When Marcus Whitney took the plunge into entrepreneurship, he realized he needed to start managing his time differently. The year was 2008, and Whitney, then 32, already had a fairly complicated life. He had two young sons, 9 and 7, whose mother he had recently divorced. Amidst all this, he had decided to found a software development firm, Remarkable Wit, out of Nashville, Tenn., where he lived.
If time management was already a challenge for Whitney, now it was a crisis. "When you become an entrepreneur, the need for your time feels like it grows exponentially," he says. Whitney spent so much time managing people that he was chronically falling behind on his own work. Someone recommended the book Getting Things Done, by David Allen (a first stop for many an entrepreneur interested in time management), which he read and tried to apply to his life. But the demands on his time only multiplied when he began dating a woman named Rachel in 2009.
Not long after meeting her, Whitney received both good and bad news on the entrepreneurship front. A VC firm was interested in one of his companies, a social commerce platform called Moontoast (later rebranded as Spendsetter). But there was a catch. The funding was contingent on hiring a CEO based in Boston—and on Whitney spending half of each month there, 1,000 miles from his sons and Rachel.
It was daunting, but it was also an offer he couldn’t refuse, so Whitney said yes to the deal. Then he holed up in Rachel’s apartment, and opened his Google Calendar. The current month popped up: August 2010. He knew that by September, he was going to be hopping a flight to Massachusetts every other week.
He wanted his company to succeed. He wanted to be a good father to his sons. He wanted his new relationship to succeed. He was facing a time-management puzzle with very high stakes.
Staring at his Google Calendar, Whitney decided for the first time in his life to do something he now does regularly: take significant time... just to manage his time. He blocked out hours in his schedule, solely to figure out his schedule. Specifically, he wanted to have an overview of how to manage his time for the next year.
He began by combing through a few important data sources, like his sons’ school calendars. He needed to know when their spring breaks fell, for instance, so he could be absolutely certain he'd be in Nashville. He gathered other important dates he wanted to exclude from out-of-town travel and threw those on the calendar. Once he had a map of things that were really important to his sons and Rachel, he went in and blocked out what looked like convenient two-week intervals to spend in Boston. The process took about two hours, he reckons, easily the longest he had ever spent tinkering with his calendar.
The other crucial decision he made—which would become a cornerstone of his time-management habits later—was to give various people access to his calendar.
First, he shared the calendar with Rachel, proofed it with her, and "let it breathe for about a week," he says, to make sure he didn’t miss any crucial dates. Now that Rachel was on the calendar, she was equipped to make quick judgment calls about whether to invite Whitney to a concert in a month, or whether (if he was traveling) to use that night to catch up with a friend.
After the week of "letting it breathe," Whitney shared it with the Boston team. They were now empowered to set up meetings for him through the year, without resorting to long and unnecessary email exchanges. "There’s nothing more annoying than an email chain that goes, ‘Hey, are you available at this date and time?’ ‘No.’ ‘What about this date and time?’ ‘No,’" he says.
As Whitney’s calendar mastery has evolved over the years, he says he now has about five calendars that he shares with different audiences. He calls his calendar "a point of communication" for important people in his life, up there with email and Slack. To schedule an event in a shared calendar is to say " "yes" or "no," "let’s" or "let’s not."
The experiment, overall, was a great success. Whitney managed to grow his business and keep his sons and new girlfriend happy. His next major crisis didn’t occur for another four years—as his and Rachel’s wedding approached.
"A wedding is like another job, while you’re planning for it," Whitney says. By January of 2014, he had proposed to Rachel, and they set a wedding date for May 17. They hadn’t planned their honeymoon; they hadn’t even set a firm timeline for when to move in together. Meanwhile, his boys were becoming teenagers, and his travel schedule had grown even less predictable.
He knew, again, that he needed to make time to manage his time. Only now there was a twist: He needed Rachel’s full collaboration from the beginning.
Whitney booked a private room at the rear of a cafe/restaurant called Pinewood Social (he knows the owners, and he says it has "some of the best Wi-Fi in the city"). They arrived around 10 a.m. on a Sunday, enjoying a tasty brunch and some Bloody Marys. Then they cracked open their laptops and got down to business.
Looking at a period of six months, they figured out when all their major life events were going to happen. They set a deadline for finding an apartment and moving in. They decided on dates for their honeymoon to Bali, and booked tickets. Soon, discussion of how they spent time became a discussion of how they spent money, too. Whitney shared with Rachel for the first time on that day a granular account of his finances and budget. "She was marrying someone previously divorced with two kids, and I felt like I owed her clarity on what she was getting into," he says.
By participating in such an in-depth "meeting" with his fiancée, Whitney was also importing a business philosophy into his personal life. "It’s hard in a company to have an aligned culture," he says. "People are naturally inclined to be misaligned, and in conflict, and skeptical." Meetings can iron out misalignments, he says. "I just thought, a similar thing was true for marriage. I know I did not do that in my previous marriage. I did not take significant amounts of time to sit down with my ex-wife and really go through things. And I knew that was one of those areas I could improve on in my next marriage."
By the time they were done, it was 6 p.m. They’d eaten dinner and graduated from Bloody Marys to stiffer cocktails.
They’d also emerged with a new habit that has stood them in good stead in their young marriage. A twice-yearly, multi-hour calendaring "date night" is now a fixture of their union.
2014 also became the year Whitney re-centered his business activities in Nashville. He joined Jumpstart Foundry, a health care innovation fund, as its president. Not long after, he also founded The Unlikely Company, a benefit corporation devoted to spotting "unlikely" entrepreneurs (it also shares business tips in a video series hosted by Whitney). On top of that, he's co-owner of Nashville FC, a pro-soccer team.
And he still finds long stretches of time to dwell in his calendar with Rachel. In fact, just after our call, Whitney tells me, he’s going to run to Whole Foods to buy some fresh fish and a bottle of wine, to be enjoyed as part of a four-hour scheduling session with his wife that very evening.
"We dress it up like a date," says Whitney. "We make sure it’s fun, going over this stuff."