Courage is Trusting You Can Figure Things Out Along the Way

Would you call yourself a brave person? Do you think you're courageous? I've learned that courage is just another word for being resourceful. It's going ahead even when you don't have all the answers. It's trusting you can figure things out along the way.

I got clear about this while sailing the Chesapeake Bay with Captain Jen on her classic schooner. She generously gave me a chance at the helm of her classic schooner the Woodwind (the beautiful yacht featured in the movie Wedding Crashers with Vince Vaughn, Owen Wilson, Christopher Walken and Rachel McAdams.)

What a thrill to feel the sails fill and the boat lift. While beaming from ear to ear, I asked Jen how she got into the business and she shared her backstory.

Jen sailed competitively through college and tried different careers but nothing “stuck.” She and her parents found this beautiful yacht, named her Woodwind, and invested their savings into buying it so Jen could start her own charter business. Jen drove up and down the East Coast searching for the perfect location to operate out of – and found it in Annapolis when she saw the Marriott had an unused dock by their waterfront restaurant.

She walked into the General Manager's office and convinced him it would be a win for the property ("Think of the extra room nights and food/beverage income from new guests.") to allow her to rent that space.

I told her I admired her entrepreneurial spirit and told her the second most-asked question on my Year by the Water was, "How did you get to be so brave?”

I told Jen I never once thought of this as being “brave.”

She smiled and said, “Me neither.”

She told me her folks (both music teachers) owned a boat from when she was a little girl and they often spent summers aboard. Jen remembered them giving her $5 and sending her off in a little dinghy to “get some ice cream.”

She laughed, “I didn’t realize until years later that was their way of getting some privacy. What I also didn’t realize was those solo forays in that dinghy taught me to trust the world. My parents didn’t warn me of the “dangers” of going off on my own. They had confidence I could handle whatever came up, so I had confidence too.”

I told her I had a similar version of that story – except with horses. My sister and I had our own horses by the time we were nine and ten. We would be gone all day, and our folks never worried. They trusted if something went wrong, we’d figure it out. If our horse bucked us off. Figure it out. If our horse ran away with us. Figure it out.

It wasn’t until later in life that I really “got” the enduring impact of those early years. Instead of seeing the world as a dangerous place, my sister and I grew up seeing the world as an adventurous place.

Instead of being afraid something might go wrong, we understood things probably would go wrong at some point, and when they did, it was our responsibility to be resourceful.

We didn’t panic or sit around and wait to be rescued, and we didn’t feel abandoned or think our parents didn’t care about us. We learned we could take care of ourselves - which is the core of courage.

Setting out with anticipation (vs. apprehension) was our norm and Jen’s norm too.

I’ve since learned that for many people, their norm was just the opposite. Their norm was to have over-protective parents who constantly warned them to “be careful.” They weren’t sent off into the world with opportunities to discover their own way; they were cautioned about the danger of strangers and were hovered over by parents who rushed in at the first sign something might go awry.

My folks are gone now – so all I can do is send up heartfelt thanks for giving us a childhood where self-sufficiency was encouraged and where the world was depicted as a wondrous place, waiting to be explored.

One of the reasons my Year by the Water (and my life) has been so rewarding is because I know in my soul that "Courage is simply trusting - that no matter what happens - I can figure it out. Bravery is simply another name for resourcefulness."

After being an entrepreneur for thirty years, and after having the privilege of working with many entrepreneurs in many different industries; I've come to understand that entrepreneurs are explorers and adventurers at heart.

Entrepreneurs revel in their independence. They're not intimidated by uncertainty, they welcome it. They find new ventures exciting (not frightening) because they trust their ability to "figure it out." Instead of being afraid something might go wrong; they jump in and proactively fix what's wrong. They know the world rewards the resourceful.

Do you want to launch something and you're scared? Do you want to start a small business, write a book, learn a new skill, return to a favorite hobby - but you don't know exactly how to do it or you're afraid you won't do it perfectly?

Do it anyway and figure it out along the way.

