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.

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