Elevate Your Time Management with a 4-Quadrant Approach

If you’re new to our weekly entrepreneur newsletter, welcome! Each week we research the issues that matter most to small business owners and entrepreneurs, then share insights, strategies, and expertise to help you solve challenges and achieve your goals. We hope you enjoy today’s edition!

In This Issue

• Why Most Entrepreneurs Struggle with Constant Firefighting
• A Principle-Based View of Time Management (Beyond Quick Fixes)
• Understanding the Four Quadrants of Time Management
• Practical Tips for Prioritizing What Truly Matters

Why Most Entrepreneurs Struggle with Constant Firefighting

Many entrepreneurs wake up each morning feeling like they’re already behind. They dash between meetings, tackle customer emergencies, and end the day too exhausted to focus on big-picture projects. Work–life balance feels impossible, and the latest “miracle” productivity hack never sticks—because it doesn’t address the root problem: reacting to every urgent demand.

A Principle-Based View of Time Management

Instead of sorting tasks by urgency alone (“Is it due now or can it wait?”), a higher-level framework also factors in importance. When you prioritize activities that align with your values and vision, you move from firefighting to foresight.

Understanding the Four Quadrants of Time Management

This simple framework categorizes every task by urgency and importance:

Quadrant 1: Urgent & Important

Immediate demands—client crises, looming deadlines. Living here means constant stress and no breathing room.

Quadrant 2: Important & Not Urgent

Strategic activities—planning, systemizing, relationship-building (including with loved ones!). These fuel growth and balance, yet often get sidelined.

Quadrant 3: Urgent & Not Important

Interruptions—nonessential meetings, emails, or “busy work” that feels pressing but contributes little.

Quadrant 4: Not Urgent & Not Important

Mindless downtime—endless scrolling or binge-watching shows—that serves as a tempting escape after too much Q1 stress.

Why Entrepreneurs Get Trapped in Q1 & Q4

Wearing all the hats makes it easy to react to every immediate need (Q1) and then crash into burnout activities (Q4). Over time, this cycle destroys work–life balance and sidelines vital long-term projects.

Practical Tips for Prioritizing What Truly Matters

1. Schedule “Important” Time: Block calendar slots for Q2 work—strategy, process improvements, or personal growth—and treat them as immovable appointments.
2. Categorize Your Tasks: Label activities as Q1, Q2, Q3, or Q4. Track where your time goes to spot patterns and decide what to delegate or discard.
3. Systematize & Delegate: For recurring Q1 emergencies, document a standard response and empower a team member (or automate) to handle them.
4. Protect Your Energy: Structure restorative breaks instead of unplanned Q4 escapes. Choose activities that genuinely recharge you.
5. Set Small Milestones: Focus on one Q2 initiative at a time. As you invest in prevention, you’ll see fewer fires and a snowball effect of increased capacity.

Effective time management isn’t about cramming more tasks into your day; it’s about ensuring the tasks you do align with your priorities and principles. By valuing importance as much as urgency, you create space for vision-driven work—and regain control of your business and life.

Schedule Your Free Strategy Session

See you next week!

Why AI Matters for Today’s Businesses

If you are new to our weekly entrepreneur newsletter, I want to first extend a warm welcome! Each week, we research the issues that are currently impacting small business owners and entrepreneurs the most, and provide our insight, strategies, and expertise to help you solve the challenges you face and succeed in achieving your personal and professional goals. We hope you enjoy the content!

In This Issue

• Why AI Matters for Today’s Businesses
• My Personal AI Journey—and How It Changed My Workflow
• Practical Ways AI Can Help You Work Smarter (Even If You’re a Small Team)
• Addressing Accuracy & Authenticity Concerns

It seems like we can’t go a day without hearing about artificial intelligence anymore. I used to be skeptical of artificial intelligence. I wasn’t sure how well it could capture my voice or bring real value to my day-to-day operations. But after months of experimenting with AI tools—like ChatGPT—I’m convinced they’re not just nice-to-have; they’re essential for staying competitive in virtually any industry. Whether we’re talking about researching topics more quickly, drafting emails, brainstorming big-picture strategy, or creating content that resonates, AI has become an essential tool for building a competitive and resilient business.

