For 25 years now, climbing Mount Kilimanjaro has been on my bucket list. And finally, a couple weeks ago, I did it.

And along the way, with my two sisters, our guide Robert, assistant guide, cook, and twelve porters from Kandoo Adventures (yes, 12), I learned a thing or two about what it takes to climb Kilimanjaro.

Here they are:

1. Go slow. “Polepole” – that means “slow” in Swahili, and that was our rallying cry. And we meant it. We might’ve been the slowest hikers there, being passed left and right, but I didn’t care. I’m told that slower you go, the better your chance of success, because you have more time to acclimate to the altitude.

Slow, small steps will get you to the top. (The tortoise and the hair, right?) As long as you’re moving forward, you’ll get where you’re going.

And after the first few bathroom stops, where Karin and Isabel and I would stand around chatting, our guide said, “You need to...

For years, I’ve wanted to climb Kilimanjaro.

I love hiking. I grew up doing it with my mom and sisters. Isabel and I climbed Mount Whitney, which is the highest peak in the continental US, and my mom and I climbed Mount Washington, which is the highest on the eastern seaboard. She and I also climbed the two highest mountains in Norway. Basically, if there’s a peak, I want to climb it.

But I’ve never done any of the really big ones. So this year, for my birthday, I decided to climb Mt. Kilimanjaro.

Stephen said I could go, as long as he didn’t have to. So I rallied my sisters, one of whom has always wanted to do it, and one of whom is reluctant (although optimistic – she was the first person to buy boots and a backpack).

As I began preparing, reading books, studying the trails – we’re going to do the longest one – I started to get scared. I was learning that the trail isn’t what gets people, but the altitude. I started...

Last month, I went to Kelly Swanson’s keynote camp just outside of Asheville, NC. There were about 20 of us staying in cabins in the woods, with no WiFi or cell service – just each other, ourselves, and the time and space to work on our keynotes.

There was one man there named Dave,  who had lived on a 26-foot yacht for fifteen years. During one of the practice sessions, he told us about the worst nights on the water he experienced.

A storm had hit – this was in the Caribbean – and it was tossing his boat around like a toy. He’d tied everything down and locked himself in the cockpit, and now he was just praying to get out alive.

Then something approached, something huge and loud, that passed just feet from his yacht – a cruise ship. Beneath the raging wind and waves, he heard the distinctive thump of disco music. Through his port hole, he could see people on the decks, laughing and dancing and having a grand old time, totally unaffected by the...

It’s February: the month where New Year’s Resolutions go to die.

I’m joking, of course. Hopefully yours are alive and well. But wherever you are in your journey, it’s a reality that change is hard. Often, we’re all gung ho at first, but then the daily grind sets in. We lose our enthusiasm, and we revert to our old ways.

Why is it so freaking hard to make a change?

Because our brains are like lawyers. They need evidence. And we’re crazy good at finding evidence of how “stuck” we are. We’re not so good at finding evidence of how powerful we are. Or that we’re capable of change.

I see this all the time around food and eating habits. Friends will order French fries, even when they’re trying to lose weight. They know there are healthier options, but choosing those options isn’t in line with their beliefs. “I’m not a person who orders wraps,” they believe, or “I just don’t like veggies....

Last week, I read an article about an art teacher who decided to do an experiment with his ceramics students.

To one half of the class, he said, “This semester, you only need to turn in one pot. It should be as close to perfect as possible, but I only want to see one.”

To the other half, he said, “I want you to turn in as much pottery as possible. I’ll weigh what you hand in, and if it’s over 50 pounds, you get an A. If it’s over 40 pounds, you get a B. And so on.”

The students worked on their pots, and at the end of the semester, the results were clear: the best pieces came from the group that was graded on quantity. The students who were instructed to make as much as possible ended up producing the highest quality.

I thought, that’s so fitting for this time of year, when we’re focused on our New Year’s Resolutions.

Sometimes, we get really dogmatic about our plans. “I’m going to lose weight.”...

The other day my dog-walker, Pam, showed up at 1 o’clock instead of 3, like she usually does.

“Wow,” I said, “Sadie’ll be so glad to see you! Her walk this morning was pretty short.”

“I should get here early from now on,” Pam said, smiling. “I finally arranged it so that my walks are all in this area. My life is a hundred times easier. And actually, that’s thanks to you. Remember that talk we had, almost a year ago?”

I remembered. One day last year, she’d come in super-late – as in, later than usual – looking really stressed. Her dog-walking business was booming, but it was wearing her out. She had clients all over Manhattan, so every day she had to rush up and down the city to get to the next dog.

“You asked me what my bigger vision was,” she said now, “for what I wanted my business to be. And it was to have all the dogs in one area. That question completely changed my outlook.

...

People often tell me they feel overwhelmed when they think about setting a big goal (or doing an outrageous act).

“All I can see is how hard it is.”

“I’m so stressed out by all the things I have to do.”

“I’m exhausted just thinking about it.”

I know, I know. Big goals are scary, and they take a lot of work. (Someone on Pinterest once said, “If your dreams don’t scare you, they aren’t big enough.”) But sometimes that overwhelm can be paralyzing. Every day, it stops someone from achieving a goal that they are capable of.

So how do you move through it?

When I feel that way, I remember my client Anna.

She called me one Sunday night sounding desperate. She was in the process of leaving a career in film to pursue one in hotel business, and she had her first job interview the next day. So, understandably, she felt overwhelmed.

“Why am I even trying?” she worried....

This summer, I played the role of the women’s rights activist Gloria Steinem, when she interviewed Hugh Hefner in the 1970s. While I was studying her for the role, I came across something she said that changed the way I think about my own life and work.

She was promoting her book Outrageous Acts and Everyday Rebellions, and Someone asked her about the title. Initially, she joked “It’s too long, don’t you think?”

“Not necessarily,” he said. “I’m just curious what it’s about.”

“Well,” she said, “A movement is really just people moving. In order to create a movement, you have to have people consistently moving toward what you want to achieve.”

She explained that whenever she gave a speech, she worried that the energy would stop when she stepped down from the podium. Her feeling was, “Okay, maybe I inspired people, maybe I’ve informed them about something they didn’t know....

As soon as I booked the plane ticket, it started.

If you’re going to New Zealand, said my brain, you’ve got to do something exciting. They’re the inventors of crazy adventurous things. They even invented bungee jumping.

Bungee jumping. Oh, boy.

I’d heard you could do it off the Auckland Bridge, which sounded cool, but I wasn’t sold. I was scared.

All during the thousand-hour plane ride, my brain went back and forth. Do it, don’t do it. It’s exciting, it’s scary. You have to, I don’t know if I’m ready.

I got to the hotel at 6:30a.m. As soon as I checked in, the first thing out of my mouth was, “Do you think I can bungee jump off the Auckland Bridge this week?”

“I don’t know,” said the concierge. “People do, but maybe not in winter. I’ll call as soon as they’re open.”

I thanked him and went up to my room. An hour later, he called up. “They go...