v16 In Defense of Short-Term Thinking

For over a decade, I was trained in the art of long-term planning—in a general management capacity that spanned strategy, operations, and full P&L ownership.

Annual planning cycles. Three-to-five-year product roadmaps. Monthly business reviews. I started in a Fortune 500 company, then moved to a Mid-Market enterprise, and later joined a late-stage marketplace Startup. At every stop, long-term thinking wasn’t just encouraged—it was the professional standard.

And then I entered the early-stage world.

Now, as Chief of Staff at a fast-moving Startup—and while learning how to build my own ventures on the side—I’ve come to a realization: the long-term planning muscles I’ve spent years strengthening? They don’t always serve me in the world of early-stage execution. In fact, they can get in the way.

Jeff Bezos once said, “People who are right a lot change their minds a lot with new data.” That line stuck with me. Because here’s the trap: when we default to long-term thinking in every context, we lose the freedom to respond to what’s happening right now.

This newsletter is about that shift. I want to unpack how different business environments—each with their own tempo and complexity—demand different mindsets. And why learning to think short-term isn’t reckless. It’s often the smartest move you can make.

Matching Your Strategy to Your Speed

Over the years, I’ve realized that different companies operate at different speeds—and your thinking style needs to match.

So here’s how I’ve come to think about it:

• Fortune 500? Cruise ship. It’s built for long journeys, slow turns, and plenty of process.
• Mid-market Enterprise? Yacht. It’s still structured, but there’s more room to steer and respond.
• Late-stage Startup? Speedboat. Fast, responsive, but you still need a strong engine and coordination.
• Early-stage Startup? Jet ski. It’s scrappy, nimble, and you feel every wave in real time.

If you try to steer a jet ski like it’s a cruise ship, you’ll sink—or stall out. And if you use jet ski instincts on a cruise ship, you’ll probably get fired.

That’s the frame I use to evaluate whether short-term or long-term thinking makes the most sense in a given context.

Cruise Ship Mode: When Long-Term Thinking Is the Job

I still remember the moment I was asked to create a three-year roadmap for a portfolio of product lines.

I had just started my career at a Fortune 500, in a general management training track. I was fresh, eager—and totally floored. Three years? I didn’t even know what I was eating for dinner that night. But the roadmap wasn’t optional. It was a cornerstone of the planning cycle, which kicked off every year in late Q3 and defined product strategy, channel shifts, and financial assumptions for the following fiscal year—and beyond.

Eventually, I found my footing. I worked cross-functionally to launch a new brand story for several product categories, which involved design updates and repositioning. It was ambitious and creatively satisfying. But something always rubbed at me: the time lag between insight and action.

We were encouraged to talk to users regularly—and I did. But anything I learned from them wouldn’t show up in a real product or revenue result for 18 to 24 months. By then, who knew if that insight would still be relevant? Or if a competitor would beat us to it?

The whole system was designed to reduce risk and manage complexity. And for a business with a mature B2B2C model, that made sense. We were steering a cruise ship: big, stable, and slow to turn. You need long-term thinking to avoid crashing into icebergs.

But it also meant I had to learn patience. And sometimes, I had to watch obvious opportunities get buried under the weight of timelines and legacy systems.

Takeaway:
Long-term thinking works when your business model is stable and your product cycles are long. But if your insights have a 24-month delay before they hit market… be prepared to watch some windows close before you can reach them.

Yacht Mode: Agility With Consequences

After my time steering the cruise ship, I moved into a mid-market enterprise role, taking ownership of all retail channel P&Ls. The setting changed, and so did the pace. The business was still structured, but it allowed for tighter turns—and quicker reactions.

We still ran annual planning cycles, but instead of monthly check-ins, I was reviewing POS data weekly. Ecommerce became my go-to lever for quick wins—especially for emerging product lines or reacting to a competitor’s surprise in-store promo. We didn’t need months of alignment to run a flash sale online. We could just… do it.

It felt more agile, more modern. But it also came with ripple effects.

I still remember the week the Amazon account manager launched a one-week promo on a product—completely uncoordinated. No one in channel management knew. Within days, we were flooded with backlash from other retail partners demanding to know why Amazon got special treatment.

That’s when I learned: even fast moves need ecosystem awareness. Speed without communication? It’s not strategy—it’s a mess.

After that fiasco, I took over all promotion planning across channels for that product category. We built a more holistic system, one that allowed us to stay nimble without burning bridges.

Takeaway:
At the “yacht” stage, short-term tactics become valuable tools—but only if you manage the long-term trust with partners. Speed alone isn’t a strategy. Coordination is what keeps the boat upright.

Speedboat Mode: Speed Isn’t Optional, It’s Survival

By the time I joined a late-stage marketplace Startup, I thought I had my cadence figured out. Weekly POS check-ins had worked in the past—why fix what isn’t broken?

Turns out, in a speedboat, weekly is late.

My CEO was a Groupon/DoorDash veteran shared this valuable lesson with me: waiting a week meant wasting six days I could’ve been learning, adjusting, or fixing something before it snowballed. Then, I started my mornings by checking the dashboard I’d built to monitor daily performance.

It changed my entire rhythm. Suddenly, I wasn’t reviewing data—I was living in it. My workdays became a cycle of “What just happened, and what do we do about it?”

