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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Business Leaders This Responsibility Rule Exemption Doesn’t Apply to You

July 2, 2020 No Comments

“You’re not responsible for the irresponsibility of others.” Or, “You can only control you, not other people.” Both are great pieces of advice to live by. Except, when you’re in a position of leadership. When you’re in charge, you are responsible for the actions of others. It’s a stark contrast to the peer-to-peer world. Because, your employees aren’t your peers. Sure, they’re good people. But, they aren’t your equal. At least, in terms of business structure. You are the authority. So, when a team member is irresponsible, you’re the one the customer will blame. It’s not fair, but it’s reality. Why Employees Act Irresponsibly Everyone does something irresponsible at some point. But, there are people who just can’t seem to get it together long-term. However, these are the exceptions, rather than the rule, a tiny percentage by comparison. You might have even been one of them, but eventually “grew” out of that phase. In almost every workplace, there is bound to be someone who isn’t pulling their own weight. When you’re an ambitious, hard-working [business owner] who is committed to growing your career and the company, it’s frustrating to work with someone who seems interested in only doing the bare minimum. —Fast Company People act irresponsibly because they just don’t take their jobs seriously. To them, it’s just a paycheck — a paycheck they can get almost anywhere. Of course, this is very short sighted but it speaks to their mindset and overall attitude. When that personality shows up in your business, you’ll have to deal with it. There is no passing it off. How to Deal with an Irresponsible Employee If you’re in this unenviable position, you’ll need to deal with the situation directly. While it’s tempting to pass this off to a subordinate who is above the person in question, letting him or her know their behavior is known at the top is very powerful. (This alone could be enough to correct him or her.) But, it’s best to be clear. Here’s how to deal with an irresponsible employee: Put the onus on him or her. Ask him or her how they can improve. Let them be a part of the solution right from the beginning. If they are unwilling or standoffish, that’s a big red flag that probably signals his or her time at the company is coming to an end. Persuade but don’t preach. You can (and should) remind him or her of the company’s policies and procedures. But explain why, instead of just hitting him or her with a litany of do’s and don’ts. Enter into a discussion rather than just making proclamations. Always lead by example. This is something you should already be doing routinely. Showing leadership not only helps others to reach their goals, it inspires others to succeed in more ways than one. Otherwise, you’re not really leading the company, you’re just a figurehead and people will instinctively understand that fact. Follow-up regularly. Obviously, you’ll need to follow-up with him or her. But, think twice about doing so on a set schedule. The element of surprise will motivate him or her to do the right thing. If they don’t, it means you’re dealing with someone who just doesn’t care and isn’t a true asset to the business. What other suggestions do you have for dealing with an irresponsible employee? Please go ahead and share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

When a Big Order Becomes a Big Problem and What Small Business Owners Can Do

November 13, 2025 No Comments

Small businesses generally run on relatively small orders. It’s usually volume that makes the difference, and it’s also why entrepreneurs desire big-ticket sales.

Common Franchise Pros and Cons

August 5, 2018 No Comments

Franchises are a great way to get into business. But, these models aren’t for everyone. There certainly are pros and cons to the systems, regardless of industry. However, it’s an effective way to start a company and it’s a quite popular method. For instance, there are approximately 400,000 franchises in the United States alone, according to the International Franchise Association. These employee nearly 10 million people and range across 75 different industries. But, is it for you? Most Common Franchise Downsides Okay, let’s begin with downsides of owning a franchise. Perhaps the largest can easily be capital expenditure or start-up costs. Some are quite large but others are relatively inexpensive. Along the same lines are the fees. You’ll pay for marketing materials, royalty payments, and more. Speaking of costs, you might be subject to sole vendor sourcing. Meaning you must purchase certain materials and supplies from approved vendors. If buying an existing business doesn’t sound right for you but starting from scratch sounds a bit intimidating, you could be suited for franchise ownership. New franchisees can avoid a lot of the mistakes startup entrepreneurs typically make because the franchisor has already perfected daily operations through trial and error. —Entrepreneur.com You must also comply with the proprietary standards, set by the franchisor. Now, you might have some flexibility with said standards, but it’s usually limited. Additionally, you could also be locked into a contract. Then, there’s the ongoing success of the franchisor. In other words, the “parent company” must continue its track record. And then, there’s always risk involved with any endeavor. Biggest Franchise Advantages Of course, franchises have plenty of upsides. If they didn’t, there’s no way these models would routinely demonstrate such high levels of success. People simply wouldn’t waste any time (or money) and the entire notion would eventually disappear. But, franchises do largely succeed. So, here are the biggest franchise advantages: It’s an already established brand. Here’s what attracts so many entrepreneurs to buying franchises — it’s a known quantity. Consumers are already familiar with the brand and its products and/or services. Which means you don’t have the burden of establishing it from scratch. Marketing and operation support. Another big benefit is that you’re not out on your own. You receive marketing and operational support from the franchisor, which is a huge plus. Proven system of employee training. Along the same line is there’s already a working system in-place for employee training. You don’t need to work your way through trial and error to refine a workable training system. Access to proprietary operating methods. Speaking of an in-place system, you also don’t have to try to peel back the veil to learn how the system works. You’ll get all the information you need to open and run the business with actionable guidelines. What other franchise pros and cons would you add to the list? What are your thoughts about buying a franchise? Please comment and share your ideas! Interested in learning more about business? Then just visit Waters Business Consulting Group.