🎁 The gifts I gave myself in May 2023

A sabbatical + moving toward a settled estate

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #6. ✨

☀️ How was your week?

I love where I live!

I put in some hard work—and enjoyed indulgences. Training for my upcoming 10k has been fun, if intense! Adding interval runs to my rotation has left me hungrier than usual, which is how I found myself running out for an emergency snack this week: a gigantic cup of vanilla soft-serve, and salty French fries straight from the fryer.

Perched at the diner counter, I paired these with my latest library pick, the poignant and compelling memoir Home Made by Liz Hauck. I can’t think of a better way to spend an afternoon.

🎁 Today’s letter is for paid subscribers—and here’s why.

When I started this newsletter, I enabled paid subscriptions on a lark.

I enjoy supporting my favorite creators on Substack and Patreon, so I figured someone might pay for a monthly subscription to this newsletter someday, when I’d published a body of work.

But as a newly-laid-off person committing lots of time and energy to my writing—well, there was zero downside to giving readers that option now. 😂

Then, a funny thing happened…

People actually availed themselves of the paid subscription option.

Some loved ones did so before the first edition was live (!!). Others, I’ve never met.

I learned two things as a result:

1. I have the world’s best family, friends, and readers. (I mean, that’s you, so: obviously.)

2. I’m intrinsically motivated to write here, and each time a reader subscribes for free, my heart just about leaps out of my chest. But when someone pays for my next month—or twelve months—of writing, it lights a fire under me. It’s a bet on my commitment to this space, and a special vote of confidence in my voice.

I’m excited to deliver on those votes of confidence via special editions of this newsletter. Writing for a more intimate group will allow me to cover personal topics that I’m navigating in real time.

You might remember my mini-manifesto about approaching life with a gift-giving mindset. In these dispatches, I’ll detail the gifts I gave my own Present and Future Self this month.

Don’t fret, free subscribers! I adore you, and the rest of my writing remains accessible to you.

On to today’s letter!

The gifts I gave myself in May 2023

The Oregon coast, captured on Kodak Portra 400 film

A gut-wrenching upheaval—whatever form it takes in our lives—isn’t just a loss to be grieved. It’s also a transition state, in which we’re concluding one chapter and beginning another. (Cue Natasha Bedingfield’s “Unwritten.”)

Often, our impulse is to motor through transition states as quickly as possible. That may be due to financial or emotional self-preservation. Other times, it’s because we’re already clear on how we want to proceed. But sometimes, we simply want to avoid the discomfort of not knowing what’s next.

I’ve used all of these rationales for speeding through change during various life transitions.

But this time is different, and here’s why:

• I’m not clear on how I want everything to unfold (particularly when it comes to my career), and

• I have the immense privilege of remaining in the discomfort of not-knowing, rather than resolving that discomfort ASAP (in the career example, by immediately seeking another financial planning role).

So! In the spirit of “sitting with the uncertainty of transition,” these are the gifts I gave myself in May.