As my son Andrew would say, "GTS it. GTS = Google that Stuff. You can find out ANYTHING you want to know in seconds. If you put "How can I start a small business? How can I start my own web design agency? How can I get funding for my startup, How can I market my new business?" into search, up will come the answers to the test. There's no mystery how to do things anymore. Experts are sharing their best practices for free and they can guide you on your way.

Print this out and take a friend to lunch today. Use this as a discussion guide to support you in seeing yourself as brave and moving forward what you would like to do.

1: Reflect and look back to clarify your beliefs: Were you brought up to trust or distrust the world? Were you encouraged to explore - to be entrepreneurial? Were you given opportunities to "figure things out?" Do you play it safe? Do you worry about things going wrong or do you expect them to and just get resourceful when they do?

2: Look ahead to clarify what you're going to believe from now on: Start thinking of yourself as courageous. Trust you can figure things out along the way. Instead of thinking, "I don't know, so I can't go," GTS what you need to know. Set things in motion. Understanding that if things can wrong, you can handle them. Picture how fulfilling life is going to be now that you see it as an adventure; how exciting it's going to be to explore new opportunities, go new place, make new friends, delight in new discoveries.

courage - trust along the way.

Freedom to Drive

On this July 4th weekend, may we be grateful for our freedoms. May we take a moment to really think about all the many things we’re free to do and send up thanks for them. freedom to drive text image

Of the many freedoms we have, my Year by the Water has given me multiple opportunities to revel in one of the most precious; the ability to travel freely, the ability get up and GO … without asking permission, without being regulated, without being told NO.

One of the first times I really became aware of how rare this is, and how many of us take it for granted (and shouldn’t) happened in the middle of a blizzard in the mountains by Yosemite.

We had booked a cabin at a family lodge that had ping pong, group dining, a huge fireplace, board games, and supposedly, snowshoeing and sledding.

Since we lived in Maui at the time, playing in the snow was a big draw for Tom and Andrew, who were about six and eight. What we hadn’t counted on was bad weather that kept us inside most of our time there.

One night, we were gathered in the main lodge and the front desk manager was really worried. A couple who were supposed to check in that afternoon still hadn’t arrived, and it was getting late. The manager was concerned their car might have gone off the narrow, windy road or gotten stuck.

Finally, with a gust of wind, the door opened and the couple walked in, much to everyone's relief.

I was standing by the desk while they explained they had gotten lost. But, and here’s the part that made a lasting impression on me, they didn’t panic because they were in America! They were originally from RUSSIA.

In Russia, if they wanted to make a long trip, they’d have to give their itinerary to the authorities. If they didn’t made a checkpoint at a certain time, they would come under suspicion, perhaps even be arrested. Here in America, they didn’t fear something bad would happen to them simply because they'd become lost. They felt safe.


That memory floated back to me yesterday while driving through the glorious Smoky Mountains during Golden Hour … and listening to the final show of A Prairie Home Companion.

President Obama called in to give Garrison Keillor a well-deserved shout-out for his 42 years of story-telling that’s “made us all a little more humane.”

When asked what he was looking forward to when he’s out of office, Obama talked longingly of getting in a car without the Secret Service and GOING FOR A DRIVE on California’s Pacific Coast Highway.


See, going for a drive is a “satisfied need.” Abraham Maslow said that once a need is satisfied – whether it’s a survival need like having food, water and shelter – or a community need like family and friends – it is no longer a motivator. We tend to overlook it, take it for granted. We don't miss it until we no longer have it.

The freedom to get in a car and just take off - anytime, anywhere, with anyone - is something we usually don’t even think about. In fact, if we think about it at all, it’s usually to complain about the traffic, the weather, or “Are we there yet?”

This weekend, if you get in a car to head to the beach, the mountains, a community or national park to celebrate with family and friends, instead of thinking how hot it is or complaining how long it takes to get where you want to go - could you instead look around and MARVEL at what it really means to have the freedom, independence and luxury to drive where you want, when you want?

As I travel this great country of ours, I am amazed and impressed with its beauty, its variety, its abundance.

Our freedoms do not deserve to be taken for granted. They deserve our attention, respect and appreciation. Happy 4th of July weekend.