In the absence of clearly defined goals, we become strangely loyal to performing daily acts of trivia.



— Unknown

So you’ve finally figured out your goal in life: To become a successful entrepreneur.

You’ve never liked working for others. You would love the freedom that comes with working for yourself. You know your wealth prospects are staggering. You visualize yourself reading the paper in your private jet, while sipping on champagne served to you by a Playboy Bunny. You see yourself sailing on your luxurious yacht, driving golf balls into the ocean with your new set of irons. You can almost feel yourself filling the sleeves of your custom-tailored Armani suits. You imagine weekend getaways to secluded European locations with your supermodel girlfriend. You’re a man on a mission, baby.

There’s just one minor detail you’ve omitted from your grand plan: What the hell does “successful entrepreneur” mean?

Make It Measurable

Some of the most exciting choices we make are in figuring what to do with our lives. Setting goals helps us chart a path into the unknown, where the action is. The only thing more exhilarating than watching the mental movie of your ideal life is realizing that you are the producer, director, and lead actor in this film, and the cameras are rolling right now.

But for our goals to be effective, they need to be specific. Defining your desired outcome in precise terms will help you figure out exactly where you need to focus your energy and attention, and make it easy to determine, at any given moment, whether your actions are bringing you closer to what you want or just distracting you from your real purpose.

To crystallize your intentions, ask yourself: Is my goal actionable? Is the output of my goal measurable? How will my external world change when I achieve this goal?

Here are some examples of goals that are insufficiently defined:

Learn to speak Spanish

Overcome social anxiety

Get in shape

Get better with women

Get better marks at school

How do you know when you can speak Spanish? At what point will you consider yourself better with women? Try stating your goals in terms of the exact output you desire, for example:

Spend 30 days speaking only Spanish

Say “Hi” to 100 strangers

Run for 30 minutes, four times per week, for at least three months

Go on one date per week, every week, for two months

Get at least 3 A’s this semester

The above goals are measurable. Even an outside observer can easily tell when you’ve reached them. They’re also carefully worded to ensure you achieve what you’re really after. For example, running four times per week for only one week doesn’t necessarily mean you’re “getting in shape”, but adding “for three months” as part of the goal’s requirements emphasizes your commitment to lasting change.

So how do you go from fuzzy dreams to concrete desires?

Define Success in Your Own Words

People often set goals using words like “expert”, “successful”, “good at”, “better at”. What do these words mean to you? Is being interviewed on CNN what you need to feel like an “expert”? Does “good at” mean being ranked in the top 10 or the top 1,000? All of these terms are subjective, so take some time to write your own rules of proficiency.

A great way to refine your definition of success is to observe what others in your field are doing. What are the most impressive attributes of those you admire? How can they be measured? What kind of revenues are they generating? What’s their batting average? What kind of clients are buying their work?

For example, at one point my primary goal was to become a Ruby on Rails expert. (For non-computer geeks, Rails is an Open Source framework for building websites.) For this goal to be truly useful to me, I had to define the word “expert” in this context. Did it mean speaking at a Rails conference? Nah, doing presentations doesn’t require expertise. Landing a Rails web development contract at an insane hourly rate? Hm, that’s more about negotiating skills. What about writing a book? Nope.

Eventually, I came up with a definition that suited me: Get a “commit bit” to the core Rails repository, which would allow me to make changes to the Rails source code itself. If the core Rails development team would entrust me with this privilege, I could definitely call myself a Rails ninja.

It turns out that while pursuing this goal, my interests shifted. After landing a few Rails contracts, I decided to shift my focus from wanting a “commit bit”, to building my own website using Rails. I used the skills I had acquired while pursuing Rails expertise to build 30 sleeps. So, even though my priorities changed, I still greatly benefited from learning Rails.

Notice the impact that a clear objective has on where you direct your energy. Had I defined “Rails expert” as “someone who speaks at Rails conferences” my actions would have been completely different from those required to gain change access to the Rails project itself.

Target the Side Effects

Some goals are tricky to nail down. How do you precisely measure “getting out of depression” or being “happy with who you are”? Emotional states are difficult to quantify, and many skills are subjective.

In these cases, think about how to turn the subjective into the objective. How would your external world change if you were “happier”? Would you go out with friends more? About how many times per week? Maybe it would include having “zero arguments this month” with your spouse. The more you ask these questions, the more you discover that even the most feel-good internal changes do manifest themselves in many ways in the external world.

This one could take some practice, so let’s consider more examples. If a major source of your unhappiness is that you hate your job, then “get out of depression” might just mean “find a new job”. If you’re trying to overcome your fear of heights, make it your goal to stand in the observation deck of a tall skyscraper for 15 minutes, at an average heart rate under 80 beats per minute. Being “happy with who you are” might just mean feeling really comfortable talking to people, so why not refine this goal to be “Say ‘Hi’ to five new people every day for a month.”

Remember, targeting the side effects does not mean ignoring the underlying issues. It just means that if your goal is to “be happier”, for example, you’ll get there much quicker if you give yourself something tangible to strive for. It might seem funny to define these things in such concrete terms, but who cares? Be creative. Have fun with it. You can always redefine your goal at a later time, especially if it’s no longer pointing you in the right direction. It all comes down to results.

Use Short Time Frames

If you give yourself six months to get a date with a hot girl, you could easily spend the first five on aimless internet reading and movie rentals. Constraints force you to take immediate action, and use your time productively.

When you aim too far ahead, you make decisions and commit to things when you have the least information to do so. For example, it’s almost impossible for me to set useful and specific revenue goals for this site in three years’ time. I have no idea what my numbers will look like that far in the future. But I can look at my current revenue and traffic growth patterns and set realistic targets to push me forward over the next couple of months.

Don’t Be Too Specific

While effective goal setting requires precision, you don’t want to box yourself in. Rather than setting your sights on dating a specific girl, define a profile of what you’re looking for in a woman. Instead of putting all your hopes on getting hired by one company, focus on what kind of work you want to do, what kind of talent you want to work with, and a salary range that suits you.

If your goals are too detailed, it’s easy to get discouraged when your results don’t match up exactly with what you want. Being flexible will expose you to more opportunities. Rather than putting all your eggs in one basket, define boundaries within which to operate and keep an open mind.

Setting goals is the first step in paving the pathway to a better life. Goals give us motivation and direction to explore who and what we are. Effective goals are not only exciting, but specific. A clear description of our desires helps us focus our efforts on the right things and makes it easier to see whether we’re moving toward or away from what we really want.

Setting clear goals sometimes requires creativity. In some cases, the best way to pursue a goal is to aim for its side effects. But by making it measurable we make it actionable, and turn our fuzzy daydreams of success into exciting challenges we can take on in the present.