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

Here’s the Big Lesson from the Mark Zuckerberg Apology Tour

Mark Zuckerberg is generating a lot of headlines. It’s too early yet to know if the old cliché “there’s no such thing as bad publicity” will eventually apply. But, what we definitely know is this is a company with too much going on at one time. Now, the merits of the scandal are in hot debate. On one hand, it’s a new practice but some marketers have come forward to explain this is just business-as-usual. Regardless, it’s started a conversation about privacy, advertising practices, and personal information security. However, this only touches the surface of the real problem — Facebook is too big. The Facebook-Google Duopoly Example Over the past few years, there’s been a lot of talk about the Google-Facebook duopoly. Now, it’s more apparent than ever these two companies are the center of the internet. Even more important is what this teaches us. Both companies are currently under heavy scrutiny — a result of their massive scales. Each company is far more than their core missions. Google is part of Alphabet, a huge conglomerate. As for Facebook, it owns Instagram, WhatsApp, Oculus, and more. Getting bigger means that you need to get more organized. Working fast and loose may have been fine for your small team of superstars, but it won’t work as well with a bigger group. As your ranks grow and positions that were filled by individuals transform into teams of people, the need to stay organized becomes amplified. —Inc.com The point here is Google is not just a search engine. Nor is Facebook only a social media network. Both are a lot more. Now, let’s distill this down to the world of small business. It’s only natural to grow and expand into new territory. The question is, when does that compromise the company’s core? In other words, growth isn’t always a good thing. How to Get Back to Business Basics One critical lesson here is the fact that when a business grows, does it grow to meet the needs of its customers? Or, does it expand to other areas for the sake of chasing profit. Of course, there’s nothing wrong with adding new revenue streams. But, there is something very wrong about letting it harm core competency. Here’s a few suggestions for how to get back to business basics: Listen to your customers. More customers are one sign that your business is growing. As your customer base increases, it becomes more and more difficult to stay in-touch. So, start listening in earnest again. There are several ways to do this beyond personal interaction, if necessary. Surveys, email, and more are valuable resources. Give your team a real voice. Just because your business is larger doesn’t mean that you need to only rely on a few key people. Chances are excellent, there are team members under management who have valuable input. Solicit from them periodically and take their insight to heart. Purge all the extra stuff. When a company grows beyond its initial offerings, it breaks its old parameters. Which means often journeying out to untested waters. Problems inevitably ensue. So, stop trying to force what’s not working and let it go. Get an outside perspective. Companies can easily lose sight of their identity. If a random person can’t immediately identify what your company does, or names off a bunch of things confusingly, that’s a bad sign. Bring in an experienced business coach to give you that much-needed outside perspective. Have you experienced a time when you needed to get back to basics? What other advice would you offer? Please share your thoughts and experiences by joining the conversation! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

3 Unconscious Mental Blocks Your Routine Creates that Hold Your Business Back

Your routine is your frenemy. Let’s repeat this paradoxical reality again. Your daily routine is your frenemy. It’s an often unspoken, difficult truth. Something most of us either ignore or just never think about. Regardless, it is inescapable, because there are two sides to everything. And your daily routine is certainly no exception. What is supposed to be highly advantageous, can also unleash equal disadvantages. So, it’s time to look at this with a curious, open mind. Biggest Daily Routine Benefits Routines obviously have their benefits. Otherwise, we would not institute and follow them at all. For example, keeping you on time and task certainly is a huge advantage. By following a routine, you are much less likely to get distracted and you’ll complete priorities in order of importance. Additionally, a routine helps with the ebb and flow of life. Which is to say, uncomfortable or emergency situations. It’s a fundamental truth that sometimes the greatest barrier to your success is yourself. Not that you don’t try, aren’t talented, or don’t have the resources to succeed–you do. It’s just that a self-limiting mindset can creep into your worldview without you realizing it, keeping the achievement of your goals forever on an unreachable horizon. —Inc.com It’s common advice that when you’re in unfamiliar territory and feel overwhelmed, settle back into your routine. This helps you to relax and look at the bigger picture. Ultimately, it gives you the calming effect of being in control. Moreover, a routine lets you to chart your progress throughout the day. You feel a sense of accomplishment with each line item you cross off your list. 3 Ways Your Routine Sabotages Your Business Although routines are beneficial on one hand, on the other, they can be downright detrimental. We usually don’t see these disadvantages because routines offer a sense of continuity and comfort — to mindsets that can be counterproductive. Here are three unconscious mental blocks that your routines create and hold back your business: You feel satisfied. There’s nothing quite like the feeling of satisfaction. It puts your mind at ease and lets you put your brain on idle. And, that’s the very problem with the mind being satisfied — the satiation is an impediment to wanting and doing more. When you are satisfied, you stop and disengage. Done too often, this is a recipe for stagnation. You’re not as creative. Have you ever noticed those “eureka” moments are now few and far between, or worse yet, absent entirely? When you started your business, you did so with enthusiasm, drive, and purpose. But, you’ve come to a point where you’re not nearly creative as you were in the past. That’s because you’re just following a routine, which means your no longer freeing yourself to think outside of the box. You can’t envision a different future Sure, the future is always uncertain. However, there’s a difference between not knowing and not dreaming. If you hit enough of your goals, you’ll probably stop thinking about reaching new achievements and that is tantamount to not reimagining your possible future. After all, as time goes by, changes occur and the future might actually look completely different than it did before. What other ways do routines undermine your success? Please take a moment to share your thoughts and experiences. Your unique perspective just might help one or several people out! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

Microsoft just Demonstrated Why the Hard Sell doesn’t Work — Again

Microsoft just undermined its launch of its newly released Edge browser by hard selling it. You may not know about this because it’s niche-worthy news. But, it’s a lesson that the company should have learned many years ago. Instead, it continues to make the same mistake over and over again. Here’s what it is, what it means, and why it proves the hard sell doesn’t work. Why the Hard Sell doesn’t Work Microsoft recently introduced a new version of its Edge browser. In order to promote it, the company shamelessly inserted a conspicuous ad in its Windows 10 menu. The advertisement “suggests” that users switch from their current browser of choice over to Edge. Of course, people don’t like this assertive tactic and are taking to social media to complain about it. Small-business owners successful at sales know the best way to sell something is not to sell it. You listen to potential customers about what they want or need, and then you introduce your product as the answer. You want people to think buying your services was their idea. —American Express Turns out that Microsoft is not willing to learn from its many repeated mistakes of the past. That is, the corporation’s insistence on pushing its customers into buying or using proprietary products and services that are promoted through the company’s various platforms. This is not only annoying, it’s obnoxious. Plus, it demonstrates the many problems with hard selling. There is no empathy, no relationship, no trust, and so it goes against human nature. Trying to badger people into becoming loyal customers is simply not a winning strategy. 3 Proven Ways to Sell without Being Pushy (or Obnoxious) So, how do you promote your products and/or services without hard selling? It’s actually easier than one would think. Better yet, it works and works very well. Here are three effective ways to sell without being pushy or obnoxious: Take your time. Rushing will only backfire. When you sell at a hurried pace, you don’t give your customer enough time to process what you’re offering. It’s confusing and overwhelming and unsurprisingly, it typically won’t work. Let potential customers do all the talking. Well, maybe not all the talking, but most definitely, the majority of it. This way, you’ll learn quite a bit about him or her and gain a better understanding of his or her needs. You’ll be regarded as empathetic and trustworthy and those two key elements are important to building any relationship. Focus on their problem, not your product or service. This goes hand-in-hand with the second point. You need to understand precisely what their problem is in order to offer an effective solution. You won’t be forcing a sale, but rather giving them answers they need. What other strategies do you use in-place of hard selling techniques? Please comment and share your thoughts and experiences! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »