Why Deadlines Are Important for Entrepreneurs

a calendar with file folders on it and dates circled leading up to a deadline on the last day of the month
Photo: Utamaru Kido / Getty Images

As an entrepreneur, deadlines are important for helping you achieve both large and small goals. However, you won't instantly find success in the world of business by just setting arbitrary deadlines for all of your projects. Your deadlines need to set you up for success—they must be strategic.

Strategic deadlines are designed to help you move closer to your goals every day, week, and month. In this way it keeps you experiencing small wins along the way, rather than simply painting a huge target that is months away which just adds to your stress levels. Even still, for most people, few things cause worry, stress, and panic as much as deadlines.

Remember the three-day, sleepless marathon you did in school just to submit a 20-page term paper on time? Or that incredibly manic week at the office when your team needed put in extra time to impress a valued client?

In these situations, many people get stressed out enough that they begin exhibiting signs of shortened tempers, which can result in poor results for everyone. On the flip side, some people just get tunnel vision and do nothing but work towards achieving the goal while neglecting other priorities. Such is the gripping effects that deadlines can have on our professional lives.

But there’s always a more effective way of doing things. Deadlines are easy to hate, but here's why you should love them instead. For one, deadlines mean you’re still in the game, that you’re in business. More importantly, deadlines can be a source of inspiration, excitement, purpose, and motivation instead of fear and—if your deadlines are strategic. 

Forget the notion of deadlines keeping you awake at night, drowning in anxiety. This is mostly just negative psychology, the planning fallacy, or a common example of procrastination. Reasonable, strategic deadlines actually do the opposite.​ Here are some reasons why strategic deadlines are important, particularly for entrepreneurs.

Deadlines Keep You Accountable for Goals

Very few things have the attention-grabbing power of deadlines when it comes to setting a purpose and defining the timeline for anything important that needs to be done. Whether a deadline has been set by a customer, manager or yourself, it places all stakeholders on the same page, working towards a common objective.

If you give yourself a personal deadline, you create a critical metric by which your action (or inaction) may be deemed a failure or a success. In these situations, only you have the sole responsibility for the outcome. 

Momentum in a Positive Direction

Because the benefits of achieving success by your definition often far outweigh the pitfalls of failure, people who set strategic deadlines tend to work (however grudgingly) towards meeting that deadline.

The closer a deadline gets, the more agitated or motivated people get. When people are agitated or motivated, they tend to move and take action. Over time as you become more comfortable working with deadlines and gain confidence in your abilities, the nervousness will give way to excitement.

Since positive action—however small—moves you closer to achieving a goal, the more progress you make towards your meaningful milestones, the more attainable the result feels. Once you’ve established the right pace for your incremental progressions, all it takes to meet your deadline is to keep the momentum going. 

Spur Innovation and Creativity

For success-driven individuals, a deadline often becomes an engaging challenge and an opportunity to generate value. Whether your deadline is for delivering client work well ahead of schedule or to submit a result that far exceeds the expectations of your customers, success-driven entrepreneurs will use deadlines as a pivot towards excellence.

Well-motivated people harness their creativity and top management skills to re-engineer their workflows and resources to finish the job faster and exceed expectations. Well-known leaders like Steve Jobs was notorious for setting “impossible deadlines” to bring out the best, most creative energy in his employees. Meanwhile, many entrepreneurs have learned to leverage deadlines as a strategic advantage in business negotiations.

Prioritize What's Most Important

Deadlines directly impact your time (and everyone else’s). Therefore, they force you to organize your tasks in order of priority, so that you're only working on objectives that move you closer to your most meaningful goals. You have to learn how to focus in on your key milestones and just say no to the rest.

Otherwise, you’ll be swamped by sifting through your email inbox, scrolling your Facebook feed, or getting roped into other responsibilities that'll cause you to deliver poorly planned and executed results on what matters most. In other words, if you don't ruthlessly prioritize how you're spending your time—which deadlines for you to do—you’ll be a mediocre performer and your deadlines will come and go right by you.

Avoids Making Promises You Can't Keep

Deadlines are for everyone’s benefit but you don’t have to say “yes” to all of them. In fact, if you recognize that a proposed deadline is too unrealistic for you to be able to deliver quality work, it's your responsibility to push back and make sure you won't sacrifice end results in exchange for rushing to get your deliverable shipped.

On the flip side, some deadlines are too lax, which will allow you time to slack off and not force yourself to get creative about how you'll need to go about achieving your goal. Assess your strengths and weaknesses relative to any deadline being proposed to you and within your own internal deadline-setting process as well.

Always go for the sweet spot where deadlines spur you to action, not lethargy; and where they encourage creativity, not cramming. Whether you're a "solo-preneur" working directly with clients or you're working with multiple employees of your own, always strive to manage expectations carefully when it comes to deadlines. Never make promises you can’t keep.

Embrace Failures and Keep Moving Forward

Some people desire nearly perfect results when it comes to their craft, business or career. That isn’t inherently bad, as it can help push you to overcome some of your current personal and professional limitations. But perfection can also become a huge roadblock to progress if you allow it to creep into every aspect of your decision-making process.

Fortunately, when you're on a tight deadline, you're forcing yourself to place the desire for perfection backseat in order to meet your deadline that's more important than endlessly tweaking your results. Do this enough times and it becomes part of your practice.

To hit your deadlines, you may have to temporarily do away with nice-to-have features and strip down your deliverable to being the absolute minimum viable product (MVP). For journalists and writers, deadlines force us to stop polishing a paragraph and focus instead on finishing the article as best as possible with the time constraints we have. 

Increase Your Confidence

Consistently meeting deadlines has the fringe benefit of making you and your team more confident in the long run. The confidence you stand to gain by shipping products and getting your creations out into the real world enables you not only to take on more customers or responsibilities in the future but also to explore new approaches, techniques and to advance your game even further.        

Prime You for Success

The ability to meet deadlines is a reliable metric for assessing performance—especially in the world of business if you're selling yourself as a service. Even in your non-work life, the practice of setting personal deadlines is also a key indicator in personal and business success. According to bestselling author and speaker Brian Tracy, setting deadlines increases the likelihood of success by as much as 11.5 times.

Setting Deadlines That Work for You

Some deadlines will hold back from achieving a good outcome, instead of making it easier to obtain. In fact, unreasonable deadlines—together with procrastination, poor time management, inefficiencies, and other factors—may contribute to the large number (52 percent) of companies failing to meet deadlines. To ensure that your deadlines help you deliver positive results time and time again, consider this.

  1. Adopt the SMART (Specific, Measurable, Attainable, Relevant, Time-bound) framework or a similar approach to setting strategic goals. Make sure to define specific and attainable goals for each stakeholder in the project so that everyone is held accountable.
  2. Set reasonable milestones and corresponding deadlines by engaging everyone and getting their feedback on how best to schedule a task or project. The deadline date should neither be too easy nor too challenging.
  3. Implement rewards and penalties for failing or meeting the deadline.
  4. Unless you directly deal with customers, involve the right people in your deadline-setting process so that you can hold yourself and your team accountable for meeting the deadlines you set.

Remember, a deadline can be painful but it’s an effective tool for getting things done. Use it to clarify purpose, motivate people and create positive change.

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