Business Education

You’ve Missed the Tax Filing Deadline (Again) But That May be the Least of Your Problems

April 15th has come and gone. Now, you find yourself in a regrettable but familiar predicament. On one hand, it’s not like you’ve missed filing your taxes before the deadline, but on the other hand, you certainly don’t look forward to the pain and cost that come with missing the final filing date. Yet, this may be the least of your worries and long-term problems. If you are constantly missing deadlines while running your business, you’re inevitably disappointing clients, and it may not be too long before you don’t have any real business left.

How Small Business Owners Can Break the Bad Habit of Missing Deadlines

For small business owners, missing deadlines can erode trust, frustrate clients, and derail growth. The habit often stems from overcommitment, poor planning, distractions inherent in wearing multiple hats, or a combination. Breaking this bad habit requires intentional strategies that balance discipline with flexibility. Here’s how to get on track and deliver on promises consistently.

Understand the Why

First, identify why deadlines slip. Are you taking on too much? Underestimating task complexity? Getting sidetracked by urgent but unimportant tasks? Self-awareness is the foundation. Track your time for a week using a simple tool like a notebook or an app like Toggl. Note what derails you—client calls, social media, or perfectionism.

Recognizing patterns helps you target the root causes rather than just the symptoms. For example, a freelance graphic designer may notice missing deadlines due to hours spent tweaking designs beyond client requirements. Once the designer pinpointed perfectionism as the culprit, that entrepreneur could address it directly.

Set Realistic Commitments

Overpromising is a trap. When clients push for tight turnarounds, saying “Yes” to secure the job is tempting. But unrealistic timelines breed stress and subpar work. Practice saying, “Let me review my schedule and confirm what’s feasible.” This buys time to assess your capacity.

Use a calendar to map out existing commitments. Block off buffers—say, 20% more time than you think a task requires. If a project seems doable in five days, promise seven. This cushion absorbs unexpected delays, like a sick day or a client’s last-minute feedback. Clients appreciate reliability over speed.

Break Big Tasks into Small Chunks

Big projects can feel overwhelming, leading to procrastination. Split them into smaller, actionable steps. For instance, instead of “complete website redesign by Friday,” list tasks like “finalize homepage layout Monday” or “source images Tuesday.” Smaller goals feel achievable and keep the momentum going.

Tools like Trello or Asana can help. Create a board with columns for “To Do,” “In Progress,” and “Done.” Move tasks across as you complete them. The visual progress motivates and keeps you focused on what’s next rather than the whole mountain.

Prioritize Ruthlessly

Not all tasks are equal. The Eisenhower Matrix—sorting tasks by urgency and importance—can clarify what deserves your attention. Focus on what’s both urgent and important, like a client deliverable due tomorrow. Delegate or delay what’s less critical, like updating your portfolio.

Learn to say no. If a new request clashes with a deadline, politely decline or negotiate a later start. For example, “I’d love to help, but I’m booked until next week. Can we start then?” This preserves your bandwidth for existing commitments.

Use Time-Blocking

Time-blocking allocates specific hours to specific tasks. Each morning, plan your day. Assign, say, 9–11 a.m. for drafting a proposal and 1–2 p.m. for emails. Stick to these slots as if they’re meetings. Silence notifications and close irrelevant tabs to stay focused.

If distractions persist, try the Pomodoro Technique: work for 25 minutes, then take a 5-minute break. After four cycles, take a longer break. This structure harnesses short bursts of focus, making tasks less daunting. Apps like Focus@Will or Forest can reinforce this habit.

Communicate Proactively

If a deadline is at risk, don’t ghost. Reach out early with a clear update: “I’m finalizing your report but need an extra day to ensure quality. Is that okay?” Most clients appreciate transparency over silence. Regular check-ins—such as a quick email on project milestones—build trust and align expectations.

For instance; let’s again use the example of a designer, who started sending clients rough drafts midway through projects. The client’s feedback helped the designer stay on track, and the customer felt involved, reducing the designer’s stress about delivering the final product.