My Personal AI Journey—and How It Changed My Workflow

A few months ago, I started to dip my toes in the AI pool and tested out ChatGPT for a few basic tasks, just to see how it works. The results were a bit clunky at first. I got a lot of inaccurate and robotic content that I had to either completely discard or do a substantial rewrite. But then I realized something crucial: the more I fed the system information about my brand, my writing style, and my goals, the better it got. Over time, ChatGPT began sounding more like me. Now, instead of spending hours writing content for my business or reworking email templates, I can have amazingly accurate and persuasive content in seconds, needing only minor edits to perfect it.

Practical Ways AI Can Help You Work Smarter (Even If You’re a Small Team)

1. Content Creation & Editing
   Draft social media posts, blog articles, or newsletters. Then fine-tune them in your own voice.
2. Customer Communication
   Respond to FAQs or simple inquiries via AI chatbots or automated email responses—freeing up time for more complex customer needs.
3. Idea Generation & Strategy
   Brainstorm new product ideas or marketing angles by treating your AI tool as a creative partner. Just feed it context about your market, and it’ll give you fresh perspectives.
4. Admin & Scheduling Help
   From setting appointments to organizing your to-do list, AI-powered task managers can cut administrative time.
5. Data Insights (Without Being a Tech Wiz)
   Many stock software solutions now have built-in AI features to help you spot trends, forecast sales, or flag inefficiencies—even if you’re not running a huge, complex system.

Addressing Accuracy & Authenticity Concerns

People often worry about using AI for fear that it will sound robotic and inauthentic. There are ample horror stories of people using AI and getting into trouble because the model spit out wildly inaccurate or low-quality content. I had the same reservations at first. The truth is, AI can make mistakes if you leave it on autopilot. But it’s a “learn by doing” kind of tool—it adapts the more you interact with it. I spent hours teaching ChatGPT about my tone, preferences, and the topics I care about. Yes, I had to correct it in the beginning. Now, it feels like a real extension of my thinking. In other words, the system becomes more “human” the more human guidance it receives.

The Bottom Line

AI isn’t just a flashy tech trend. It’s a powerful ally that can supercharge your efficiency, creativity, and competitive edge—once you teach it who you are. Don’t get stuck in the old ways while everyone else speeds forward. Embrace AI now, and watch it help you work smarter, not harder. And if you’re worried about authenticity, remember: you’re the one in control. Train it well, and you’ll get an invaluable assistant that amplifies your voice, rather than drowning it out.

Click here to schedule a free business health assessment now!

See you next week!

Reclaiming Control: How to Grow Your Business Without Burning Out

If you’re new to our weekly entrepreneur newsletter, welcome! Each week we research the issues impacting small business owners and entrepreneurs, then share insights, strategies, and expertise to help you overcome challenges and achieve your personal and professional goals. We hope you enjoy the content!

In This Issue

• A Personal Challenge: Losing a key employee during growth
• Applying The Pumpkin Plan Principles: Staying sane and profitable
• Hiring, Training & Automation: Building a business that works for you

The Challenge: Growth + a Vacancy

These past few months, I’ve faced a challenge that many entrepreneurs encounter at some point: I lost a key employee—someone responsible for managing the day-to-day operations for our bookkeeping clients—right when we were bringing on several new clients and ramping up our growth efforts. The conflicting demands of serving existing customers at a high level while also onboarding new ones put our team under intense pressure. Although we’ve been thrilled to see our revenue projections on track, the stress and potential burnout threaten to undermine these wins.

Turning to The Pumpkin Plan

As we scrambled to fill the vacancy and maintain quality service, I was reminded of the very principles we share with our clients—namely, those found in The Pumpkin Plan. The core idea is that a business should serve its owner’s vision, not the other way around. When day-to-day chaos dominates, we can easily lose sight of what really matters: creating a profitable, systematized enterprise that supports our lifestyle and ambitions.

