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

Employees are Quitting Instead of Returning to Work and That’s a Good Thing — Here’s Why

Leading news organizations continue to report a substantial number of employees are quitting their jobs rather than returning to work. The headlines are stark and alarming. They are also good news. Yes, it’s actually not cause for alarm. Instead, it’s a blessing in disguise, a silver lining to a cloud. Read on to learn why. Quitters Never Win? It’s a cliche, “Winners never quit and quitters never win.” But, we all know there are certainly exceptions. Put another way, sometimes quitting is the right choice, the best option, for an employee. Moving on and into something new can prove extraordinarily fortunate and fulfilling. However, it can also reveal qualities that aren’t net positives for businesses. After spending more than a year at home, some don’t want to go back to commuting, preferring the flexibility of remote work at least a few days a week. Others are simply burned out from logging long hours while also balancing child care and remote school, sometimes all at once. And nearly all employees are ready to see what else is out there. —CNBC Practically anyone who chooses to walk away and be part of what’s currently referred to as the “Great Resignation” is doing so for almost entirely personal reasons. And, that could very well point to a deficiency not previously exposed to co-workers, administrators, and owners. This of course being, unwanted characteristics, such as laziness, lack of passion or even interest, and just showing up for a paycheck. All of those are things a business can really do without. 3 Top Employee Qualities On the other side of the equation is the qualities that are the most beneficial to businesses. Companies should always look beyond resumes and take full advantage of the interview process (perhaps even going so far as to an informal interview over lunch or dinner). Here are some of the top qualities good employees naturally exhibit: Strong work ethic. Someone with a strong work ethic will obviously be productive. But also, concerned about the quality of work he or she is producing. But, be careful not to mistake a workaholic or the extreme statistics of the Japanese “karoshi,” people who literally die as a result of overworking. Strong work ethic isn’t the same and will offer a much more well-adjusted person to your team. Enthusiasm for the job. An enthusiastic individual is quite fortunately fairly easy to spot and even more thankfully, easy to distinguish from a phony or fake. (Phonies and fakes often exhibit many telltale signs they are just not genuine.) These people usually speak with zeal and great pleasure about their work. What’s more, will also talk about their work in a very focused yet informal and understandable manner. Team cooperation and collaboration. Place this quality in the “obvious” column, but one that’s definitely worth including. A person who is a true team player tends to be an individual who loves to listen to the input and perspective of others. Also, someone who can follow instructions without a bad or negative attitude, but can just as easily step into a leadership role, yet relinquish control for the good of the company. What other suggestions do you have? Please take a brief moment to share your thoughts and experiences so others can benefit from your unique perspective! You might just help out someone in a profound way. Interested in learning more about business? Then just visit Waters Business Consulting Group.

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 »

Thinking About Introducing Summer Fridays to Your Employees? Here’s What Small Business Owners Need to Know

Summer Fridays are a type of alternate scheduling that allows employees to either leave the office early or take the day off at the end of the week. As the name suggests, these reduced hours occur during the summer months and apply only to Fridays. Obviously, team members appreciate the option and this policy can be beneficial to both employees as well as businesses. Just What are Summer Fridays? Again, workplace Summer Fridays refer to a flexible work policy where employees are granted reduced work hours or time off on Fridays, typically during the summer season. The specifics of Summer Fridays can vary depending on the company, but the most common approach is to allow employees to leave early or take the entire afternoon off after completing their required work hours for the week. Reasons to Incorporate Summer Fridays Summer Fridays are a popular perk that can be a great way to boost employee morale and productivity, but it’s important to carefully consider the pros and cons before implementing this practice in a small business. Here are the advantages companies can expect to gain: Increased employee morale and engagement. Offering Summer Fridays can boost employee morale, satisfaction, and motivation. Knowing they have extra time to enjoy summer activities or spend quality time with friends and family can increase overall happiness and job satisfaction. This, in turn, can enhance productivity and reduce burnout. Improved work-life balance. Small businesses often face challenges in maintaining a healthy work-life balance for their employees. Summer Fridays provide an opportunity for employees to recharge, reducing stress levels and preventing burnout. The increased flexibility can also allow employees to schedule personal appointments, attend children’s activities, or engage in hobbies, which can positively impact their well-being. Attraction and retention of top talent. In a competitive job market, small businesses may struggle to attract and retain skilled professionals. Implementing Summer Fridays can be an attractive perk for prospective employees, differentiating the company from competitors. Additionally, existing employees are more likely to stay with a company that values work-life balance and offers flexibility. And, last but certainly not least – increased productivity and focus. Shortened work hours can lead to increased productivity as employees strive to accomplish their tasks within a condensed timeframe. Knowing that they have limited hours available can encourage employees to prioritize their work, minimize distractions, and focus on completing their assignments more efficiently. Considerations Small Businesses Need to Take into Account Before Implementing Summer Fridays Of course, there are always some potential drawbacks or downsides that go along with just about any type of change, regardless of intention and promise. Here are some things small businesses need to consider about Summer Fridays: Impact on operations and client expectations. Before implementing Summer Fridays, small businesses need to consider the potential impact on their operations and client relationships. Adequate planning and communication should be in place to ensure that reduced work hours or the absence of key employees on Fridays do not disrupt workflow or negatively affect customer service. Scheduling and staffing challenges. Small businesses often operate with limited resources, and adjusting schedules to accommodate Summer Fridays may present staffing challenges. Careful consideration should be given to workload distribution, cross-training employees, or arranging for temporary help to ensure essential tasks are covered. Consistency and fairness. It is crucial to establish clear guidelines and policies for Summer Fridays to ensure consistency and fairness among employees. Setting expectations, defining eligibility criteria, and addressing potential conflicts can help avoid misunderstandings or negative feelings within the team. Communication and transparency. Effective communication is key when implementing any new policy. Clearly communicate the details, benefits, and expectations of Summer Fridays to employees. Openly address any concerns or questions and be transparent about how the policy aligns with the company’s goals and values. What else would you include in the pros and cons of instituting Summer Fridays that small businesses should know about? Please take a few moments to comment and share your thoughts and experiences so others can benefit from your unique perspective! Interested in learning more about business? Then just visit Waters Business Consulting Group to learn more about us and the services we offer.

Read More »