Now that you know my belief that starting a company is your best hope of living the life you want, here's the next logical question: When should you get started?
1. You're young
The best time to start a company is when you are young. The younger, the better. Youth is a beautiful thing. It's the perfect combination of ignorance and innocence. Stupid decisions are excused as learning experiences and the worst outcome of most youthful transgressions is a few days in juvenile prison, or, worse, going broke.
Blogger Michael Arrington recalled a conversation with a venture capitalist last year that "entrepreneurs are like pro basketball players. They peak at 25, by 30 they're usually done."
I don't agree with the blanket statement, but I do agree that it's easier to pour your life into a company when you're young, creative, fresh, and fired up.
When I graduated from Northwestern in 1996, my primary asset was time and passion. I decided to focus these assets on two goals: making money and finding women who would date a geek in glasses with crossed eyes and a bum heart.
Starting a business killed two birds with one stone. I grew my first company into what became a publicly-traded firm (University Wire and Student Advantage) and I met my future business partner, best friend, lover, and wife at a wedding at age 22.
I've never met an entrepreneur who said, "Wow, I wish I hadn't started so young." The world is full of regrets and one of the main ones is from entrepreneurs and would-be entrepreneurs lamenting that they didn't start off earlier.
2. You're miserable at work
Life is too short to sit behind a desk and be miserable. Show me someone who makes a million dollars a year but hates his job and I'll show you an unhappy guy. Show me someone who makes a tenth of that and I'll show you someone who is 10 times as unhappy.
I've always believed that misery loves company for a reason. Look inside any company and you'll find a boatload of misery, the best fuel to start your own company. We grow up rebelling against our parents. Many grow companies to rebel against former bosses.
Use your nights, weekends, and lunch breaks to form your ideas and network and start laying the groundwork for your eventual prison break. And when you're confident you're on to something, jump. I assure you that you'll never look back, even if all you have at the end is less money in the bank and a learning experience.
3. You're out of work
There's nothing like a good ol' fashion layoff to turn you from a worker into an owner. It shocks and beats the comfort out of you. It's a mini death forcing the least introspective to examine all aspects of their lives.
Let's be clear, everyone who is laid off should not start a business. But a layoff is a great catalyst if you're already thinking about making the move.
When you're fired or let go, many fall into the trap of focusing energy on the people who "wronged" you. Just the opposite. Look at the firing as a blessing in disguise and motivation to reevaluate your life. Put everything on the table—new opportunities you have been ignoring, industries you're interested, and starting your own gig.
4. You have no responsibilities
Start-ups and life responsibilities are often inversely related, if not mutually exclusive. The more responsibilities you have, the less likely it is that you will start a business.
I have many friends who have been speaking to me about starting businesses for 15 years now. And for many, they now feel it's too late to jump in.
While age and responsibilities are often related, they aren't always. So start a company when you have the time and the energy and the freedom to do so. Don't wait until it's too late and you're trapped by a mortgage, private school tuition bills, and annual family vacations that you need to fund.
Starting your own firm has a ton of rewards—excitement, accomplishment, the promise of financial freedom, and more. But don't kid yourself, it also has a ton of downsides—you won't see your friends or family as much, your income will approach zero, the time you used to spend working out is now being spent networking, meeting, recruiting, and traveling.
Providing for others and keeping up with a lifestyle you've grown accustomed to makes it hard to start companies, especially for the first-time entrepreneur. If you are single, married without kids, or thinking about getting married and starting a family—and considering jumping on the entrepreneurial train, do it now before you decide that it's just too late.
5. You have an incurable obsession
Our great country was founded on the idea that anyone with an idea can strike it big. John D. Rockefeller, the son of a traveling salesman, founded Standard Oil, and in the process became the nation's first billionaire whose fortune swelled to more than $500 billion.
The Rockefeller story is a great one. But don't get seduced by the myth, the money, the adventure, and the allure of being a self-made person. Starting a company is the hardest thing you will ever do professionally. It's you versus the world. And the world wins 90% of the time.
Start a company after you sit on your idea for a while—and you can't get it out of your head. You're obsessed. You're incurable. No matter how much you try not to think about the business, it keeps coming back. You start working on the idea during all your free time. You can't stop talking to friends and family about it. And you feel like you will never forgive yourself if you don't take a chance.
This incurable obsession must be consistent over an extended period of at least three months. Let it sit. Let it settle. And don't confuse it with the entrepreneurial seizure, a more temporary excitement that will wane if you give yourself time to really think about the idea.
6. You are an "intrapreneur"
I am starting to spend time with more and more entrepreneurs who came to the game late but are in an ideal position to thrive. They have launched stuff inside large companies (also known as "intrapreneurs") and have put some money in the bank. Despite having responsibilities and being older then 25, they are in a position to invest in themselves.
Just look at David Rochon and Michael Libenson from SavingStar, a mobile savings company I invested in and sit on the board of directors. David had 25 years experience in the grocery industry and Michael was a former consultant who spent 20 years building other people's businesses.
The two launched Saving Star, which in December 2011 TechCrunch called the "Groupon of Groceries." The two are well on their way to creating a formidable business that will revolutionize how consumers save money through a network of 24,000 grocery and drug stores nationwide.
It's well documented that college dropouts create great businesses (Facebook, Microsoft, and Dell, to name just a few). But data also shows that age and entrepreneurial success aren't tied. The Founders Institute released research last year that shows that being older increases the likelihood of success. They theorize that the "combination of successful project completion skills with real world experience helps older entrepreneurs identify and address more realistic business opportunities."
The Kauffman Foundation reports that the Great Recession of a few years ago drove more people to start their own business than any time in the past 15 years. And the fastest-growing group of business starters? Old fogies like me (those who are older than 35)!
7. Do it today
You can try to pick the best time to start a business. When you are old, young, rich, poor, fat, thin, with hair or balding. But any attempt to do so won't make you more or less likely to succeed. Entrepreneurs come in all sizes, shapes, ages and colors. And, believe it or not, our country doesn't have a monopoly on business creation.
Great businesses have been created in times of prosperity. Great businesses have been started when we the country was facing its darkest hours and the entrepreneur was at her lowest low.
If you're reading this story, you're interested in starting your own business. And if you are reading to the end (yes, you! I'm talking about you!), you're about to jump and seriously consider it. Why else would you read 1,500 words about a topic you weren't passionate about?
So let me make it simple for you—the best time to start a business is TODAY. Not tomorrow. Not in two weeks. Not after you get promoted, pregnant, married, or your MBA. TODAY! You're not getting any younger. Your life is not getting any simpler.
See that cliff in front of you that you're scared to go over? Run up to it once again. But this time, actually jump. What you will find below is the life you wanted to live and all you need to do is get over the fear that's keeping you back.
To see more about how I decided to start my first company rather than take a job, and how fear is getting in your way, check out my talk from late last year.
I'm going to be answering questions next week in my column. So please ask anything you'd like about starting a company in the comments below.