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

Comic illustration

Effective Ways to Deal with a Setback

Setbacks are inevitable. They come in many shapes and sizes and some appear from out of the blue. When you encounter a setback, it triggers different emotions. You feel shocked, unprepared, perhaps angry or down. It’s only natural to feel bad after a setback but it’s how you handle it that really matters most. How to Overcome a Setback Everyone experiences setbacks, large and small. During these times it’s easy to feel overwhelmed and maybe even unappreciated. (This is especially true when it involves an interpersonal relationship.) Minor setbacks throw us off for a few hours but others are much more significant and really throw us in a tailspin. While we will all experience roadblocks, we will differ in how we handle them. Some of us have the resilience to just pick up the pieces and move on. Others find it difficult to let go. Either way, how do we learn from the tough times? —Entrepreneur.com Whatever the cause and no matter the size, it’s important to understand you aren’t out of options. Sure, you feel helpless to one degree or another. And, it does bring into question what’s all that time and effort for, anyway? But, if you put things into perspective, you’ll begin to realize it’s not the end-all, be-all. Effective Ways to Deal with a Setback We all know adversary helps to build character. Although, no one welcomes tough times, whether in the form of a setback or something else. So, here are some effective ways to deal with a setback you can put to use: It’s only temporary. Very few setbacks are insurmountable. And, most are only temporary. Realize it is just a temporary situation that will pass. It will only linger and bother you the longer you allow it. If you put it into perspective, it’s merely one of many temporary obstacles. Your goals remain. Sure, it does bring into question what all your hard work is for in the first place. And, it undermines your sense of accomplishment and success. While these are certainly true, it doesn’t change your goals. Refocus on your goals to help you overcome. Reset the timetable. Any setback will throw off the timeline, there’s little way around this fact. But, that doesn’t mean you can adapt and readjust your timetable to make it workable again. Take action, right away. Of course, the worst response is to do nothing at all. It will not get you past the situation and will only serve to make it haunt you even more. Take action straight away and you’ll start to feel better immediately. What other methods would you suggest to get past a setback? Please share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »
Money illustration

What to Do with an Unwanted Inherited Business

Owning a business is not something that everyone aspires to do. Sure, many people like the idea of being their own boss. But, there are definitely individuals who prefer to avoid the stress and anxiety of being an entrepreneur. Of course, there are many different sets of circumstances. For instance, children who follow their parents and run the family business, taking it over after their parents retire. Or, people who unintentionally fall into their own business without actually setting out to do so. For example, someone who inherits a business from a relative. Although this might seem a bit far-fetched, it does happen more often than one would think. So, what options are available to an heir who really does not want to take over the business? Types of Inherited Businesses Probably the most common form of an inherited business is a family company. Usually, the children grow up in and around the operation and are at least familiar with it. Other times, the children aspire to follow their own career path and never work in the organization. Additionally, there are heirs who inherit a family-owned business that they have never really been acquainted with whatsoever. If you’ve inherited a company, there might be a lot of questions on your mind. You might not want to be an entrepreneur, or even if you do, you might prefer to work in a different industry. Even if you’re ready to take on the business, you might be unsure about how to deal with current employees and suppliers. —Nerd Wallet Though these circumstances are far less common, they do occur. One prime example is someone who inherits a commercial property. That property is leased by several other businesses and generates a profit. The owners may not even be directly involved with the day-to-day operation and rely on a firm or individual to handle the necessities. These would include things like maintenance, repairs, negotiating leases, upgrades, and more. What to Do with an Unwanted Inherited Business Your first instinct could be to just sell it and be out of the situation as quickly as possible. But, if it’s generating a consistent profit, that might not be a wise idea. On the other hand, even if it does generate a profit and you’re completely unfamiliar with it, it could turn into a gigantic mess. Here are some possible options to explore: Learn about the business. Regardless if you’re set on selling it or remotely considering taking it over, you’ve got to know what you’re dealing with first. It’s imperative that you educate yourself about the business in order to make an informed decision as to which way to go. Don’t make the mistake of letting your emotions take over. Instead, take at least a little time to understand precisely what it is and more importantly, how much it’s really worth. Consider being an absentee owner. Although this is quite common in the business world, it’s always a risky proposition. And, it’s probably why you don’t want to get involved in the first place. If you let other people run it, you’re putting your trust into others and that could easily lead to a very regrettable set of circumstances. However, if it is something like commercial property and your relative was also an absentee owner, at least give it some serious thought. Invest in the business. If you do want to give it a try, don’t go it alone. Bring in a business coach to guide you through the process of taking on an entrepreneurial role and become familiar with all it takes to head up this type of operation. If you find it isn’t a good fit, you can always sell it and move on. What other suggestions would you give someone in this position? Please take a moment to share your thoughts and experiences so others can benefit from your perspective! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

