Changing Lanes

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The Perils of Following Your Bliss

Plenty have made the passion-to-profession shift, but there are challenges that can make the proposition less alluring than it first appears. Chief among the pitfalls for professionals thinking about a transition are the following:

What's creative and personal on a small scale can quickly become mechanical and rote when writ large. Ask yourself: Would I still love this activity if I spent almost every waking hour on it? Would my creative juices still flow if my production increased to thousands of units per month, and would I get as much gratification from building a team to produce the product or service?

The typical drop in income can be daunting. Consider whether the demand for your niche can support at least one full-time income. Will the marketing expense needed to spread the word beyond friends and family leave you money to plow back into your company?

Investing in your business will mean forgoing luxuries you take for granted. Rough up as realistic and conservative a five-year financial model as you can for a sense of the money your new career may provide. Then list luxuries you'd be willing to part with. Too deep a bite and you could regret the decision.

—Edited by Liz Ryan

How to Slide Smoothly into a Side Business

In an ideal world, you'd develop your dream business after putting in the hours at your real job. When you were ready, you'd slip seamlessly into the new venture.

But real life doesn't play out quite so neatly. So early on, consult a lawyer, particularly if intellectual property is involved. You don't want to find out that your employer is entitled to a share of a venture based on your after-hours work because of an agreement you signed years ago.

Document the time spent on your new venture, the equipment you use, even conversations and e-mails you have in connection with it. You may need to prove you didn't use company time or resources to build your new business. And don't pursue deals or do research using company equipment or funds—for instance, piggybacking on a day-job trip to China to line up clients for your business.

As your venture gains momentum, stay fanatically productive at your day job. Suss out how your managers reacted to other desk-jockeys-turned-entrepreneurs before sharing your plans. And when you do leave, give lots of notice. Your former employer could become a client.

—Edited by Liz Ryan