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.

Like this article?

A Competitor Wants to Buy Your Small Business: Now What?

April 24, 2025 No Comments

When a competitor comes knocking with an offer to buy your small business, it’s a moment that can spark excitement, anxiety, and a flood of questions.

2 Strong Signs You’re Actually Successful, Even if You don’t Believe It

October 21, 2018 No Comments

What does success look like? More particularly, what does success feel like? These are, of course, quite objective. But, there are some signs you’re successful, even if you don’t particularly believe it yourself. It’s always worthwhile to take stake in where you stand — especially when you feel as though it’s less than inspiring. 2 Strong Signs You’re Actually Successful, Even if You don’t Believe It Aside from the hard numbers, how do you know you’re successful? Sure, you can always look at the books and see the bottom line. However, these figures don’t tell the whole story. One such example is when you feel comfortable that you can’t change everything but do change what you can. We’ve all experienced those days when we feel like an absolute failure. It’s a normal feeling when things don’t go as exactly planned. And, when we feel like that, it’s challenging to think of yourself as a successful individual. Here’s the thing about success though – no one can agree what that word means. Even though we all have our own definitions of success, there are also a number of signs that we’re overlooking that can let us know that we’re actually more successful than we could have ever guessed. —Inc.com Or, if you don’t feel stressed out at every bump in the road. People who aren’t struggling just don’t usually sweat the small stuff. It’s really that simple. When you’re making it, little setbacks are regarded as valuable lessons and not nightmare scenarios. Top 3 Signs You’re Making It, Even if it Doesn’t Feel that Way Now, if those don’t apply to you, let’s take a look at a few more telltale signs you’re actually making it — even if it doesn’t quite feel that way: You see the bigger picture. When your focus is large in scope, you are able to think more clearly. Which means you look into the future instead of fretting on every little component in the now. In other words, you’re more comfortable with the bumps along the way because you know it’s just part of getting to the next goal. You feel excited to keep at it. If a person feels excited to keep on with their role, there’s definitely a reason for that. Fulfillment is a sure sign that you’re successful. Otherwise, you’d feel quite different, more pessimistic and gloomy. And, you most assuredly wouldn’t feel energized or enthusiastic about your role. You look forward to the next challenge. Another sign you’re successful is you’re looking forward to the next big challenge in the future. After all, you’ve had to achieved a level of success in order to get to this point. In other words, you’ve had to racked up some successes in the past because there’s still more to go. What other signs of success do you think go unnoticed? Please share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Less Texting More Face Time Equals More Success in Business

September 12, 2017 No Comments

No, I am not talking about the Facetime application … I am talking real, live one-on-one face time! Texting has become as normal a standard in our world as eating and sleeping, and in some cases it has become more important to some people than eating or sleeping! With texting, the level of trust is low. Texting does not allow for relationship building and real relationship building is required to develop trust. Texting only provides tentative, at best, minimal trust. It’s important to understand that low trust does not translate to success in business! Why Personal Contact Always Beats Out Texting in Business Ok, I am as guilty as anyone using text to communicate. Texting is an efficient and immediate form of communication that allows the sender and recipient to respond on their own terms. It’s very convenient. The benefits of texting are numerous, but the problems that texting develop or cause are now beginning to surface as we track data; auto accidents, pedestrian accidents, sleeplessness, lack of productivity, poor communication skills … and now less success in business due to limited and poor planning! Texting has its place, but not while walking, driving, during meetings, or especially at the dinner table. You want to improve your relationships with family, friends, and business associates, along with clients/customers? Call them, meet them for coffee or lunch, and build a relationship with eye-to-eye contact instead of sending texts. We never talk any more: The problem with text messaging – From CNN Tech Web site By Jeffrey Kluger As texting use rises, the phone call is becoming a dying institution American age 18-29 send an average of nearly 88 text messages a day Psychologists worry social skills in young texters won’t develop Habitual texters may hurt relationships, miss out on new ones Because texting is convenient and can be done almost anywhere, it tends to substitute proper planning in advance for last minute texting to coordinate meetings, directions, critical information, etc. Recently, it hit me why last minute texting is a pet peeve of mine. Why? It minimizes our need to plan because we expect immediate responses. So why plan in advance when you can text at the last minute? Is it not more convenient? Does this rationalization sound familiar? Let me provide a real-world example. When texting or cell phones didn’t exist, we all had to plan out our days, our travel, our meetings … our whole day-to-day life. It required goal setting and developing a plan because there was no cell or text to connect at the last minutes. We had to pre-plan even if the plan was just meeting someone for lunch, or meeting someone at an event. Today, I hear many people say, “We’ll figure it out; I’ll text you.” Real success occurs when you plan in advance by writing down your goals and when you have a plan to achieve those goals. Or in the case of meeting or connecting with someone, you plan in advance so that you minimize the use of text while driving to the meeting! Achieving Your Goals Statistics show more than 70 percent of people never have goals. And, only 28 percent say they have some kind of goals, with just a meager 2 percent having written goals. Moreover, it’s estimated that this 2 percent controls over 90 percent of all income. Goals require planning. This includes planning your weekly business calendar of priorities which are part of your strategy to achieve you goals. So, if you have a plan, you can easily set a meeting and location based on your schedule. If you have no plan, and your plan is to “figure it out and text” at the last minute, then your potential for success diminishes greatly. Align your plan with your goals, by scheduling your plan in a calendar. Instead of texting for directions or meeting locations or times at the last minute, usually while driving and walking, pre-plan your meeting in advance and call or e-mail the information. Then use the time while driving to clear your mind and prepare for your meeting. That will produce far more effective and successful meetings than texting at the last minute. “By failing to prepare, you are preparing to fail.” –Benjamin Franklin Try this for 2 weeks Take 1 hour to plan your week by pre-scheduling all the priorities you need to accomplish in your plan for achieving your goals for the next two weeks. Put each priority in your schedule under a block of time. Allow time for travel, meals, errands, family, work outs, etc. (This takes thinking in advance, but by pre-planning, you will address any logistical challenges in preparing your plan and be able to adjust prior to your meeting or event.) Call and use your voice to communicate your plans with those you are meeting. When you get to the meeting or event, avoid texting and focus on eye contact and listening to your client, customer, vendor, or associate. In doing so, you will have less stress, higher productivity and greater success … with less aggravating, last minute, in between traffic lights and phone call texts … I guarantee it! So, put down your mobile device and start planning for Less texting and more real face time that will help you succeed in business!