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.

Like this article?

Entrepreneurs Can Use These 5 Tricks to Fight Drowsy Days

September 14, 2017 No Comments

Everyone pushes through drowsy days. In fact, a study by the Centers for Disease Control and Prevention reveals 35 percent of adults ages 18 through 60 do not get the recommended 7 hours per night. That leads to a perpetual sense of tiredness. And, if this affects you, you know full well it’s not good for your productivity. But, if you’re unable to get a decent night’s sleep, you’ll need ways to cope to get through the workday. 5 Ways to Beat Drowsy Workdays There’s a lot you can stop doing to be successful in business. When it comes to sleep, you can also stop doing a few things. First and foremost, give yourself some tech-free time in the evening, particularly before you go to bed. About an hour before you go to sleep, turn off or silence your phone, tablet, laptop, desktop, and other devices. Also, get in a routine. Go to bed and wake up at the same time. We live in a fast-paced world where everything is quicker and more urgent. In leadership, in business, and in life, it seems we’re always behind: It needed to be done yesterday! It needs to be done now! Why isn’t it already done? Our days are hectic and our nights are busy. We constantly have to be on and available. Unsurprisingly, the side effects of this constant rush include an epidemic of fatigue. —Inc.com When you’re an entrepreneur, you work long, hard hours. And, it’s not easy to just relax and unwind at night when you have so much idle time. It’s natural to mull over the day and to plan ahead for tomorrow. But, you need a good night’s rest to be your best. However, you can’t let go and toss and turn through the night. Now, that familiar mid-afternoon 3 o’clock yawn grips you. What do you do? You need to make a good impression when you have a face-to-face meeting. Even if it’s just another day, without a big agenda, you might still need to fight fatigue. Here are a few helpful suggestions for beating those drowsy workdays: Leave your workspace. Being in the same environment for hours can easily lead to boredom (especially if you’re already tired). So, do yourself a favor and get outside. A walk around the block. A trip to the nearest mall for some quick window shopping. Just get out of the office for 15 or 20 minutes. Have a quick, healthy snack. Fruits, vegetables, and nuts are excellent sources of nutrition. And, some even help perk up your blood sugar levels. That’s enough to give you some more energy. It’s also a great way to counteract the effects of a big lunch that bogs you down. Do a little exercise. You don’t necessarily have to go outside to reinvigorate yourself (although it does really help). You can exercise right in your workspace. Do a few stretches and follow-up with some simple calisthenics. Tackle a few no-brainers. Tiredness can also be made worse by staying on a difficult task. One solution is to go with a few mundane chores. Take out the trash, clean the kitchen, organize your desk, anything that doesn’t require a lot of concentration will do the trick. Play some music. It’s a well-known fact that music stimulates the brain. And, it also impacts the body itself. So, put on some of your favorite tunes and get into the rhythm. Your attitude will quickly improve and you’ll feel reinvigorated. What do you do to power your way through a drowsy afternoon? What methods allow you to cope the best? Please share your thoughts and experiences by leaving a comment! Interested in learning more about business? Then just visit Waters Business Consulting Group. [shareaholic app=”follow_buttons” id=”26833294″]

My Biggest, Most Important Client is #!@_&% — How can I Keep Them and Not Go Crazy

