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“The size of your dreams is in proportion to how much you trust yourself.” Erik Orton

My family didn’t think I could take a vacation where I genuinely unplugged. If you had received an email from me between January 5th -10th, their judgement would have been correct.

We haven’t taken a proper family vacation in years. Yes, at times, there have been financial constraints but if we are motivated, time off can fit almost any budget size. We didn’t vacation because none of us really understood the S Curve of vacationing.

Now that I am back on premises (and I did in fact vacate and unplug), here are a few things I learned:

  1. Listen to your loved ones. Our children had been saying they wanted more family time, more family experiences—awesome! But we had hesitated for so long, we were on a collision course with a Cat’s in the Cradle moment: “We’ll have a real good time then….”
  2. Be open to opportunity. In mid-October, Erik and Emily Orton (podcast episode 101) offered to host us for a few days of sailing. The Ortons wrote the NY Times Best Travel Book of 2019 titled Seven at Sea about their shoestring family adventure (they are not wealthy––they saved for five years to make this happen) living on a sailboat. Now they’re experimenting with making a business of it. Were we in?
  3. Logistically prepare. The plan was to sail from Tortola. To do this, we had to be COVID free. We were tested before we left home and then tested again upon arrival. Quarantined for four days. Tested again. Wait another day for results. Only then could we leave our lodgings and set sail. There was a lot of advance planning required. Fortunately, we were COVID free but we did have to leave our college-age son behind for a day because he required a different kind of test. And we launched a day later than expected because of quarantine restrictions.
  4. Emotionally prepare. Beyond logistics, emotional preparation is required. I have had several vacations derail because I wasn’t emotionally prepared to be in a different place doing different things with different people. I have since said no a few times, deterred by anticipated awkwardness and unfamiliarity. I recited to myself more than once, “I can jump to this new S Curve. It’s going to be awkward, but I can do this.”
  5. Schedule time to transition. We did not plan this part; it resulted from travel restrictions. But because of the quarantine, we had a few days to wind down work commitments – essentially, slowing our lives to a vacation pace. By the time we sailed physically, we were ready to be present emotionally.
  6. Unplug. If you don’t do anything else, do this. If I wouldn’t have my phone on in a major presentation, why would I have it on while on vacation with my family? I am grateful to my wonderful team, who made being disconnected possible. Being able to focus lowers the stress of doing something new.

During one of our evening conversations, Erik said, “The size of your dreams is in proportion to how much you trust yourself.” In the past we’ve scheduled family weekends and I canceled them at the last minute. Or spent the entire time working. This time I didn’t. I can trust myself more now. My dreams are now bigger.

What can you do to maximize your self-trust? Maybe it’s a vacation… Maybe a different S Curve. How will you expand the horizon of your dreams?

Our podcast this week features Margo Georgiadis–––CEO of Ancestry.com. Her career has been remarkable, but what I most loved about the conversation was hearing her family stories. I’ve been doing some family history of my own. I think it’s no coincidence that this has led me to want to make history with my own family.

Happy January,
Whitney

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