Some people are perfectly happy with their corporate jobs, but have always had the desire to challenge themselves with a new experience like starting a business.

Whatever your reasons, in order to gather the strength for what lies ahead, you must feel deep inside that it is worth the time, energy, and money required to explore entrepreneurship.

Are you feeling it? Good.

If Not This, What?

KEY

Find out what makes you purr.

When you realize that you are not able to continue in your current line of work, the next logical question is: What should I do?

This strikes fear in some people’s hearts since they have been on autopilot for a long time and have not considered their passions in many years. When I used to teach presentation skills to corporate salespeople all over the United States, I would always use the same practice topic: a one-minute presentation entitled “I am passionate about . . .”

I was amazed at how few people had an immediate answer to this question. Most looked at me with a blank stare. Others were annoyed and even hostile, since they could not believe that I would ask them to complete such a difficult task with so little preparation.

So a big part of your job at this stage is to reawaken curiosity, your muse and your creativity. This will require time, attention, and focus in order to get real results.

In the year 2000, in Phoenix, Arizona, at a Fast Company conference about design, I had the privilege of listening to Jim Collins, author of the best-selling books Good to Great and Built to Last. In his highly personal keynote, Jim talked about his own career path, which took him from professor of entrepreneurship at Stanford to, in his words, “an entrepreneurial professor.”

He referred to the ultimate work situation as your “sweet spot.” This is the intersection of three interlocking circles:

• The first circle is “what people will pay you to do”—marketable skills and abilities that you have developed over your working life.

• The second is “that which you have great passion for”—areas of interest, hobbies, ideas, or causes that make your heart race.

• The third, and most elusive, is “that which you are genetically encoded to do”—the things that you were brought on this earth to accomplish that no one else on the planet can do as well as you.

Where these circles interlock is your “sweet spot” and the place where you should spend your working life if you want to feel alive and full of joy.

Jim started his investigation by gathering data on himself much as a scientist would observe an insect in its native habitat. So when he was stuck in meetings, or listening to Brahms, or involved in a variety of other activities, he would document his behavior in a notebook he called “A Bug Called Jim.” He would notice when he was engaged, or bored, or sad, or angry.

His process of discovery lasted years, and he supplemented his data gathering with personal mentors and lots of reading. After a while, he began to see patterns, and made steps each year to bring his working life closer and closer to his ideal picture.

EXERCISE

“A Bug Called You” Notebook

To start this exercise, purchase a notebook that will be easy to carry around in your bag or briefcase. It can be as simple as a lined notepad, or as fancy as a custom-engraved Moleskine. The key is to always have it handy and take note whenever you notice significant things about yourself. Here are some starter questions. Feel free to add your own:

What interests me?

What repels me?

Which topics are exciting?

Which environments make me feel open and relaxed?

Which environments make me want to crawl out of my skin?

Which kind of people do I like to be around?

What time of day do I feel most awake? Energized? Relaxed?

What do I really love to do?

What do I daydream about?

Which kinds of stores make me feel good?

Where is my favorite place in nature?

Who in my life is a bloodsucking leech?

When do I feel the most free?

When do I feel the most imprisoned?

When do I feel “in the zone,” “flowing,” and so preoccupied that I literally lose track of time?

Every week or so, read over your notes and pay attention to any patterns that emerge.

Through this process of introspection, you will soon begin to answer these questions:

• Who am I? You must get to know yourself deeply and completely if you want to act from a place of truth and self-confidence. This will include gaining insight into both your essential and social selves described in chapter 2, in addition to the part of yourself that is more creative and spiritual.

• Who are my people? These are not just those people who would grudgingly fork over money for your product or service; they are people who would clamor to do business with you because you are the exact answer to their problems. They are your ideal partners, clients, customers, and mentors. These are people whom you like to spend time with, who embrace you despite your perceived warts, mistakes, and flaws and who are deeply affected by your work.

• What work do I love to do? We often think of career development as answering the question “What do I want to be when I grow up,” insinuating a job title or specific profession like lawyer, doctor, or accountant. The problem with this is that as you change, your ideal work situation can change too. So while you may revel in being a high-flying consultant in your unmarried twenties and early thirties, the constant time away from home can start to wear on you once you are married and have kids. A better question to understand is “What work do I love to do?” These can be things like “educate and inspire people,” “write code,” or “rid the world of ugliness by applying my clean and beautiful design aesthetic.” You can package these basic skills and areas of interest in many different ways, depending on the nature of the market and your life situation.