Key Principles We’ve Prioritized

1. Refine Hiring & Training
   We improved job descriptions, interviewed more methodically, and invested in structured onboarding. A consistent process ensures each new team member aligns with our culture and is equipped to succeed.
2. Efficient Knowledge Transfer
   We documented recurring tasks and built SOPs (Standard Operating Procedures). Storing these guides in a shared hub reduced new-hire learning curves and minimized interruptions for senior staff.
3. Focus on High-Value Activities
   Instead of doing “all the things,” we identified tasks that truly needed our attention—strategic planning, client relationships, refining offerings—and delegated the rest. This shift keeps growth on track without sacrificing quality.

Growing a Business That Supports You

Following these steps has eased our workload and refocused our energy on big-picture goals. Here’s how you can do the same:

• Identify Your Ultimate Vision: Define the lifestyle you want, then align your business model accordingly.
• Select the Right Clients & Offerings: Concentrate on services you excel at and customers you can serve profitably. Prune low-margin or high-hassle offerings.
• Develop Systems & Automation: From SOPs to scheduling tools, build repeatable processes that don’t require constant oversight.
• Empower Your Team: Provide training, resources, and decision-making authority so employees can handle routine tasks and free you for strategy.

The Bottom Line

Even the most promising growth phase can become a burden if you’re not intentional about where you spend your time and resources. By prioritizing a smarter hiring process, efficient knowledge transfer, and focusing on high-value work, we’ve regained control in our own firm. I encourage you to do the same: embrace The Pumpkin Plan principles to refine, automate, and delegate—so your business can flourish without burning you out.

Schedule Your Free Business Health Assessment

See you next week!

How to Find a Tax Accountant Who Protects Both Your Wallet and Your Business

If you are new to our weekly entrepreneur newsletter, I want to first extend a warm welcome! Each week, we research the issues that are currently impacting small business owners and entrepreneurs the most, and provide our insight, strategies, and expertise to help you solve the challenges you face and succeed in achieving your personal and professional goals. With tax deadlines coming up, we wanted to take some time to provide some tips for getting the most value from your relationship with your tax accountant. We hope you enjoy the content!

In This Issue:

• Common Pitfalls of Bad Tax Accountants
• Why Specialization Matters for Effective Tax Planning
• Balancing Tax Savings with Healthy Cash Flow
• Where to Turn for Help and Advisory Support

How to Find a Tax Accountant Who Protects Both Your Wallet and Your Business

Not too long ago, a business owner asked their tax accountant how to reduce their tax bill before year-end. The advice? Spend thousands of dollars on equipment and supplies—items the owner didn’t truly need. Sure, it shaved a bit off their tax liability, but it also left them strapped for cash when they needed it most. This scenario captures a fundamental problem with many tax professionals: focusing so heavily on short-term tax savings, they miss the bigger picture of maintaining a healthy, profitable business.

Common Pitfalls in Tax Accounting

• Barely responsive, often only available once a year.
• Charging by the minute, without considering revenue or complexity.
• Failing to offer genuine guidance beyond plugging numbers into tax software.
• Overemphasizing quick tax reductions—like pushing unnecessary expenses—at the expense of long-term financial stability.
• In the worst cases, an under-qualified accountant might even risk filing inaccurate returns, opening you up to scrutiny or penalties if you’re ever audited.

Why Specialization Matters

Some CPA’s try to handle both tax filing and day-to-day bookkeeping, which can dilute their expertise. They end up spending so much time on basic data entry that they have little bandwidth left to explore advanced tax strategies. Look for a tax accountant who focuses on tax law and strategy so they can devote their energy to where they provide the most value: strategic tax planning and saving you money. When an accountant specializes, they often have a deeper grasp of industry-specific regulations and creative, yet legally compliant, tactics to reduce liabilities.

