Thinking about taking an extended leave from work? Find out how one dad did it -- and brought his son along for the ride. By Lisa Gerstner, Contributing Editor May 4, 2012 If "very aspirational and a little bit crazy" sounds like the kind of sabbatical you'd love, take a cue from Charles Scott. Three years ago, he and his son, Sho, spent 67 days bicycling 2,500 miles between Japan's northern and southern tips. Scott connected a child's "trailer cycle" to the back of his bicycle so that Sho, who was 8 at the time, could pedal behind him.SEE ALSO: Turning a Passion Into a Second Career Scott, 44, of New York City, had set a life goal of going on adventures with his kids before they grew up. "We got a little carried away" as the idea evolved from a weekend jaunt to a months-long journey, says Scott, an endurance athlete. Sponsored Content The timing was far from perfect. Scott introduced the plan to his manager at Intel Capital in November 2008—as the economy crumbled and Intel's profits took a dive. On top of that, Scott wanted to take the trip during his 12th year with the company—meaning that he wouldn’t be able to take advantage of Intel's sabbatical policy, which allows employees a paid two-month break every seven years. Instead, he had to use two weeks' paid vacation and negotiate two months' unpaid leave. Advertisement At first, management wasn’t receptive. But the trip had a charitable component that helped turn Intel into a supporter. Scott and Sho raised money for a United Nations campaign to plant seven billion trees, and they gained international exposure as two of the U.N.'s "climate heroes." "It was more than just taking time off to spend with my child," says Scott. "Intel saw it as something substantive and meaningful." Plus, as a result of the campaign, he was able to expand his network in the clean-technology field—an area that he was exploring through his venture-capital work at Intel. Giving your boss several months’ notice and evidence that you'll come back a better worker—whether it's because you'll recharge, enhance your job skills or both—bolsters your case. So does ensuring that your absence will be as painless as possible for your employer. Scott trained his temporary replacement and created a plan for making sure his work was completed over the summer. And because he and Sho settled on their idea a year and a half in advance, Scott had time to set aside money each month in a savings account; he estimates that he spent $10,000 on the trip. Taking a sabbatical isn't risk-free. Scott could have been laid off during his leave (though with the shaky economy, that could have happened if he'd been working all summer, too). "In an ideal world, a sabbatical complements your work. But I think it's more about feeling empowered and pursuing a passion," he says. "Once you do that, you've got greater confidence, motivation and focus to build your career." Advertisement Or maybe you'll be inspired to start a new career. In June 2011, Scott left his job at Intel and spent the summer bicycling the perimeter of Iceland with Sho; his daughter, Saya; and his wife, Eiko Ikegaya. Today, he's self-employed as a writer, speaker and consultant, and he has more time for adventures with his family. Sell your boss on your break Compose a "sabbatical proposal." Keep it to one page, suggests consultant YourSabbatical, and hand it to your supervisor during your first meeting on the topic. List key points, such as who might take over your duties. Suggest that your absence could enhance other employees’ skills as they train to cover your work and make the company more flexible. Get job assurances. In later meetings, ensure that your job will be there when you get back, and arrange to continue benefits such as health coverage—even if you have to pay extra for it. If your employer won't offer full pay during your sabbatical, see whether you can be paid on a scale—say, full pay the first week, 80% the second week, and so on. (But you may have to settle for zilch.) Advertisement Give plenty of warning. Propose your sabbatical at least three months in advance (more time is better). Top performers and people who have been with a company at least a few years have the best chance of success. "If you think you've earned it, go for it," says Nancy Bearg, coauthor of Reboot Your Life: Energize Your Career and Life by Taking a Break.