Begin at the End: Create a Picture of Your Ideal Life

KEY

Design a life that will make you happy.

Once you begin to get some insight into your interests, preferred working style, and business ideas, a common inclination is to dive into business planning right away.

The danger in this is that you will become an unwitting hunting dog, following the blood of the market. You might chase a business opportunity that has great financial potential but will not match your ideal life whatsoever.

This is a very common trap for new entrepreneurs, who find that despite business success, they still are working crazy hours and aren’t exactly thrilled with their life. Instead, first define the type of life that will make you happy, healthy, wealthy, and wise.

EXERCISE

Your Ideal Life

As you complete this exercise, it is important that you escort your social self out the door, since it will only get in your way. If you find yourself saying things like “but that would never work,” or “no one would ever pay me to sit around talking about Dalmatian breeding,” or “Brad Pitt is obviously sticking with Angelina, how could he be living with me? ” kindly escort those voices to the door.

I suggest you do this exercise in an uncluttered environment, with time to daydream, and plenty of tools around you to take notes.

INSTRUCTIONS

For each of these areas, read the questions and write notes about your ideal life situation. Write in the present tense, as in “I live in San Francisco, California, in a house that overlooks the Golden Gate Bridge,” or “I live in a yurt in Upper Mongolia, with a warm fire in the center of the house and a large herd of horses outside my door.”

HOME

• Where do you live?

• What is your physical home like?

• What surrounds your home?

• What is the neighborhood like?

• What are the characteristics of the community? Is it an urban or rural setting? Is it a close-knit community, or does everyone live a private life?

RELATIONSHIPS

• How do you treat yourself?

• What is your relationship like with your spouse/partner?

• What is it like with your kids? (If you have them, or want to have them)

• With your pets?

• With your friends?

• With your family?

• With business partners?

• What are ideal partners like?

• What strengths do they have that complement yours?

HEALTH

• How much do you sleep?

• What exercise do you do, at what frequency?

• What do you eat?

• How does your body feel most days?

• Write down anything else important about your ideal state of health.

WORK STYLE

• Do you work by yourself or with others?

• Do you work in an office or work from home?

• Are you home a lot, or a road warrior?

• Do you have a regular, structured schedule or do you work when you feel the muse?

• How many hours a week do you work?

• Is it the same each week, or does it change depending on what you do?

NATURE OF YOUR WORK

• Are you creating something from scratch?

• Providing a service or selling a product?

• Working with your hands?

• Inside or outside?

• Do you prefer to:

Create something and pass it on to someone else to manage?

Manage the details of what someone else creates?

Both create and manage?

• Add anything else you can think of that describes the general nature of work that makes you happy.

FINANCIAL LIFE

• How much money do you make per month?

• What kinds of benefits and insurance do you have?

• What is the nature of your income stream? Do you have regular, predictable income, or does it ebb and flow depending on what you are doing?

• How much money do you have in savings?

• Write down anything else that is important to you in terms of your financial life, like levels of debt, spending habits, etc.

If you have a family, your life plan is created as a joint effort. Each person in the household (wife/husband/partner/kids/parents if you are caring for elders) should weigh in on the kind of life that would be ideal. Of course everyone won’t agree with all the others’ priorities, but you should be able to gain agreement on some major areas.

Once you have a life plan in place, it becomes very easy to make decisions about the kind of business you want to create. The best part is that it ensures that once your business takes off and you experience financial success, you will be happy with the life that you have created. I cannot tell you how many miserable multimillionaires I met in my years in Silicon Valley. I believe they were miserable because they got too enamored with business growth at all costs and didn’t see creating a great business as a means to live a great life.

For a downloadable template of the life plan, go to www.escapefromcubiclenation.com/book.

Find the Business Needle in the Idea Haystack

KEY

Identify a specific idea.

As you have thawed out your frozen soul, reawakened creativity, observed the kinds of things that interest and energize you, and created a snapshot of your ideal life, it is time to look for specific business ideas.

If you are like most people, when you are in brainstorming mode, you will be plagued by pesky thoughts like:

• No one will pay me to listen to music/drink Red Bull/analyze my pet’s problems!

• I will never be able to make it as a writer—that is one of the most competitive fields ever!

• Artists never make money!