February 10, 2022 No Comments

Fill in the blank. Angry, anxious, cheapskate, short-tempered, impatient, annoying, hard-to-please. No one enjoys dealing with difficult business clients, but sometimes we have to. These clients can be demanding, angry, and anxious. They can sap our energy and make us feel like we’re going crazy. But don’t worry – there are strategies for how to deal with them. Running a Business Means Dealing with Challenges No one ever said that running a business would be easy. In fact, it can often be downright difficult to deal with the various challenges and situations that come up. Whether you’re struggling to keep afloat or trying to figure out how to take your company to the next level, there are some effective ways to deal with difficult business situations. Many small business owners have ‘em—you know, the clients who make you cringe when you see that they’re calling. The ones who drain your energy, criticize everything, and are slow to pay. Difficult customers exist in every business, for every company, and even though you may want to kick them to the curb some days, you know that it’s better to keep them if you can. So, how might you keep your difficult clients and your sanity? —American Express The key attributes are persistence and patience. Entrepreneurs who stay the course but don’t rush into things tend to be the most successful over the long term. They push when necessary and recognize futility for what it is. In other words, they act appropriately to the circumstances they experience and do not try to bend reality. Best Strategies for Managing Impossible Clients Dealing with difficult business clients can be a nightmare. They can be demanding, angry, and anxious, and they can really put a damper on your day. However, with the right strategies in place, you can manage them effectively and keep them from ruining your business relationships, like the following: Keep your cool. One of the most important things to remember when dealing with difficult clients is to stay calm and collected. If you start getting angry or frustrated, it will only make the situation worse. Take a few deep breaths and try to relax. This will help you think more clearly and come up with a plan of action. Put on their shoes. Another thing to keep in mind is that these clients are just people. They have their own problems, and they’re probably stressed out too. Try to put yourself in their shoes and see things from their point of view. This will help you understand where they’re coming from so you can better address the problem at hand. Don’t retaliate in anger. If possible, avoid getting into arguments with these clients. You might think this is impossible, but it can be done. Stay calm and collected — even if they’re yelling at you or cussing you out. If necessary, take a break from the situation. Politely end the phone call or meeting and go for walk outside. This will give both parties time to cool down and reset. Walk the walk, talk the talk. Finally, always try to stay professional. These clients are probably already angry and frustrated, so don’t add to the problem by being rude or unprofessional. Address the issue at hand in a polite and respectful manner. You’ll be surprised how much this can help diffuse the situation. What other strategies would you use to deal with difficult customers? 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.

How to Manage Your Teleworking Staff

April 9, 2020 No Comments

Managing a staff remotely presents a number of challenges, some of which are completely unexpected. When a business first goes to a telecommuting or teleworking structure, it naturally undergoes some growing pains to adjust to the new dynamic. Although it is ostensibly more beneficial, cutting down on some expenses, and providing more convenience to staff who no longer have to commute, there are still some issues which can arise. So, it’s best to know what to expect. The Upsides of Telecommuting for Small Businesses There are a number of advantages to remote work situations. It gives team members more flexibility with their schedules. Also, it cuts down, if not nearly eliminates, office politics. Additionally, another benefit is that it can reduce operating costs, having to rely less on a dedicated, physical location. Particularly for small businesses, telecommuting seems an effective strategy for maximizing a workforce while still keeping costs low. You don’t need to pay for a centralized office space or deal with a drive to work, but you do have to contend with YouTube, Facebook and myriad other online distractions. —American Express But, it also means having to wrangle with coordination efforts, relying on different forms of communication, along with various other things to work out. With just a bit of tweaking here and there, it’s possible to make it work and even to reach a point where pretty much everything flows seamlessly. Ways to Manage Your Teleworking Staff Of course getting from Point A to Point B requires a combination of ingenuity, cooperation, and some out of the box thinking. To effectively manage a remote staff, you’ll need to do the following: Clarify roles. Each team member must clearly understand his or her role within the organization to eliminate duplication of effort, gaps in productivity, and more troublesome issues. Every person should have a defined, central role, as well as alternative responsibilities, just in case there is a need. Set expectations. In addition to defining everyone’s role, you’ll also need to clearly delineate your expectations. Otherwise, people won’t know exactly what you want out of them, and that’s a recipe for disaster. Develop procedures. It’s pretty straightforward to set up and explain and demonstrate procedures in a face-to-face environment, but presents quite a challenge with remote staff. This is where most of the initial communication will be necessary, in order to coordinate how things should be done. Set Regularly Scheduled Conference Calls. Regular communication is key with your staff in order to develop relationships and high trust cultures with accountability. Have a set time and day with a set agenda on key performance metrics and results, project updates, review current challenges and opportunities and collaborate openly so that there is a sense of community. Use a video conference application like ZOOM or GoToMeeting.com or other for more effective communication. Understand security issues. With remote work comes the risk of work-product being compromised. You need to learn about and address any potential issues by being proactive as possible. Reach out for help when needed. Lastly, if things just don’t seem to work, you should seek help with the right people. you might need to consult or hire a technical professional in order to get everything you need in order for the system to be fully functional. What other suggestions do you have? Please, share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.