Calendar Habits of High Achievers: What Michelle Obama, Richard Branson, and Others Know That You Might Not

Want to be more successful and happier? Start with your calendar.

According to socio-economist Randall Bell, people who regularly use a calendar and to-do list are nearly three times more likely to become millionaires than those who don’t.

While most people use their calendars to plan meetings or track appointments, some of the world’s most respected leaders use theirs to intentionally shape their lives. From personal time and family events to daydreaming and rest, these high achievers schedule the non-negotiables first, leading to better focus, stronger relationships, and less burnout.

If you’re ready to build a better life, take a page from the playbooks of these five influential leaders.

Michelle Obama: “I Have to Plan My Happiness”

During the Obama Foundation Summit, Michelle Obama made it clear that structure isn’t just for work; it’s essential for life.

“I’m very ruthlessly efficient,” she said. “But I have to be organized about myself.”

As a mother, she learned early that running a family alongside public duties required serious planning. She and Barack would coordinate with their children’s schools a year ahead, locking in school plays, recitals, and events into their calendars.

But she doesn’t just plan logistics, she plans joy.

Before accepting invites for work or events, Michelle asks herself:

• When will I exercise?

• When will I see friends?

• When will I take a breath?

If self-care isn’t on the calendar, it doesn’t happen. “We think happiness just happens,” she said. “But you’ve got to work in some happiness too.”

Richard Branson: “Block Time to Dream”

Virgin Group founder Richard Branson is known for his adventurous spirit and massive business empire. But one of his greatest productivity secrets? Making space to dream.

In a blog post, Branson shared that he treats unstructured time as a top priority, writing long to-do lists and scheduling dream time like any other important meeting.

“Too many people get caught up in doing,” he said. “You have to make time to think and feel.”

Whether it’s a few hours or a full vacation, Branson says blocking out this mental breathing room helps him zoom out and see the bigger picture - something every leader needs.

Mary Callahan Erdoes: “Own Your Calendar”

As CEO of JPMorgan Asset Management, Mary Callahan Erdoes operates at a fast pace, but she credits one habit above all others for keeping her on track: calendar discipline.

“Calendar management is the single most important thing, especially as you get busy,” she told CNBC.

Her method? Look both short-term and long-term. Know what you need from others, and what they need from you. Keep a pulse on your priorities every day. Be intentional, not reactive, with your schedule.

Erdoes calls it being “maniacally focused” on managing time and says it’s the secret to avoiding overwhelm as responsibilities multiply.

Jeff Weiner: “Schedule Time to Do Nothing”

For years, former LinkedIn CEO Jeff Weiner built buffer time into his schedule - intentionally leaving 30- to 90-minute blocks open each day to think, reflect, or simply step away from the grind.

At first, it felt indulgent. But over time, he discovered that these breaks weren’t a luxury; they were a necessity.

“I realized these pauses were absolutely essential for me to do my job well,” he wrote on LinkedIn.

Whether he used that time to catch up on reading, think through strategy, or take a walk, Weiner said this habit became his #1 productivity tool and helped prevent burnout.

Robert Herjavec: “If It’s Not on the Calendar, It’s Not Real”

Entrepreneur and “Shark Tank” investor Robert Herjavec takes his calendar seriously, speaking with his assistant 20+ times a day to stay in sync.

His golden rule? If it’s not scheduled, it doesn’t exist.

Herjavec books his year far in advance, often sitting down at the start of each school year with his assistant and his kids’ counselor to input every school play, swim meet, and holiday. That way, no work commitment ever trumps family time.

“I’d fly across the country just to be there for one day,” he said. “That’s the beauty of owning your own business. You have the power to choose where your time goes.”

The Bottom Line: Schedule Like Your Life Depends On It

Whether you're a CEO, entrepreneur, or simply someone trying to get more out of each day, one thing is clear: Time is your most valuable asset.

These high achievers don’t wait for balance or happiness to show up on its own; they block it off in ink.

So before your calendar fills up with other people’s priorities, ask yourself:

• What matters most to me this year?
  

• When will I rest, reconnect, and reflect?
  

• What do I want to protect on my calendar?
  

Success may start with what you say "yes" to, but it’s sustained by what you schedule.

Source: CNBC