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

Small Business Owners in the Trades – Should You Provide Your Techs with Tools or Have Them Supply Their Own?

Trades-based small business owners, from plumbers and electricians to HVAC and carpenters, often ask one question that sparks debate among newcomers and seasoned professionals alike: should you provide your technicians with tools, or should they bring their own to the job? This decision is far from trivial because it can significantly impact your business’s operations, finances, and even team dynamics. On one hand, supplying tools ensures consistency and control over equipment quality, but it comes with substantial upfront costs and ongoing maintenance responsibilities. On the other, having techs supply their own tools can reduce your overhead and potentially attract more experienced professionals, but it may lead to inconsistencies in work quality and create liability concerns. With this in mind, it’s important to take a close look at the pros and cons of each approach, exploring how this choice can affect your bottom line, workforce satisfaction, and overall business efficiency. Whether you’re a seasoned trades business owner re-evaluating your current policy or even a newcomer to the industry trying to make an informed decision, this short but informative guide will help you navigate this crucial aspect of managing a trades-based small business. Tools of the Trade: Should Small Business Owners Provide Them or Let Techs Bring Their Own? When you’re running a small business in the trades, every decision counts. One big question you might face is whether to provide tools for your techs or let them supply their own. This choice can shape your business culture, affect costs, and influence your workers’ morale. So, what’s the right move for you? Well, it depends on several factors, some of which are more consequential than others. Now, let’s get into the nitty-gritty and provide a few answers. Why You Might Want to Supply Tools Providing tools shows commitment to your employees. Just think about it: when you hand over a quality tool, it sends a message. It says, “I trust you to do your best work.” Plus, you can control the quality of the gear. If you’ve ever used a low-quality drill or a dull saw, you know how much it can affect the job. When you supply reliable tools, you ensure that your team has what they need to get the job done right. Consider this scenario: you have a new tech on your team. You give them top-notch tools. They feel valued and more confident about their work. That confidence can translate into higher-quality results and fewer mistakes. When you supply the tools, you can also streamline your operations. Everyone uses the same gear, which means less time wasted figuring things out. But, don’t forget about cost factors, either. Supplying tools means you’ll have to spend money upfront. Depending on your business size and the number of employees, this can add up fast. If your workers have their tools, you can save some pretty penny while also encouraging them to bring their best selves to work. The Case for Techs Bringing Their Own Tools On the flip side, letting your techs supply their tools can encourage a sense of ownership. When someone buys their tools, they’re likely to take better care of them (and not forget them on a job site). That personal investment can lead to pride in their work. Also, if your techs have their own favorite tools, they probably know how to use them best. This familiarity can speed up jobs and enhance quality. When the tools are owned by your employees, they’re the master of their domain. No need to seek approval from anyone – not even the boss. This makes their freedom palpable. Techs don’t have to wait for a painfully slow approval process. Plus, they don’t have to suffer delays to wait for the tools to arrive. All they need is right there, ready for them to pick up and put to use. Techs who own their own tools feel empowered to work on their term. They can dive into a project without bureaucratic hurdles or logistical roadblocks. Finding the Right Balance So, where does that leave you? It’s not always black and white. Some businesses choose a middle ground. For example, you might provide basic tools and let your techs bring specialized ones. This way, you maintain quality without breaking the bank. Additionally, think about offering incentives for tool maintenance. A tool bonus could encourage your employees to keep their gear in shape, whether it’s yours or theirs. The Team Factor Now, let’s look at team dynamics, which play a crucial role in this decision. If you have a collaborative environment, having similar tools might strengthen that bond. Everyone’s working with the same equipment, which can foster teamwork. On the contrary, if your crew thrives on individuality, let them shine with their personal tools. Moreover, open communication is key. Ask your techs what they prefer. You might discover a shared sentiment that could guide your decision. Creating a culture of inclusiveness not only builds trust but also enhances productivity. Consider the Following Whether you provide tools or let your techs supply their own is a complex choice, shaped by your business goals, team dynamics, and budget. Whichever path you choose, prioritize your team’s needs and consider the long-term implications. Remember, successful businesses don’t just focus on profit; they also invest in their people. In the end, your decision will set the tone for your workplace, creating a space where everyone can thrive. Want to Accomplish More? Do you want your company to grow faster and earn more while you spend more time with your family doing all the things 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,

Read More »

