(photo by Benjamin Burgh)

A picture of my ideal situation, I kid you not. For more on this, read on. As for why this somehow represents my ideal self to me, I couldn’t tell you. Actually, the more I look at it, the more I realize that it’s not a great fit – I hate leather, after all. Still, it’s more the organization – the feel, rather than the actual items – that speak to me. Calm, collected. That’s what I want.

So, I have a big problem with even referring to whatever I’m about to talk about as entrepreneurship. It sounds mannered. It sounds pretentious.

To me, this stuff is as natural as breathing, and I do not mean that in a self-glorifying way. As I’ve mentioned before, I am a serial project-starter, serial business-creator. I like the beginnings of things. It’s addictive, it’s creative, and to me, building some kind of organization around whatever I happen to be doing is so natural that I actually have to try to turn it off just to maintain some level of sanity and focus.

So, no fancy-pants talk. I’m not making Google. I don’t want an IPO and I don’t want to sell companies to giant corporations for millions of dollars (well, you know. Unless they want to buy. If that’s the case, I was kidding before).

I’m interested in lifestyle businesses – another fancy-pants internet term – businesses that are meant to improve your quality of life by engaging you in something you enjoy, empowering you to make your own economic decisions, and making the world a better place.

My Dad always used to say that money is freedom, but you can always be free and miserable. It isn’t the end goal; the process is. You shouldn’t want to retire.

Keeping this in mind, I’ve been going through multiple transitions lately (from student to student teacher, from student teacher to unemployment, from rollicking single guy to serious relationship)(well, I was never actually “rollicking”), and the need to make more money has been fairly intense. I have bills to pay, debts incurred while student teaching.

In response, I started two companies, both of which have been doing fairly well. The process has been much, much easier than in the past, which made me realize that my incredible list of spectacular failures has actually bestowed on me a respectable body of knowledge on how this all works. It isn’t that hard, if you know what you’re doing. Kind of.

Since I’m planning on teaching a few adult education classes on the subject, and actually have my first-ever career coaching client right now (she isn’t paying, mind you – this is a test run, which I’ll talk about later), I thought I’d walk you all through the process I’m going to walk them through. I’ll develop the materials, you read it, follow along, tell me what you think, start awesome companies, make tons of money and give me ten percent.

Deal? Deal.

Now, on to

Part 1. Goals.

I am a huge believer in goals, as you may have noticed. And I think it is fair to say that if you give even the slightest thought to things like this, you’re probably pretty goal-oriented yourself.

Goals are almost entirely overlooked, however, when people start thinking about starting a business. Even when they do have goals, they are often completely worthless, and sometimes do more harm than good. This is because all of us – including myself – want to jump right into the nitty gritty of starting a business and building our empire. That enthusiasm is great, but it’s dangerous as well; remember, this is a marathon, not a sprint.

Starting any long-term endeavor without some kind of plan is just begging for trouble. There are a few reasons for this, but essentially it all boils down to two things: Motivation and Direction.


The number one reason you fail at things is because you give up.

Think about it: if you had kept up with those piano lessons you took when you were 8, how good would you be now? What about that band you started in high school? Or that blog you put up, then forgot about?

We all do this, and failures and abandoned projects are by no means worthless. However, if your goal is to succeed it’s important to realize that your biggest obstacle will be your own loss of motivation. You can plan for this, you can trick yourself, but if you don’t make that realization now, it will mean trouble down the road.

Goals help with motivation because human beings are universally motivated by progress and demotivated by frustration. This is part of our evolutionarily-honed pattern recognition process: try something, note the results, change action accordingly. This is great if you’re tracking wild boar in the jungle, but for difficult projects that require a fair amount of groundwork it can lead to abandonment.

We can short-circuit this process by developing goals that give us actionable, realistic milestones. We give ourselves an endpoint, a destination, and then can judge our progress towards it. This has the effect of creating an awareness of progress, helping us to stay motivated.


The other benefit of effective goals is direction. We spoke in the paragraphs above about how goals are really milestones – objectives that allow us to gauge progress and stay motivated. Those milestones, however, serve a second function: they let us know if we are going in the right direction.