Build Accountability

Share your goals with someone—a mentor, peer, or even a client. External accountability adds pressure to follow through. Alternatively, join a mastermind group or online community of entrepreneurs. Regular check-ins with others facing similar challenges can inspire discipline.

You can also self-enforce accountability. Set reminders on your phone or use apps like Habitica, which gamifies task completion. Reward yourself for hitting deadlines—a coffee treat or an evening off. Positive reinforcement strengthens the habit.

Reflect and Adjust

Review what worked and didn’t at the end of each week. Did you overestimate your capacity? Did a tool help or hinder? Tweak your approach. You may need stricter time blocks or fewer meetings. Habits form through repetition, so small, consistent adjustments compound over time.

Breaking the cycle of missed deadlines isn’t about perfection—it’s about progress. By understanding your pitfalls, planning realistically, and staying disciplined, you’ll build a reputation for reliability. Clients will notice, stress will shrink, and your business will thrive.

Want to Accomplish More?

Do you want your company to grow faster and earn more while spending more time with your family doing everything you started your business to do?

We can make that dream a reality. Give us 30 minutes and we will show you how to get your life back. Skeptical? Good! Put us to the test.

You can call us for your free appointment at 480-636-1720, or, if you prefer, Waters Business Consulting Group to learn more about us and the services we offer.

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Is It Time to Grow? 7 Signs Your Small Business Is Ready for the Next Step

July 2, 2025 No Comments

Running a small business is a thrilling journey – taking it to the next level can be daunting

How to Turn YOLO into Action

January 10, 2019 No Comments

YOLO — You Only Live Once. It’s true and that’s precisely the reason to give that business idea you have a real go. Really. What you’re waiting for isn’t likely to happen. You have to make it happen. So, let’s get right to it. Why Most Business Start-Up Roadblocks are Imaginary Okay, you need money, right? Wrong. But, you need an extensive business plan. Nope. You need a retail store, an office, a professional space. Probably not. Whatever the reasons, you’re probably talking yourself out of it rather than being thoughtful and careful. There are no limits on who can become a great entrepreneur. You don’t necessarily need a college degree, a bunch of money in the bank or even business experience to start something that could become the next major success. However, what you do need is a strong plan and the drive to see it through. —Entrepreneur.com While thoughtful and careful are good qualities, you need a healthy dose of impulse. In fact, almost every “roadblock” is merely you making an excuse. It’s no more complicated than you making it more complicated. 4 Simple Steps to Start a Business In reality, there are very few steps to start a business. With all the technology at your disposal and a little can-do attitude, it’s entirely possible. All you need is to do the following: Do a bit of research (but not too much). Learn about the product or service and its industry. You don’t need to become an academic expert. Research enough to get acquainted and feel more confident. Although, there’s a point of diminishing returns. If you keep going, you’ll eventually become overwhelmed. In other words, don’t get stuck in the paralysis of analysis or you’ll never actually get started. Test it out in a few different ways first. Whatever it is, test it out and don’t expect to charge — at least in the very beginning. Instead, ask for feedback and listen carefully. Others will give you invaluable input and that’s more valuable than money when starting out. (Now, if someone is willing to pay, give them a nice discount.) Start spreading the word, far and wide. Use social media, your family, your circle of friends, and acquaintances to spread the word. But, don’t hard sell. Just let people know about it. Make changes as you go and learn along the way. More than likely, you won’t hit the ball out of the park at first. You’ll need to make changes as you go. Be flexible and you’ll enjoy the ride a whole lot more. What other advice would you give to people who want to start a business? What motivated you? Please share your experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Most Common Scams that Target Entrepreneurs

