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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3 Ways Business Owners and Entrepreneurs can Find more Free Time

March 8, 2021 No Comments

A substantial percentage of established business owners and fledgling entrepreneurs have experienced significant change over the course of the past year. Some had to make very difficult decisions and enact hard changes in order to survive. Conversely, some have been in the fortuitous position to thrive. Regardless of their circumstances, too many entrepreneurs and business owners struggle to find free time. Fortunately, there are some effective strategies to find more free time and enjoy it. The Dreaded Free Time Paradox The most common problems business owners have when it comes to free time is either not recognizing it, or failing to indulge it. In other words, when there’s free time available, business owners and entrepreneurs most often either prefer to spend it working, simply defaulting to a workaholic mindset. So, it’s often the case that they don’t have any free time, as much as it is they won’t take time to actually enjoy it. Time freedom is about spending your time doing what you really love doing with the clients and people who mean the most to you. Having more freedom of time is about having the ability to live a full life and have the time to pursue other interests outside of work. But finding time freedom for entrepreneurs can be tough. — Thrive Global This creates a cyclical scenario where any ostensible free time is put either toward their work or, is spent on distractions. That’s often more advice given about business owners seeking free time. That is to say, to identify and eliminate distractions, because they divert away from the task or relaxation at hand. Because entrepreneurs are action-minded people, they mistake any type of work as being valuable. Of course, that’s just not true. 3 Ways Business Owners and Entrepreneurs can Find more Free Time The advice usually given to free up time is to rely on technology, innovative tools of the trade, and eliminate redundancies. Those are all great ways to help streamline your operation, but these mostly work around the margins, and don’t address the core problems. Here are three ways business owners and entrepreneurs can find more free time: Stick to a schedule. It’s very difficult, if not impossible, to find free time in an unstructured environment. The old Friedrich Nietzsche philosophy of “out of chaos comes order” simply doesn’t apply to this situation. So, get yourself on a schedule and follow a routine. It can be flexible and should not be rigid, but should provide you with structure. This will greatly cut down on distractions, and force you to focus on the highest priorities, and work your way down to the lowest. Put your business on a budget. Before you scoff, remember this — a budget doesn’t always mean spending less, it means always spending smartly. Too many business owners either spend their time worrying about their finances. Others know their general financial situation, but dwell on every possible contingency. In either case, they waste a great deal of time worrying, because they really don’t have a plan for their company finances. Money just comes in and goes out, but with very little accountability. Creating a realistic budget allows you to operate your business with a lot more certainty, and that in turn, will create more free time. Hire (back) help. You might have responded to the pandemic and ensuing chaos in a number of ways. Perhaps, it was necessary to reduce your payroll and take on more responsibilities yourself. Or, you’ve been taking on more work personally, because you haven’t found the time to hire people to help. The longer this unnecessary stress goes on, the more you risk burning out. It not only steals away valuable downtime, it is also counterproductive. So, get yourself on a schedule, lay out a budget, and hire on some help when and where needed. What other suggestions do you have for creating more free time? 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.

How to (Re)Establish Business Relationships Post Shutdown

June 3, 2020 No Comments

As you reopen your company, people you previously did business with might or might not return with you. Or, it could be the same people, but in different positions, not necessarily having the same latitude and/or resources at their disposal. These individuals, vendors or customers, will most likely continue their relationships, but it will probably be one that’s changed. So, you’ll need to re-establish said relationships and do so in a thoughtful and careful manner. Why Business Relations are Now more Important and Fragile than Ever Of course, whether or not you’re dealing with the same individuals and/or roles Will depend on a number of factors. It’s important to understand and accept the fact that you have no control over these situations. That means you’ll have to make adjustments on your end, in order to make the relationships work. Hopefully, the people you deal with will have some say of their own, but it’s best to hope for the best and plan for the worst. In the early months of 2020, the COVID-19 pandemic prompted wide-sweeping shutdowns and shelter-in-place orders across the United States. Now, as parts of the country look to start relaxing these strict measures, small business owners need to think about what’s next and how they will adapt and move forward safely and sustainably. —U.S. Chamber of Commerce As you reopen, some of the individual vendors and customers you previously worked with might not come back. Also, there’s the inevitability of personnel change among vendors you worked with prior to the shutdown. This means they’ll be some level of give and take, and you’ll need to temper your expectations from time to time until the new relationship takes form. How to (Re)Establish Business Relationships Post Shutdown Going forward, This new and strange dynamic will present its own set of challenges. But, with a bit of patience, tact, and along the way analysis, you can either establish new business relationships or re-establish old ones. Here’s how: Reach out. Obviously, this is where you’ll start. Reach out to those you had the strongest relationships before. Then, to others and go down the list to eventually get to those you only occasionally worked with prior to the shut down. Listen carefully. When you do speak to vendors and customers, make a conscious decision to actively listen. Don’t give into the urge to carry on about your business. Instead, take the time to listen carefully to them and learn about their circumstances. Communicate clearly. By the same token, be honest about your situation, exactly where you stand, and where you expect to be in the near future. In short, under promise and over deliver. Offer Meeting options. Not all clients, customers or partners will feel comfortable meeting in person so offer them options. We have asked our clients; would you prefer to do a video or ZOOM conference or have us meet you in person. Just asking shows you are sensitive to their concerns. Pay on time, every time. Also, be sure not to get too far ahead of yourself so you’re always in a position to pay on time, every time you receive an invoice. Otherwise, you’re opening yourself for trouble. Refer good vendors to others. Another thing you can do is to refer your favorite vendors (and customers) to others to show your appreciation. 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.

