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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Custer’s Last Stand, the Dade Massacre, and Your Business

January 10, 2025 No Comments

Small business owners often wear many hats, juggling the roles of visionary, manager, marketer, and more. While confidence is a crucial trait for any entrepreneur, unchecked arrogance and overconfidence can lead to a series of missteps that can threaten the very survival of a business.

Coronavirus Presents an Opportunity to Teach Your Children about Business

June 16, 2020 No Comments

The Sword of Damocles tells a very important story about the stark reality of being in a position of power. For those unfamiliar, Damocles is a court sycophant or flatterer, who pines for the power of King Dionysus II. The king gives his throne to Damocles, who in-turn enjoys fine food and drink, opulence, and entertainment, only to be surprised by a razor-sharp sword dangling over his head, held in-place by a single horsehair. In an instant, Damocles learns power comes with a price. That every leader is under constant threat of being replaced or worse. Crisis can Turn into Opportunity A pandemic was probably the furthest thing on any business leader’s mind prior to the outbreak of COVID-19. Now, hindsight being 20/20, it’s easy to see the sword comes in many forms. And, it’s a great time to teach your children about the inevitable ups and downs of owning and running a business. By becoming an entrepreneur — whether it is simply putting up a neighborhood lemonade stand, launching a landscaping business or developing a new app — kids can learn about budgeting, saving, spending and investing. —CNBC.com You can teach many lessons by having your kid(s) start and operate a small business. But, as we adults know, failure is where the hard but necessary lessons lie. Use this crisis to show your children how to cope and face adversity. It’s a terrific time because there’s no shortage of awareness about the outbreak and quarantines. Meaning, there’s a lot of context and therefore, makes it easier to use real-world examples. Three Lessons the Coronavirus Business Owners can Teach their Kids The moment we’re all experiencing as business owners, managers, and team leaders causes us to question a whole lot of things. And, that’s not a bad thing, especially when it comes to teaching business lessons to children who can later use that information. Here are three important business lessons entrepreneurs can teach their kids: Debt. Everyone knows the risk accumulating debt carries. But, it’s so commonplace, we just don’t appreciate how dangerous it can be when things go wrong. While debt is very often used by companies of all shapes and sizes, when there’s a disruption in the economy, it remains an obligation that can’t be ignored. Debt is sometimes necessary but when it’s used in excess, it can financially ruin a business and even personal lives in a devastating way. Hard choices. Another important lesson to teach is about having to make tough decisions. Being able to evaluate the circumstances, choose essential personnel, and identify where cuts can be made certainly isn’t easy. But, it’s a wonderful life lesson to relate that will make a life-long impression. Streamlining. Call it identifying redundancy or creating efficiency. If you take an honest look at everything inside your business, you’re going to find unnecessary duplication or just flat out waste. Use these examples and make them relatable on an age-appropriate level. What other lessons would you add to this list? Please share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Effective Ways to Deal with an Unpredictable Schedule

June 3, 2021 No Comments

An unpredictable schedule is a chaotic one. And, it can confuse and/or frustrate anyone who experiences such uncertainty. After all, it’s better to know what’s coming and have a heads-up, in order to be prepared. But, that’s not always the case and it can wreak havoc psychologically and emotionally. Eventually, an unpredictable schedule can lead to total burnout. So, read on to learn some of the best ways to cope and take control of an otherwise unpredictable schedule. Chaos is Counterproductive Some entrepreneurs claim they really like uncertainty and the surprises associated with “going with the flow.” At least, they may say this to others, but when it comes down to it, aren’t very keen on unpredictable schedules. They’d much rather have their days planned out in order to maximize their productivity and budget their time wisely. These things can’t really be accomplished when schedules fluctuate too much. It’s just not feasible to effectively plan and execute when every little thing is completely on-the-fly. Workers at the top and bottom of the economic spectrum feel the loss of control dearly, and technology is often the culprit. Whether it’s a buzzing smartphone or software that tracks our whereabouts, the more hard to predict our schedules become, the less real flexibility many of us have. —Harvard Business Review Although this may work in a micro sense, like during the course of an ordinary day that’s gone a bit awry, or during free time, such as vacation, a truly unpredictable schedule is tumultuous. And this breeds confusion, anxiety, as well as a sense of being out of control. Those simply aren’t good emotions to experience while running a business, so it’s necessary to make adjustments in order to produce a more predictable schedule. Effective Ways to Deal with an Unpredictable Schedule The business owners who succeed not only have a vision, but an actionable plan to follow. Of course, it’s not possible to plan out every scenario. But, it is advantageous to take as much control as you can. Fortunately, there are effective strategies for dealing with an unpredictable schedule: Structure your non-work day. The very first thing you need to do is begin structuring your non-work time. While this might seem strange, it helps you to build a healthy habit and there’s no better place to start than your non-working days, which are often free-for-all situations. If you can put even a loose schedule to your non-working days, you can most certainly do that in the office or out on the road. Establish work-related boundaries. One of the most difficult things for any entrepreneur to do is establish boundaries between their free time and their work time. Business owners, by their very nature, are concerned about their companies well-being and take every opportunity to ensure that it’s running properly. But, this all too frequently leaves to work intruding into free time, which can severely detract from personal relationships, particularly when it comes to spouses and children. So, set boundaries for your work and personal times in order to maintain a healthy balance. Allow for work flexibility and continuity. If your schedule changes quite substantially from day to day, that’s okay too. Instead of scheduling and entire day from one appointment or task to another, set aside blocks of time and prioritize accordingly. This way, you’ll be able to accomplish what you most need to, when you are able, instead of trying to pound a square peg into a round hole. Reward yourself when you accomplish goals. As always, it’s a good idea to reward yourself when you accomplish a goal, be it big or small. Part of the process can be redefining or redesigning your schedule to be more predictable and therefore, allow you to be more productive. What other suggestions do you have? Please take a few minutes to share your own thoughts and feelings so that others can benefit from your experiences and perspective! Interested in learning more about business? Then just visit Waters Business Consulting Group.