Reader Q+As: Chic Lunchboxes, Wedding Shoes, and My Squiggly Path to Success.

Q: I just received the 20z water tumbler you blogged about and love (in blush)! I now feel like I need a more stylish way to tote in my packed lunches to the office. Any finds or favorites?

A: So glad you like the tumbler! YAY! My first thought for toting lunches was to look at Scout Bags. I have one of their insulated lunchboxes and find a trillion different ways to use it, even though I don’t carry my lunch to work anymore. I use it for picnics, carrying my daughter’s lunch around, car trips, Subway trips, etc. I like this versatile style, though I personally own and love this style, which is convenient in the sense that it can be packed into a bigger bag a bit easier than the other one. I love this brand because it was founded by an incredible, strong woman (and mother to four or five kiddos!) who was looking for a stylish solution for everyday toting needs while she had all of her kids. She thought — “I need a big bag for toting sports gear! And a roomy, wipeable diaper bag! And a lunch bag!” And she created them all in the cutest prints.

Q: What Myers-Briggs or enneagram personality type are you?

A: I’ve never taken an enneagram test before, but I am an INFJ on the Myers-Briggs. I remember when I first took the test in high school I was ashamed and appalled that I was an introvert, and kept telling my friends I was “very borderline — a few points off from being an extrovert.” I think back on this now and cringe, but have come to understand why: we live in a culture that favors extroversion (read more about this in the overlong but interesting book Quiet) and it felt like I was revealing my inner dork by labeling myself as an introvert. In general, I think these tests are principally helpful in the workplace, where they can give employees/colleagues a common language and framework in which to understand and peaceably work around personality differences, i.e., “oh, she is such a FEELER versus THINKER in this particular context.” Outside of the workplace, the applications are fuzzier.

Q: I’m recently engaged and on the hunt for wedding shoes. I know that seems backwards, but I am a shoe maven so that’s where I’m starting. I had originally planned to purchase matching pairs of Aquazzura Powder Puff slides and heels for the day but they seem to be only available in random sizes and colors around the internet. Do you have any other ideas of fun shoes for something like this? I’m not stuck on the traditional white/ivory, and the shoes don’t need to match my wedding colors at all. I’m looking for a pair of heels and a pair of flats that are just once-in-a-lifetime fun. No need to match! I am just overwhelmed with the options right now.

A: CONGRATS! This was SUCH a fun inquiry and I’m so flattered you asked.  I had fun looking for options.  Here goes:

+My first thought was a pair of Malone Soulier Marguerites.  I have been lusting after this label for months now.  They come in all different colors and prints, but I’m drawn to the femininity of this pair, which feel appropriately bridal and elegant.  BUT — if you’re not a pink gal, just check out the entire collection!

+My second thought was — glitter!  Not sure if that’s your vibe either, but how special and FUN would these glitzy heels be?  They are a kind of once-in-a-lifetime-ultra-festive snag.  (If the heel height is an issue, these ombre Jimmy Choos get the look, too.)

+Manolo “Hagisi” brooch pumps are a classic and elegant pick, too.  Maybe in bold blue (your “something blue”?) or the pretty blush/champagne hues.

+These LRs just look like a party to me.  I feel like I’d wear them and be ready to dance.  Plus, the stacked heel looks comfortable.  This would be for more of an informal vibe/outdoor wedding situation I think.

+I know you said you’re not “wedded” (HA!) to white/cream heels, but these are the ultimate bridal shoe.  I love that dramatic bow at the ankle…I would probably lean toward these or the Malone Souliers if I was getting married tomorrow 🙂

+My Alexandre Birman Clarita sandals are probably my most-worn evening shoe.  They go with EVERYTHING and cut such an elegant line.  They come in white, too (<<on sale!).  These are unfussy and chic and I promise you’ll get a TON of use out of them.

+For practicality — in an outdoor wedding/if you’ll be walking on cobblestone or uneven terrain — these are perfection.

+Finally, THESE ARE SO ELEGANT AND FUN.  What a statement!!  I’m in love.

Q: Where did you get the pillows and curtains from in this post?

A: Hi! Sadly, the pic at top of that post is not from my own home. (A gal can dream…) I found it on Pinterest! BUT. I found some great similar (affordable!) valences here. For pillows — I actually own a few different ones myself in various blue prints, and got several of them from Caitlin Wilson Design. I love this, this, and this mixed together to achieve a look similar to the one above.

Q: Can you describe your writing process? How long does it take for you to write and edit a post?

