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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Is Finding Skilled Trades Employees Impossible? Think Again!

May 1, 2025 No Comments

What’s the biggest problem facing most small businesses in the trades? If you ask an owner-entrepreneur, one answer stands above the rest—finding good employees who want to work, do a good job, and are consistently reliable.

How to Avoid People Who Waste Your Time

May 24, 2017 No Comments

Successful business entrepreneurs obsess over their companies and know instinctively the phrase, “time is money,” is true. It’s why business owners hire others to do tasks they could otherwise do themselves: accounting, marketing, paperwork, and so on. However, not everyone in the world of business is adept at executing, some, talk and do so a lot — a whole lot. They procrastinate, squander time on trivial tasks, and have long conversations without an objective. What’s worse, is some of us are not only susceptible to time wasters, we’re also enablers. How to Avoid People who Waste Your Time Enablers are generally very caring, thoughtful individuals and they don’t like to hurt others’ feelings. Even business people who are laser focused and get things done are time waster enablers, because they interact and hire them. While it seems completely counterintuitive, you don’t really know a person’s qualities until you get to know him or her through your work together. Someone might appear to be just as focused and enthusiastic but appearances can be misleading. We’re all too busy, spending our days in back-to-back meetings and our nights feverishly responding to emails. (Adam Grant, a famously responsive Wharton professor, told me that on an “average day” he’ll spend 3-4 hours answering messages.) That’s why people who waste our time have become the scourge of modern business life, hampering our productivity and annoying us in the process. —Harvard Business Review You contract and hire individuals based on their previous work but it isn’t until you really begin to interact with them you learn their true character traits. While you might be impressed with their body of work, you probably aren’t at all eager to become a victim of someone who wastes your time. The really big problem to overcome is to spot time wasters and that’s very difficult, because it could be anybody, not just an employee or contractor, but also a partner, vendor, customer or client. The trick is to identify as soon as possible those who are most likely to waste your time from those who get things done. You can do this by looking for certain personality extremes: Negative individuals. Head down, slumped shoulders, complete with a scowl or frown, negative people tend to broadcast their misery physically with body language. Even those who manage to look composed will definitely show their true colors when speaking. They portray themselves as victims, bring you and others down, and worst of all, waste your time. Super happy people. Happy-go-luckily, big smile, with large, enthusiastic stride, super happy individuals might be a blast and cheer others up, but, these people can be a bit too exuberant. These can easily be signs of immaturity and even though jubilant, they’re not serious about much of anything. These individuals will definitely liven up a room, but, they’ll also waste your time and do so with a big grin and bellowing laughter. You’ll be trying to get things done while they’re cracking jokes and carrying-on. Gossip spreaders. People who can’t wait to tell you the latest about this or that with him or her are to be avoided at all costs because they’re involving you in the drama as well, even if you don’t know it. Individuals that take gossip to a whole new level aren’t interested about getting things done, they are only interested in spreading rumors and stirring-up drama to justify their agenda. Emotional people. Speaking of drama, those who revel in spreading rumors and gossiping can also be very prone to being emotional. They go from one extreme to another and never seem to be on an even keel. These individuals do little else than waste their own time, as well as others. They tend to be irrational and irritable and ought to be completely avoided. Another two personality types who can be total time wasters are attention seekers and self-centered individuals. The former will always want to be the center of attention, no matter where they might be, while the latter will step on toes and cross lines in a self-serving manner. This is why it’s imperative to surround yourself with positive, focused individuals who get things done and share your enthusiasm so that you can achieve your goals. Want to find out about what a business coach can do for you? [shareaholic app=”follow_buttons” id=”26833294″]

How To Network during Periods of Instability

October 15, 2021 No Comments

Despite the reopenings across the country, many places have still yet to return to normal, pre-pandemic schedules. Several offices continue to allow employees to work entirely from home, or only require minimal in-office workdays, usually just one or two. Meanwhile, small business owners also continue to experience disruptions in their operations, due to a labor shortage, shortage of materials and supplies, and other abnormalities. Plus, several professional associations are not holding annual meetings, or have greatly altered, meaning mostly reduced, their events and in-person get-togethers. All of these unusual occurrences have likewise lead to fewer opportunities to network, but this form of relationship-building still remains essential. The Importance of Networking Consistently Even during normal times, regular networking is important for career professionals and entrepreneurs alike. It provides them with the opportunity to meet new people and gain a new perspective. Networking also helps them discover other types of opportunities, including career advancement, product innovations, and possible future alternative routes. Networking has always been essential to small business owners because it costs little to nothing and helps them create brand awareness. Small business owners use networking as a means to form relationships with others, in like or related fields, that help to expand their business’s ability to find new customers, partner, and grow. A key element to effective networking is to make you known. The premise being that the more people you meet, the more people there will be to get to know and remember both you and your business. You should use every professional and social opportunity to meet and connect with new people.–Olympia Benefits Networking also offers a few other benefits, such as improving social skills, being exposed to new environments, and forming new relationships, both professional and personal. In other words, networking isn’t just about selling products and services, it also is a prime environment for self-enrichment. Too few people see these qualities and only network purely for the sales aspect. Regardless, this relationship-building activity still remains extremely important, even though there are many abnormalities that persist, even well after the pandemic reopenings. How To Continue to Network during Unstable Times There have been periods in the past that have completely disrupted the entire business and economic landscape. Perhaps the most recent and largest in modern history began in earnest in 2008, continuing for several years and what is now referred to as the Great Recession. Although this was mostly related to the housing sector, its effects reached practically every corner of commerce in one way or another. Both business owners and consumers had to adapt, with people leaving long careers to go in entirely different fields of work. Similarly, business owners changed their models in order to survive and return when economic circumstances permitted. During this time, networking became very important not only to sell products and services but to find new opportunities. Here are a few helpful suggestions for networking during such times of upheaval: Change your mindset. Perhaps the biggest obstacle to overcome isn’t in external factors but is entirely internalized. That is to say, it’s very difficult to not only identify but change one’s mindset. Your attitude and outlook will have much to do with this and it’s critical to understand how your approaching the world as so many people’s lives and other businesses are still in a state of disruption. Be flexible with your schedule. Your old way of networking might still be partly or mostly intact. If so, that’s very good news and you won’t have to make many adjustments. However, if very little has returned to normal or is still in a state of flux, you’ll need to be flexible in order to find the time and places to network. This is also a great opportunity to think outside the box and identifies places where you did not network before. Temper your normal sales approach. Since things are not completely back to normal for everyone, it’s best to pull back on the sales talk. Instead, make it more about building new relationships, whether they are professional or personal. This might not be of big benefit now but could prove very advantageous in the future. What other strategies can be used to network during unusual economic times? Please take a few minutes to share your thoughts and experiences so others can benefit from your input! Interested in learning more about business? Then just visit Waters Business Consulting Group.