Jay Georgi

TL;DR (elementary worldly wisdom): If your business feels “fine,” that’s often when you should worry. Stagnation usually isn’t bad luck. It’s a predictable pile-up of human folly: protecting the old game too long, underinvesting until you’re desperate, worshipping a plan that’s already obsolete, tolerating misalignment, clinging to the wrong people in the wrong seats (including yourself), starving the future, and refusing to update your beliefs. Use inversion: study what causes stagnation, then systematically avoid it.

The Decision Point Every Mid-Market Leader Faces

Let’s keep this simple and honest. You’ve built a business. People rely on it. You sign the checks. You carry the worry. And at a certain point you look around and realize: nothing is “wrong,” but nothing is really getting better either.

That “fine” feeling can be very expensive.

So instead of asking, “How do I grow?” try inversion. It’s a better tool than optimism.

Ask: “How do I guarantee stagnation?”
Then don’t do those things.

Most stagnation is self-inflicted. Not because owners are stupid. Because owners are human. And humans are wired to protect comfort, avoid embarrassment, and postpone pain. That wiring is useful if you’re trying to survive. It’s terrible if you’re trying to build something that lasts.

Here’s a workable list of the common ways to kill momentum—told plainly, with no incense burning.

First: deny reality while calling it loyalty. You keep the old model because it worked once and you feel attached to it. It’s familiar. It made you money. It made you proud. And changing it feels like admitting you were wrong.

You weren’t wrong. You’re just late.

Kodak is the famous case. They built the digital camera and still protected film. That’s not a lack of intelligence. That’s incentives, denial, and fear. Fujifilm did the opposite. They accepted the unpleasant truth and rebuilt the business into something broader—healthcare, materials, imaging.

If you want to avoid stagnation, don’t wait for humiliation. Make a habit of asking: “What is getting weaker that we’re pretending is fine?” If you can’t name it, you’re not paying attention. If you can name it and do nothing, you’re bargaining.

A practical habit: once a quarter, write down three things: what’s working, what’s fading, what must change. Then do one thing from the “must change” column. One. Not fifteen. Just one that actually ships.

Second: starve the business of capability, then act surprised when growth is painful. This is the classic mistake. You treat systems, talent, and training like luxuries. You wait for “extra cash” to invest. Extra cash rarely shows up on schedule. Pressure shows up. Then you buy what you should’ve built earlier, but you buy it in a panic, at a premium, with everyone already exhausted.

This is like refusing to maintain the brakes because the car is still moving.

Avoiding stagnation means accepting a boring truth: you have to invest before you feel ready. Not because it’s exciting. Because it’s sane.

A practical habit: reserve a fixed portion of your resources for future capacity—tools, training, process, talent. Treat it as a cost of staying in the game, not a reward for winning it.

Third: worship the annual plan. People love plans because they reduce anxiety. They also create a special kind of stupidity: commitment to a story that stopped being true.

Markets change. Customers change. Costs change. Technology changes. Your plan sits there looking confident while reality walks past it.

Netflix adapted. Blockbuster didn’t. That’s the whole story. Blockbuster had plans and assets. Netflix had the willingness to change its mind and cannibalize itself.

So don’t fall in love with a calendar. Fall in love with feedback.

A practical habit: shorten the loop. Work in quarters. Pick a few outcomes. Re-check assumptions. If something important changes, update the plan like an adult instead of defending it like a politician.

Fourth: let misalignment rot. This is where owners lose years.

People say they want growth. Then they resist every change required to earn it. Systems that worked at one size start to fail quietly at the next size. Partners that fit yesterday’s model start pulling against tomorrow’s direction.

If you want stagnation, here’s a great method: upgrade the CRM and ignore behavior. Hire strong people and keep weak processes. Announce a new strategy and keep incentives tied to the old one. You’ll get theater instead of progress.

Avoiding stagnation is not inspirational. It’s mechanical. Align incentives, roles, systems, and partners with where you’re going—not where you’ve been.

Fifth: protect the wrong people in the wrong seats because it feels “nice.” This is where business becomes emotional, and most owners try to pretend it isn’t.

Your business will not outgrow its leadership. That includes you. If you are the bottleneck and you refuse to change, the company will politely stop growing around you. It won’t announce it. It’ll just slow down.

Sometimes the founder can scale. Sometimes the founder needs to change how they operate. Sometimes you need different leaders in key seats. This is not moral judgment. It’s matching talent to the job.

Apple is the famous case people argue about forever. Jobs was pushed out in 1985. When he returned in 1997, he led with a different posture and built an ecosystem and team that could execute. The point isn’t the drama. The point is that leadership fit matters, and refusing to face it is very costly.

Sixth: optimize the present until you’ve eliminated the future. If you want stagnation, cut every “non-essential” investment—innovation, exploration, new products, adjacent markets—because the core is busy and you want nice-looking short-term numbers.

That produces a clean spreadsheet and a dead company.

Amazon didn’t stay a bookstore. They expanded—electronics, cloud, grocery, entertainment—because they understood optionality and long-term compounding. Expansion isn’t always wise, but starving the future is almost always unwise.

If you want to avoid stagnation, keep a deliberate slice of attention and resources aimed at what’s next. Protect it from the tyranny of the urgent.

Seventh: refuse to update beliefs. Pride is a killer. People say they want “consistency,” but what they really mean is they don’t want to admit they were wrong.

Continuous reassessment is not chaos. It’s discipline: watching what’s true, comparing it to what you assumed, and adjusting.

Microsoft missed major shifts for a period, then later leaned hard into cloud under Satya Nadella and changed the trajectory. That’s what updating beliefs looks like at scale.

A practical habit: once a month, ask three questions:

1. What did we assume that might not be true anymore?
2. What are customers telling us with their behavior (not their words)?
3. What are we stubbornly defending?

Now, if you want the blunt summary—the Munger-ish version—it’s this:

• Stagnation comes from denial, then underinvestment, then misalignment, then pride.
• Growth comes from clear thinking, early investment, alignment, and the humility to change your mind.

None of this is fun. It’s not supposed to be. If building a durable business were easy, everyone would do it and nobody would pay you for it.

So the question isn’t, “Do you have a strategy?” Most people can print one.

The question is: are you systematically avoiding the standard ways humans mess this up? Because if you’re not, the default outcome is “fine”…until it isn’t.

Sources

1. Harvard Business Review – "Breaking Out of Stagnation" – https://hbr.org/2019/01/breaking-out-of-stagnation
2. Forbes Business Council – "Why Some Businesses Grow While Others Stagnate" – https://www.forbes.com/councils/forbesbusinesscouncil/
3. McKinsey & Company – "Strategic Planning in an Uncertain World" – https://www.mckinsey.com/capabilities/strategy-and-corporate-finance
4. Inc.com – "Leadership and Business Growth Research" – https://www.inc.com/leadership

TL;DR

Most growth strategies fail because of avoidable mistakes: misaligned teams, scattered focus, weak market research, unrealistic projections, wrong KPIs, poor customer understanding, and trying to do everything at once. The fix? Get clear on priorities, align your team, ground decisions in data, and focus on execution over excuses.

Your business hit $8M last year. Now you want to double it in three years. Sounds great on paper. But here's what usually happens: six months in, you're burned out, your team is confused, and you're no closer to that goal than when you started.

Growth strategies fail not because the market turned or competition got tougher. They fail because of internal mistakes, mistakes you can fix today.

Mistake #1: Your Teams Are Fighting Different Wars

You've got sales chasing enterprise deals while marketing targets small businesses. Operations is optimizing for efficiency while product is launching features that complicate everything. Everyone's working hard. Nobody's aligned.

The Reality: When growth accountability sits with one person or department, everyone else treats it like someone else's problem. Your VP of Sales thinks growth is their job. Your CFO thinks it's about margins. Your head of operations thinks it's about capacity.

The Fix: Create one shared vision document, literally one page. State your growth target, the 3-5 strategic initiatives that will get you there, and how each department contributes. Review it monthly with your leadership team. When decisions come up, ask: "Does this serve our shared vision?"

Think of it like a GPS. Everyone in the car needs to see the same destination. Otherwise, you've got backseat drivers arguing about routes while the driver takes you in circles.

Mistake #2: You're Playing 10 Games Poorly Instead of 3 Games Well

Last year you tried LinkedIn ads, SEO, trade shows, partnerships, a podcast, and cold outreach. You dabbled. None of it worked particularly well because you never gave anything enough attention to actually master it.

The Reality: Mid-market companies rarely win by doing everything. They win by doing a few things exceptionally well. Your competitor with the same revenue probably focuses on 2-3 channels max.

The Fix: Pick your top three growth initiatives for the next 90 days. Shut everything else down or put it on maintenance mode. Go deep before you go wide. Master one acquisition channel before adding another.

Look at how Marvel built its universe. They didn't launch 10 franchises simultaneously. They perfected Iron Man first. Then they added carefully, one at a time. DC tried to rush their universe to compete, and it collapsed under its own complexity.

Mistake #3: You're Guessing About Your Market

You "know" your customers want your new feature. You "know" there's demand in that adjacent market. You "know" your pricing is competitive. Except you don't actually know. You're guessing based on a few conversations and your gut.

The Reality: Bad market research killed more growth plans than bad execution ever did. You can't execute your way out of a market that doesn't exist or competition you didn't see coming.

The Fix: Before committing resources to any growth initiative, answer these questions with data:

• What's the actual size of this market segment?
• Who are the top 3 competitors and what's their market share?
• What do 20+ potential customers say they'll pay for this?
• What are the real barriers to entry?

Spend 5% of your growth budget on research before you spend 95% on execution. It's the cheapest insurance you'll ever buy.

Mistake #4: Your Financial Projections Are Fiction

Your growth plan shows 40% year-over-year growth. When asked how you'll get there, you point to "market opportunity" and "increased marketing spend." Your projections look great in the pitch deck. They're also completely detached from reality.

The Reality: Inflated projections don't just mislead investors. They mislead you. You make hiring decisions, lease commitments, and inventory purchases based on revenue that never shows up. Then you're in a cash crunch wondering what went wrong.

The Fix: Build your projections from the bottom up, not top down. Start with: "We have X sales reps who close Y deals per month at Z average contract value." Then model what happens if you add resources or improve conversion rates by realistic percentages, not fantasy numbers.

Use three scenarios: conservative (75% of plan), realistic (100% of plan), and optimistic (125% of plan). Make decisions based on conservative. Celebrate when you hit realistic.

Mistake #5: You're Measuring the Wrong Things

You track revenue. Maybe you track some vanity metrics like website visitors or social media followers. But you're not measuring the things that actually predict whether your growth strategy is working.

The Reality: Most KPIs either measure outcomes too late to matter or measure activity that doesn't correlate with results. You need leading indicators, metrics that tell you 30-60 days in advance whether you're on track.

The Fix: Identify the 3-5 metrics that directly drive your growth model. For most B2B companies, that's:

• Qualified pipeline generated
• Sales cycle length
• Win rate
• Customer acquisition cost
• Net revenue retention

Review these weekly. Set thresholds for action. If qualified pipeline drops below X, you know you have a problem before it hits revenue three months later.

Mistake #6: You Don't Actually Know Your Customers

You've been in this industry for 15 years. You know your customers. Except the market changed. Your customer base shifted. Their needs evolved. And you're still selling based on what worked in 2019.

The Reality: Customer understanding isn't a one-time exercise. The software company that succeeded selling to IT departments five years ago now needs to sell to procurement. The manufacturer whose customers valued speed now faces buyers who prioritize sustainability.

The Fix: Talk to 10 customers every quarter. Not sales calls, actual conversations about their business, their challenges, their buying process. Ask:

• What's changed in your business in the last year?
• What problems keep you up at night?
• Who else are you evaluating?
• What would make you switch vendors?

Record these conversations. Share insights with your team. Update your strategy based on what you learn, not what you assume.

Mistake #7: You're Trying to Boil the Ocean

You're expanding into two new markets, launching three new products, implementing a new CRM, restructuring sales territories, and opening a second location. All at the same time. Your team is drowning.

The Reality: Organizational capacity is finite. You have X amount of leadership bandwidth, Y amount of capital, and Z amount of employee focus. Spread them too thin and everything suffers. Quality drops. Execution slows. Good people burn out.

The Fix: Use the "Rule of Three" for strategic planning. Pick three major initiatives per year. No more. Within each initiative, identify the three most critical components. Focus quarterly sprints on making real progress on these priorities.

Everything else? It either waits, gets delegated completely, or gets cut.

Think about Kodak versus Fujifilm. Both faced digital disruption. Kodak tried to protect film sales while investing in digital cameras while diversifying into pharmaceuticals and chemicals. They split focus and went bankrupt. Fujifilm picked their battles, they went deep into cosmetics and medical imaging. They survived and thrived by focusing, not by doing everything.

The Bottom Line

Growth isn't complicated. But it's hard.

Hard because it requires saying no to good opportunities to say yes to great ones. Hard because it means aligning people who have different incentives. Hard because it demands you face uncomfortable truths about your market, your projections, and your execution.

The businesses that grow from $5M to $50M don't have secret strategies. They just avoid these seven mistakes. They stay aligned, stay focused, stay grounded in reality, and execute consistently over years, not months.

Which of these mistakes are you making? Pick one. Fix it this quarter. Then move to the next.

Sources

1. "Common Growth Strategy Mistakes and How to Avoid Them" – Business growth alignment and KPI research
2. "Financial Projection Errors in Business Planning" – Market research and forecasting best practices
3. "Strategic Planning for Mid-Market Companies" – Priority management and capacity planning
4. "KPI Selection Framework for Business Growth" – Performance measurement research
5. "Market Research Methodology for Business Expansion" – Customer research and market validation approaches