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

Signs an Employee is Quite Quitting

Quite quitting is currently making all the rounds on social media and in corporate environments. And, it’s generating a whole lot of attention. Quite quitting isn’t just the latest buzz phrase, either. (Although, it is a bit misleading, given that it doesn’t mean preparing to turn in a resignation letter. Instead, it means doing as little as possible while still collecting a paycheck. Or, what was previously known as “coasting.”) However, this differs because employees who “coast” usually depart in the near future. Quite quitting is about staying onboard, but performing just enough to get by without being noticed. Quite Quitting Explained The term quiet quitting has only recently emerged and it’s gained quite a bit of traction in a very short time. The phenomenon is thought to arise from the aftereffects of the pandemic and shutdowns, which gave people a lot of time to reflect and reprioritize. The theory goes that employees realized that they can have a more fulfilling life experience by doing less at work and putting emphasis on their personal lives. Not taking your job too seriously has a new name: quiet quitting. The phrase is generating millions of views on TikTok as some young professionals reject the idea of going above and beyond in their careers, labeling their lesser enthusiasm a form of ‘quitting.’ It isn’t about getting off the company payroll, these employees say. In fact, the idea is to stay on it—but focus your time on the things you do outside of the office. —Wall Street Journal Obviously, this has a number of profound effects – not least of which is the fact that businesses are still paying them the same, though their production steadily declines and quality of work will likewise suffer. That’s just an unfortunate reality, but there are also other deleterious effects. Rather than make the person engaging in this practice happier, it will likely have the opposite effect, since numerous studies have clearly shown that work adds value and purpose to people’s lives. So, it is imperative to know the signs of quiet quitting in order to spot it when it starts to manifest, and before it becomes a problem. Top Signs an Employee is Quite Quitting The good news about this new phenomenon is that it’s actually a kind of reincarnation of an age-old problem. As stated above, it was previously known as coasting, something employees did when they were about to leave their position. But, this new version is far more concerning, because the employee who is quiet quitting has no intention of actually leaving their job. So, here are the top warning signs an employee is quietly quitting: They disengage. An employee who previously stayed in the mix and was eagerly part of the day-to-day operations and activity will start to disengage. At first, it might not be obvious. But, over time, managers and business owners will probably notice it. They stop keeping up. Similarly, an employee who is quietly quitting will no longer keep up with the latest that’s going on inside the company. Instead, he or she will fall out of the loop or just remain on the margins in order to appear that he or she is keeping up with what’s happening – even though that’s not what’s really transpiring. They no longer take initiative. This should come as no surprise. By its very definition, quiet quitting means doing as little as possible in order to remain employed but definitely not contributing any more than necessary. Fortunately, this is a fairly easy sign to spot, especially with people who were previously go-getters who now just seem to show up and do the bare minimum. They keep their ideas and opinions private. This sign isn’t overtly obvious, but it does point to the distinct possibility an employee is quietly quitting. However, if it is someone who previously contributed good ideas and shared their thoughts and opinions and now doesn’t, then such a change might be a red flag. What other telltale signs would you say are indicative of quite quitting? Please take a moment to share your thoughts and opinions – and/or experiences – so others can benefit from your suggestions! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

Most Effective Ways to Improve Customer Satisfaction

Improving customer satisfaction is a never-ending pursuit. It’s not like any company can fully reach 100 percent customer satisfaction. Although, that certainly doesn’t mean it isn’t worthwhile to strive for as high as rate as possible. So, just how do you improve customer satisfaction? Best Methods to Improve Customer Satisfaction Let’s start from a realistic baseline. We’ll blow-up the old adage, “the customer is always right.” Because, we all know, this is a good rule of thumb but isn’t universally true. However, it’s equally as true, happy customers help sustain and create additional business. As business owners, we’d all like to think of ourselves as providers of great customer service. As small business owners in particular, it’s quite possibly your biggest differentiator. After all, how often is it that you walk into a national chain restaurant and are greeted by name, handed your favorite drink and made to feel like part of the family? But great customer service is also about knowing how to handle problems, responding to and resolving issues—something at which agile small businesses can often excel. —U.S. Small Business Administration One of the best ways to improve customer satisfaction is to eliminate repetition. Now, this is a difficult task but it’s not impossible. A full 72 percent of consumer attribute poor customer service to having to explain their problem to multiple people. Meaning, people seriously dislike repeating themselves to multiple employees. Instead, funnel such situations straight to where they must ultimately go. Most Effective Ways to Improve Customer Satisfaction Now, that’s a huge piece of improving customer satisfaction. But, it isn’t the only way you can make your customers happier. Here are a few more helpful suggestions: Monitor social media. An old statistic states if someone is dissatisfied, they’ll tell 7 to 10 people. But if pleased, will only tell between 2 and 3 other individuals. Today, those numbers are much larger due to social media. So, that’s a key place to follow. Lend a helping hand. Somethings require a bit of a learning curve to understand and eventually master. If you are selling something requiring a learning curve, offer a means to explain it. A manual or a video will work nicely. Give customers rewards. No, not every customer should receive a reward. But, your most valuable definitely need such adulation. If possible, make it personal for an added touch. Provide flexibility. Along the same lines of eliminating repetition should be the ability to offer flexibility. Simply put, give more team members the power to make decisions that can resolve issues. Prevent problems. Another great way to improve customer satisfaction is to prevent problems. For instance, if someone purchases two items and they aren’t compatible, offer a heads-up and alert them. What other practices improve customer satisfaction? Please share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

How to Turn YOLO into Action

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.

Read More »