Sailing Through 2020

Sailing Through 2020


Words by Callie Murray


One January, I created a spreadsheet to track each of my goals. Every day, I noted my workouts, my early mornings, and my clean eating, and I kept a list of quarterly benchmarks in my personal and professional life. I’d start a supper club! I’d do that triathlon! I’d launch a new venture! I envisioned the year ahead like a college crew team: determined, in sync, and rowing power-fully toward my destination.

However, the surprises that came with start-ups, babies, and my husband’s military career, led to a life that looked far from that streamlined watercraft. A friend called me during the summer—long after my spreadsheet had been abandoned—with this (more accurate) vision: 

“I know this is weird Callie, but I feel like God gave me a picture of you on a sailboat. You’re trying to paddle it, and you’re exhausted. I feel like you need to know that sailboats aren’t meant to be paddled, and you should wait for the wind.” 

Not long after this phone call, my husband and I were gifted a trip to Greece where we found ourselves in the middle of the Aegean on—you guessed it—a sailboat. As we sat on the deck one morning, my husband made the vision concrete. “Imagine trying to paddle this giant ship, Callie. That would be ridiculous!” We watched the crew walk by, calm but with purpose. “Instead, watch how the crew wakes up every morning and points the ship in the direction they’ve charted. They raise the sails. And then they trust the wind.”

My goal-setting at the beginning of that year led to much more discipline and intentionality in how I stewarded my capacity, and that was such a good thing! But how do we approach time management and goal-setting when life isn’t predictable? How do we stop ourselves from paddling and keep ourselves from the unproductive circling that comes with striving? How do we recognize when the best path forward is to wait for the wind to catch our sails?

If you’re looking at the year ahead with a sense of fear, shame, or exhaustion, may I suggest the following approach to tackling vision-setting and productivity.


Chart the course. The marriage counseling app I worked for, Lasting, did the research on personal goals and found that you’re far more likely to hit your goals if they’re rooted in a sense of meaning. Knowing what you value and where you’re ultimately headed will keep you on track. What holds meaning and value in your life? Where do you want to land? 

Find your crew. We need people on our ship. This maybe for accountability, for an extra set of hands, or for enjoyment. Honestly, sometimes it feels like it’s for sheer survival. Who is riding the waves with you? Do they know how valuable they are? 

Raise the sails. Laying down the paddle doesn’t mean that you quit the work; it just means that you put your efforts into the right work. What’s your next step in the right direction?

Trust the wind. Sometimes it comes in gusts, and some-times it’s just a whisper. After the sails have been raised, what is powering your ship? As hard and counter intuitive as it may feel, when all the planning is done, ask yourself, “Is it time to trust?”

Callie Murray is the founder of The Big Fake Wedding and now helps other businesses grow through a mix of marketing and operational strategy. Most recently, she worked with Lasting, the No.1 couples counseling app mentioned above. Find out more about Lasting at, and follow along on Callie’s adventures @calliemurray.