We're down to the home stretch of 2020. Based on what I see on the interwebs most everyone can't wait for this year to end. Yet less I put a damper on the joys of opening a brand new year, most all that made 2020 so 2020 is still going to be with us come day one of 2021. Amazon has a philosophy that every day is Day One. Every day is a chance to make or break it.

On the plus side, we'll see a change of administrations to one who actually appreciates science. And a vaccine starting to roll out. But we're still in the woods. Even if your 'woods' lack any requisite trees. We're lucky on the west coast to have some amazing woods by the way.

Last week I challenged you to check in with your vision and create a framework that takes you there. This week I want to highlight the cold realities of technology and work and talk about your keel design.

Built for cruising slowly or built for speed?

How is your keel designed? Keel you ask? I'm not a sailor. What's that got to do with me? Let's talk about the purpose of the keel on a sailboat. When a boat is built, this is the first thing laid. It’s the critical piece attached to the bottom of the hull of a sailboat which provides stability and keeps it upright. It prevents the boat from blowing sideways too. When a keel breaks off - which is rare - the boat loses control. Sometimes to the detriment of the crew.

Ever been told to keep things on an even keel? Well, that's all about ensuring that things are calm and steady. You want to stay upright. You need to be - want to be - on an even keel. Off kilter you and you fall over. Often it's what we can't see that makes the biggest difference in our performance.

Life is like piloting a sailboat. Think of your keel as made up of all the things that keep you grounded and resilient.  In addition to the keel supporting your direction, you need to adjust your sail to stay the course based on changes in the wind. A sail boat never travels in a straight line to its destination. It zig zags just like you do towards yours.

"A sailor is an artist whose medium is the wind. Live passionately, even if it kills you, because something is going to kill you anyway." ―Webb Chiles

Several years ago I learned to sail on a small boat with a tiller - that lever at the rear you steer with. You move it in the opposite direction you want the boat to go. Often in life we need to do things counter to what we would expect in order to find success. On calm days, you didn't have to hold on to the tiller very hard. It was relaxing but you moved dang slow. Sometimes you needed the iron sail (that would be an engine).

But once the wind starts a blowing, you gotta be alert and hang on tight. That's when you need a strong keel to keep the boat from tipping over. On the most exhilarating runs, I would find myself standing on the side of the boat with the rails nearly in the water holding the tiller tight as we sailed briskly down the river.

You feel like you might tip over, yet with everything and everyone on the boat working well together, you wouldn't. After such runs my arm felt every bit of it. You trust your boat and crew that all will be well.

Trusting your boat comes from knowing it inside and out. And knowing it’s been thoughtfully maintained. There are keels that fail because the bolts holding it on rust off.

Sailing takes focus and constant adjustment. You need to 'read' the wind and the water. Ignore the elements and you'll be buffeted around. Just like in life. Those that let life happen to them rather than design their life rarely achieve their potential.

Sailboats and keels come in many different shapes depending on their purpose. Think about where you're going in your life. Now think about what kind of keel you need. Do you need one solid and simple to keep you cruising along? Or do you need one designed for speed like those used on the America's Cup?

What is your crew made of?

Who are the people you need to get where you want to go? What kind of sail - i.e. tools - do you need? Last week I talked about picking the essential and simple tools. When you're sailing, there's a lot going on when you're adjusting sails, changing tack. Everything and everyone needs to work together. And better stand out of the way of the boom (what the sail attaches to) when tacking lest you get bonked overboard.

When  I later sailed a larger boat across San Francisco Bay that had a wheel instead of a tiller I learned how much easier it was with a wheel. One tool I didn’t mention last week is Airtable, which brings spreadsheets and databases together in the cloud. Highly customizable and scalable, it’s great for one and also great for team collaboration. Think of a spreadsheet as a tiller and Airtable as a wheel.

It’s true. The hustle is hard.

Achieving outsized success takes a lot of work and intention. Success rarely comes from the newsworthy actions we do. It comes from showing up every damn day. Success is in the execution. We want the dramatic flourish. I use the analogy of sailing to hopefully deepen your thinking about what you need. And what keeps you upright when a proverbial storm blows.

Side hustles - made more possible than ever with the tools and platforms available - are glamorized. The glam is in the success. What you don't see is the work behind the scenes. For a little reality check, the odds are not always in your favor. Those 1% at the top see much more success than the 99% combined.

The algorithms favor the connected and famous. Those with the largest followings. There is no trickle down economics in social. Not that there ever was trickle down economics anywhere. Those with a big audience have a much easier time monetizing that audience. And selling new products.

Many will not succeed and will give up. Purpose will keep you going when you fail. And let’s put failure into context. In this podcast, Libby DeLana talks about how failure needs a rebrand. I like this notion for that’s what gets you closer to your success. When you’re designing your work, you can design your potential failures so they’re not fatal.

In this world - often called the passion economy - the economics show that successful creators on Poshmark work 40 hour weeks and end up earning just $12.50 an hour. Hardly worth the effort involved. Same with Uber, Fiverr and other platforms that promise you a life where you’re in control of where and when and how you work.

Platforms like Poshmark need a lot of people in order to work. The catch is you want to be the platform and not one of the people. This is why it's important to intentionally design your 'keel' and have a vision. You need to build something you can own. If you rely on a platform, not only are the odds against you, but if the platform goes away, you're back to zero.

“I was amazed that what I needed to survive could be carried on my back. And, most surprising of all, that I could carry it.”—Cheryl Strayed

In the case of a resale platform like Poshmark, you're selling a fixed quantity of goods. Your marginal costs are high and inventory limited. If you're selling a digital good, your marginal costs are near zero and distribution potential infinite. Many say the most beautiful businesses are platforms, software and digital products for this reason. Shopify was created to sell physical goods but became the focus over the goods when Tobi, the founder, recognized both the need and the opportunity.

Thanks to people like him, you have access to the same kinds of tools behemoths like Wal-Mart have. Imagine being able to compete with a Wal-Mart next week? This is the amazing world we live in. The upside of the challenges faced. And if you are keen to sell physical goods, look at those where the margins are high. Gives you much flexibility in how you price and market. Trends.co just released a report on the high margins in laundry detergent and perfume. Someone's cleaning up nicely! Or turning scents into dollars.

Last week I launched Walloy, my online gallery of fine art photography. I know it will take time to build a following and reach critical mass. Because it's such a part of who I am, I'll invest the time. And I am not counting on it delivering food to table (yet) 🙂. But I do look forward to it funding my penchant for cool camera gear and travel.

So what if it’s hard?

Society tells us to look for the easy and avoid the hard. But sometimes what’s hard is deeply satisfying. Especially if it’s what floats your boat. So keep after it, okay?

I’ll leave you with a ‘theme’ song for this letter:

Hint: my suggested takeaway is make sure you’re the windshield.