Tacking: How we imagine forward progress should be and what it actually looks like

Collecting small zigzags

In sailing, to move upwind, you need to tack. It’s possible to angle the sails so that the wind will actually propel you upwind if you travel at a 45 degree angle across it. So, to move straight upwind you need to zigzag back and forth.

Credit: Hatteras Sailing

On average, you’re moving directly against the wind. But the moment by moment experience feels like you’re sidestepping the real progress.

This looks like forward progress only when you zoom out far enough that the little zig-zags blur into fuzzy line pointing in the direction you want to go.

Though I’m not a sailor, I try to remind myself that tacking often (almost always?) describes the progress we make in other areas of life. It’s easy to look back at a single day, week, or even month and feel as though we were avoiding facing the resistance head on, side stepping the true work by making orthogonal progress.

I tend to make a lot of sharp turns in life, dropping one path and quickly switching to another. But the tacking metaphor helps me realize that while it might feel like I’m just flitting back and forth in place, those hard turns might all be hard tacks across a wind direction that I’m meant to be traveling.

Even if I’m not sure of the ultimate destination, all the zigzagging is leading somewhere. I’m accumulating progress and compounding skills along the way.

Finding purpose probably isn’t about setting a direction and moving headlong into it. It’s probably about figuring out the direction that all of your little tacks — the ones you’re forced to make and the ones that you can’t help but make — are leading.

I also find it empowering to remember that it’s possible for wind to propel you in the exactly opposite direction that it’s blowing. But only when we learn the skill the angle the sails just right. And only when we learn the patience to accumulate a bunch of small tacks and release our expectation that we should be able to march directly up wind.

A Related Thought and an Invitation

In the men’s journal club that I host, we recently reflected on the prompt: where have you compounded the most? Especially areas that might not have been intentional?

Similar to this tacking metaphor, I think we are all constantly compounding skills, relationships, and experience. The professional and intentional ways that we do this matter, but I think it’s far more interesting to ask yourself about the areas where you’ve been doing this but simply following your curiosity or your passion.

When asked how he got so good at tennis, Novak Djokovic is supposed to have answered, “I just love hitting the ball.” What are the tennis balls that you love hitting?

If you’re a man and interested in thinking about these types of questions with other thoughtful men, you might like attending my men’s journal club. It’s free, welcoming, and has quickly become my favorite 90 minutes of the week. It’s Friday mornings at 6AM Pacific time. DM me or reply to this email if you are interested in joining.

Personal Updates

Our boy is four and half months old which means he’s rolling, slobbering, and shrieking with glee pretty much non-stop.

My younger brother just got married in the most debauchery-filled evening I’ve ever been a part of. I’ll probably share a few stories with the journal club dudes, if you need extra incentive to check it out ;)

Skate & Create, the skateboarding and art program that Marika and I are building within our local school district is getting so, so, so close to launching.

I’m running the Cerro Gordo Silver Run on May 24. It’s an 8-mile race up to an old silver mine that gains nearly 5,000 ft, topping out at 8,500 ft. There’s a few spots left and it’s 20% right now with the code FRIEND. Sign up here. I hope to see you out there!