Last week, I messaged Theresa from the aisles of a store: “How much trouble will I be in if I go a little over our gift budget?”

On this, our third holiday season together, Theresa and I set a $50 gift budget based on the idea that we both have what we need and much of what we want, and that we treat each other throughout the year anyway. That messaged conversation, though, illuminated that neither of us was particularly chuffed at how it was feeling shopping in that budget. We were both having a distinct sense of meh.

Later, we talked about the purpose of giving each other gifts at the holidays, acknowledging the piece that’s about social norms and going with expectation without a whole lot of thought. We talked about bringing some curiosity to how we’d like to feel and what we could shift next year in order to get to those feelings, rather than to some dollar amount or number of packages. We’ve got most of a year to explore before we run our next experiment in holiday gift giving – perhaps a mutually agreed upon couple’s gift? – after which, we’ll evaluate and perhaps adjust again, with another experiment come winter 2021.

It’s ultimately a tiny little thing. And yet it exemplifies a conversation I have just about every day with the people I coach, especially those starting businesses or looking into some significant life change. At such times, we want to know what the outcome will be – Will this business idea be financially successful? Will my relationship withstand my new evolution as a person? What will it feel like to engage with change in this way? Will Theresa even like the things I picked out for her?

And the truth is, we don’t get to know outcomes.

Yes, we can and, especially in the case of business, should explore what we can proactively – market research and running numbers and all of that stuff, even if only in a back-of-the-envelope way. At some point, though, there’s only a best guess paired with a leap of faith.

Then, just like with our holiday gift buying guidelines, we evaluate, adjust, and leap again.

And then we do it again because with most things, there’s not a perfect answer. For most things, we benefit by staying on our toes, noticing how our changing responsibilities and opportunities and selves require a slight shift here and a big one there.

Most of us would trade a lifetime of holiday gifts – and birthday gifts and anniversary gifts and all the rest – for even a modicum of certainty. As it is, we pay a lot of money to programs and products that offer the promise of such, the snake oil of solid ground.

Since I can’t give you that, I’ll instead offer you this holiday wish: That in this season and all of the ones to come, you dip more and more deeply into your existing well of courage as you face uncertainty and embrace curiosity and experimentation.

And that you remember that you have creatively and deftly survived every moment of the ground crumbling beneath your feet so far; my certainty lies in knowing that you – and I – will survive the next one, too.

A crew can be mighty helpful in navigating those shifting landscapes; yours awaits you via my weekly email. It includes my weekly posts, bonus insights and ideas, and access to our weekly community gathering, Chomp & Chat. We’re excited for you to join in!

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