If I Could Restart My Career Knowing How To Make Better Bets, Here's What I'd Do Differently
By Atticus Li, Growth & CRO
Almost a decade has passed since college. In that time, I've watched countless peers navigate their careers, and I've spotted clear patterns in who thrives versus who merely survives.
Some of my classmates are now leading teams at startups. Others are stuck in jobs that pay well but drain their souls. The difference isn't always talent or luck—though both matter. It's something more fundamental that I wish I'd understood in my early 20s.
If I could restart my career with one piece of knowledge, it would be this: Your opportunities right now are limited by your imagination, not the market.
The Phone Search Test That Changed How I Think About Opportunities
Here's a simple exercise that illustrates what I mean. Right now, search "best phone 2025" on Google.
You'll probably see articles from TechRadar, CNET, or Tom's Guide. Maybe some YouTube reviews. The results feel comprehensive, authoritative even. But here's the thing: you're only seeing what these sites want to rank for, filtered through Google's algorithm and your search history.
Now try this: go directly to GSMArena or PhoneArena. Sites that live and breathe mobile device comparisons. Look at their spec databases. Check their camera tests. Browse phones by specific features you actually care about.
Suddenly, you'll discover devices you never knew existed. Phones with better cameras than the iPhone, longer battery life than Samsung flagships, or unique features that solve problems you didn't realize could be solved.
This is exactly how most people approach career decisions. They limit themselves to what's immediately visible on job boards, what's trending in their LinkedIn feed, or what their immediate network suggests. They never dig deeper to find the career equivalent of GSMArena, the specialized resources where the real opportunities live.
Here's what I learned after running 200+ experiments across multiple industries: the biggest wins come from testing ideas that others aren't even considering yet. Just like the best phone for your specific needs might never appear in those generic "best phone" articles.
Why I Wish I'd Taken More Calculated Career Risks
Early in my career, I made a classic mistake. I focused too much on what my economics degree could "get me" in terms of traditional job titles. Analyst roles, banking positions, consulting gigs. I was optimizing for job descriptions that explicitly mentioned "economics background preferred."
The result? I got good at fitting into predefined boxes but missed the exponential opportunities where my economics trained brain could actually thrive.
It wasn't until later that I shifted my thinking. Instead of asking "What jobs want economics majors?" I started asking "What problems could benefit from an economics trained mindset?" That's when I discovered more opportunities.
Here's what I learned: Most people are making career decisions based on incomplete data and limited sample sizes. They're matching degree labels to job titles instead of matching cognitive strengths to market problems.
The False Positive/False Negative Framework for Career Bets
In experimentation, we worry about two types of errors:
False Positive (Type I Error): Thinking an opportunity is good when it's actually not
False Negative (Type II Error): Dismissing a good opportunity as bad
Most people optimize to avoid false positives—they're terrified of taking a "bad" job or making a "wrong" career move. But this strategy optimizes for the wrong metric.
Early in your career, false negatives are far more costly than false positives.
Here's why: If you take a risk that doesn't pan out, you learn valuable skills, expand your network, and gain experience. If you avoid taking risks, you learn nothing new and stay exactly where you are.
The Three Levels of Career Opportunity Perception
Through my work in behavioral economics and growth, I've identified three levels of how people perceive career opportunities:
Level 1: The Obvious Opportunities
These are the jobs posted on LinkedIn, the career fairs at your school, the companies everyone knows. Competition is fierce because visibility is high.
Level 2: The Network Opportunities
These come through connections: friends, mentors, alumni networks. Better odds, but still limited by your existing circles.
Level 3: The Created Opportunities
These don't exist until you imagine them. They require combining insights from different industries, identifying emerging trends, or solving problems that others haven't recognized yet.
Most people never get past Level 1. They're competing for the same visible opportunities as thousands of others.
How I Expanded My Opportunity Perception (And You Can Too)
1. Study Adjacent Industries Obsessively
When I moved from e-commerce to fintech, I brought behavioral economics principles that weren't widely used in banking. This combination made me valuable in ways that traditional finance backgrounds couldn't replicate.
Your action item: Pick an industry that's 2-3 steps removed from yours. Study their challenges, tools, and success metrics. Ask: "What would happen if I applied [technique from Industry A] to [problem in Industry B]?"
2. Follow the Talent, Not Just the Companies
I started tracking where smart people from companies I admired moved next. This led me to discover growth opportunities at startups that weren't on anyone's radar yet.
Your action item: Identify 10 people whose career moves you admire. Set up Google alerts for their names. When they move, research why.
3. Develop "Future Skills" Before They're Mainstream
In 2020, I started learning about customer data platforms (CDPs) when most marketers were still focused on basic email automation. By the time CDP expertise became hot, I had 2+ years of hands-on experience.
Your action item: Identify one skill that feels "too early" right now but could be essential in 2-3 years. Spend 30 minutes per week learning it.
The Compounding Effect of Better Career Bets
Here's what happens when you consistently expand your opportunity perception:
Year 1: You take a role that others overlooked. Competition is lower. Learning is higher.
Year 2-3: The combination of unique skills makes you valuable in unexpected ways. Your network expands beyond traditional boundaries.
Year 4-5: You start creating opportunities rather than just finding them. Companies seek you out for problems they didn't know how to solve.
This isn't theory. It's exactly what happened in my transition from traditional marketing to growth and experimentation roles. The path wasn't obvious, but it led to opportunities worth millions in revenue impact.
Your Next Move
The biggest career mistake I see people make is treating their next job like their last job. They optimize for immediate comfort instead of long-term learning and network expansion.
Here's your homework:
This week, spend one hour researching opportunities outside your normal search radius. Look at:
Companies that recently raised funding in adjacent industries
Job postings that combine two of your skill areas in unusual ways
Problems you keep hearing about that don't have obvious solutions yet
The goal isn't to apply immediately. It's to expand your mental model of what's possible.
Remember: your current perception of available opportunities is a local maximum, not a global one. The question isn't whether better opportunities exist—it's whether you're looking in the right places to find them.
FAQ
What if I take a chance and it doesn't work out? Early career "failures" are rarely true failures if you approach them strategically. Focus on roles where you'll learn valuable skills, work with smart people, or gain unique experience.
How do I know if a career opportunity is worth the risk? Apply the "regret minimization framework": In 10 years, will you regret not trying this more than you'd regret it not working out? Also consider: What unique skills or network access will this provide?
Should I always choose the less obvious opportunity? No. Sometimes the obvious choice is correct. But most people have a systematic bias toward over-weighting obvious opportunities and under-weighting hidden ones. Consciously counteracting this bias usually improves outcomes.
How do I expand my opportunity perception if I don't have a strong network? Start with adjacent skill development and content consumption. Follow people in adjacent industries on Twitter/LinkedIn. Join communities (both online and offline) where your target opportunities might be discussed. Create content about insights you're developing.
What's the biggest mistake people make when taking career risks? Taking random risks instead of calculated ones. Good career bets have asymmetric upside. limited downside but potentially unlimited upside. Bad career bets have symmetric or negative risk-reward ratios.
Author Bio:
Atticus Li is a growth strategist and experimentation leader with 10+ years in SaaS, banking, and energy. His work in CRO, analytics, and behavioral economics has helped startups and Fortune 500s drive over $1B in acquisitions and major revenue gains. He writes at experimentationcareer.com, helping students, practitioners, and decision-makers apply experimentation to build smarter products, careers, and teams.