Sails Not Anchors
You may feel safe in a calm harbor, but what are you missing out on?
"A ship in harbor is safe, but that is not what ships are built for." - John A. Shedd
Every boat needs both sails and anchors. Without a sail to catch the wind, a boat can’t take you anywhere. Without an anchor, a boat can drift and crash into the rocks. But an anchor doesn't just prevent the bad outcome. It also prevents every good outcome that requires you to leave the safety of the harbor.
People rely on sails and anchors as well. Sails are anything that helps you move forward on your journey and make progress towards a destination. Sails can be the people in your life that motivate and inspire you. Or they can be the experience and education you build up to give you momentum in your career. Anchors are the people and mentality that keep us grounded, but also hold us back from going anywhere.
Like boats, people need both sails and anchors in their lives. What I have found is that far too many people rely on their anchors more than their sails. They stay in the safety of the harbor, never venturing out to explore or take journeys, because they are afraid of the rough waters. They never find out how far they can go and miss out on the new places that their sails can take them. It’s depressing to think about how many brilliant lawyers, accountants, doctors, and engineers are quietly miserable and have no idea how to leave the harbor they're sitting in.
The Anchors We Inherited
Most Asian Americans and children of immigrants were raised by parents who only taught us how to drop an anchor, but never showed us how to raise a sail. The irony is that they boldly set their sails (some literally) to get here. They relied on anchors, because they had sailed through torrential storms. They left behind their homelands and loved ones, to go to a foreign country where they knew no one, could barely speak the language, and only had a few dollars to their names. They prioritized security and stability over everything. Because anchors were how they survived the storms.
That scarcity mindset kept a generation of immigrant families afloat. It is also, I've come to believe, the single biggest thing standing between a generation of their children and the life they actually want for themselves.
After weathering the violent open waters, our parents settled in calm harbors. They expressed their love to us by not wanting us to endure the same suffering. So they pushed us into careers that would be reliable and pay the bills. Their idea of what is best for us, is to stay in the harbor and play it safe.
Playing it safe isn't actually safe. It's just a bet you've made without admitting you made it. A bet that the harbor will always be calm, that the credentials will always be enough, and that stability is the same thing as security. It rarely is. I've watched people ride the "safe" path straight into a layoff, a burnout, a mid-life reckoning. I also know people who feel trapped in a harbor of their own making. What is the real cost of this “security"?
I frequently get messages from miserable people who are in terrible situations at their jobs, but they can’t leave because they are afraid they can’t find something better. Their identities are inextricably tied to their brand name company or firm. Their self worth is tied to their title. They are worried that no one else will want to hire them. They are scared that they will fail if they go out on their own. They are terrified to leave the harbor. Even though they’ve spent their lives building up their sails with their resumes, they can’t pull up their anchors.
Trust Your Sails
Sails don’t work by fighting the wind, they work by catching it and using its force to go somewhere. A sail requires you to trust something you can’t fully control. That is precisely what a scarcity mindset cannot tolerate, because scarcity thinking believes control is the only thing standing between you and disaster. Scarcity thinking gives you the false sense of security that if you eliminate any risk or uncertainty, that you are in control.
But I’d argue the opposite is true. The people I’ve watched build real, compounding, exponential lives: the founders in my portfolio, the executives I’ve profiled on my podcast, the friends who left “safe” careers to become writers, investors, builders, didn’t succeed because they controlled every variable. They succeeded because at some point they stopped asking permission and raised the sail anyway, trusting that the wind would take them somewhere even if they couldn’t chart the whole route in advance.
I didn’t ask permission to start a syndicate to invest in Asian American founders. I didn’t ask permission write a letter in the Wall Street Journal letter signed by CEOs and a former president. I didn’t ask permission to finance a documentary that would win an Emmy Award. I didn’t ask permission to start a fund or build a media platform out of nothing. Every one of those was a sail, not an anchor. None of them were safe. All of them compounded into the next opportunity, and the one after that. None of this could have happened while parked in a harbor, avoiding the unpredictable open seas.
Honoring the Anchor, Choosing the Sail
Morris Chang was 55 when he started TSMC. He was a VP at Texas Instruments, where he was respected and compensated handsomely. But after being passed over for the CEO position, he decided to move back to Taiwan, where he pioneered the dedicated semiconductor foundry business model, allowing tech companies to outsource chip manufacturing. TSMC is now worth almost $2 trillion and is the backbone of the AI boom.
On the flip side, Sarah Guo was named general partner at Greylock Ventures at the age of 28. She was the youngest ever GP since the firm was founded in 1965. Instead of staying at a prestigious firm with lucrative carried interest, she left to start her own fund aptly named Conviction. She has gone on to invest in 6 of the 21 AI-native companies that are valued at over $10 billion on revenue run rates above $100 million.
Both Morris and Sarah had the security that every immigrant and child of immigrants longs for. They were already financially successful and had extremely respectable positions. But that wasn’t enough to satisfy either of them. They didn’t want to set their anchors down, because they weren’t done writing their stories yet. Their success, their networks and their reputations were massive sails that they leveraged to take them even further.
Surround yourself with people who will be your sails: People who encourage and support you to pursue your big dreams. People who will indulge you in your crazy ideas. People who will make introductions to others who can facilitate and enable those ideas to become reality. People who have gone ahead of you on that same path who can mentor you. People who will invest in you and believe in you. People who will celebrate your success and not begrudge you for it.
None of this is a rejection of our parents sacrifice. In fact, it’s a direct result of their love and scarcity mindset, that we can even consider these options. I’m not saying you should cut your anchors loose, because you will always need them. You just need to know when to use them to weather real storms. Stop using anchors as a crutch because you’re afraid of what will go wrong. Those are the hypothetical storms we create in our own heads to avoid opening our sails, because we’re so afraid of where they might take us.
Apply for that new job. Move across the country. Move to a new country. Make that career change. Start that new business. Write that book. Create that content. Every choice you make can take force your sails in a new direction, but first you have to open them.
You only have one life to live. It seems a waste to spend it anchored in a harbor just to avoid uncertainty. Imagine if you raised those sails that you’ve invested your entire life building up, how far could they take you? The networks you’ve created. the experiences you’ve had. The skills you’ve learned. You are more than equipped to navigate the unpredictable waters. You may not know where the wind will take you, but that’s what makes life an adventure.
What are the anchors in your life that are holding you back? What are the outcomes that you’re missing out on outside the safety of the harbor?
You owe it to yourself to raise your sail and find out just how far you can go.