Serious Goals for the Serial Entrepreneur

It is the entrepreneur’s cliché cash-out: idling away lazy afternoons on a white-sand, tropical beach. Success certainly affords, among other things, an excuse to relax and enjoy the fruits of one’s labor.

But as many dyed-in-the-wool entrepreneurs have discovered, there is only so much time you can spend fly fishing or lounging in a hammock before the urge to do something new starts gnawing deep down. Soon enough, everything around you suggests a new or overlooked opportunity. Every cocktail napkin becomes a sketchpad or whiteboard. Or that great idea, long stowed away, keeps you awake late at night.

Indeed, success also provides resources, credibility, experience and—most of all—the confidence to attempt things. The only thing harder for an entrepreneur to pass up than a good idea is that same idea coupled with the knowledge that “I’m good at doing this sort of thing.”

Entrepreneurs therefore need no prodding or motivation to get up and try something new. It just happens. They can’t help it.

What is not so automatic is the notion of attempting something ambitious. By that, we mean ambitious relative to what you’ve already accomplished. In short, if you’re attempting something that doesn’t make you feel at least a bit uncomfortable, then you probably aren’t growing. You may be successful at completing an unamibitious project, but it will be a hollow victory, as anticlimactic as an author’s second book that breaks no new ground. Worst of all, you will fall far short of your own potential.

Serious Goal-Setting

If you’ve found this article, you probably need no explanation of the power of setting goals. What is not so well-known is that a few of your goals should deliberately be very difficult.

That’s right, difficult. Just plain hard; in fact, as hard as they can be, so long as you still believe that the goal is possible. In numerous studies, research has demonstrated that effort and performance are directly proportional to the goal’s difficulty level, up to the point where the goal becomes no longer believable (at which point effort tends to cease altogether).

But here’s the clincher: Performance is maximized even when the goal is not achieved!

How is this possible? If you look closely, most things that people attempt are not truly binary, meaning they’re not measured as all-or-none, pure success vs. pure failure. Most outcomes are a matter of degree and incremental gains are key. A marathon runner may not finish her first race but she might run further than she’s ever run before. A smoker might fail to quit smoking altogether but might cut his nicotine consumption in half. A salesperson might reach only 90% of a large sales target. In all of these cases, the goal was not reached, but performance was improved.

The research thus overwhelmingly suggests a new approach to goal-setting: Set very difficult goals for yourself and then recognize and reward partial success. It’s better to earn 80% of a $1 million income goal than to earn 100% of a $500,0000 goal.

This can be hard to get used to for highly aggressive, old-school goal-setters who writhe in pain at the thought of failing to meet a goal by its deadline. Fear not. The research also shows that failure to reach the goal (regardless of whatever gains were accomplished) is still highly motivating to people, especially when you missed your goal by a narrow margin. Reaching 80% of your goal stimulates you to try that much harder next time and reinforces your overall belief in the goal’s attainability.

True, there are bigger risks when attempting bigger things. But that’s the whole point. Working to minimize risk is what it’s all about. After all, it’s the fear that creates the stress, and it’s the stress that forces the mind to adapt, coming up with ever better approaches and solutions that minimize the risk. The very act of eliminating risk is what raises us to the next level.

What if my goals depend on other people or things out of my control?

If you choose to set a goal in which the outcome is dependent on the actions of somebody else, acknowledge now that, through no fault of your own, you may not reach that goal. For example, the goal “To toilet train my daughter by the end of the week” is largely dependent on your daughter’s cooperation. That doesn’t mean it’s not a good or worthy goal, it simply requires a more flexible frame of mind—you can’t force someone else to adhere to your plan.

Matters of chance or competition are similar. Winning a game, a pageant, or admission to a particularly selective school may be worthy of your efforts and a good goal. But again, accept that the outcome, though influenced by your actions, is not entirely in your control.

If you pursue one or more goals like this, be sure to set and pursue several other goals in which you are entirely in control of the outcome. Your life shouldn’t be left too much to chance—take control of as much as you possibly can. Wherever possible, aim to accomplish tasks that tilt the odds in your favor.

What if my goals conflict with each other?

Almost all goals require some of your resources: time, money, effort, attention, and so on. Because these resources are limited, goals can often appear to be at odds with one another—working on one can mean slipping on the other.

Good management of your goals as a group is important for avoiding frustration:

  • Stay focused. Don’t set too many goals to come due at the same time. A large number of goals (7+) is okay if the goals are small or simple (such as a goal to shampoo the carpet) but be realistic and don’t expect to build a business while getting a law degreewhile training for a triathlon while raising a family.
  • Always have at least one simple goal and one difficult goal at any given time.The simple goals motivate you as you accomplish them rapidly. The difficult goals keep you challenged and growing.
  • Always have at least one short-term and one long-term goal at any given time. As with simple goals, short-term goals help assure that you’ll have frequent victories. Long-term goals (two years or longer) keep you headed in the right direction.
  • Prioritize but be flexible. Decide which of your goals (and tasks) are most important and assign your due dates accordingly. Be willing to change due dates or even put a goal on hold for a while if necessary.
  • Spread out your due dates. Avoid setting a large number of difficult goals with tasks due at the same time.
  • Look for ways to combine goals and tasks. For instance, if you have a goal to take a vacation and a goal to get better at photography, consider taking a travel photography class that spends a week in the wilderness snapping pics.
  • Most of all, strive for balance. Make sure to set goals (whether easy or hard) across different areas of your life: health, finance, family, relations, learning, experiencing, career, etc. For instance, don’t set ten career goals but then neglect your health, friends, and family.

New Feature: Habits on Dashboard

We have just launched a new feature, which allows you to quickly check off any habits that you have kept for today. Basically you will see a “habits” section down below the “active tasks” section. To check a habit, simply click on the checkbox before the habit name. Once it’s checked, it will disappear from the dashboard, and at same time a checkmark will be placed on the habit’s calendar.

Habits on Dashboard

Habits on Dashboard

So basically this is the same as you check your habits on the calendar from the Habits page, but just a quicker way to do it. Many people request this as many of their habits are indeed kind of daily tasks that they do. So it makes sense to put it on Dashboard page to allow the fast access.

How to deal with actual failure?

This is important: “Failure” only occurs when you fail to try in the first place or when you give up on a goal you want to achieve without having first given it your all. Missed deadlines are not failures. Setbacks are not failures. Unexpected challenges or changing priorities are not failures (in fact, they’re quite normal). Feeling discouraged doesn’t mean you failed. You can only fail if you quit, and there’s an easy solution to that:

Keep going or start again.

So long as you are working toward your goal and following a plan, you haven’t failed. If you stop, just start back up again. And remember, every step forward, every single task you check off as completed is a small accomplishment unto itself. Focus on just taking that next baby step, then the next, then the next. If the tasks are too difficult, then break them down into absurdly simple tasks, ones that you’re guaranteed to complete. It may seem ridiculous to break down something as simple as cleaning a garage into forty individual tasks, but in doing so, you can build momentum with each task checked off. It’s a bit like playing a game with yourself, but it really works.

How do I know if a goal is realistic?

A goal is realistic if you stand reasonably good odds of accomplishing it, given enough time and effort—and indeed, mountains can be moved if given enough time and effort. “Good odds” is a subjective measure, but one that you have most control over when success or failure depends on what you do, as opposed to what other people do or random events (such as goals “to become an astronaut” or “to win the lottery”).

The majority of the goals you set should be very realistic or you risk becoming frustrated if you do not accomplish any of them. However, there is nothing wrong with attempting things that defy the odds or that you expect to be extremely difficult. Such goals require courage, defined here as “attempting something even though you might not succeed.”

Almost any goal, no matter how difficult, can be made easier by breaking it down into several smaller goals, to be tackled one at a time. The completion of so-called “baby steps” is one of the best ways to build confidence, momentum, and a track record of performance.

And finally, when you create or update a Goalplan, ask yourself, “Will completing these steps lead to completion of the goal?” If not, then modify the obstacles, tasks, or due dates until a viable plan exists.

To Reach Goals: Bypass Resistance & Gather Assistance


To reach goals, consider this illustration:

If you see roadblocks up ahead on a journey you take a diversion. No one in their right mind would just drive on and hit the obstacle head on just hoping they get through!

Bypass Resistance

When you set a goal and if you are going to successfully reach goals, you need to write down a list of potential obstacles you may face.

Are there people who won’t understand your goal and discourage you?

Do physical limitations or unfavorable circumstances stand in the way?

Then list them, analyze them and develop a strategy.

With a roadblock you can turn off before you get there or go over, under and around.

Do the same with obstacles that may seem to make it impossible for you to reach goals you have set.

Is there any way you can bypass the objects of resistance you are likely to face?

Preparation like this is invaluable.

If and when you reach the obstacle you know what to do.

You have already made up a contingency plan so you can move ahead and reach goals you have set!

Gather Assistance

At the same time, it is important to identify the knowledge you will need to acquire or the people or organizations that could give you essential help to reach goals before you.

Research the subject and educate yourself.

Become knowledgeable on what you are trying to achieve.

Do you personally know people who have accomplished what you are seeking?

Talk to them. Get input.


  • How did they do it?
  • How did they feel once they were able to reach goals they had worked towards?
  • Can you link up with other persons in that field?
  • What organizations exist with support or information you could use?

The internet is almost a bottomless ocean of knowledge. Through persistence you can find pretty well anything you need to know.

So, to reach goals, bypass resistance and gather assistance.

