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.

Like this article?

Share on Facebook
Share on Twitter
Share on Linkdin
Share on Pinterest

Related Posts

Entrepreneurs — Post-Pandemic, This One Single Word will Become Your most Powerful Tool

Just one word can serve as your most powerful ally in a coming post-pandemic business world. It’s actually one of the shortest words in the English language, but wields an incredible amount of influence. It’s a single syllable that can save you from a lot of trouble, and even one that can help you realize a profit. This magical word? It’s “no,” and it will be very difficult to utter in the coming months. Why “No” will Become Absolutely Necessary Risk is inherent in entrepreneurship, and that’s why it’s so difficult to turn things down. Business owners realize when they do not seize upon a seeming opportunity, they ostensibly lose out in one way or another. Call it FOMO or fear of missing out. Call it pride or even stubbornness. Whatever it is, there’s an impulse to accept things as they come. It’s easy to say yes and hard to say no. Anyone who has children knows how effortless it is for kids to learn the word ‘no.’ They love to say it—all the time! So, it’s curious that as we get older, the word ‘no’ becomes a distant memory and ‘yes’ is the order of the day. This is especially true if you are a people pleaser. Let’s face it, deep down we all want to be liked. For an entrepreneur, learning to say no is crucial because it can mean the difference between success and failure. —Forbes This isn’t to say it’s necessary or even smarter to avoid risk, but rather, to measure it on a case-by-case basis. And in a time when you’re in a position to help others out in their time of need, it will be extra tempting to accept rather than pass. This can easily become detrimental to your business in a very short period of time. So, it’s critical that you learn or relearn how to say “no.” How to Say “No” The real problem with saying “no” is that you’re not saying “yes.” If you think about it for a moment, that becomes fairly profound. In other words, “yes” carries a positive connotation, while its antonym is, understandably negative. But, that doesn’t mean that saying “no” can’t have a positive income. Here’s how to say “no,” when you impulsively want to say the opposite: Suggest alternatives. Instead of just posing an objection and leaving it at that, suggest alternative scenarios. It will help you to feel a sense of usefulness and even a sense of accomplishment, perhaps pride. This way, you’re offering solutions rather than shutting the other person out. Explain your reasoning. Although we’ve all heard the phrase “No is a complete sentence,” in many instances, it’s just not enough. So, take a moment to explain why you’re saying “No thanks,” and don’t belabor the point(s). After all, if you do prolong the situation, you’re opening yourself up to self-doubt. Don’t rationalize your decision.This goes right along with the last point. If you begin to rationalize, you’ll send yourself out on a path to going the opposite way to “yes.” And, that defeats the entire purpose of saying “no” in the first place. What other suggestions would you add? Please share your thoughts and experience by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

Help! My Sibling is Sabotaging Our Small Business – What Should I Do?

Help! My Sibling is Sabotaging Our Small Business – What Should I Do? We all know that running a small business can be challenging. It requires a lot of hard work, dedication, and the right team to make it successful. But what happens when the person who is supposed to be your right-hand man or woman turns out to be the one sabotaging your business? Below, we’ll discuss some practical steps you can take if you find yourself in this unfortunate situation. Recognizing the Signs of Sabotage Before we dive into the solutions, let’s first discuss the signs that your sibling might be sabotaging your business. Here are some common indicators that something is seriously awry and that you’re suspicions are probably valid: Your sibling consistently misses deadlines or fails to complete tasks. He or she spreads negative gossip or talks poorly about the business to others. They withhold important information or resources from you. Your sister or brother makes decisions that negatively impact the business without consulting you. They take credit for your ideas or successes and do so without including you or specifically attempt to exclude your time and effort. If you notice any of these behaviors in your sibling, it might be time to take action. But, don’t just leap without thinking things through. You need to take a step back and look at the entire situation with a realistic perspective. Addressing the Issue with Your Sibling The first step in dealing with a sabotaging sibling is to have an open and honest conversation with them. Make sure to approach the conversation calmly and objectively, and avoid making accusations or placing blame. Instead, focus on how their behavior is affecting the business and your relationship. During the conversation, try to understand the reasons behind their actions. Perhaps they are feeling overwhelmed or frustrated with their role in the business. Or maybe they are dealing with personal issues that are affecting their work. Whatever the reason, try to work together to find a solution that benefits both the business and your relationship. Creating a Plan of Action Once you’ve had a conversation with your brother or sister, it’s time to create a plan of action. This plan should address any issues that were brought up during the conversation and outline clear expectations for both of you moving forward. Some things to consider when creating your plan of action include: Clearly defining each person’s role and responsibilities within the business. Establishing regular check-ins to discuss progress and address any concerns. Setting up a system for open communication and feedback. Identifying any areas where additional support or resources may be needed. Remember, the goal of this plan is to create a healthy and productive working environment for both you and your sibling. It’s not – by any means – to establish a rivalry or force a hierarchy. Seeking Outside Help If you’ve tried addressing the issue with your sibling and creating a plan of action, but things are still not improving, it may be time to seek outside help. This could mean hiring a business coach or consultant to help you navigate the situation, or even seeking the advice of a professional mediator if the situation is particularly difficult. Remember, there is no shame in asking for help. Running a small business is hard enough without the added stress of dealing with a sabotaging sibling. Seeking outside help can provide you with the guidance and support you need to overcome this challenge. What We’ve Learned Dealing with a sabotaging sibling in your small business can be a difficult and emotional experience. However, by recognizing the signs, addressing the issue, creating a plan of action, and seeking outside help if needed, you can overcome this challenge and continue to build a successful business. Want to Accomplish More? Do you want your company to grow faster and earn more while you spend more time with your family doing all the things 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 602-435-5474, or, if you prefer, send us an email. You can also visit us at Waters Business Consulting Group to learn more about us and the services we offer.