The process of starting a business (or doing anything, really) can be hopelessly overwhelming. You have to find clients, craft proposals, know what you’re selling, build a website, get business cards, make a Twitter account, get a Facebook page, tell all your friends, build an email list, post flyers, work on a resume…

…You see what I mean. There is a near-infinite number of things you can do. How do you choose between them? How do you prevent freezing up in the face of all these possibilities? How do you judge what’s worthwhile, and what’s a waste of time?

Goals let you do this. Whenever you’re in a situation in which you must decide whether to pursue a specific course of action, go back to your goals. Think about where you are, and then apply this criteria to your decision making process:

If it does not move you closer to your goal, you do not do it.

I call it Barrett’s Razor (well, I wish I did, anyway). You should be applying this rule to every single decision you make. Whatever your goal is, whether it’s to get your very first client or to maintain a million-dollar contract, you must keep it in mind at all times and always be moving towards it. Everything else? Cut it. Time and effort are finite resources; you have to be careful where you allocate them.

I’ve discussed this theoretical basis for goal-setting in such detail because of one simple fact: most people don’t set goals. Even now, after I’ve been praising goals from top to bottom for who knows how many paragraphs, you’re probably thinking about skipping this step. “I already know my goals,” you think. “I want to make more money.”

You’ll see why that’s a horrible goal as we move forward, but I really can’t stress this enough: You must do this part. The success rate of people who go through this process versus that of people who do not is striking. If you skip it, you’re setting yourself up for failure down the road.


Putting It Into Practice

We know we need goals, but how do we put that knowledge to use? How do we create goals that actually benefit us?

We’ll be working on two separate goal setting exercises, both aimed at maximizing your Motivation and Direction. But first, let’s talk about what makes some goals good, and some goals bad. What makes one goal better than another?

The answer is definability and actionability.

Definability means that your goal can be quantitatively defined; you actually know what it means. This sounds simple, but a surprisingly large number of our goals are undefinable. For example, if someone told you their goal was “to be happier,” what would that mean? For everyone, the actual, physical or mental definition of “happiness” will be different. Some people are happiest when working all the time; for others, laying on the beach means happiness. If you can’t define your goal, how do you start? What do you do?

“I want to get three paying clients” is a definable goal – you either have it, or you don’t. “I want to lose ten pounds,” is definable. “I want to sell 1,000 copies of my new record.”

“I want to make more money,” on the other hand, is not definable. How will you know when you have “more?” How much is that? If you find a penny, you’ll have more money – have you achieved your goals?

If you really want to know if your goal is definable, ask yourself if it’s measurable: How will you measure your progress? How will you know when you are done?

Actionability, on the other hand, means that you can actually perform some action that will help you achieve that goal. “I want to be happy,” even if you could measure “happiness,” is still not actionable. How do you become more happy? What do you actually do every week, every day, every morning? Good goals have things that can be done to help achieve them. Even if you have no idea what those things are right now, you have to know they exist.

Let’s look at an example of how we can use these principles to turn a bad goal into a good goal. We’ve been using “I want to be happy” so far, so let’s stick with that.

“I want to be happier” is super vague – both undefinable, and unactionable. Let’s start with our definitions of happiness, and work our way down.

Take Diane. She’s a 40-year old businesswoman with two kids. Diane is the one that wants to be “happy,” but isn’t sure what that means.

There are a lot of things she can ask herself to work through this problem – why does she want to be happier, anyway? Is she not happy now? Well, It isn’t that she’s not happy now, she thinks – she has a family and a good job. She’s just been stressed out lately, overworked and overtired, with not much free time.

It’s the stress and lack of free time that’s the problem, not “happiness,” which doesn’t really mean anything anyway. Knowing this, she adjusts her goal to “I want to be less stressed.”

Of course, “less stressed” is still undefinable. How stressed is less stressed? Should I be picturing the Dalai Llama here, or something less extreme? It’s also unactionable – how is she supposed to become less stressed? If there was an obvious way to do this, wouldn’t she have done it?

Let’s focus in even further. When Diane thinks about her stress levels, it really boils down to not having any time to herself – between her work and her kids, she’s busy all day, every day. Perhaps she changes her goal to something like, “I want more time to myself.” Better, but still a bit undefined – what does time by herself look like? Maybe she changes her goal again to “I want more time in the house, in total quiet, so I can read.”