A: I’m flattered you would ask, but the unsatisfying truth is that it varies considerably! Some of my longer thought and memoir pieces take days to write and edit, and I’m often incubating them for weeks prior, as phrases and ideas on a particular subject flit through my mind sporadically. (This post took me weeks to write and edit, and I was sitting on pins and needles waiting to hear what you readers thought; I still feel that its publication was dicey.) I’ll capture some of these snippets in my iPhone notes, where I also keep a running list of post ideas as they come to me, most often while I’m out walking Tilly or tossing and turning late at night, and then I often find myself running over to my computer to write and revise these longer pieces in fits and spurts whenever I can get a quiet minute — during mini’s nap, late at night, first thing in the morning. But for less recherche pieces — say, posts on a fashion trend or a round-up of items on my radar — my routine is fairly consistent: I sit down at my writing desk after my nanny arrives (on Monday, Wednesday, and Thursday mornings) with the goal of writing or completing/editing two posts within the seven hours I have my nanny. (Note that I also almost always spend a portion of my nanny days running errands, walking the dog, taking care of admin tasks, etc — so I’d say active writing/editing time is about four or five hours per nanny day, which means most posts take about 2-3 hours from start to finish. Probably an hour or so longer if I include the time I spend thinking about them and making mental edits while away from my desk.) Some days, I just sit down and begin to write with no idea where I’m headed. Other days, I refer to my iPhone list for post inspiration.

Caveat to the above: When I started writing more intensively here about two years ago, I resolved to prioritize volume over quality, which was initially a challenge for me as a Type A. But I was conceptually more interested in writing prolifically and consistently (publishing every day) than I was in turning out perfectly-polished pieces. Some days I cringe when I re-read my posts and note a glaring typo or a poorly-worded sentence, but most of the time I see the writing of this blog as a consistent exercise in self-improvement.

Q: What are your thoughts on cloth versus paper napkins for everyday use?

A: I wish we used cloth napkins daily! It would be better for the environment and more conducive to creating an elegant family ritual (why not eat on your best china every day, too?!). But, for now, while I’m already doing laundry nearly every day, we use paper napkins. Incidentally, one of my favorite sources for cloth napkins is Sur La Table. I’ve gotten so many sets from there over the years. I love these and these (D&G vibes, right?) right now.

Q: How are you handling crib/bed transition and prepping mini for the new baby?

A: Hi! We are waiting until mini tries to climb out of her crib to make the transition. (Until then, we’ll enjoy her containment in the evening — ha! This is something several readers suggested in comments; why rush things? This has been our M.O. in general with mini, FWIW: she’ll get there when she gets there. For example, it took us a long time to wean mini off of bottles and onto sippy cups for milk. Like, over six months. Closer to ten. We kept trying different cups and she would scream for her bottle or just not drink her milk. I worried I’d be sending my daughter off to school with a bottle in hand. But, we kept trying, making small tweaks like offering her milk with her dinner versus separately/before bed, getting excited about the design of the sippy cup (“Minnie Mouse cup!?!? What does Minnie Mouse say?!?”), giving her a new style in her Advent calendar gift roundup, etc., and gradually got rid of all of the bottles. But, I digress.) In terms of other preparations for the new baby, we talk about the baby in my stomach and the fact that she is going to be a big sister fairly consistently. We also pray for baby brother every night when we say our nightly intentions before bed. I wasn’t sure she was absorbing any of it, but just the other day, Mr. Magpie said: “What’s in mommy’s tummy?” and she said: “Baby!” So, we will see. She is still really young and has such a limited concept of time; I have noticed that if I talk about something too far in advance (i.e., “In four days, we’ll see Mimi and Grandpa!”), she gets confused, so I’m trying not to lay it on too thick too early since we still have over three months to go. We do model caring for the baby with her babydolls — patting and burping, diapering, shushing, putting the baby to sleep. She loves this, and always has. Our neighbors had a baby a few months ago and whenever we hear her cry, we pause and say, “Oh, poor baby. Baby must be hungry/tired/need a diaper.” Now she’ll do that on her own — “Oh, Avery,” she’ll say, when she hears the baby. “Baby hungry.” I suppose these are small ways we are acclimating her to the idea! The only other “preparation” I have made is trying to think about how to involve mini in the everyday caring of the new baby. I’m a little skittish about how I’ll fare on my own after Mr. Magpie goes back to work (he has three weeks of paternity leave) and am trying to be proactive in thinking through how we’ll structure our days on our own. My dad sent me a really good article on this general topic that I found chock-full of practical advice, especially the ideas on “non-messy breakfast in bed,” making nursing sessions special for the toddler, and taking communal bathroom trips. Mainly, the article reminded me to take things really slow and set expectations really low during those first few weeks.

But. Seasoned moms: please share your sage advice in the comments!

Q: How do you organize Emory’s bows?

A: When mini was really little and I had smaller bows and a smaller collection in general (insert grimacing face), I kept her bows in a pretty mercury glass compote bowl. I’ve since upgraded to this fun monogrammed bow holder, which I hung on the inside of her closet door. I keep her hair elastics and barrettes in these little 3×3 acrylic organizers in one of her dresser drawers. I also love this pretty painted bow holder, which would be a sweet gift!

Q: London fashion — help! Headed there in May for a wedding!

A: My sister just moved to New York from London and said that women are more understated and sophisticated there. Less flashy trends, more elegant basics. She’s still rocking that vibe here, wearing things like an elegant topcoat (<<she owns this exact style in the chic forest green color; I’m currently swooning over the sophistication of this topcoat), tailored sweaters, and polished leather boots. Extrapolating this vibe for slightly warmer weather, I’d opt for “grown-up,” tailored pieces in solid colors — think anything by the label Goat, often worn by the royalty. I like this dress (get the look for less with this) and this coat.

Basically — I’m imagining myself dressed as an adult in sophisticated cuts, tailored waists, and principally neutral/solid colors. A couple of other chic finds: this knit dress (with these boots!), this dress with these sandals (look for less with these), this white trench dress, and this jersey jumpsuit (could be worn with pointed toe flats — look for less with these — or chic white leather sneakers.)

For the actual wedding, depending on formality, I like this polka-dotted beauty (on sale for under $140), this, and — for a major splurge — this or this.

Q: Engagement ring buying. Particular online retailers or stores? Would love vintage!

A: Ahhh, I am OUT OF MY ELEMENT, but two things came to mind: my family has used family-owned Pampillonia Jewelers in D.C. for generations. My father has commissioned countless pieces for my mother from there, Mr. Magpie had my engagement ring made there, and my brother-in-law used them as well. They create new pieces and have vintage/estate pieces as well. We’ve always had good experiences there, and my father really trusts the head jeweler. My other thought was Stephanie Gottleib, sort of a buzzy jeweler here in New York. Her Instagram account is NUTS. Lots of inspiration and stylish, contemporary options.

Q: Would love to hear more about your overall path — where you grew up, UVA, NYC, career!

A: I was born and raised in Washington, D.C., with a brief stint in Connecticut for a few years of my childhood. My parents had an incredible stone house on the top of a hill right by Rock Creek Park that was built in 1920 and that I lived in for the majority of my youth. I have nothing but fond memories growing up there with my four siblings. I attended Montessori for pre-K and K (my mother was a Montessori school teacher before she had her children), then a small parochial Catholic school (Annunciation), and then an all-girls Catholic prep school (Georgetown Visitation), before attending UVA for undergrad as an Echols Scholar. I was very close to going to Duke University instead, but my father had attended UVA Law and we’d grown up visiting the Boar’s Head Inn and Wintergreen and attending UVA basketball games, so I had an irrational emotional pull to it. (I also liked being close to home, and Charlottesville is about a two hour drive from D.C. I am very close to my parents and siblings.) I essentially triple majored in French, American History, and Literature, but UVA only permits double majoring, so technically I’m a double major in history and literature, though I earned the credits for — and completed — all three. While at UVA, I fell in love with and started dating Mr. Magpie. After I graduated, I worked for a small consulting firm focused on government procurement (falling asleep typing those words) while living at home for a year and then matriculated to Georgetown University for an M.A. in literature, where I specialized in high modernist poetry and poetics (and yes, I need to use those terms of art — HA!). At that point, I moved into the garden apartment of a beautiful row house on R Street with my best friend, from which I could easily walk to campus. While pursuing my degree, I started this blog as a creative outlet. Those were happy years.

I intended to pursue a Ph.D. in literature (Georgetown only offers a terminal M.A.), but I had curtsied into a part-time editing role for a foundation that was building free, online, open courseware (MOOCs! Do you remember that phrase?) and became its second full-time employee in short order. The foundation was backed by a billionaire business mogul in D.C. and it was a great learning experience for me — a ton of responsibility; a wide open, creative space; and an opportunity to flex my editing and academic muscles, as I oversaw about 100 contributing faculty members from all across the U.S. hard at work designing cost-free courseware. At the time, online education was a burgeoning new field, and it was exciting.

I married Mr. Magpie at this time and then he moved us up to Chicago to pursue a job at Groupon after graduating from his MBA program. For almost a year, I traveled to D.C. every other week for a week at a time. It was exhausting and I was unhappy. I found a new job headquartered in Chicago for a start-up non-profit focused on financial education for low-income youth and was hired as the Chief Innovation Officer there, overseeing a new digital program they were rolling out that was backed by Citibank. The fintech aspect of the job was new to me, but I had a strong background in education and, thanks to my nearly five years at the foundation, educational technology and online courseware in particular. The position was a crash course in tech development, as I worked with visual designers, interaction designers, and engineers and even had the privilege of teaming up with the renowned design firm IDEO, from whom I learned a ton. I also had occasion to learn a lot about social entrepreneurship, b-corps, and the modern face of philanthropy and non-profit work, especially after I applied and was accepted into Stanford University’s executive program in social entrepreneurship, which was FABULOUS. Oh my God. Fabulous.

Over the course of these two jobs, I wore every hat you can imagine — HR, operations, recruitment, fundraising, grant-writing, marketing, video production, public speaking, product management and design, project management, and even (yikes) legal, having being in a position to write more than my fair share of offer letters and contracts. Those years were exhilarating. I learned a lot about how to build and run a business, even though I was working in the not-for-profit sector.

Mr. Magpie is a serial entrepreneur and I suppose I’ve always had an entrepreneurial — or at least industrious — bent as well. (While in grad school, I also established a small “editing practice” and took on various projects with faculty at Georgetown that led to few days a week at an academic press downtown.) We are always kicking around new ideas and we’d been obsessing over one in the HR technology space focused on providing real-time feedback to employees. We were both managers of large teams and found that people management was the single most difficult part of our jobs. (You learn technical skills in school, but no one teaches you how to be a good manager — you learn trial-by-fire, or by observing the missteps of your own superiors.) I made tons of mistakes as a 20-something with no business running a team of folks more tenured than I was. One piece that Mr. Magpie and I talked about ad nauseum was how hard it was to provide constructive feedback in a timely way — and how opaque it is as an employee to understand how your performance is being perceived, except for at annual review time, which is an archaic and ineffective process anyway. So, we set out to build a lightweight technology that would facilitate real-time managerial feedback, and we integrated it with Slack, which was being used prolifically by our test market (small tech start-ups). We both left our jobs and lived off of savings for two years. At that point, Mr. Magpie had developed expertise in sales and sales operations while at Groupon and had a solid grasp on the business logic side of things, and I had been leading the development of educational technologies, overseeing designers and engineers, and felt competent in designing a tool we could test. We worked on this company for nearly two years. We had paying, active customers and managed to raise a decent pre-seed round of financing. We were frenetically busy. But the business did not grow at the pace we expected it to and we made the difficult decision, shortly after our daughter was born, to shutter. Around that time, a job opportunity dropped into Mr. Magpie’s lap seemingly out of heaven and we packed up and moved our family to New York City. Selling our home in Chicago was shockingly emotional, but we were both thrilled to get back to the East Coast and I don’t think I’ve ever been happier than I have here.

Since we closed our business, I’ve been working half the week on this blog and half the week as a stay-at-home mom, but I also serve on the boards of two private foundations — work that keeps me busy and alert.

WHEW. I feel like I could write for hours about all of these decisions and movements, but when I zoom way out I am always astounded at the number of enormous risks I have taken in my career. I often encourage the younger women in my life that come to me for career advice to take big risks in their 20s. It’s a great time to explore, change course, and try new things. Starting our own business in our 30s was dicey — I wish in some ways we’d done it earlier, as there are more responsibilities (financial and otherwise) to contend with as you age. But it has all worked out shockingly well and has reminded me of a wisdom I once picked up from a tenured businessman: “Most successful people have squiggly paths to success.” And I have managed to somehow translate a degree in the humanities into an executive role in the non-profit world within a few years, launch a business with my best friend, and launch a second business (this blog!) on my own. Mr. Magpie and I often joke with one another that we are both “jacks and jills of all trades, masters of none,” and I do occasionally envy friends who have committed to a career and are now deep experts in their fields. I, on the other hand, know a small amount about a lot of different things but wouldn’t call myself an expert in any one area — except writing. That’s been the through-put in my career. I have always had to write a lot and manage a ton of content, even as CIO and then COO at my last two formal places of employment. They say that if you do anything for 10,000 hours, you are an expert in it. I am fairly confident I’m close to that total in terms of hours spent writing at this point!

P.S. For those of you who loved my leopard dress from Ganni, here is a lookalike for less!

P.P.S. More Q+A, my most recent musings on the shuttering of our business, and one of my favorite more academic-minded posts.