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?

Share on Facebook
Share on Twitter
Share on Linkdin
Share on Pinterest

Related Posts

3 Top Business Relocation Considerations

Thinking about relocating your business? It’s something that many business owners think about, particularly when there’s a radical change in the economy. Or, they’ve had an immense increase in their growth or experienced a substantial decline. Regardless of the circumstances, entrepreneurs may consider relocating their companies for a number of reasons. But, when thinking about the move, get lost and frustrated within the many details. So, let’s focus on three of the biggest things you need to consider if you’re really thinking about relocating your business. The Relocation Conundrum There’s always pros or cons to relocating. For instance, you might be trying to escape a tight regulatory environment. But, your customer base is very broad and strong, and moving elsewhere might invite other obstacles. Or, there’s a huge upside to moving to a state with lower taxes, however, doing so means that you’ll have to take on less work in order to maintain your same level of quality with your current client base. Businesses grow. Products change. Economies flourish or flounder. Any combination of these or other factors can lead you to consider the possibility of relocating a business. As you consider the reasons to relocate your business, your primary concern has to be how the move is going to affect your bottom line. Don’t make any move without first considering all the factors for relocation and determining what the move may do to your customer base. —Houston Chronicle Small Business Obviously, there are upsides and downsides to almost any business decision. And, it is up to you to examine those advantages and disadvantages in order to decide whether or not it’s right to make a change. That’s where the “paralysis by analysis” phenomenon begins, causing you to overthink the situation and abandoning the idea altogether. 3 Top Business Relocation Considerations Because it’s such a big decision, it’s best to focus on just a few of the most basic questions. So, let’s take a look at some of the top business relocation considerations you start with: Overall cost. This not only includes the cost of moving, but expenses you’ll incur thereafter, such as taxes. Moving isn’t cheap, particularly if you have a large operation already in place. Then, there are the long-term costs, such as the aforementioned taxes. Think and project the most realistic scenario in order to gain an understanding of the feasibility of relocating. Work force pool. If you do move your business to another location, whether it’s to a nearby city, a neighboring county, or an entirely different state, the workforce pool will likely change, at least somewhat. Give this some serious thought and do a little research into possible relocation areas in order to make yourself aware of the local workforce pool. Growth potential. Obviously, if you’re reconsidering locating your business because of a downturn, make sure you’re not moving laterally to another destination that will resign you to the same fate. You should pick potential relocation areas based on your ability to grow your company over the long-term. Although we’re focusing on these three factors, what other elements would you consider to be among the most important? Please take a moment to comment to share your thoughts and experiences so others can benefit from your prospective! Interested in learning more about business? Then just visit Waters Business Consulting Group.

Read More »

Are You Delegating or Demanding

Throughout the course of building a business, you’ll learn over time to delegate tasks and responsibilities to various people with the right skill sets. Some of the most successful entrepreneurs, like Sir Richard Branson and Mark Cuban, state no one can do it alone. That’s certainly true, you can’t do everything on your own and for those who attempt to do so, learn the hard way it’s an open invitation to trouble and even outright failure. The best business owners know their strengths and weaknesses and through this recognition, develop strategies and relationships which maximize their professional potential. Are You Delegating or Demanding? Delegating responsibilities is just part of doing business. Done smartly, this increases productivity and gives companies potential to grow and prosper. It also allows team members to realize their potential and creates a healthier and happier work environment. Delegating shows your confidence in someone and gives them pride to take ownership of certain areas. In addition, delegating allows you to focus on what’s most important while others can put their efforts into other tasks. Delegating is a great way to ensure that more tasks get done in less time, and it also builds team capacity. Unfortunately, a lot of managers don’t pay enough attention to the delegation process, and thus fail to reap the benefits. —Fast Company Another aspect of delegating is it gives you the opportunity to evaluate a person’s performance. When you give a team member responsibility, their approach and results will speak volumes about what kind of work ethic he or she has and what he or she believes are acceptable standards. In addition to evaluation, delegating gives you the ability to learn which of your team members are best suited for certain tasks. All of these things are great about delegating — if you are sincere. However, there is a real difference between delegating and demanding. Demanding does the opposite of delegating. It stifles creativity, decreases productivity, and poisons the workplace. It also drives a wedge between you and your employees, as well as creates tensions among your team members. Demanding doesn’t give you a true chance to evaluate, either, because it puts unnecessary pressure on people. Here are some signs that you’re demanding and not delegating: You rationalize unrealistic expectations. When you demand, you know it to be the case, as does the other person. This creates a need to rationalize unrealistic expectations, not only to the other person, but to yourself. In the end, no one is fooled, but, it gives you at least a pretense of having reason to demand. Your employees mislead or lie to you. If you get the feeling or learn that an employee is misleading or lying to you, there’s definitely a reason. Before jumping to conclusions, you should look back and think about the overall situation. For instance, if you interrogate an employee who wants time off, you’re creating an atmosphere where there’s little choice and lying becomes the only viable option. You create emergency situations. We all know that unexpected things crop-up from time to time, but, if you’re turning every surprise into an emergency, you’ll feel an undue urgency and that can easily lead to demanding. You justify your actions as legitimate and/or legal. If you ever have to ask if something is legal just to get it done, that’s troubling. You shouldn’t have to walk such a fine line because if you are, chances are excellent that even if it is legal, it’s not entirely ethical. You don’t want to deal with this or that. Delegating is done because it puts the best talent where it is most needed. Demanding comes from a need to get something done, particularly a task that you don’t want to deal with personally. Another sign that you’re demanding rather than delegating is your willingness to take credit or give credit to the person who deserves it. If you are taking credit of the work of others and not giving credit where it is due, that’s unethical and will undermine your entire organization. In summary, your employees are your greatest appreciable asset. Invest in them through servant style leadership by delegating with clear expectations and the kind of results you are looking for … then ask; “what can I do to help you succeed with this responsibility or project?” Want to find out about what a business coach can do for you? [shareaholic app=”follow_buttons” id=”26833294″]

Read More »

How to Get Business Referrals in Secretive Industries

Referrals are one the most important parts of a successful business. When these come in and you deliver, more are likely on the way. In addition, these are a surefire sign that those you serve are more than satisfied and want to show support and appreciation. Unfortunately, there are industries which operate under a significant amount of discretion (read: secrecy). Examples are sports agents, investment bankers, ghostwriters, healthcare providers, and even business development professionals. Because of this, it’s a lot more difficult to get referrals. You can’t necessarily ask your clients to spread the word since they don’t want others to know what you’ve done for them. To the outside world each client is successful on his or her own and not because you provided advice, action plans, and of course work product. Although you feel a sense of accomplishment and pride, you can’t just use these experiences freely. How to Get Business Referrals in Secretive Industries Referrals are a cornerstone of doing business, and it’s what entire entities are based upon — examples include Angie’s List, Yelp, Healthgrades, and Home Advisor. These services provide consumers with real customer reviews and that relatable trust is what gets people to pickup the phone. In some industries, like those listed above, the provider might not be able to tap into the same resources. Your best source of new business is referrals from happy customers or clients. You cannot receive a better lead than one that has been sent your way with a strong referral. You cannot have a more motivated prospect arrive in your store or restaurant than someone sent there by a raving fan. —Forbes If you want to get referral business, but are in a business that’s subject to secrecy, you can still do so you just need to be a little more creative. This is especially true if it’s not just based on discretion but also guaranteed with non-disclosure agreements. Here are some ways to get business referrals in secretive industries: Use a “degrees of separation” approach. One way to get referrals when you’re subject to secrecy is through former industry insiders. Connect with individuals who use to be in the business and speak with each about being a brand advocate. The friend-of-a-friend approach is also worth giving a try to get more referrals. Ask a willing client to speak on your behalf. You might have a current or former client or two that are willing to speak with others about doing business with you and their experiences. Take advantage of this and show your appreciation with a gift, discount, or another way of saying, “Thank you.” Give potential customers more control. One thing that scares new prospects is the fear of making a big and/or long-term commitment. To overcome this objection give potential customers flexible and short terms. Openly demonstrate your plans. Possible customers might also be unsure of what you’ll be able to deliver — because of this, the secretiveness balloons into a larger problem. To combat issue openly demonstrate your plans and let him or her evaluate and ask questions. Another thing you can do is to give away a little to entice potential clients to doing business with you. By doing so you’re demonstrating your confidence in your abilities and willingness to do what it takes to earn his or her business. Want to find out about what a business coach can do for you? [shareaholic app=”follow_buttons” id=”26833294″]

Read More »