Balancing Tax Savings with Healthy Cash Flow

A good tax accountant recognizes that while saving on taxes is important, it shouldn’t come at the expense of your business’s cash flow and growth. Buying unnecessary equipment for a $20,000 tax write-off might save you $5,000 on your return, but it still depletes $15,000 of your working capital—a decision that can cause financial strain later on. Ideally, your CPA should understand your long-term vision, personal goals, and immediate business needs, crafting tax strategies that improve profitability without depleting cash reserves.

Where We Can Help

While we don’t file taxes at our firm, we can still help you! If you’re not sure how to find a reliable, responsive tax accountant, we can make referrals to professionals we have used and trust. Alternatively, we can help you vet any accountants you’re already considering. We know the right questions to ask, how to recognize tax accountants that will really work in your best interest, and we speak their language.

Plus, our own bookkeeping and advisory services are available to ensure you have clean, up-to-date financials ready to hand over—reducing the time (and fees) a tax accountant spends piecing together your numbers. The bonus? With real-time, accurate financial data, you can make smarter decisions year-round instead of waiting until tax season to see how you did.

Click here to schedule a free strategy session now!

See you next week!

Transforming a Highly Seasonal Business: A Profit First Success Story

If you are new to our weekly entrepreneur newsletter, I want to first extend a warm welcome (it’s finally getting warm outside!). This week, we’re going to take a slightly different approach. We’d like to spotlight an amazing success story one of our clients recently experienced. We hope this can spread a bit of hope for struggling business owners and maybe even inspire you to take greater control of your business’ cash flow to achieve the same success in your business!

In This Issue:

• A Success Story: Transforming a Highly Seasonal Business
• Profit First and Seasonal Adjustments: How They Smoothed Cash Flow All Year
• The Impact on Personal Goals and Emotional Well-Being

In a bustling city known for summer events and tourism, a specialized hospitality business had operated successfully for several years, routinely surpassing $1.5 million in annual revenue. In 2023, they hit a record $2 million in sales. At first glance, you’d think the owner was living the dream—yet behind the scenes, the business faced an all-too-common issue for businesses that experience inconsistent cash flow (and don’t we all at times): their revenue flooded in heavily during the late spring and early summer, aligned with peak festival and wedding season, while the remaining months lagged.

Although their variable costs (materials and subcontractors etc.) moved up and down with the number of clients served, their fixed expenses remained the same year-round—rent, equipment leases, and most payroll costs had to be paid monthly, no matter how much (or how little) income arrived. With no concrete plan to handle the severe difference between Q2’s strong inflows and the slower rest of the year, their cash reserves dried up by fall—leading to a precipitous drop in profit and nerve-wracking debt obligations. Instead of relaxing during the holiday season, the owner was left battling insomnia and financial stress.

Enter Profit First

Earlier last year, before the busy season began, we started working together with them to implement the Profit First system and set up a cash-flow budget that would even out the highs and lows. We calculated a clear “Target Income for Allocation” (TIFA): the monthly amount of revenue needed to cover fixed expenses, taxes, owner’s pay, profit allocations, and any materials or subcontractor costs.

Armed with that TIFA figure, we devised a plan: once their busy season produced enough revenue to meet those budgeted needs each month, any additional cash flow would go into a seasonal adjustment account. During the lean months, when sales dipped and revenue wasn’t enough to fully cover expenses, the company would draw from this fund. Essentially, the summer spike funded the year’s quieter periods, sparing the owner from the dreaded “shortfall panic.”

A Smoother Ride and a Surplus on the Horizon

The results were striking. With strong early-season bookings—plus a disciplined approach—this company had fully set aside funds to handle fixed expenses, taxes, profit, and the owner’s compensation for the year already by the time they finished with their busy months. Within 2 months of starting their busy season, they even surpassed their annual TIFA goal based on realistic sales projections. That translates into a significant surplus by year’s end for every dollar earned above their annual budget—an incredible turnaround compared to last year’s cash crunch.