• Well, that is a stupid idea! Who do you think you are, Richard Branson?

At this stage, these thoughts will just get in your way. Don’t get me wrong: you will absolutely need to use research, testing, and planning to find evidence that your vague business idea has some merit in the real world. But many people dismiss potential business ideas based on vague, unsubstantiated hunches before they do real testing in the market.

After lots of brainstorming, sorting, musing, research, writing, and playing around, you will start to see specific business ideas emerge. Clues that you are on the right path with your ideas at this stage are that you feel real excitement, joy, and energy when you work on your business ideas. And fear, of course—but once you see fear as a natural part of doing anything worthwhile, it will not be quite as ominous.

Figure Out the Money

KEY

Make sure you don’t live in a van down by the river.

Money is a deep concern for aspiring entrepreneurs, as it should be. Before you get too far developing your idea, you want to make sure that you have the financial wherewithal to seriously consider entrepreneurship. And depending on your situation, you may need to spend considerable time saving and/or paying down debt in order to have a safe cushion when you start out. So evaluate your financial situation early.

Just about every seasoned entrepreneur I speak with says two things: if at all possible, have at least six months of living expenses saved up before you launch your business, and conserve cash like crazy when you get started. There is always risk involved when starting a business, but having a solid, realistic financial plan will give you a better shot at success. We’ll go over this in greater detail in chapter 12.

Define the Spirit of Your Brand

KEY

Learn how to stand out from the crowd.

No matter the type of business you are considering, if there is a viable market, there are bound to be competitors.

If you want to be successful, you must create a compelling, authentic, and sticky brand that will draw your ideal customers to you like flies to honey. The good news is that people are hungry for real, interesting, and authentic communications with people who solve their problems.

Unlike a broad, generic corporate brand that has a vague name like “Initech” and marketing copy that aims to appeal to everyone, and therefore appeals to no one, your small business brand should hit people in the gut with its clarity or humor or utility. Some examples:

• Legal Sanity, advice on work-life balance for lawyers

• Help a Reporter Out, a free public relations service

• Grammar Girl, a podcast and blog with practical tips on grammar for anyone who reads or writes for a living

A great brand does a number of things:

• Takes a stand: Communicates a feeling, tone, personality, and spirit that is uniquely yours. Brand expert Rick Julian of QV Brands says to “zig where your competition zags.”

• Makes you feel: Creates an inviting picture of what it will feel like to work with you by using colors, writing, images, and sounds that all communicate the spirit of your brand.

• Invokes trust: Makes potential customers trust you and want to work with you because you appear clear, competent, and authentic.

• Solves a problem: Your customer should immediately recognize what problem you are solving. Escape from Cubicle Nation: From Corporate Prisoner to Thriving Entrepreneur is an example of stating and solving a problem within a succinct brand name.

With today’s Internet and social media tools, you do not need to pay an agency $15,000 to create your brand for you. You can start simply and polish your image as you go.

Recruit Your Tribe

KEY

Identity the people who will support, guide, and partner with you.

What I have found is that when you have the right group of people around you, you will assume less risk with more rewards, grow faster, make fewer stupid mistakes, and have a lot more fun.

If you are like most long-term corporate employees, your social circles have long been defined by your company connections. You might not know even one successful entrepreneur, besides those you read about in your local paper or who author the books you read. Your immediate family might be extremely skeptical about your becoming an entrepreneur, which is why I devoted chapter 15 to helping you explain your motivations to them.

So reaching out to complete strangers when you are in the midst of doing something totally new can bring up the following feelings:

• Imposter syndrome: Who am I to pretend that I am an entrepreneur when I have no idea what I am doing?

• I’m not worthy: What have I done to make anyone important want to pay attention to me?

• Sleazy, hype-filled sales guy: People will run screaming from me when they find out I am just trying to hustle them for some money.

Trust me, it is normal to feel these insecurities when you are first starting out. But contrary to what you may have experienced in the corporate setting, sharing honestly and vulnerably is actually celebrated and admired in entrepreneurial circles. If traditional networking strikes fear in your heart, don’t worry. Chapter 7 covers specific, nonslimy ways that you can connect with people who will support you in all aspects of starting and growing your business.

Test and Prototype

KEY

Find out if you actually have a business worth quitting your job for.

Venture capitalist Guy Kawasaki says that most pitches he views from start-up founders state that “a conservative estimate for our market is 50 million people.” But how many of those 50 million people will actually take out their credit card and pay you?

I once worked on a program with fantastic, smart partners who had a great reputation, raving fans, and connections with a huge market. We all “knew” that our product idea would be just what people needed. So instead of testing the idea with a small group, we designed the whole program and rolled it out.

No one bought anything. Zip. Zilch. Nada.

The funny thing was that everyone thought everyone else was buying. We got e-mails from friends and clients that said “Great idea! I can’t afford it, but I am sure that you guys will kill the market.”

This valuable lesson taught me that the only way to know whether or not an idea is viable is to test it in little bits in the real world.

• If you think your baked goods will make Mrs. Fields run home crying to her mommy, start selling your cookies on the corner.

• If you think you have a “space-changing, curb-jumping” application, slap together a prototype and try it out with some potential customers.

• If you think you have what it takes to be a great coach, start coaching your seatmates on the evening train on the way home from work.

Every little bit of testing will give you great information and will either validate your big projections or send you back to the planning bench to craft an entirely different solution.

Let me put it to you this way: Would you rather invest a huge amount of time, money, and energy in something that could very easily crash and burn, taking your savings and ego with it, or would you be more willing to test a little and tweak frequently and come up with a much more bankable business model?

Chapter 11 will give you lots of ideas for how to test your product or service, which will give you the data to inform your final decision: Should I stay or should I go?

Prepare to Leap . . . or Not

KEY

Make a decision.

If you feel that your current job at your current company is the only option you have to make money, you might want to first take some steps to shore up your employment options in general. You don’t want to make a decision to start a business as a desperate move, jumping on any opportunity that is slightly less sucky than your current situation.

It is like being in a horrible relationship with an abusive, controlling, unemployed narcissist. Compared to him, just about anyone with a pulse and a steady paycheck would look good. But don’t you want a little more than a man (or woman) with a pulse?

The best way to feel like the move will be a good one for you is to spend the time to really get to know yourself and the kind of business that would bring out the best in you.

If you decide to take a risk and jump, you want to be as smart as possible. At a minimum, you should have the following things in place:

• A basic business plan

• Feedback from the real world with real customers that your business idea has merit and people will pay you for your product or service

• A clear and honest picture of your finances, and at least six months’ worth of expenses saved

• A clearly defined backup plan with a few options for employment if your self-employed gig doesn’t work out

You must balance your desire to be thorough with the knowledge that there is no way to really know if your business is a “sure thing” until you try it. At the same time, you must realize that your “stable” corporate job may not last forever either. On many occasions, I have received e-mails from blog readers who had spent years holding back their business plans because they were worried that self-employment was too risky. Then, with no warning, they lost their jobs. Me? When pushed into a corner, I would rather have three ways out. The sooner you get moving on your plans, the more quickly you will know if you want to go full-sprint into entrepreneurship.

If You Are Going to Do It, Do It All the Way

If you make the decision to leave your job and start a business, do not hold anything back. Throw yourself into it with everything you’ve got. Social media favorite and TV.WineLibrary.com host Gary Vaynerchuk threw out some motivating concepts for aspiring entrepreneurs at a Web 2.0 Keynote conference in New York in September 2008 that are worth repeating:

• Stop doing what you hate! Gary’s slogan is the sum of Jim Collins’s advice to “find out what you are genetically encoded to do” plus Gary’s concept of “Hustle 2.0.” Basically, once you know what work you can “kill at,” do it full out, every day, until you make it a viable business.

• Work your face off! Gary is not one who believes in working four hours a week to launch a business. He advocates doing whatever it takes to grow your brand, connect with your customers, and monetize your business, even if it means working on your side business from nine p.m. to one a.m. for a year or two.

• Stop watching f*ing episodes of Lost! Despite feeling like there is no extra time in the day, many people waste time on pursuits like cheesy television shows and meaningless Twitter conversations. If you want to make your business happen, you will have to be ruthless with your time.

• Legacy is more important than currency. How do you want to be remembered by your children and grandchildren? Will they be more excited by their grandma who diligently trudged into her cube at 7:58 each morning and clocked out at 5:00, or by Grandma 2.0, with strong opinions, passions, and an unwaving dedication to making a difference in the world?

Now that you have a better idea of what is actually involved in your path from corporate employee to entrepreneur, I will share a few guideposts that will make your journey a bit easier.