Ways Business Owners can Deal with Personal Crisis

May 18, 2017 No Comments

Entrepreneurs, by their very nature, are self-reliant. They set goals and achieve them with confidence. When a personal crisis strikes a business owner, it can be very damaging to their corporate environment and even its micro-culture. Suddenly, the dynamics change and can lead to irreparable harm. We’ve all heard the advice not to bring personal problems into professional space, but, some are so large they have a nearly uncontrollable effect. It’s best to bring the situation into perspective, but, doing so might be difficult to accomplish. Ways Business Owners can Deal with Personal Crisis In some instances, it’s possible to prepare a business for a crisis. When it’s impending and inevitable, business owners should prepare by speaking with their team members about delegating and assigning responsibilities, seek legal advice (if applicable), and focus on what’s most important. There will be difficulty in maintaining balance but by being proactive, you’ll have less to worry about. Eventually it happens to the best of us. Something occurs in our personal lives that is so devastating, we have difficulty concentrating at work. It may be the death of a loved one, a divorce, a financial crisis, or serious damage to our homes. When our personal lives are in chaos, it can be hard to focus and get what we need to do done. —Inc.com Unfortunately, it’s often the case that a personal crisis strikes without warning. When it does occur, it can be very burdensome to get through. Even the toughest entrepreneurs will have difficulty trying to deal with upset in their personal lives while continuing to run their businesses. Here are some ways business owners can deal with a personal crisis: Outsource and be willing to ask for assistance. It’s okay to let go and farm-out work during turbulent times, especially if you’re having trouble staying focused and concentrating. Also, there’s no shame asking for assistance from your team — it’s actually a smarter choice. Be upfront with customers. As soon as possible, let your clients know about the situation. You don’t have to go into details, but you ought to alert them to what’s going on, particularly if you’re not able to work as usual. You’ll find most to be understanding and that helps to give you some peace-of-mind. Surround yourself with positive people. This is something that successful entrepreneurs naturally do but it’s very important when you’re going through tough times. Personally, I lean on others as well as my faith and prayer to shoulder the burdens of crisis. It’s uplifting and it can be a way to see the silver lining knowing others are walking with you. Give team members more flexibility. Your employees are huge assets to your business and during a personal crisis, can be the best go-to source for carrying-out day-to-day operations. Give them the flexibility that’s needed to keep your company running smoothly. Do not put undue pressure on yourself. If there’s one thing entrepreneurs struggle with, it’s the fear of not getting the job done. When you are dealing with personal issues, give yourself permission to lighten your workload. Take time to reflect on what’s most important. This is an ideal time to put everything in perspective. Give yourself time off and reflect on what’s truly important in your life. In addition to these, you should be honest with yourself about your life’s direction. Some business owners who experience a personal crisis use it as a learning tool advantageously, but others allow the event to cloud their judgment and make rash decisions. When you’re not thinking clearly, be willing and ready to ask for advice from someone you trust. In my life, I have found great opportunity comes from crisis because of my willingness to reflect and make changes. How have you overcome crisis and remained focused and successful with your business? Want to find out about what a business coach can do for you? [shareaholic app=”follow_buttons” id=”26833294″]