The owner recently asked, “What do I do with all that extra cash at year’s end?” That question is music to any advisor’s ears because it opens doors to achieving their long-term financial and personal goals:

• Paying down or completely eliminating debt
• Meeting tax obligations easily, without scrambling
• Enabling the owner to finally tackle postponed personal projects, like home upgrades or family vacations

More important than the bottom-line numbers is the new sense of calm and confidence the owner experiences daily. With business and personal finances on track—even during slower months—peace of mind has replaced the sleepless nights.

The Takeaway

This story proves how a strong cash-flow strategy can transform a business that’s profitable in peak times but falls short the rest of the year. By applying Profit First principles, calculating TIFA amounts, and creating a seasonal adjustment account, the company effectively eliminated the roller-coaster ride of feast-or-famine months.

If you’re dreading an upcoming slowdown or constantly chasing money after sales suddenly dip, remember there are proven methods to safeguard your cash flow and mental health. By planning ahead, allocating funds as they come in, and making your revenue work for you, you can avoid the trap of seasonal struggles—and finally find the freedom and confidence every business owner deserves.

Click here to schedule a free consult now!

See you next week!

Adam Litster
Certified Profit First Professional and Pumpkin Plan Strategist
(816) 500-5779
adam@betterbizinfo.com
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Working “In” vs. “On” Your Business: Finding the Right Balance

If you’re new to our weekly entrepreneur newsletter, welcome! Each week we research the issues impacting small business owners and entrepreneurs, then share insights, strategies, and expertise to help you overcome challenges and achieve your goals. Enjoy today’s edition!

In This Issue

• Defining “In” vs. “On”: What these terms really mean and why it matters.
• Ideal Time Allocation by Revenue Milestone: Insights from The Pumpkin Plan on where you should focus your efforts.
• Shifting to Big-Picture Leadership: Practical steps for delegating, automating, and systematizing.

In vs. On: What Does It Really Mean?

In the Business are day-to-day activities directly tied to operations and revenue: selling, delivering services, invoicing, troubleshooting, and managing emergencies. It’s the hustle that keeps the lights on.

On the Business are high-level, strategic tasks: planning new offerings, building systems, guiding your team, and setting the long-term vision. These activities take your company from where it is now to where you want it to be.

Most founders start by doing almost everything themselves. Over time, scaling requires shifting more energy “on” the business—leading and shaping it rather than getting buried in the details.

The Right Balance at Different Revenue Stages

According to The Pumpkin Plan, the ideal split between “in” and “on” evolves as you hit revenue milestones. Use this as a guideline to self-assess:

• Under $100K: ~80–90% In, 10–20% On
• $100K–$250K: ~75% In, 25% On
• $250K–$500K: ~60% In, 40% On
• $500K–$1M: ~50% In, 50% On
• $1M+: ~20–40% In, 60–80% On

If you’re feeling overwhelmed by daily tasks while revenue climbs, it’s time to shift more attention “on” the business.

Making the Shift: Practical Steps

1. Delegate & Empower
   • Identify non-core tasks you can hand off.
   • Train and authorize your team to make decisions—reduce emergencies landing on your desk.
2. Automate Wherever Possible
   • Use tools for billing, scheduling, email marketing, and other repetitive workflows.
   • Document each process so anyone can follow the same steps.
3. Systematize Your Offerings
   • Focus on your most profitable products/services.
   • Prune low-value offerings to simplify operations and free up your time.
4. Schedule “On” Time
   • Block weekly or monthly slots dedicated solely to strategic planning and innovation.
   • Treat these blocks as unbreakable CEO appointments.
5. Measure & Adjust
   • Track how you spend your hours.
   • If “in” tasks creep back up, revisit delegation and systemization until you find the right balance.

The Bottom Line

At every stage of growth, the balance between working “in” and “on” your business must shift. By delegating, automating, and systematizing, you free yourself to lead with vision and strategy—building a company that supports your long-term goals and gives you the freedom to enjoy both work and life.