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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5 Words Smart Entrepreneurs Always Avoid

We all have our quirks when it comes to language and nowhere is it more prominent than email. Because there is no body language, gesticulations, facial expressions, and attitude, we are left to find context, solely from the words we read. When you think about that for a moment, it’s a wonder that any business gets done from day-to-day. Ironically, just two years ago, a study conducted in the United Kingdom, surveying 2,500 office employees, revealed that an astounding 94 percent preferred email over telephones. It’s clear that email is our number one means of communication, and, because it’s become so commonplace, we don’t regard it in the same way as we do face-to-face encounters. Our demeanor, tone, and delivery differs greatly from email to spoken word. Since email is so important to business, you would think that it’s used in the utmost professional manner, but, it’s not. 5 Words Smart Entrepreneurs Always Avoid The fact is, we just don’t pay attention to what we’re writing most of the time. To many business professionals, it’s an informal method of communication, and, it’s closest cousin, texting, is even more relaxed (read: lazy). However, that’s simply not the case. Email is important, so much so, it can make all the difference. The words you type or tap are going to be read by someone else. That person or persons will not only read what’s in the message body, but read into the message itself. If you want to become more successful as an entrepreneur or in your career, you can start by making a habit of talking and thinking more like the people you know or read about who are already successful. —Entrepreneur Let that stir a moment and go back to the introduction. Since there’s no interpersonal communication, every word matters. This is why smart entrepreneurs are conscience about what they write, how it’s phrased, and what message is delivered. If you aren’t practicing the same discipline, you might be sending more than an email, you might be sending a message that you lack confidence, are somewhat lazy, or, unsophisticated. Here are the top five words you ought to avoid: Might. The word “might,” is generally used in different ways, but often, it’s meant to point out a possibility. When you use the word “might,” you are essentially communicating that you’re unsure. That’s okay in casual, social situations, but dangerous in business communication. Likely. When you use the word “likely,” you are making a very unsure prediction. What you’re really doing is opening wide and wild interpretation. Here again, use of this word in social and casual conversation is fine, but, when you’re using it in the business world, you’re telling the recipient that’s it’s unlikely you are in-the-know. Alot. First of all, this is not how the phrase is spelled–it’s two separate words, “a lot.” Because it’s run together so often, it’s become commonplace for people to write it incorrectly. It’s the reason the ampersand was dropped as the last letter of the alphabet. It used to be recited, ending with “x, y, z, and ‘and per se,’” which evolved into “ampersand.” If you write, “alot,” you’re taking a risk that the recipient won’t notice you don’t know this. Won’t. This is one of the best ways to ensure a negative vibe, along with a lot of frustration. While you’re being emphatic, you’re also demonstrating just how stubborn, or, unwilling you are in your ways of doing things. Usually. This is the opposite of the pithy directive delivered so often by the Joe Friday character from Dragnet. It tells the recipient that you don’t have all the facts, nor do you care. Here’s a bonus: “irregardless.” Though there are some who say that it’s fine to use, it’s just unnecessary. Instead, use “regardless.” And remember that communication is made up of words, tone and non-verbal communication. Based on multiple studies, non-verbal carries the largest percentage of influence in communication while words carry the least amount of influence. So, picking up the phone to use your words and tone is more effective than just text or e-mail. When it is possibly or efficient, use Skype or Google Video or an actual face to face conversation to communicate more effectively. Business gets done through trusted relationships, and these are built on solid communication which ultimately requires words, tone and non-verbal. Now go build your business with good communication. Who do you need to improve your communication with this month to grow your relationship, your business or career? Want to find out about what a business coach can do for you? [shareaholic app=”follow_buttons” id=”26833294″]

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Reasons Why Small Business Loans are Denied

Small business owners can easily find themselves in the unenviable position of needing capital, but, not having ready access to cash. It presents an age-old problem, buying equipment ties cash up, even though said equipment is considered an asset. Such assets can depreciate, which worsens the situation all the more. On the cash liquidity side, there are tax consequences to having a certain level of retained earnings. This is why debt instruments are a part of doing business. However, even profitable small businesses can be denied for a loan, and, there’s ample evidence to support this phenomenon. In the first two quarters of 2014, about half of applicant businesses received any funds, according to a survey conducted by the Federal Reserve Banks of New York, Atlanta, Cleveland and Philadelphia. Reasons Why Small Business Loans are Denied Unfortunately, present trends don’t show much improvement in the access to capital, or, in reducing operational costs. In fact, since November 2014, three out of ten businesses reported more difficulty in trying to reduce operating expenses, and, one-quarter reported unexpected expenses too hard to plan for, according to a study conducted by Nav (formerly Creditera), a business credit management company. If your company recently applied for business credit and was rejected, you’re not alone. So what can you do if your business credit application is denied? Start by trying to find out why. The Federal Trade Commission suggests submitting a written request for the reasons within 60 days of the denial, and the creditor must give you the specifics in writing within 30 days of the request. Consider discussing any concerns you have with your lender, and you may be able to resolve the issues. —Washington Post Within the same survey, about 20 percent of participant companies considered closing their doors, citing two primary reasons: lack of growth and issues with positive cash flow. These factors are likely why 53 percent of all companies applied for lines of credit or loans over the past half-decade, with more than one-in-four attempting to access capital numerous times. During the same five year period, one-fifth were denied and of those, 45 percent reported being turned down more than once. Twenty-three percent of all those denied loans or lines of credit did not know the reason why their applications were denied. So, why is this happening and what makes it appear so prevalent? There are reasons why small business loans are turned down, and, it’s actually not complicated. Here are some of the most common reasons small business loans are denied: Having no credit or even bad credit. Some business owners do not realize they have two credit scores: their personal credit and their business’ credit. What’s worse, some owners have relied on personal lines of credit and have seriously driven their DTI or debt-to-income ratio into dangerous territory. Making payments on-time, keeping a low balance, and not seeking to continually open new credit lines are all necessary to improve both personal and business credit. Too little collateral. Since most business owners aren’t willing to sign a personal guarantee, leveraging their personal vehicles and home to secure a loan, there’s little to nothing left to pledge as collateral. Lenders aren’t keen and will not provide financing that constitutes an unnecessary risk. Anemic cash flow. After all other expenses are paid, lenders want to see demonstrable proof there’s enough cash to repay the loan. Too tight a margin and banks won’t be willing to approve a business loan. Lack of strategic planning. It’s often true that business owners don’t understand the loan process, including the application itself, and all necessary documentation and that can lead to being turned down. Applicants must provide a clear forecast and show a realistic, actionable plan. Under capitalization on loan applications. There are sometimes more assets available to claim than applicants realize and as a result, their loan application makes the organization appear under capitalized. Some assets aren’t immediately clear, which means all potential assets ought to be identified. Another reason businesses might have trouble securing debt instruments is industry-specific difficulties. For instance, a construction company that’s operating in a locality where people are moving away from, or, a taxi company that’s facing tougher licensing regulations or an industry disruption as we have recently seen with Uber. The best solution in the short term is to reduce your Cost of Goods (labor and materials) to improve Gross Margins and reduce Expense Overhead to increase Net Profits which will help with cash flow and operating capital. Also, negotiating terms with your Receivables and slowing growth will allow for an influx of cash. 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Imagine Selling Your Business…

How Would Your Life Change?

You didn’t start your business just to stay busy—you built it to create freedom, security, and options for yourself and your family. Selling your business can be life-changing, but the real question is whether you’re intentionally building toward that outcome or simply leaving it to chance.

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