How to Set Business Product and Service Prices

Pricing products and services is difficult for any new business owner. Though it might seem to be a simple equation, that’s hardly the case. There are quite a few factors which go into setting your price or prices. Even within industries that buy from manufacturers to sell directly to consumers, there are variables from one vendor to another. Location is part of pricing, not just distance, but also demand and population. Services aren’t much different in this respect. Let’s say that you’re a dietitian, and you work with various doctors, hospitals, and gyms over a large geographic region. You travel quite a bit, so you go from big cities to rural communities. Chances are excellent you’ll charge more for your professional services in the metropolitan area than you will in sparsely populated rural areas. How to Set Business Product and Service Prices One important aspect to keep in mind when setting prices for goods and/or services, is they are promises to your customers. A price reflects value and consumers are careful about which products and/or services they choose. This means that price, while a very important factor, isn’t the only consideration consumers take into account when purchasing. For instance, a big bag of individually wrapped chips complete with select flavors is priced for $6.99. Next to it is a generic store brand priced at $4.99. Based solely on price, you’d opt to save $2 and go with the store brand. After all, you’ll save money and the chips will taste the same. Price is the most important factor in determining profit. Yet countless businesses fail to get their pricing strategy right. The price you charge for your products or services is directly related to your Cost of Goods (labor & materials to produce the product/service), your overhead and the competition or demand. Your focus needs to be on your desired Gross Margin. Price is a major way you communicate your firm’s value in the marketplace. Yet many small business owners set prices arbitrarily or sheepishly follow the crowd. —Bloomberg Business Now as you wind your way through the grocery store you visit the meat department. Inside the display case there are four ready-to-cook hamburger patties made mouthwatering with fresh bacon bits and cheese and is priced at $12.49. Right across the aisle in the frozen section there’s a 10-count box of plain, frozen hamburgers for $9.99. Suddenly, saving $2.50 doesn’t seem worthwhile and you splurge because the fresh, mouthwatering ready-to-cook hamburgers are simply irresistible. The point, of course, is perceived value — you’ll have to base your business’ product and service prices on their value. However, that’s just one factor of many others which go into pricing. Here are some steps you can take to help you set the right price: Learn about demand in your area. No matter how wonderful your product or service might be, if there’s no demand for it in the area, it won’t sell. Think about the old sales joke, “Selling ketchup popsicle sticks to customers in white gloves.” Obviously, people wearing white gloves have no need for such a mess. The same holds true for demand in your area. If you’re selling snow shovels, it’s should be to consumers in climates where it snows. Check out competitors’ pricing. This is a simple way of learning what consumers will pay for a product or service. Of course, you should only rely on established prices by flourishing businesses. Always factor-in costs. There’s no getting around the fact that it costs money to run a business. Even freelancer contractors have operating costs. For brick-and-mortar operations, there’s rent, utilities, insurance, inventory, employee pay and benefits, and other costs. Be willing to discount. One way retailers sell products is by offering discounts. This is a great strategy, if it doesn’t wipe-out your margin, or it’s a one-time deal to establish a relationship for future business. Don’t undercut simply to attract business. A big mistake that some new to business make is to undercut competitor pricing, only to learn the hard way they can’t deliver. After all, it does no good to attract business if customers aren’t receiving what they expect. Pricing is a science and an art. The science is an equation based on your Labor + Materials (Cost of Goods) divided by your desired Margin or divisor. If you desire a 40% Gross Profit Margin (the amount left over after you cover your Labor and Materials), then your divisor is 60% and not a 40% markup. Using a 60% divisor based off your Cost of Goods will yield a 40% Gross Profit Margin. A mistake many businesses make is to mark up their Cost of Goods which yields a lesser Gross Profit Margin closer to 28%. We call this “Profit by Accident”. Because it is feasible to guarantee your business makes a profit, we developed our “Profit by Design” strategy. Contact us for a complimentary consultation to review your pricing strategy and learn more about “Profit by Design”. Now, what about the art of pricing? The art is in the research, testing, creative marketing and demand for your product or service and how you promote its value. The art is in your ability to pivot and massage all of the components (labor, materials, overhead, marketing, value, customer perception, etc.) to work together. Combined, you will develop a pricing strategy that proves out in your bottom line profits and more money in your pockets! Pricing is a delicate balance, but with some research and a bit of critical thinking, you’ll be able to set prices for your business’ products and/or services. Do you know and understand your pricing strategy, or is yours Profit by Accident? [shareaholic app=”follow_buttons” id=”26833294″]

Read More »

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.

Sign up below for a free consultative session to learn what your business could be worth today and in the future! 

Thank you for your interest in learning what your business is worth. We will be in touch shortly.