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?

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.

How to Push Forward Starting a New Business when Few People Believe You can Make It

March 15, 2023 No Comments

Entrepreneurship is a journey that is full of challenges, and it is not uncommon for entrepreneurs to experience moments of self-doubt and a lack of motivation. However, it becomes even more challenging when the people around them are negative and tell them that they cannot succeed. How Entrepreneurs can Stay Motivated and Focused Even when People Around them Say they Can’t Succeed Negativity can weigh heavily on an entrepreneur’s mind – leading to a lack of focus and plenty of unnecessary second-guessing. So, let’s go ahead and discuss some strategies that entrepreneurs can use to stay motivated and focused even when the people around them are saying they can’t succeed. Believe in Yourself The first and most important thing is to believe in yourself. You must have confidence in your abilities and trust that you are capable of achieving your goals. If you don’t believe in yourself, it will be difficult for you to stay motivated and focused when others doubt you. Surround Yourself with Positive People Surrounding yourself with positive people who believe in you and your vision is essential. Negative people can bring you down and sap your energy. Seek out individuals who are supportive and can offer encouragement and constructive feedback. Focus on Your Vision Stay focused on your vision and goals, and don’t allow others to deter you from your path. (This isn’t easy because we all have self-doubts and are unavoidably influenced by the opinions of others – particularly the people closest to us.) Entrepreneurs have to make a lot of tough choices each day and it can take a toll. Throughout the rest of the day, though, they tend to limit decision-making to keep things simple. It’s a great tool for motivating entrepreneurs because it keeps them sharp when their abilities are needed elsewhere. —Inc.cdom Remember that success often comes after a series of failures and setbacks, so stay the course and remain committed to your vision. If you can put failures in perspective, you’ll have a much better chance of persevering when things don’t go right. Celebrate Small Wins Entrepreneurship is a journey, and it is essential to celebrate small wins along the way. Recognize the progress you’ve made, no matter how small, and use it as motivation to continue working towards your goals. Take Breaks and Practice Self-Care Running a business can be overwhelming, and it’s crucial to take breaks and practice self-care. Take time for yourself and do activities that bring you joy and help you relax. This will help you stay on task and keep your drive to succeed healthy in the long run. Keep Learning and Growing Entrepreneurship is a continuous learning process, and it’s essential to consistently grow and develop your skills. Attend seminars, conferences, and networking events to learn from other entrepreneurs and industry leaders. This will help you stay motivated and focused as you work towards your goals. Embrace Failure Finally, it’s essential to embrace failure as part of the learning process. Every entrepreneur has failed at some point, but what sets successful entrepreneurs apart is their ability to learn from their failures and use them as motivation to keep pushing forward. Summing it all up, staying motivated and focused as an entrepreneur can be challenging, especially when others doubt your ability to succeed. However, by believing in yourself, surrounding yourself with positive people, focusing on your vision, celebrating small wins, taking breaks and practicing self-care, keep learning and growing, and embracing failure, you can stay motivated and focused on your path to success. What other strategies and/or attitudes would you add to this list? Please, take a few minutes to share your own thoughts and experiences so others can benefit from your perspective! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Hey, Entrepreneurs, If You Want to Succeed, Stop Seeking Advice from People Who’ve Failed

November 10, 2022 No Comments

Everyone has an opinion. But, everyone can’t be right. There’s always a set of best practices and then there are ways to do things that fall short of success or lead to bad outcomes. So, this is why people seek advice from their family and friends when they want to start a small business. The trouble with this approach is that the people the entrepreneur is speaking to may not be the owner of a profitable small business. While it’s certainly understandable to seek advice from people you trust, that doesn’t necessarily mean they’re the best or only sources. Remember, Real Friends are Supportive Here’s another problem. There are a lot of individuals around you who will tell you that you can’t do it. Usually, this is based on fear, but can also manifest from those who are envious that you’re willing to take a risk to improve your life and be professionally successful. Then, there may even be people around you who went into business for themselves, but it didn’t work out. Ask business owners who specialize in the same niche as your startup if they have any tips. Business owners in your market know about accountants, lawyers, and recruiters who might be a good fit for your needs. They can make recommendations and point you in the right direction. —Entrepreneur.com While the reason that their businesses failed might not be direct to their own decisions, it’s generally a safe bet. Even if it was circumstances beyond their control, successful business owners are the ones who find a way through tough times, endure, and come out on the other side. To put it much more plainly, if you’re seeking advice from people who have failed in their own business ventures, you’re speaking to the wrong people, unless they have gone on to succeed in other ventures by learning from their failures. Failures can be the precursor to success if we learn from them. Best Places to Seek Business Advice Fortunately, there are a few places you can go to get reliable, actionable advice about starting your own business. Here are the best places to seek entrepreneurial advice that will help you get started in the right direction: Successful individuals in the industry. Sure, this sounds all too obvious. But, a lot of people who want to go into business for themselves are fearful of speaking with people that are already successful in the industry. Now, that sounds strange, but it makes sense if you think about it in a different way. Those who avoid successful individuals in the industry into which they want to enter, typically don’t want to give up their plans – which is to say their strategies and secrets. So, they make the mistake of being protective of their ideas, without knowing if said ideas are actually good or bad. Small business development groups. There are small business development groups that can help you get some of the logistics worked out and even provide a little friendly advice that you may not have thought of on your own. But, here again, you must be willing to share your ideas with others. Doing so will allow other people to gauge your ideas and their merit. Local industry trade associations. These industry trade associations exist to promote their industry, which is their sole purpose. You’ll learn a lot about the industry, and perhaps your own niche, along with some tricks of the trade and how your competition deals with its challenges. Of course, it’s just as wise to consult someone who specializes in starting and growing small businesses. An experienced business consultant and coach brings a wealth of information and is someone who can not only provide valuable input but also be supportive. Where else do you recommend people starting a small business seek advice? Please take a few minutes 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.