Now we’re getting somewhere! That’s a clearly defined goal, but it isn’t measurable. Let’s set a number, so we can measure exactly how close to or far away from our goal we really are.

Diane’s final goal looks like this: “I want one hour every day, in total quiet, so I can read.” That goal is well-defined, it’s actionable, and it will serve as a powerful tool as Diane works on ways to carve out that time for herself – perhaps by hiring a maid to take care of household chores, going in to work an hour earlier and leaving early to spend time in the library, arranging for her husband to pick the kids up, etc.

All right, enough talk! Now it’s time for you to apply these principles yourself, creating a set of broad and specific goals that will help you stay motivated and move in the right direction. This isn’t some list you’re going to write down and forget about – these goals are going to be an integral part of the process, so take your time. Write them down in a safe place.

Ready? Here we go.

Step 1: Long-Term Visualization and the 12-month plan.

In this step you will visualize your end-goal: your ideal situation. From there, we’ll decide what kind of work you truly want to do, and how to best approach starting your own business. Answer the questions thoroughly and thoughtfully. Feel free to let your imagination go.

12 months from now…

1. What kind of work will you be doing? I mean literally – are you outside, inside? Working with your hands? On the computer, in an office?

2. Who will you be paying you? Is it individual clients, or an employer? Profile them – size, revenue, number of people, even gender. Who’s your “boss” – the person you’re accountable to? What are they like?

3. How much money will you make a month? A year (write down both)?

4. How will you be using that money? Be realistic – what does it go to? Are you saving, making extra money for dinners out, spending on gadgets, feeding the kids? Be specific – break it down.

5. Where will you be working? Literally – what place? What does it look like? What surrounds you? How do you get there? Picture it.

6. How much time will you spend working – per day, per week, per year?

7. What does your Monday look like?

8. What does your Saturday look like?

9. Who will know your name in your field?

10. Who will you be having lunch with?

11. What will your family and friends think of what you do?

12. Find an image – online, in a magazine, a catalog, wherever – that symbolizes your ideal situation and how it will feel. The image need not be literal – it needs to evoke the emotion you’ll feel when you achieve your goal. Clip it out or save it to your hard drive.

Step 2: Immediate Goals and Quick Wins.

Long-term planning is absolutely crucial for motivation, but there’s also an inherent risk: long-term plans can mean long stretches of work without immediate reward. Immediate reward is essential to maintaining your motivation and effort – remember, if we see no effect we tend to change course.

Immediate goals are meant to circumvent this problem. Immediate goals are definable, actionable, and most importantly, they are achievable within a limited time frame.

Making immediate goals is simple. Just complete this sentence:

In 3 months, I will…

Remember, you need to pick something – just one thing – that is clearly defined, achievable within only 3 months, and easily measurable. Examples might be:

…make my first $1000 from my business.
…have 3 paying clients.
…compose, record, and release 3 songs for download.
…have 200 pages written in my novel.

The key is that it has to be doable within 3 months, but not so simple (“I will have emailed 5 companies about a job,” for example, is far too easy) that it won’t take work.

This immediate goal will serve to motivate you by providing a clear direction to head in right now, but it’ll also tell you whether you’re on the right track. If your goal was to make $1,000, and you’ve only made $5, it’s time to change strategies.

Now, here’s the important part: Take everything you just put together, including the image. Print it out, paste it together, tear it out of the book – whatever you need to do – and hang it somewhere you will see it every day.

Put the image as your desktop background. Make it the background image on your phone. Hang your goals on the refrigerator, and above your desk. Put it anywhere and everywhere. Everyday, take a moment to look it over. Read it to yourself. Remind yourself why you’re doing all this work in the first place.

In many ways, goal-setting and visualization exercises have been given a bad name by wishy-washy new age types who seem to think that visualization somehow magically affects the universe and makes wishes come true. The reality is much more prosaic: people who have a clear idea of where they want to go are much more likely to get there. People who don’t are much more likely to waste time and give up.

It’s that simple, and it’s that important.

Next time: Picking the business that’s right for you.