One of my favorite moments: I spotted a sudden spike in sales for a specific cruise brand. At first, I assumed it was a one-off. But a deeper look revealed it was one of our most profitable offerings. No one had flagged it—it was just hiding in the noise. We quickly elevated it into a featured promo, gave it headline placement, and rode that momentum to increase organic traffic and sales.

That kind of nimbleness would’ve been unthinkable in my Fortune 500 days. But here, it was the norm. Necessary, even.

Of course, the speed came at a cost: it created a ton of motion. Strategy and execution blurred into one. I had to work cross-functionally to keep everyone aligned—sometimes hourly. But that’s the price of responsiveness.

Takeaway:
In late-stage Startups, short-term thinking isn’t chaotic—it’s clarity in motion. The market tells you things daily. Your job is to listen, translate, and act before the opportunity vanishes.

Jet Ski Mode: Ruthless Focus, Relentless Execution

After years of owning product lines and P&Ls, I made a pivot. I stepped into a Chief of Staff role at an early-stage Startup—not to run a channel or launch a category, but to drive operational excellence and execution.

Translation? I’m no longer steering a business unit. I’m helping steer the business itself toward product-market fit—and doing it in a way that’s scalable.

It was a huge mental shift.

At first, we followed a quarterly planning cadence. It felt familiar, but too slow for the pace we were operating at. One of our most active advisors — who’s built and exited three Startups, including one acquired by Amazon — pushed us to rethink it.

Ultimately, we landed on a 45-day planning cycle with a 30-day check-in. And the difference was immediate.

People dropped projects that didn’t belong. Discussions stopped getting postponed. We began aligning not next week—but right now. Execution became the centerpiece.

If Fortune 500 was a cruise ship, and mid-market was a yacht, then the late-stage Startup had been a speedboat: fast, responsive, but still requiring some structure and coordination.

This? This was a jet ski.

Lean. Sharp. Zero buffer. You feel every wave. Every decision makes a splash. And if you hesitate too long, you risk tipping over. You’re steering, balancing, and accelerating—all at once.

Takeaway:
In early-stage Startups, short-term thinking is precision under pressure. The goal isn’t to abandon strategy—it’s to make it so focused that it fuels real progress, fast.

Which Boat Are You Steering?

Different business models and company stages demand different planning rhythms. There’s no “best” approach—only the one that fits where you are and what you need now.

Here’s a quick breakdown of the four planning modes:

Early-Stage Startup (Jet Ski Mode)
Adapt + Learn
• Time Horizon: 1–2 months
• Feedback Loop: Instant
• When you're testing for product-market fit, you don’t need a perfect plan—you need short cycles, tight execution, and the humility to course-correct fast.

Late-Stage Startup (Speedboat Mode)
Scale Fast
• Time Horizon: 3–6 months
• Feedback Loop: Fast
• You’ve found early traction. Now it’s about scaling what works, staying responsive to data, and building systems that can keep up with growth.

Mid-Market (Yacht Mode)
Balance
• Time Horizon: 6–12 months
• Feedback Loop: Moderate
• Your model is mature but still evolving. You need to balance strategic bets with operational discipline—fast enough to grow, steady enough to sustain.

Fortune 500 (Cruise Ship Mode)
Optimize
• Time Horizon: 1–3+ years
• Feedback Loop: Slow
• In a stable environment, long-term planning is essential. You’re optimizing for scale, efficiency, and minimizing risk—turns are slow, but powerful.

Takeaway:
Your planning style should reflect your reality. Match your strategy to your speed—and don’t be afraid to switch boats when your business evolves.

Where I Am Now: Letting Go of the Old Playbook

If you told me a few years ago that I’d be leading 45-day planning cycles, measuring progress daily, and deprioritizing long-term initiatives in favor of what we can execute this month—I probably would’ve laughed (politely) and pointed you to the annual planning document.

That’s what I was trained to do. That’s what I knew how to do. Long-term thinking wasn’t just a skill—it was my identity as a professional.

So this shift? It’s not just tactical. It’s personal.

I had to unlearn parts of my training, stay open-minded, and embrace a different rhythm. Not because long-term thinking is wrong—but because it’s not always right for now.

Adapting to short-term thinking has been one of the biggest mindset changes of my career. And it’s also one I know I’ll carry forward—not just in my current role, but in the future companies I’ll build.

Because at the end of the day, it’s not about short-term or long-term. It’s about having the wisdom to know which one will actually move you forward.

What about you?

Where do you find yourself on the spectrum right now—cruise ship, yacht, speedboat, or jet ski? What kind of planning cadence is actually serving your stage of business—and where might you be defaulting to old habits that no longer fit?

🎧 P.S. Now My Newsletter Talks Back

Prefer to listen instead of read? I turned this exact newsletter into a podcast episode — so you can take it on a walk, a drive, or just hit play while hiding in your closet for ten minutes of peace. No judgment. Because sometimes hearing the words makes them land a little differently — and you deserve to feel less alone, in whatever format works for you. Or if you want to share it with a friend who prefers podcast.

▶️ Listen to “In Defense of Short-Term Thinking” on Spotify (Spotify link here).