Elon Musk, Twitter, and Bogus Business Numbers Teach this One Simple Lesson

Elon Musk’s acquisition of Twitter is full of drama. It’s one of the biggest deals in the world of social media. What makes it so fascinating is the many bomb drops that continue to detonate, drawing huge public attention. Among the latest is about the actual number of bots on the microblog. Musk threatened to walk away if the company can’t provide proof positive about the percentage of fake accounts, citing his offer was predicated on official SEC filings. Turns out, there might be a lot Twitter is hiding from the public and this is a prime teaching example. Why Businesses should Never Mislead the Public or Consumers As a business owner, you should be aware of the consequences of misleading the public. When businesses knowingly deceive their consumers, it can lead to disastrous results. Not only can it ruin your reputation and cost you customers, but it can also lead to legal trouble. In this article, we will discuss the consequences of misleading the public and why honesty is always the best policy. One of the most influential propositions in marketing is that customer satisfaction begets loyalty, and loyalty begets profits. Why, then, do so many companies infuriate their customers by binding them with contracts, bleeding them with fees, confounding them with fine print, and otherwise penalizing them for their business? Because, unfortunately, it pays. Companies have found that confused and ill-informed customers, who often end up making poor purchasing decisions, can be highly profitable indeed. —Harvard Business Review Deceptive advertising is one of the most common ways that businesses mislead the public. This can take many forms, such as false claims about a product’s effectiveness, exaggerated claims about sales figures, or even making false promises about what a product can do. In some cases, businesses may even resort to fraudulent activities, such as selling counterfeit products or engaging in bait-and-switch schemes. Consumers rely on businesses to be truthful about their products and services. When businesses engage in deceptive practices, it erodes consumer trust and confidence. This can lead to lost business and customers turning to your competitors. In addition, if you are caught deceiving consumers, you could face legal action from state attorneys general or the Federal Trade Commission. The bottom line is that honesty is the best policy when it comes to running a business. Misleading the public may seem like a quick and easy way to make a profit, but in the long run, it will only lead to problems. Be truthful about your products and services, and you will build trust with your customers that will last for years to come. Have you ever been misled by a business? How did it make you feel? Share your story in the comments below. And if you’re a business owner, remember – always be honest with your customers! It’s the best policy for ensuring long-term success. Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

The Landlord is Seriously Raising My Business Space Rent – What are My Options?

Commercial tenants can expect their rent to go up every year. In fact, it’s a bit unusual for the rate not to increase at the end of a lease. But sometimes, unscrupulous landlords will take advantage of their tenants’ naivete and exercise a somewhat obscure clause that allows them to up the rental rate substantially. So much, that it can increase by a relatively high percentage, thus making it virtually unaffordable. Fortunately, there are some options commercial tenants have in these situations. Business Owners, Know Your Lease Although it may seem completely obvious or self-evident, don’t just skim over any commercial lease. If necessary, pay an attorney to look it over and explain it to you on a very elementary basis. Or, go over it carefully yourself and if you don’t understand something, be sure to research it on your own – do not just take the landlord’s word for what it truly means. There’s no standard agreement for commercial leases. In fact, negotiating the terms of commercial leases is usually expected. Depending on the state of the commercial real estate market, a business may be able to obtain significant concessions from a landlord. A property owner with a largely vacant business park, for example, will most likely make allowances. On the other hand, the business renting the space will have less control over the terms of a lease in a hot rental market or when renting a premium space. —FindLaw Small Business We’re not going to get into commercial lease types, because there are many kinds. But, it is quite common for leases to contain various expenses besides just renting pure square feet, including common area maintenance and repairs, and other expenses. However, it certainly isn’t unheard of that tenants get stuck with even more expenses related to their business rentals. So, again, be sure to understand the lease before you sign on the dotted line in order to avoid any confusion or surprises in the future. What To Do When Your Business Rent goes Up Unexpectedly If the commercial space you’re leasing for your business goes up dramatically, you do have some options available, though they may not always be the best. Here are a few things you can do if the landlord raises the rental rate on your commercial space: Do your research first. Start by getting a firm grasp on your state’s commercial rental laws. This won’t necessarily be a fun task, but a very necessary one. If you understand how these laws work, you may find something in your favor. At the very least, you’ll have more knowledge about how the landlord-tenant laws work in your state and will be wiser to make better decisions in the future. Survey the local market. The next thing you should do is to start looking at other commercial spaces immediately. You just may find some deals out there that would allow you to either lower your current rental rate or be competitive. Because of the pandemic disruption, many commercial landlords are desperate for tenants, since so many businesses have adopted work-from-home and hybrid models. Try to renegotiate your current lease. Another option is to try to renegotiate the lease on the property you are currently occupying. You can use your newfound knowledge of the law and of the local market opportunities to your advantage. This is especially helpful if you really want to avoid the hassles of moving your operation elsewhere, and the landlord is willing to be reasonable. How else would you deal with a sudden commercial rent increase? Please take a few moments 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.

Read More »