nicholas Taleb. Here’s how he defines it in his book by the same name:

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. 

From Antifragile: Things That Gain from Disorder (via Farnam Street)

Dealing with volatility, randomness, risk & uncertainty is an inherent part of an outlier tech career. Unlike other industries, tech is ruled by ruthless power law outcomes that are driven by tremendous leverage (software), high scalability with minimal marginal cost & top talent that creates intense competition by starting, operating & investing in new ideas. Given these dynamics, capital & talent rushes into prospective outlier companies, all of whom then execute with intensity. Ultimately, a handful of market leaders remain standing in each space, and the rest die. The cycle then resets – rinse & repeat.

While the above pattern seems obvious on reading, most tech employees remain oblivious to the “high risk-high reward” game they are playing. While early-stage founders, startup employees & venture investors understand this more than others, this downcycle is showing that even FAANG & scaled enterprise software jobs aren’t as derisked as everyone thought. This isn’t surprising, given the sheer pace & intensity of creative destruction in most tech verticals. And if we go by how things have played out since the dotcom crash in ’01, this disruption will only become more brutal in the next 2 decades.

So coming back to the anti-fragile career (& life!), I have been asking this question to myself for more than 5 years now. I started thinking on these lines much earlier than usual, probably ‘cos I have a tendency to keep disrupting myself in order to chase large opportunities & therefore, I have subjected both my professional & personal lives to significant stressors over the last decade. From leaving a lucrative VC career in India to move to the Bay Area with just 2 bags & no job in hand, to giving a shot at driving Alibaba’s global expansion pre-IPO when few knew about it, then doing my own startup through the pandemic in a very lean way, while in parallel to all these adventures, also angel investing with my own salaried money in 20+ companies, many of them at an idea stage.

Having been on every side of the table over the last 15 years (founder, startup operator, big tech operator, angel, VC), one thing I internalized very soon was that chasing large outcomes in tech is a high failure rate, multiple-shots-at-the-goal kind of game. It’s hard to know with high certainty what product/ company/ investment will become an outlier & when, so staying power becomes super-important. In this context, another mental model from Taleb (originated from his days as a public markets trader) really resonated with me:

Avoid risk of ruin.

Nassim Nicholas Taleb

I combined the 2 models of creating an anti-fragile career and avoiding risk of ruin, to design & practice my life in a very specific way. Sharing some of my key life rules for the benefit of anyone with similar goals & context:

  1. Embrace risk – rather than ignoring or avoiding it. ‘Cos risk will find you anyway. The best starting point for managing risk is to acknowledge its perpetual presence in your life.
  2. Regularly practice adapting to change – over a long lifetime, change will creep up on you whether you like it or not. It’s important to keep your muscles trained during peacetime, to deal with big changes during wartime. Going out of your comfort zone & routinely taking up low-risk, micro changes go a long way in building muscle memory. Eg. take up the mini-project at work that you don’t feel ready for, overcome your inertia & go to the networking event, or push yourself to have that tough conversation you have been avoiding.
  3. No complacency – remember the best-seller ‘Only the Paranoid Survive‘ by the legendary Intel Founder & CEO Andy Grove? Oh man, it’s so true! The key to thriving across cycles in tech is to never be complacent in your success. It only takes one black swan event, one war, one economic crisis, or one new competitor to take it away.
  4. Acquire & continuously improve real-world skills – whatever is the space, stage or timing in the economic cycle, core operating skills are always going to be valuable for building any business. In tech, the 2 core “L1” skills are a) ability to build a software product and b) ability to sell a software product. These are then surrounded by other “L2” skills such as operations, finance, human resources etc. Whether you are 25 yrs old or 45 yrs old, acquiring & improving these L1 skills (backed by specific L2 skills you are good at) should always be your North Star.
  5. Execute your skills with hustle – an armory of relevant skills is irrelevant unless it’s backed by strong execution. Be it a tech startup or a publicly-listed Big Tech, superior execution is key to winning & retaining market share. In this context, the word I really like to use is “hustle”. In my book, hustle means “doing whatever it takes to get the job done”. Unfortunately, everyone’s hustle-quotient goes down in bull runs, as returns become increasingly uncorrelated with effort & more correlated with (rising) macros.
  6. Hone your specific “competitive edge” – as with companies, talent gets rewarded the most when it figures out its specific edge & brings its skills+hustle to a team that needs that edge the most. Like the way any good founder or leader evaluates their product, view yourself as a ‘product’ too. Keep asking yourself the question – “where do I have the strongest product-market-fit?” to figure out what your edge is.
  7. Nourish a high-quality network – to start the go-to-market of your ‘product’ (skills+hustle+edge), you will need the support of your network to do lead-gen of relevant opportunities. The best opportunities are almost always behind the firewalls of relationships & cliques. And it’s difficult to break into it cold when you really need it. Important to keep investing in & nourishing a wide-enough network, especially as loose connections typically give the best access.
  8. Play repeated games with the most-valuable relationships – while building a wide network, it’s also important to identify a small set of people you have the most professional synergy & personal resonance with at any point in time. Once you know who they are (<10 people in most cases), consciously make an effort to reach out, help them achieve their goals & look for ways to collaborate with them. Behind every game-changing opportunity is prior trust & reputations at play. The best way to build real trust is to play repeated games with a small set of high-quality people & show up with consistency in them.
  9. Minimize leverage – history shows that the most frequent reason behind the ruin of both companies & individuals is leverage (debt). And interestingly, the propensity to take on more debt rapidly increases during bull markets. Of course, home mortgages are an important source of cheaper, long-term debt but even that needs to be done with discipline wherein your monthly cash flows should line up well even if the going gets tough. I grew up in a middle-class Indian household and as every Indian of this background will tell you, we are taught to be wary of debt since childhood. Now I know why!
  10. Maintain low household burn – even the highest salaries cannot sustain a lifestyle that goes beyond means, leave alone the scenario of tough times wherein the salary itself goes away for an extended period of time. To keep playing the game during both good and bad times, I always like to remember Benjamin Franklin’s age-old virtue of “frugality”. Living below your means is key to avoiding ruin & getting your freedom back.
    • Bonus point: to lead a quality life even while staying frugal, I have found “focusing on value-for-money (ROI) over penny-pinching” as a good framing to achieve goals that are important to you while minimizing personal conflict.
  11. Create multiple sources of income – as the current layoffs are showing, even if you are the most talented & hardworking employee, your salary can go away in an instant & due to reasons that are completely outside your control. I strongly believe that a monthly salary as the single source of family income is a major personal finance risk. Whatever your life stage might be, it’s important to continuously work towards creating other sources of income. These could be dividend income from public market investments, rental income from real estate, side-hustles like operating an Amazon store, weekend consulting or contracting work in your area of expertise etc. Though it might take several years of focus & discipline to put these non-salary cash flows together, once this system gets set, it will compound without much effort and give you freedom & flexibility when you call on it.
    • Bonus point: while setting up these supplemental income streams, it’s equally important to do the basics of personal finance & money management well. These include 1) paying off high-cost/ short-term debt (eg. credit card, auto, personal loans etc.), 2) saving x% of income every month & investing it in your desired asset classes, 3) taking full advantage of relevant tax benefits including maxing out retirement contributions (401k, Roth, IRA, 529 etc.), 4) avoiding large-ticket, cash-flow-foolish decisions at every life stage.

These are some core rules I have discovered while attempting to create my own anti-fragile career (& life!). The virtues behind them are all from grandma’s wisdom – discipline, humility, less ego & more sacrifice. As it turns out, grandma’s wisdom is more relevant than ever in this age of AI & Crypto 🙏🏽

Sending you my very best wishes, as you navigate these turbulent times. This too shall pass, and when it does, I hope to see you stronger (& anti-fragile) on the other side ⭐️


to my weekly newsletter where in addition to my long-form posts, I will also share a weekly recap of all my social posts & writings, what I loved to read & watch that week + other useful insights & analysis exclusively for my subscribers.

Author: Soumitra Sharma

Operator-Angel I Product Leader I US-India corridor I Believer in Power Laws I Love building & learning

One thought on “Building an anti-fragile career (& life!)”

Leave a Reply

%d bloggers like this: