Entrepreneurs face a lifetime of career decisions. In the beginning, they must decide whether to wander out far and in deep into entrepreneurial waters and solely dedicate their time and efforts to starting a business or to maintain a job and work the start-up on the side. Later in life, they have to decide whether to maintain the course they are on and stay with the business they started or become a serial entrepreneur. Let’s begin with the discussion by examining the pros and cons of working more than one job. Sarah Needleman believes the process begins with a little introspection and asks, “Could you juggle both a full-time job and your own fledgling business?” [“How to Juggle Entrepreneurship and a Job,” Wall Street Journal, 10 April 2011] She continues:

“[People who do that], in general, … say doing double duty requires putting in an extraordinarily long work day. You need to get up early enough in the morning that you can put a few hours into your start-up before heading to your day job. Once at work, you use your lunch break to send and respond to emails for your company. When you get home, you go back to working on your start-up for however long you can handle. And then, there’s the weekend. Mike Schwarz says such a hectic routine can be exhausting. In mid-2008, he accepted a temporary product-management position with a large Internet company while building RibbedTee Designs, a maker of men’s undershirts in Los Angeles. ‘I was wearing myself out at the time,’ he says. ‘On average, I was getting four to five hours of sleep at night.’ Still, Schwarz managed to wear two hats for more than a year.”

Wearing yourself out when you are unattached is one thing. Working those kinds of hours if you are married, in a serious relationship, or have a family is quite another. Those relationships cannot help but be affected by the long hours, the frustration, and the obvious lack of attention. Needleman continues:

“For Stephanie Burns, working a day job while growing a start-up means not having to fret about paying bills or making rent. She launched Chic CEO, a Web-based start-up that provides women with information about entrepreneurship, in 2008 and has been holding a marketing job at a health-care company since 2010. ‘It’s definitely really hard,’ she says. ‘It’s amazing I have the energy to do it.'”

Burns reason for working two jobs is probably the most common — using money from a “real” job to help fund the start-up. That’s why, in another article, Needleman asks, “If you recently launched a business to dodge unemployment, the thawing job market may be creating a sticky situation: Should you continue growing your start-up or go back to earning a steady paycheck?” [“Should You Take That Job Offer?” Wall Street Journal, 10 April 2011] Despite the challenges Needleman notes above, she says that if you don’t have a safety net of funds “and are struggling to make ends meet, you don’t necessarily need to put your start-up to bed.” She explains:

“You may be able to juggle both [your start-up and a job]. ‘Take some of the money you’re making with that new salary and fund your business,’ [J.T. O’Donnell, a career coach in Hampton, N.H.], says.”

Needleman goes on to relate the experiences of several people juggling jobs and start-ups, including Schwarz and Burns. Emily Maltby writes, “Many entrepreneurs say they don’t sleep much. But is that because they choose to sacrifice dream time to grow their businesses or because they wouldn’t be sleeping anyway?” Mike Schwarz talked about getting 4 to 5 hours sleep a night. The question Maltby is asking is, “Do entrepreneurs like Schwarz have a different physiology that permits them to work longer and sleep less?” Maltby continues:

“Perhaps, they are ‘short sleepers,’ or folks who can run on just a few hours of shuteye. Classic type-A entrepreneurs fit most, if not all, of the characteristics of the sleepless population described in a recent WSJ article – energetic, outgoing, optimistic and ambitious. There is no way for people to teach themselves to be short sleepers, according to the article. Out of every 100 people who think they need five or six hours of sleep, only about five really do. Still, some entrepreneurs say they’ve managed to train their bodies to function on minimal sleep.”

I believe what Maltby is saying is that you shouldn’t try and fool yourself into thinking that you are a short sleeper if you are not one naturally. What are your chances of being a short sleeper? According to the article mentioned by Maltby, “just 1% to 3% of the population” are natural short sleepers. That means the odds are stacked against you. The inevitable result of fooling yourself into thinking you are a short sleeper will be physical exhaustion and failure. If, however, you are a short sleeper, you might be able to tackle starting a business and holding a regular job. But, as I mentioned above, even short sleepers can’t juggle two jobs and relationships without something having to give. You not only have to know yourself, you have to be honest with yourself.

Let’s switch gears from talking about multiple jobs to discussing multiple careers. Entrepreneur Luke Johnson writes:

“I have always been transfixed by those who lead multiple careers. They are the ones who refuse to be typecast but instead break convention by embracing a variety of roles, sometimes simultaneously, more often consecutively. To me they are among the most impressive businesspeople, switching vocations and accumulating new skills as they go, achieving great feats across different disciplines. Undoubtedly one of the true joys of being an entrepreneur is that you are not trapped in one stifling occupation but are free to roam.” [“Multiple careers are better than one,” Financial Times, 15 February 2011]

Johnson, a serial entrepreneur who has had multiple careers, believes that society is a bit prejudiced against career shifters. He writes:

“There was much less prejudice against such wholesale reinventions in previous eras. Characters such as Benjamin Franklin were not seen as dilettantes, despite the fact that he was an author, inventor, printer and politician – among myriad other activities. Above all, he was a man who believed one should make one’s mark in the world and not waste time. I have a poster on my wall from the RSA, where he was a fellow, with a marvelous quote from him: ‘If you would not be forgotten as soon as you are dead and rotten, either write things worth reading or do things worth writing.’ These sorts of legendary polymaths must be human whirlwinds, forever in motion, leading three lives while the rest of us struggle to make progress in just one. But there is no good reason why anyone should be obliged to stick neurotically to a single work trajectory for half a century. We shall probably all have to earn a living until the age of 70, so why not plan to convert to a different field of endeavor in midlife? It is the way to avoid the boredom of sticking to just one discipline.”

Although Johnson makes switching careers sound easy and fun, Alicia Clegg warns that changing careers “can be a perilous step, even for the talented and powerfully connected.” [“The reality of a career switch,” Financial Times, 25 April 2011] Clegg continues her piece by writing short case studies of several Wall Street banker-types who leaped (or were forced) into second careers — including New York mayor Michael Bloomberg. Despite the challenges facing those who switch careers, Johnson writes:

“Surely the experience accumulated across a range of crafts can be immensely valuable. If you focus for decades on one narrow speciality, then you risk becoming blinkered and stale. I accept that ‘domain knowledge’ is essential to excel in any calling. But 20 years must be sufficient to become truly expert. What then? Clearly, casting aside all that training, those qualifications, networks and reference points, is a scary step. Yet where is the excitement in an existence of routine and predictability? We should all attempt to pursue life-long learning in pastures new as a fundamental goal.”

I certainly agree that the pursuit of life-long learning should be a way of life. One thing that being an entrepreneur has given me is the opportunity to be exposed to a number of disciplines. Each new area I learn about deepens the reservoir of knowledge from which I can draw. I consider that a blessing. Johnson concludes:

“Ronald Reagan is another great example of defiance towards those who would pigeonhole you. Initially he enjoyed reasonable success as a Hollywood actor, served in the US Army, and then became a union boss, as president of the Screen Actors Guild. Subsequently, he worked as a spokesman for General Electric and was later elected governor of California. In the 1980s, he was twice elected US president and is considered by many of his countrymen to be the most successful holder of that office in modern times. Reagan skilfully used his early jobs to gain public recognition, master the art of public oration, understand leadership and develop an appeal to ordinary citizens. A rather more interesting way to gain judgment and credibility than working as a party hack, which so many of today’s politicians appear to do as their form of apprenticeship. Not everyone can afford to make wholesale changes to their livelihoods while in their prime – but many actually fail to do it through fear or laziness. Yet even cautious individuals can enjoy renewal once they are notionally retired from a first career. Everyone possesses a range of talents; and we should all aim to have second or even third acts in our working lives.”

Whether you are considering taking on multiple jobs or pursuing multiple careers, you need to be a bit of a risk taker. You also need to be physically and emotionally up to the challenge. Most entrepreneurs that I know love life and try to live it to the fullest. On the other hand, life loses its enjoyment if you grind yourself into the ground by taking on more than you can bear. Socrates had it right — “Know thyself.” All good decisions about your life’s work must begin with that knowledge.