Jenny Just, How To Actually Set Goals and Critical Thinking Skills
Alex Brogan
Most goal-setting frameworks fail because they mistake activity for strategy. You write down objectives, break them into tasks, track progress religiously — and still end up optimizing for the wrong outcomes entirely. The real work happens before you ever touch a goal-setting template: deciding what's worth pursuing in the first place.
That's the diagnosis William Deresiewicz delivered to West Point cadets in 2009, though he was talking about leadership, not quarterly planning. We've become "the greatest technocrats the world has ever seen," he argued — people trained to execute flawlessly but incapable of determining direction. The result: leaders who can fulfill goals but don't know how to set them.
The Fintech Contrarian's Playbook
Jenny Just built her career on asking different questions than her competitors. When she co-founded PEAK6 Investments in 1997, the options trading industry was dominated by firms optimizing for speed and volume. Just focused on user experience instead.
That sounds obvious now. It wasn't then. Trading platforms treated interface design as an afterthought — functionality mattered, aesthetics didn't. Just's insight: the complexity of financial instruments doesn't require complexity in execution. Her teams constantly asked, "How can we make this better for the user?" That question drove product decisions that competitors dismissed as frivolous.
The approach worked. PEAK6 grew into a major player in electronic trading. Just's latest venture, Apex Fintech Solutions, provides clearing and custody services to major brokerages — the infrastructure layer that most fintech companies outsource rather than build. She spotted an opportunity in the plumbing while others focused on the fixtures.
"Building a great team is crucial. I look for people who are passionate and aren't afraid to challenge the status quo."
Her hiring philosophy mirrors her strategic thinking. Most leaders say they want people who challenge assumptions. Just actually hires them. The difference shows in results.
The Snack Empire's Distribution Gambit
Mondelez International emerged from a 2012 corporate split that carved Kraft Foods into two companies. The grocery-stable division kept the Kraft name. The snack business — Oreo, Cadbury, Trident — became Mondelez, a neologism meaning "world of delicious."
The new company inherited iconic brands but faced a strategic puzzle. Traditional food conglomerates were losing ground to smaller, health-focused competitors. Local brands were stealing market share in key regions. The obvious response: compete on product innovation, launch healthier options, fight for shelf space in saturated categories.
Mondelez chose a different path. Instead of treating competition as product versus product, they reframed it as distribution versus distribution. Their competitive advantage wasn't superior cookies or better chocolate. It was relationships with retailers in 150 countries — a network that takes decades to build and costs billions to replicate.
This insight shaped their acquisition strategy. The $4 billion purchase of Enjoy Life Foods in 2015 wasn't just about adding healthy snacks to their portfolio. It was about leveraging existing distribution to scale a smaller brand faster than competitors could build equivalent reach.
Your moat isn't your product. It's your distribution infrastructure.
The Goal-Setting Framework That Actually Works
Most goal-setting fails at step one: choosing what to optimize for. The standard advice — make goals specific, measurable, achievable, relevant, time-bound — assumes you've already solved the hardest problem. It doesn't help you distinguish between goals worth pursuing and goals that feel productive but lead nowhere.
Here's a different approach:
Start with Systems, Not Outcomes
Before setting goals, map the systems that drive your most important outcomes. If you want to grow revenue, identify every component of your revenue engine: lead generation, conversion rates, average deal size, retention, expansion. If you want to improve health, map the daily habits that compound over time.
Goals become targeting mechanisms for system improvements. Instead of "increase revenue by 20%," you might set goals around specific system components: "increase qualified leads by 30%" or "improve trial-to-paid conversion from 15% to 22%."
Apply the Regret Minimization Framework
Jeff Bezos used this when deciding whether to leave his hedge fund job to start Amazon. Project yourself forward to age 80. Which choice would you regret more: trying and failing, or never trying at all? The framework forces you to separate temporary discomfort from permanent consequences.
Most goal-setting focuses on maximizing upside. Regret minimization focuses on avoiding the outcomes you absolutely can't live with. Different calculations entirely.
Test the Vision Deficit
Return to Deresiewicz's challenge: Are you setting goals because they're measurable, or because they're directionally correct? Can you articulate why this goal matters independent of whether you achieve it? If you hit the goal but the underlying system doesn't improve, was it worth pursuing?
The best goals change how you operate, not just what you accomplish.
The Vision Deficit Crisis
We're producing more technically skilled professionals than any generation in history. We're also producing fewer people capable of setting direction. The two trends are connected.
Specialization creates expertise. But expertise within narrow domains often comes at the cost of broader perspective. You become incredibly good at optimizing within existing frameworks, less capable of questioning whether the framework itself makes sense.
"We have a crisis of leadership in America because our overwhelming power and wealth, earned under earlier generations of leaders, made us complacent, and for too long we have been training leaders who only know how to keep the routine going. Who can answer questions, but don't know how to ask them."
This shows up everywhere. Companies that obsess over efficiency metrics while missing fundamental shifts in customer behavior. Investors who can model discounted cash flows flawlessly but can't spot when entire industries are about to be disrupted. Professionals who climb every rung on the ladder, only to realize they've been climbing the wrong wall.
The solution isn't less specialization. It's developing the capacity to zoom out periodically and question the direction you're optimizing toward.
Critical Thinking as Competitive Advantage
Critical thinking isn't skepticism. It's the ability to separate what you know from what you assume, what you can control from what you can't, what's correlation from what's causation.
Most thinking failures happen because we mistake pattern recognition for understanding. You see that successful companies do X, so you implement X. You notice that high performers share trait Y, so you try to develop trait Y. The patterns might be real, but the causal relationships might be backwards.
The Eigenquestion Method
Before solving any problem, ask what Shishir Mehrotra calls the "eigenquestion" — the question that, if answered well, makes all other questions easier to answer. Most problem-solving starts with the symptoms. Eigenquestions start with root causes.
If your conversion rates are declining, the obvious question is "How do we improve conversion rates?" The eigenquestion might be "Why are we attracting visitors who aren't good fits for our product?" Different question, different solution set.
Elements of Effective Thinking
The most effective thinkers share certain habits:
They actively seek disconfirming evidence for their beliefs rather than just collecting supporting data. They separate conclusions from the reasoning that led to those conclusions, questioning both independently. They look for what's missing from any analysis, not just what's present.
They reframe problems multiple ways before settling on a solution approach. They consider second and third-order effects of their decisions, not just immediate consequences.
Most importantly, they maintain intellectual humility — the recognition that being wrong is information, not failure.
The Hidden Pattern Question
What are you seeing that no one else is seeing?
This isn't about having access to secret information. It's about processing widely available information through a different lens. Jenny Just saw user experience as a competitive advantage in financial services before most people thought interface design mattered in trading. Mondelez saw distribution as their core asset when competitors focused on product differentiation.
The patterns are usually hiding in plain sight. The insight comes from asking different questions about the same data everyone else has access to.
The question forces you to articulate your contrarian beliefs — the areas where your perspective differs from conventional wisdom. If you can't identify any, you're probably not thinking independently enough. If you can identify several but can't defend them with logic and evidence, you might be contrarian for its own sake.
The sweet spot: contrarian beliefs that you can defend rigorously and that, if correct, would significantly change how you operate.
That's where competitive advantage lives. Not in executing better within existing frameworks, but in identifying when the frameworks themselves need to change.