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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Reconstruction Red Shirts Relay a Valuable Lesson Entrepreneurs Can Still Use Today

October 3, 2024 No Comments

You may not believe it, but the experiences of the Red Shirts during the post-Civil War Reconstruction era provide a powerful lesson for today’s small business owners in recognizing when a cause is futile. Why? Well, the Red Shirts were a paramilitary group that fought against Reconstruction efforts in the South, often with overwhelming odds stacked against them. Their struggle, despite fierce resistance, ultimately failed to stop the sweeping societal changes brought by federal authority. For business owners, this history can highlight the importance of recognizing situations where their efforts are likely to result in little or no success, despite emotional or ideological investment. You see, sometimes, persistence can be misdirected, leading to wasted time, resources, and energy. Instead of relentlessly pursuing a failing strategy, business owners should focus on adaptive strategies, learning when to pivot or walk away from a failing investment. In today’s business environment,, just as with the Red Shirts, recognizing when a fight is unwinnable can prevent further losses. Entrepreneurs should focus on evaluating their goals, assessing market conditions, and knowing when to change direction before a venture becomes unsustainable. Resilience in business does not always mean continuing a doomed effort, but sometimes, recognizing when to change course entirely. Learning from the Red Shirts: When to Quit Let’s recap to get the most out of this analogy. The Red Shirts, a white supremacist paramilitary group active in the American South during the Reconstruction era, faced numerous setbacks and failures in their attempts to suppress black voting and maintain white dominance. While their actions were abhorrent, their experiences can offer valuable lessons for today’s small business owners about recognizing futile situations and knowing when to give up on certain pursuits. This is particularly difficult for entrepreneurs because these self-starting, self-reliant individuals often believe they can make any situation work. With enough determination, grit, positivity, and a willingness to push past obstacles, entrepreneurs can fall into the trap of pursuing futile endeavors. So, it’s super important to recognize when something isn’t worth the time and effort. Identifying Futile Endeavors Lack of support. The Red Shirts struggled to gain widespread support, even among white Southerners. Similarly, small businesses may find it difficult to sustain themselves without adequate customer base or investor backing. Opposition. The Red Shirts faced fierce opposition from both sides, residents of the North, and the South and federal forces. Small businesses may encounter obstacles such as competition, regulatory hurdles, or negative market trends. Limited resources. The Red Shirts often lacked the necessary resources, such as funding and manpower, to achieve their goals. Small businesses may face similar constraints, such as insufficient capital or a shortage of skilled employees. Now, here’s the real kicker. It’s not just about identifying when something is futile, it’s about knowing when to give up. That’s not an easy thing for any entrepreneur to do, but on some occasions, it’s not only entirely necessary but appropriate. Knowing When to Quit Persistent failure. If a business consistently fails to meet its objectives despite repeated efforts, it may be time to reassess the situation. This could involve re-evaluating the business model, target market, or even the viability of the venture. Exhaustion of resources. When a business has exhausted its financial resources or is unable to attract additional funding, it may be necessary to consider closing down. Negative impact. If a business is causing significant stress, financial hardship, or damage to relationships, it may be time to cut losses and move on. Learning from the Past While the Red Shirts’ actions were reprehensible, their experiences can provide valuable insights for small business owners. By recognizing the signs of a futile endeavor and knowing when to quit, entrepreneurs can avoid wasting time, money, and emotional energy on ventures that are not likely to succeed. It’s important to note that giving up on a business can be a difficult decision. However, sometimes it is the most prudent course of action. By learning from the past, small business owners can make informed decisions and increase their chances of long-term success. 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,

My Business Partner is Hiding Clients from Me — How Do I Deal with this Situation?