Read More »

The Most Common Characteristics Successful Business Owners Possess that New Entrepreneurs can Emulate

Starting a new business is a risky venture, and unfortunately, many start-ups do not make it. According to the U.S. Bureau of Labor Statistics, approximately 20% of small businesses fail within the first year, and this number increases to 50% within the first five years. While there are many factors that contribute to business failure, there are a few common reasons why so many start-ups don’t make it. To gain an advantage, successful business owners employ a number of traits and these help them overcome various obstacles that might otherwise derail their plans for building a profitable organization. The Biggest Reasons New Companies Fail Businesses fail due to a wide variety of reasons. But, the most prominent reasons come down to just five. First and foremost is the lack of planning. Many businesses fail because they do not have a solid business plan in place. Without a clear plan for how to generate revenue, manage expenses, and achieve their goals, businesses may struggle to succeed. Another common reason for business failure is a lack of financial resources. Many start-ups do not have enough capital to cover the costs of launching and operating their businesses, which can lead to financial difficulties down the line. Poor management is also a notorious culprit. Successful businesses require strong leadership and effective management, and those that lack these qualities may struggle to succeed. Poor management can lead to a lack of direction, disorganization, and conflicts within the company, which can ultimately lead to failure. It takes the lucky convergence of opportunity and ambition to create success. Successful business owners, regardless of industry, share a few critical traits that set them apart from the rest of society. Leveraging these skills allows them to turn their business ideas into profitable realities. —Forbes.com An inability to adapt is another factor. The business world is constantly changing, and those who are unable to adapt to these changes may struggle to stay competitive. Businesses that are resistant to change or unwilling to try new things may find it difficult to meet the needs of their customers and keep their businesses relevant. Finally, many businesses fail because there is simply not enough demand for their products or services. Without a sufficient customer base, businesses will struggle to generate revenue and may eventually go under. Successful Business Characteristics Entrepreneurs can Copy Starting a business is no easy feat, and it takes a certain type of person to be successful in the world of entrepreneurship. While there are many characteristics that successful business owners possess, there are a few that stand out as particularly important. By emulating these traits, new entrepreneurs can increase their chances of building profitable companies. Passion. Successful business owners are passionate about their ventures and the products and/or services they offer. This passion drives them to put in the hard work and long hours necessary to make their businesses a success. As a new entrepreneur, it’s important to be passionate about what you do, because this will help you persevere through the tough times and keep you motivated. Determination. Starting a business requires a lot of hard work and perseverance, and successful business owners are determined to see their visions through to the end. They are not easily discouraged and are willing to put in the effort necessary to overcome obstacles and achieve their goals. As a new entrepreneur, it’s important to be determined and never give up, even when things get tough. Adaptability. The business world is constantly changing, and successful business owners are able to adjust to these changes in order to stay competitive. They are willing to pivot and try new things in order to stay relevant and meet the needs of their customers. As a new entrepreneur, it’s important to be adaptable and open to new ideas, as this will help you stay ahead of the curve and keep your business moving forward. Confidence. Successful business owners are confident in their abilities and the value of their products or services. This confidence helps them to sell their ideas and convince others to invest in their ventures. As a new entrepreneur, it’s important to be confident in your business and your ability to succeed, as this will help you persuade others to believe in your vision and support your endeavors. Vision. Successful business owners have a clear vision for their businesses and are able to communicate this vision to others. They have a long-term plan for their company and are able to inspire and motivate their team to work towards a common goal. As a new entrepreneur, it’s important to have a clear vision for your business and to be able to communicate this vision to your team and potential investors. By emulating these characteristics, new entrepreneurs can increase their chances of building successful and profitable businesses. Remember that starting a business is not easy, and it will require hard work and determination. However, with the right mindset and approach, it is possible to achieve your entrepreneurial goals and build a successful company. What other qualities should entrepreneurs emulate from successful business owners? Please, go ahead and take a moment or two to share your own thoughts and experiences so others can benefit from your perspective! Are you interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »