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This morning, re-publishing a modestly edited essay from the archives because it touches upon a couple of motifs that have come up in conversations with friends over the past few weeks. I think that when we are in the midst of a transition, a career pause, a lane shift, our insecurities come rushing out, and we find ourselves doubting the path we’re on — we’re exposed, we’re starting something new, we’re hearts on stilts, we’re taking those fawn-like first steps, all wobbly ankles and ungainliness, and we long for the seasoned stroke of competence and tenure. All of this is doubly hard because we are interrupting stories we’ve been telling about ourselves for a long time. Just think of the ease of answering “and what do you do?” exactly the same way for your entire life. You have your self-pitch down. When you change directions, you must figure out how to explain your new path to yourself, and then also perform it hundreds of times to other people, who may or may not receive it with gentleness. I’m here to cheerlead you and to share a few mantras that have been helpful to me over the years, especially when crouching at the start line of something new:

It’s not your job to prove yourself to everyone; focus on the work itself

The only people who you should try to impress are your 8 year old self and your 80 year old self

You are not for everyone, and that’s OK

There is no “one way” to do life

You can start anything today, and with no one’s permission

It’s healthy to change the stories you tell about yourself

*****

During our entrepreneurial days, Landon and I used to joke that we were “jack and jill of all trades, and masters of none.” At the time, we envied our friends who had chosen more structured career paths, and had cultivated deep expertise in their fields. By contrast, we felt unimpressively generalist. I kind of understood design, kind of understood sales, kind of understood technology, but I was far from an authority in any of those areas. I am thinking now of a friend who, when asked whether she could help with a technical issue on my site, responded: “Sure. I mean, I know enough to be dangerous.” Ha! Like, I can do something that will either implode your site or catapult you to the next level — we’ll see.

I have so many thoughts on this now. First, I think that many people in their 20s and 30s, especially those who switch or shift career paths a few times, feel this way (“the unimpressive generalist”), and don’t yet see that they are building up a unique register of insights and experiences that will eventually serve them in surprising ways. For example, I am shocked by how much design thinking percolates my approach to my writing, to my business, to even the everyday administration of my life. Product design was a short chapter in my life, but it has touched almost everything that followed. The same is true of writing, of course, although it only occurred to me in the past few years that I could consider myself any kind of specialist, or tradesperson, in it. (It takes a long time to become.) And yet how I think about writing, how I practice it, conditions everything else I do. It startles me that every daily encounter — how I experience beauty, how I read, how I make my way through times of irresolution — is rooted in wordplay, and the patience required of drafting and editing, and the specific kind of listening that goes into writing a sharp line.

I also think that entrepreneurs must, as a matter of survival, be “practicing generalists” whether they want to or not. No one else is going to clean the toilets of your restaurant when staff is out sick; no one else is going to figure out that billing issue. You don’t have enough money to pay for a full-time CMO; you’ve got try something on your own.

And, finally, I think there’s merit to Elizabeth Gilbert’s “are you a jackhammer or hummingbird?” question — the notion that some of us are consumed by a singular passion, and others move from tree to tree, trying this and that. No one approach is better than the other. And the most surprising thing of all is that I have thought myself to be a hummingbird for all my life, but it turns out I’ve been jackhammering away at writing the entire time. I suppose that happens when you take a hobby and make it a career.

What about you, friend? Do you consider yourself a jackhammer or a hummingbird? A jill of all trades or a master of one? Has that evolved in your life?

I think it’s important to note that you can experience “greatness” as a hummingbird or a jackhammer — that you can be great at a specific skill and also great across a career, or a lifetime. I know several people whose jobs have changed over time but who have consistently demonstrated what I would classify as “greatness,” glossed as talent, commitment, curiosity, leadership, ambition. I am thinking first of my dad. He is an attorney by trade but it’s not the first thing that comes to mind when I talk about him. He brings intensity and passion to absolutely everything he does, whether it’s woodworking, flyfishing, philanthropy, casual mealtime conversations (my brothers-in-law used to joke that they’d read the WSJ cover to cover before meeting him for lunch). What does it mean to be “great”, after all? And what can we learn from it?

Post-Scripts.

+On shaking hands with the empty page.

+The first job each morning.

+On falling in love with Landon. (Thrill of the chase.)

Shopping Break.

+Sezane just launched a spectacular fall capsule. These boots, this chic cropped jacket, this macrame cardigan (!), these chocolate trousers!!! I want to be this woman this fall. All the gorgeous textures and layers of espresso, mustard, olive, chocolate! Also obsessing over their Victor bag. It has such Toteme vibes for less $$.

+Almost to cord season. I ordered these, in Frame’s bestselling Palazzo silhouette! (Frame also sells this silhouette in leather — so incredibly chic.) Anthro has a pair similar in shape for less, as does J. Crew.

+If you’re into a straight leg cord style, I love this sleek pair. Boden has a good look for less, too.

+Classic J. Crew tees on sale for under $20. A great buy. I live in white tees!

+This cubby bookcase is somehow 50% off in the white. I actually think I might order this for my son’s room. We have a taller bookcase that has been pretty impractical for him; I like the idea that he can reach everything and also use the top surface to display all of his Lego pieces. I’m still astounded by the price!

+This cable knit half zip is so dreamy. I love the idea of it paired with the aforementioned brown cords. Gorgeous looks for less here and here.

+While we’re talking Varley, how gorgeous is this brown wide leg set for fall?! The definition of elevated athleisure!

+I shared this Longchamp-inspired bag in my “what to wear to a concert” post and realized it’d be handy, too, for sporting events this fall.

+Pink Chicken has the cutest back to school collection; I love the painterly motifs, like these pencils, this blacktop/hopscotch print, and this PB+J dress. I got the latter one for my daughter. She doesn’t love frilly dresses, and the simplicity of this cut (and the whimsical pattern!) are perfect for her.

+I think these are my favorite joggers I’ve ever worn. They have a great lean, lengthening effect and fall just perfectly.

+These chic magnetic travel container sets (I LOVE mine) are currently on sale.

+Loving this polka dot top and skirt set.

+Fun Bento lunch boxes for kids.

+Gorgeous marbleized notebooks.

+Eyeing this Alice Walk sweater jacket. Which color?!

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