September 7, 2021 No Comments

You’ve just found out that your business partner has been hiding clients from you. Of course, this has a number of important implications including, but not limited to: revenue, reputation, day-to-day operation, and a variety of other issues. All of these, not to mention the breach of trust and value of the interpersonal relationship. It’s a very difficult set of circumstances to deal with, but obviously, you can’t just ignore it. You must take action, not only for your own sake but for the sake of your career and the business at large. Dealing with a Bad Business Partner Emotions Anger. Disbelief. Disappointment. Resentment. Shock. Sorrow. You could easily cite any one of these negative emotions because you’ll experience at least one or more of them. Before you do anything at all, it is essential that you understand your gut reaction and the long-term feelings you’ll probably encounter as time goes on. While you will get past this situation, you’ll probably never completely get over it. And, that’s okay. Not all partnerships or deals work out well. Some just can’t formalize because of extraneous factors affecting the agreement, while others can be impacted by poor communication skills or a lack of flexibility on goals or approaches. This means that it is essential for leaders to stay aware of the state of a pending deal or partnership, especially if there are quiet signs that things aren’t going as well as they’d like. —Small Business Trends You’ve no doubt experienced difficult circumstances in the past, and this is really no different. While it may be new, it most certainly won’t be the last time. The point being, do not allow pure, raw emotion to dictate your actions. If you give in to your negative feelings, you will make rash, poor decisions that will only make things worse. You need to approach this from a calm and rational perspective. So, give yourself a little time to vent and get those negative emotions out of the way. How to Deal with a Dishonest Business Partner Who is Hiding Secret Clients Once you feel calm and collected, you’ll need to methodically approach how you will deal with the situation. Here is a brief but effective guide for the steps you can take to deal with a business partner who has been hiding clients from you: Learn as much as possible about these clients. This probably won’t be easy or pleasant. If you are able, learn as much about these secret clients as possible. You might even go so far as to contact them yourself under the guise of following up with regular business. The whole idea is to try to get the best picture you can about these secret clients. Thoroughly examine all the business’ finances. The very next thing to do is look through your business’s financial documents. While these might not reveal anything at all — if your business partner was clever and deceitful enough — it could reveal an unseen pattern that you never detected before. At the very least, you might find some discrepancies, or this revelation will reveal past discrepancies you could not explain before. Formulate a couple or few separation scenarios. After you’ve done your detective work, it’s time to concentrate on how to best move forward. Since this is such a big betrayal of trust, it’s probably unrealistic to think that you can just patch things up and go on as if nothing has happened. So, you need to formulate at least a couple of ways that you can break up the relationship and do as little damage while causing as little disruption as possible. Talk to your business partner about ending your arrangement. This will most likely be the hardest part of resolving the situation. If you are able, don’t simply cut off communication and walk away. Instead, talk to your business partner in order to gain an understanding of his or her motivations. Although this certainly doesn’t excuse his or her behavior, it might help you in the future to detect when something’s awry when you otherwise wouldn’t. What other suggestions do you have for dealing with a dishonest business partner who is hiding something important? Please take a moment to share your thoughts and experiences so others can benefit from your unique perspective! Interested in learning more about business? Then just visit Waters Business Consulting Group.

I Want to Create a New Position for My Small Business – So How Do I Go about It?

September 9, 2022 No Comments

Entrepreneurs wear many, many hats. It is not at all unusual for a small business owner to perform several different roles. But, this Jack of all trades, master of none can’t go on in perpetuity. The longer it lasts, the less chance there is that the business can scale up. In order to grow a company, it’s necessary to have help and many business owners reach a point where it is unavoidable. So, they make a few hires but still continue to perform various functions until they realize that a new position will free them up to pursue their main goals. Hiring should Equal Growth It’s very common for small business owners to be nervous about their first hires. However, they eventually get past this and the team settles into a comfortable routine. This can easily result in a false sense of security and it’s not at all unusual for the owner to slip right back into or continue bad habits. If a heavy workload causes your employees to feel overwhelmed and frustrated, it may be time to add new positions to your department. Hiring an additional staff member or two can help you split tasks between employees more equitably and give employees the time they need to devote to their work. —Houston Chronicle Sure, someone has to perform those functions and the owner typically feels it is his or her responsibility. But, there comes a time when it’s clear that handing off at least some of those tasks to someone else would be very beneficial. What generally holds a business owner back is not having a clearly defined position, as they did with previous hires. Fortunately, there are some steps you can take to create a new employee position. How to Create a New Employee Position for a Small Business When it becomes obvious that you’re taking on too much, be it administrative tasks or something else, it’s time to seriously consider hiring someone to do that work for you. Here are some steps you can take in order to create a new employee position: Estimate its ROI. Before you start posting job openings, take some time to work out the most likely return on investment. Ask yourself if one or more of your current employees can assume these responsibilities. If not, then it is more likely you need to create a brand new position. Just work out a realistic scenario on how much this will add to expenses and what size return of investment you’ll get for this potential hire. Determine if it’s part or full time. Next, you’ll need to determine whether this is a part-time or full-time position. Go over your schedule and create a ballpark figure of how much time you spend on these tasks. This will give you a pretty good idea of the number of hours you’ll give over to a new employee. Plus, it will tell you how much time you gain back doing more important things. Compile a list of applicable skills. Now, you’ll need to create a list of applicable skills that a new employee would need to possess. This will also tell you if these responsibilities are truly interrelated or if they are a mixed bag. What’s more, it will point you in a more specific direction and help you to hone in on the right personality. Advertise the new position and interview potential candidates. Last but certainly not least, it’s time to fill the new position you’ve created. Write a job description that defines the role and your company’s expectations, then advertise it in trade publications, and on social media. What other suggestions do you have for an entrepreneur who is considering creating a new team member role? Please share your experiences and thoughts so others can benefit from your input! Interested in learning more about business? Then just visit Waters Business Consulting Group.