#93: Why most career advice is wrong

How to build an Antifragile career

Jan 26, 2025

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Hey Friends,

Welcome to the 92nd edition of my newsletter.

It’s been a busy week, especially since I returned to work after my one-month parental leave. I’m still trying to adjust to the schedule in which I go to work, write for my MBA assignments, write online, go to the gym, and spend time with my family. And ideally not in this particular order.

It’s not easy, but I’m getting there. I just need to keep in mind what my priorities are every day and act on them. And to remember that every time I say “yes” to a commitment, I am actually saying “no” to others.

Things are still a bit messy, but I’m getting there, slowly.

I’m also trying to accommodate at least one coaching call per week, as they are quite fulfilling for me. For example, we had a public holiday this Friday, and I had a short conversation with a 21-year-old student who is studying finance and wants to get into tech. This conversation led me to the topic of this newsletter.

Most Career Advice is Wrong

So, during the coaching call this week, I got this revelation about career advice.

Most career advice assumes life is predictable: set your goals, follow the plan, and success will follow. But in a world of rapid change and uncertainty, the best careers aren’t just resilient—they’re antifragile. They don’t just survive chaos; they thrive on it.

When I was in high school, everyone was telling me to choose one career path and stick with it. Ideally, it should have been engineering, medical school, or law practice.

These were “safe bets," and you just couldn’t get it wrong with them.

You had to go to the university and follow the linear path to becoming successful. Eventually.

In this newsletter, I’ll show you why this type of career advice often fails and how to build a career strategy that benefits from uncertainty.

The Problem with Traditional Career Advice

Most career advice centers around deliberate planning.

Set your 5-year goals
Follow your passion
Stick to the plan

On paper, it sounds great. But life rarely works that way. Markets evolve, industries are disrupted, and even our own priorities shift. Here’s where traditional advice gets it wrong:

The illusion of control: Advice like “chart your path” assumes you can predict the future. You can’t.
Resilience isn’t enough: Bouncing back from setbacks is good, but in a chaotic world, you need strategies that help you grow stronger through uncertainty.
Ignoring emergent opportunities: Rigid adherence to a plan can blind you to unexpected chances that could transform your career.

The Antifragile Alternative: Combining Deliberate and Emergent Strategies

Careers, like complex systems, thrive when they’re designed to adapt. Clayton Christensen’s How Will You Measure Your Life highlights the importance of balancing deliberate strategies (planned goals) with emergent strategies (opportunities that arise unexpectedly).

To make this even more powerful, we add an antifragile layer: designing your career to grow stronger from change and chaos.

Here’s how to mix deliberate strategies with emergent ones, all with an “antifragile mindset.”

Anchor to Your Core Values
Know what truly matters to you. These are your compass, guiding your efforts even as circumstances change.
Example: You may deliberately seek roles where you can lead teams, innovate, or solve meaningful problems.
Invest in Optionality
Develop skills and relationships that open multiple doors, rather than locking you into one path.
Example: Learn decision-making, strategic thinking, or AI integration—skills that stay relevant no matter the industry.
Experiment Constantly
Treat your career as a series of experiments. Say yes to roles, projects, or industries that pique your curiosity.
Example: A side project in automation could reveal a passion for optimization, leading to new career paths.
Pay Attention to Weak Signals
Notice trends, conversations, or tools reshaping your industry. These weak signals often lead to emergent opportunities.
Example: Dive into learning AI tools when you see their impact growing in your field.
Turn Volatility into Opportunity and Seek Discomfort
Seek situations where others see risk. Chaos often holds hidden opportunities.
Example: During organizational changes, volunteer to lead an initiative others are hesitant to take on.
This is especially useful when you are at the beginning of your career and don’t have anything to lose. High risk→ high reward, but with almost no downside in case you fail.
Growth happens outside your comfort zone. Actively pursue challenges that stretch you.
Redefine Failure as Feedback
Treat setbacks as data to refine your strategy.
Example: If a project or role doesn’t work out, reflect on what you learned and adjust your path.
Build Robust Networks
Surround yourself with diverse connections who expose you to new ideas, opportunities, and challenges.
Example: Engage meaningfully on LinkedIn or in other spaces where you can find like-minded people, not just to connect but to join conversations in adjacent fields.

I’ve lived both deliberate and emergent strategies.

Early in my career, I followed the “perfect” plan: climbing the ladder in a specific industry.

In 2007, networking was a big thing in Romania. And I’m not talking about networking with people at events, but about devices like switches and routers connected through a network (physical or wireless). Companies from North America were opening offices in Bucharest, and it was the best chance of getting hired in technology.

So, like many of my peers, I started as a networking engineer, testing these devices. Manually.

I was very passionate about it, and for a while I thought this was going to be my career forever. I didn’t imagine myself doing something else.

Then, about 2 years into my manual testing career, there was a new thing called “automation” becoming more and more popular. Writing scripts that would automate the steps we were doing manually. A new team was formed, and my manager asked for volunteers.

Most people thought this was a fad, and it’s never going to replace manual testing, so they didn’t want to join the initiative.

I decided to take on this challenge. This led me to the opportunity to go for 3 months in California and become a team leader when I got back home.

Everything happened in 6-7 months. From manual tester to automation tester to team leader.

All because I chose to be curious, to be uncomfortable. It pushed me into uncharted territory. It was uncomfortable but transformative, opening doors I never anticipated.

After 8 years in telecommunications, I changed to automotive. A different industry, with different projects and different people. I actively pursued an opportunity people were afraid to pursue.

Seven years later I moved to consulting, in Tax Technology. Again, something completely new.
Was I afraid of these changes? Of course.

Did they take me outside my comfort zone? Definetely.

Did it help me grow and build an antifragile career?

No doubt about it.

Your turn

Ask yourself:

What’s one small experiment you can try this month—a skill, role, or side project—to test a new direction?
What’s one area of discomfort you could embrace to grow stronger?

I’d love to hear your thoughts. Share your experiments, stories, or ideas with me by replying to this email. Let’s build an antifragile community together.

Your career isn’t a puzzle to solve; it’s a dynamic story.

By blending deliberate planning with emergent opportunities—and embracing antifragility—you can turn uncertainty into your greatest advantage.

Recommendations:

I finished the first season of “Ted Lasso,” and I loved it. It’s a comedy show full of leadership lessons that apply in all domains, not only in sports. One of the best things out there, and I fully recommend it.