Including these two elements in your goal setting can make the difference between a failed attempt at the target and a bull’s eye!

The Top 10 Steps to Set and Achieve Your Goals – Every Time!

By Dr. Philip E. Humbert

It’s been said that everyone has goals, whether we know it or not. We have goals to keep our current job, or to get a different one. We have goals to save for the future, or to travel, take a vacation, or purchase the things we need and want to make our lives more enjoyable. An important distinction, however, is that top achievers are very intentional and focused on their goals, while many of the rest of us are not.

Top achievers know that the wording, structure, timing and format of a goal can make it’s achievement much easier – or far more difficult. Top achievers understand the basic skills for setting and reaching their goals, every time! They know how to design goals that create success. Here are the 10 most important steps to set and achieve your goals:

1. Reachable goals are SPECIFIC.

Top achievers know that to reach their goals, the brain must know exactly, precisely, what they are trying to accomplish. Never word a goal with vague terms like “some” or “a little bit”, or “more”. Be specific! If you want to lose 10 pounds and reach a weight of 175, specify those exact numbers. If you want to save $200 this month, be exact. Your brain can help you accomplish almost anything if it knows precisely what you are aiming for.

2. Reachable goals are SIMPLE.

Many people describe their goals in complex terms of retiring on the beach in Hawaii, with nice cars and lots of money, and…. Their list goes on and on. Any ONE of those things is a great goal, but the combination becomes over whelming and the brain gets confused. If you want to retire in Hawaii, just say so! If you want to increase your sales by 10% this month, say so! Keep your goals simple, clear, and focused.

3. Reachable goals are SIGNIFICANT.

No one can muster the enthusiasm, hard work and courage to reach a goal they don’t really care about. A reachable goal is one you really, really, REALLY want! It’s something that will change your life, enhance your health or wealth, and make you proud. It gets your juices flowing, gets you up in the morning, and keeps you going all day long, because it is important! Set goals that are worth achieving!

4. Reachable goals are STRATEGIC.

High achievers know that the best goals accomplish many great outcomes, all at one time. Running a 10K race will almost certainly: 1) feel great! 2) help you lose weight. 3) lower your cholesterol level 4) strengthen your heart 5) lower you risk of heart disease 6) boost your energy and stamina, and 7) improve your outlook. Design your goals to strategically impact as many areas of your life as possible. You’ll have more reasons to reach your goal and more excitement when you do!

5. Reachable goals are MEASURABLE.

A goal without a measurable outcome is just a pipe-dream. You can’t achieve a pound of “happiness” or 6 inches of “self-esteem”, but you CAN get a new job. You CAN run a mile in under 7 minutes, or do 100 sit-ups. Someone has wisely observed that, “What gets measured, gets done.” Define your goals in terms of height, weight, dollars, inches, or hours. Then measure your progress until you achieve your desired outcome.

6. Reachable goals are RATIONAL.

To reach your goal, you will need a plan, a path, and a vehicle for getting there. Your goals must make sense! When you explain them to friends and family, your goals should create excitement, draw support, and encouragement. Your goals should be just out of reach, but not out of sight! You want to stretch to be your best, not strain after impossible dreams. Set goals you CAN and WILL achieve!

7. Reachable goals are TANGIBLE.

Choose goals that you can see, hear, smell or touch. Go for things you will enjoy and that you can clearly visualize. The brain has hard time going for “financial security”, but it can visualize a bank statement with nice, large numbers on it! Define your goals in terms that excite the senses, then go for it with all your heart!

8. Reachable goals are WRITTEN.

High achievers always know precisely what they want, because they’ve written it down. Often, they write a short description of their goals every single morning, as a personal reminder of their priorities and their objectives. The act of writing your goals down vastly increases your chance of success. Write it down! Then, keep your notes where you can see and read them every day.

9. Reachable goals are SHARED.

We are far more likely to stick to our plan and reach our goals if we know our friends and family support us. Being part of a team increases our determination, our stamina, and our courage. Caution: Never share your goals with anyone who may ridicule, tease or discourage you! The world is full of doubters and you have no time for them. But, find a support team, a group of cheerleaders, and a coach who will encourage you every step of the way. High achievers count on and work with other winners!

10. Reachable goals are CONSISTENT WITH YOUR VALUES.

One of the biggest reasons people fail to achieve their goals is that they have conflict between their behavior and their values. However, when your values and your goals are in agreement, there is no stopping you! Clarify your values first, then set simple, specific, measurable, tangible, written goals that are consistent with those values. You will achieve them, every single time!

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Keep Your Goals On Track and Get Things Done

Any progress made on your goals has to be achieved through completion of your daily tasks. GoalsOnTrack‘s Dashboard and Day Planner are great features to help you plan out the day, focus on tasks at hand, and boost your overall productivity.

Give it a try today. Find out more >>

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