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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You Don’t have to Meet a Politician to Find a Hypocrite — Your Mirror Might just Reflect One

March 1, 2019 No Comments

Rep. Alexandria Ocasio-Cortez just moved into a luxury apartment in Washington D.C. It doesn’t contain one affordable housing unit. In fact, the complex doesn’t even comply with D.C.’s Affordable Dwelling Units program. This, after campaigning on a platform which included “Safe, affordable, adequate housing for all.” George H.W. Bush infamously said, “Read my lips. No new taxes.” LBJ promised the country not to escalate America’s involvement in the Vietnam War. George W. Bush campaigned, in-part, against excess government spending. Then, expanded several federal programs. How Hypocrisy Hurts Businesses The list goes on and on and on. Bernie Sanders, who rails against wealth inequality, owns three houses, has a net worth of about $2 million, and earns a six-figure salary. You get the idea. And, these are just a handful of politicians. It doesn’t include entrepreneurs, celebrities, professional athletes, and other public figures. As a business owner or manager, it’s important to practice what you preach. If you require employees to be available 24/7 while you’re MIA, or you’re constantly texting on the job while you prohibit employees from using their phones, for example, your hypocritical behavior is sending the wrong message to employees, and they may resent you for it. —Business News Daily Of course, hypocrisy is everywhere. When it occurs in a business environment, it’s very harmful. Hypocrisy undermines your ability to lead. After all, it’s essentially telling your employees to literally do as you say, NOT do as you do. You lose respect. It compromises your standing. Plus, it makes it very difficult for others to even work with you. 3 Key Ways to Avoid Hypocrisy as a Business Leader Hypocrisy is a dangerous trait. It essentially subverts morale and threatens the very viability of a business. It can even go so far as to cause a self-inflicted implosion. So, just how do you avoid being hypocritical? Here are a few helpful suggestions for how to avoid hypocrisy as a business leader: Practice self-awareness. You might call this “practice what you preach.” It’s an obvious reminder but one definitely worth mentioning. Every day, you should stay vigilant and stay self-aware about your own behavior. While it’s not rocket science, it’s quite difficult to put into practice. Be consistent with decisions. It’s almost impossible not to have or even show bias. We all do it in a variety of ways. You might treat team members differently due to your own personal biases. When making decisions, consider all sides of the equation. Actively solicit constructive criticism. It’s always good to encourage feedback from your employees (as well as your customers). And, doing so could reveal hypocrisy you commit but don’t consciously act against. What other advice would you give about avoiding hypocrisy? Please share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

How Smart Businesses are Adapting to the Quiet Vacationing Trend

January 2, 2025 No Comments

Last summer, several families skipped the usual bustling theme parks and crowded beaches for a serene cabin tucked away in the mountains.

How You’re Sabotaging Your Own Business

May 16, 2017 No Comments

You put a lot into your business and have a commitment to make it grow. It’s likely that you want to do more than provide for your family, you probably would like to leave a legacy, and, feel the satisfaction of accomplishment. However, what’s holding your company back from its potential isn’t necessarily sinister, uncontrollable, outside forces–it’s you who is the culprit. That might sound strange, but it’s a reality that plagues many organizations, from the mom and pop brick and mortar, to software as a service, to large community companies. While you’re busy being busy and worrying about this and that, you’re likely missing some behaviors and practices you personally do to sabotage your own business. Sure, you know about your propensity to push yourself and try to keep a sound balance between work and home life, but, there are other ways you could be causing harm. How You’re Sabotaging Your Own Business Entrepreneurs have a dedication to an idea, and ironically, it’s that commitment which can cloud judgment, or, cause myopia–not seeing the bigger picture. There’s more to building a business than recruiting the right people, networking, and delivering a good level of service, along with the products or a services you offer or provide. Success begins with you, and, while you might have the drive to make it a worthwhile venture, you might also be impeding growth. Most entrepreneurs have the drive and desire to succeed. It’s what we grow up learning and what we want from an early age. But many of us have also been adversely wired by negative experiences in ways that sabotage or hinder our chances of personal and business success. The good news is that we can rewire ourselves in ways that not only neutralize our negative programming, but also put us on an even stronger path to success. —Forbes Most business owners understand that the right pricing, marketing, and brand building are crucial factors for success. What goes largely unnoticed is certain behaviors and practices that can inflict real damage, some of which can be long lasting. So, if you’re doing one of these things, identify them, and settle on a fix. Over-promising. It’s easy to give-in to pleasing your customers, and, doing so is laudable. However, when you over-promise, you run the very real risk of coming-up short. That’s a bad place to be and finding a way out of such a situation won’t be simple. Micromanaging. When you have every member of your organization under your thumb, you are sending a message that says you believe them to be incompetent. What’s more, you’re indirectly telling them they are only a tool, not an asset to your company. Not delegating. It’s one thing to micromanage, but it’s not the same as not delegating. You can be hands-off and not delegate, which can create chaos and decrease efficiency, as well as output. You ought to delegate to streamline your organization and make it work better. Keeping dead weight on staff. When you keep toxic team members on-board, you are sending a bad signal to others. What’s more, that particular person can project a negative image to your customers and to the outside world. Not setting achievable goals. You’ve probably heard the Zig Ziglar quote, “If you aim at nothing, you will hit it every time.” That’s certainly true, and, it’s just as true of setting goals that aren’t realistic. Set workable goals, reach them, and then repeat. Another way you can easily sabotage your own business is to take things personally. There will be setbacks, even outright failures, and, you’ll lose good people along the way. Don’t take things personally because you’ll make emotional decisions, not sound ones. [shareaholic app=”follow_buttons” id=”26833294″]