June 2, 2023 No Comments

Starting a new business is an exciting and challenging venture. However, amidst the hustle and bustle, entrepreneurs need to remain vigilant and protect themselves from potential scams that can derail their success. Scammers often prey on the vulnerabilities and limited experience of new business owners. Most Common Scams that Target Entrepreneurs Okay, let’s get ahead of this right now. Entrepreneurs are proud people and willing to take risks. So, they can be a little more susceptible to scams. Even the most skeptical can be fooled. And that means knowing the most common schemes can be very informative. Now, let’s delve into the types of scams that entrepreneurs are most likely to encounter and provide essential steps they can take to avoid falling victim. Fake Invoice Scams One of the most prevalent scams is the fake invoice scheme. Scammers send fraudulent invoices for services or products that were never ordered or received. The invoices may appear legitimate, using logos and details similar to genuine suppliers or service providers. New business owners, caught up in the chaos of managing operations, may inadvertently pay these invoices without realizing the deception. How to Avoid Fake Invoices Implement strict payment protocols: Establish a clear process for verifying and approving invoices. Maintain a record of authorized suppliers and cross-reference all invoices against this list. Double-check all invoices: Scrutinize each invoice for any discrepancies, such as changes in payment details or unexpected price increases. Contact the supplier directly to confirm the legitimacy of the invoice before making any payments. Train employees: Educate your staff about invoice scams and the importance of verifying invoices. Encourage them to report any suspicious invoices or requests for payment. Business Opportunity Scams Entrepreneurs, driven by the desire for success, can become susceptible to business opportunity scams promising quick riches or high returns on investments. These scams often present themselves as legitimate-sounding franchise opportunities (or pyramid schemes or multi-level marketing programs). However, they typically rely on recruiting more individuals rather than selling legitimate products or services. How to Stay Away from Business Opportunities that Sound Too Good to be True Research extensively: Thoroughly investigate any business opportunity before committing. Seek independent reviews and testimonials from individuals who have engaged with the organization and look for the good and bad. Anything that strikes you as a red flag should give you ample pause. Take a step back and look objectively: This is much easier said than done, but it’s worth mentioning. Get some perspective and ask people you trust. Let them evaluate the offer and give you their honest feedback. Phishing and Email Spoofing Phishing and email spoofing scams remain a constant threat to entrepreneurs. Scammers send deceptive emails, often posing as trusted organizations, financial institutions, or even government agencies. These emails attempt to trick recipients into revealing sensitive information, such as passwords, credit card details, or social security numbers. Entrepreneurs may unknowingly compromise their own and their business’s security by falling for these scams. Best Ways to Protect Yourself from Phishing and Spoofing Be cautious with email links: Avoid clicking on suspicious links or downloading attachments from unknown sources. Hover your mouse over links to reveal the actual destination before clicking. Verify email senders: Scrutinize the email address of the sender carefully. Phishing emails often use slight variations or misspellings of legitimate email addresses. When in doubt, contact the organization directly through a trusted source to confirm the authenticity of the email. Utilize security measures: Install reputable antivirus software, spam filters, and firewalls to protect against phishing attempts. Regularly update software and keep your systems patched to minimize vulnerabilities. Business Directory Scams This is an old one, but it’s still in use today. And it targets new entrepreneurs in various forms – usually digital but sometimes, still hardcopy. Scammers may contact business owners, claiming to offer inclusion in a prestigious online directory or publication for a fee. They employ persuasive tactics, promising increased exposure and enhanced credibility. However, these directories often have limited visibility and fail to deliver any real benefits. Effective Protection Tips Conduct thorough research: Before investing in any directory or publication, research its reputation and reach. Look for genuine testimonials and reviews from other business owners. Question unsolicited offers: Be skeptical of unsolicited calls or emails from unfamiliar directories. Ask for detailed information about their services and cross-check their claims with trusted sources. Verify legitimacy: Contact established industry associations or local business bureaus to verify the legitimacy of the directory or publication. What other types of scams would you add to this list? Please take a moment to share your thoughts and experiences so others can avoid making costly mistakes and being victimized by nefarious individuals or criminals. Interested in learning more about business? Then just visit Waters Business Consulting Group to learn more about us and the services we offer.