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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7 Challenges Every Bootstrap Entrepreneur Faces

May 16, 2017 No Comments

The entrepreneurial experience is one of duality, a paradox, that’s both exciting, full of hope, and, anxious, stymied by fear. Two very different states of mind and emotion, however, in the majority of instances, one set is preceded by the other. It comes with that spark of the proverbial, “ah ha!” moment–excitement and genuine, heartfelt belief that whatever it is, it will work. Often, this elation is short lived and it’s little wonder why. We grow-up with expectations and more than enough are not fulfilled. So, we learn skepticism, caution, and to examine our actions before blindly leaping. This is precisely why extreme success stories remain so unfathomable–often accompanied by the phraseology, “against all odds.” These sets of circumstances cause us to look at those odds and be honest about the entrepreneurial journey, which more often than not, requires a lot of work, much dedication, and, the ability to see and believe what others don’t. 7 Challenges Every Bootstrap Entrepreneur Faces When you start your own business, it might be a side gig, something that only takes a few hours out of your week and is intended to grow incrementally. It could also be the resort of finding yourself suddenly unemployed and the opportunity to take control of your own future provides all the drive necessary to start and never look back. Others partner together and use old fashioned sweat equity to get their businesses off the ground. Whatever the case might be, there will be obstacles. Regardless of size, most businesses face many of the same challenges every day. Maximizing profits, minimizing expenses and finding talented staff to keep things moving seem to be top challenges for both SMBs and large corporations. —Entrepreneur.com It might come as a surprise, but new companies fail for two primary reasons: too little business, and, too much business. In the former instance, there’s obviously a lack of revenue; but, the latter seems counterintuitive, perplexing, though perfectly explainable–overwhelming demand. These dynamics are usually out of the company’s control but there are others, and, just one of these can be enough to cause failure: Stability. While you might have a marketable and sellable idea, possess the talent to sell it, and have enough resources to get it out there, you don’t control the economy. Being employed provides a sense of security, though arguably, it’s a false one. There is no guarantee your vision will come to fruition in the way you now imagine it, or, at all. Income. It’s a fact that many entrepreneurs don’t take any salary for the first several months, even for a year or more, because the money’s better spent rolled back into the business. Having to forego a steady income, even temporarily, can be too much to bear for some, it’s looking to the future and taking stock of gains that provides the remedy. Sustainability. The marketplace changes and some businesses become near or completely obsolete. In the wake, new opportunities emerge, but that doesn’t undo the damage suffered by those caught on the wrong side. Pivoting when times begin to change is a necessity to embrace. Comfort. One thing that seems strange is what’s obvious by its absence–being the boss. Sure, it will be you who’ll be in charge, which means you will be making the tough decisions, you will be the one responsible for company mistakes, and you who must put your foot down. Schedule. Your work and personal lives will intersect many times during your startup period and here again, it’s because you’re the boss. While you’ll have set boundaries, you’ll have to do so smartly and be flexible. Sleep. Lying awake, brainstorming, putting in a lot of extra hours to get something done, having to meet this deadline or be present for a meeting, all of these are common. Try to find a schedule that largely works and take advantage of downtime. Seventh on the list is confidence, and, it’s among the most powerful of influencers. Your confidence will be challenged many times, but this just comes with the territory. You will have doubts, falter, and make miscalculations, but these are only as hurtful as you allow. Finally, if you have a viable business model with a demand for a product or service, then much of your success falls on you ability to persevere. Many businesses fail or fall “three feet from gold” because the entrepreneur quit. In the toughest of times, I encourage my clients, as I did for myself, to take Action every day on something that will help to grow your business. Sitting, worrying or praying does no benefit without Action. And, Action helps to resolve anxieties and fear. So, go out and pursue our dream today, and take Action every day to building your business! [shareaholic app=”follow_buttons” id=”26833294″]

Entrepreneurs Avoid the Top Mistakes that Put New Companies Out of Business

March 30, 2023 No Comments

Starting a new business is an exciting venture, but it’s important to be aware of the risks involved. According to research, about 20% of new businesses fail in their first year, and about 50% fail within five years. While there are many factors that can contribute to business failure, some are more common than others. Big Mistakes New Entrepreneurs should Avoid The numbers above aren’t the only ones that are out there. Other studies reveal the new business failure rate is as high as 75% (depending on how “failure” is defined.) However, most findings agree fewer than half will survive long enough to celebrate their fifth year in business. …being an entrepreneur and founding a successful startup is difficult. It’s a long and difficult road, and you will make mistakes, regardless of how hard you try not to. In fact, there are a few common mistakes that entrepreneurs make, especially during their first time attempting to start a business. Thankfully, the key to mitigating risk from those mistakes, and hopefully avoiding them altogether, is understanding as much about them as possible. —Forbes.com What’s more, of the less than half that do make it to their fifth year, a mere 33% of those entities will go on to celebrate their tenth year in business. So, let’s take some time to explore the most common reasons new businesses go broke and how entrepreneurs can avoid failing. Lack of Market Research One of the most common reasons new businesses fail is a lack of market research. It’s important to understand the needs of your target audience, as well as the competition, in order to create a successful business. Entrepreneurs who skip this step may find that their product or service is not in demand, or that they are unable to compete with established businesses in the industry. To avoid this mistake, conduct thorough market research before launching your business. This may involve surveys, focus groups, or other methods of gathering feedback from potential customers. By understanding the needs of your target audience and the competition, you can create a business that is more likely to succeed. Poor Financial Planning Another common reason new businesses fail is poor financial planning. Entrepreneurs may underestimate the costs involved in starting and running a business or fail to secure adequate funding to cover these costs. Additionally, some entrepreneurs may overspend on non-essential items, such as fancy office spaces or unnecessary equipment. To avoid this miscalculation, create a detailed business plan that includes financial projections and a budget. This can help you estimate the costs involved in starting and running your business, as well as identify potential sources of funding. It’s also important to keep track of your expenses and income and to adjust your budget as needed. Lack of Marketing and Branding Even if your product or service is high-quality, it’s important to effectively market and brand your business. Entrepreneurs who fail to do so may find that they are unable to attract customers or establish themselves as a reputable business. To avoid this blunder, create a marketing plan that includes branding, advertising, and other promotional efforts. This may involve creating a logo and website, networking with potential customers and industry professionals, and investing in online and offline advertising. Poor Management Effective management is key to the success of any business. Entrepreneurs who lack management experience may struggle to make important decisions, delegate tasks, or create a positive company culture. Additionally, entrepreneurs who try to do everything themselves may become overwhelmed and burned out, which can negatively impact the business. To avoid these missteps, hire experienced managers and delegate tasks effectively. It’s also important to create a positive company culture that promotes productivity, teamwork, and employee satisfaction. Inflexibility Finally, entrepreneurs who are unwilling or unable to adapt to changing market conditions may struggle to keep their businesses afloat. This may involve being unwilling to pivot the business model, invest in new technologies, or adjust pricing and marketing strategies. To avoid this foil, remain open-minded and adaptable. This may involve regularly monitoring market conditions, soliciting feedback from customers, and being willing to make changes when necessary. As we all know, starting a new business is a risky endeavor, but by avoiding common mistakes and implementing effective strategies, entrepreneurs can increase their chances of success. What other mistakes would you include and warn entrepreneurs about? Please take a few brief moments to share your experiences and more so others can benefit from your input! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Why NFL Teams Can’t Run the Pinkerton Play and Neither Can Your Small Business

January 31, 2025 No Comments

Super Bowl LIX will pit the Kansas City Chiefs against the Philadelphia Eagles. During the game, both teams will vie to out strategize their opponent. Undoubtedly, there will be internecine struggles and those internal conflicts will test their ability to operate and execute as a cohesive team.