Help, I need somebody!

I may have mentioned that I have an executive function disorder. That is the category AD(H)D falls into. What that means for me is that it is often a lot of work for me to make decisions and organize tasks. All of the traits that make me an excellent systems thinker, like holistic views, consideration of concepts outside the standard solution, and interrelationships are present all the time.

Most people, when they go to book a hotel room, get on a site like Travelocity that triages by price and distance, and they just pick something. What I do is do that, and then think about how much it would take to get Lyft to and from where I need to be and if that’s a savings worth staying further away, and is there anything else I need to visit while I’m there, and is it in my 3 loyalty networks, and does it have late-night room service, and is it close to someplace that I can get groceries, and does it have a fridge, or a microwave? Is it in the loose budget my company asks for? Is there a reason that it’s more expensive, such as holidays or major events? How does that compare to the per diem for federal employees, which is what I use as my heuristic for judging which cities are just annoyingly expensive?

I think all those things pretty much every time. And I think in that scope for almost everything. I used to think that loyalty programs like airline mile memberships and hotel points were for a) optimizers b) rich people c) frequent travelers. I’m really only a member of c), but it turns out that they’re also great for d) people who need to reduce computational complexity.

I went to 44 events this year, I think (accurate year-end roundup later). Are you exhausted thinking about that level of planning? I was. And then I was facing down 3 weeks in Europe and I complained to my boss and he told me that a personal assistant was an allowable business expense.

I’m working with a lovely woman named Carly, from an organization called Aim2Assist, and it is making my life so much better. Suddenly, I understand why executives get executive assistants and why it matters to their productivity. Because I can delegate.

How does it work?

Yes, I have signed over a great deal of personal information to this person. There’s no way around it. The way I did it was to share LastPass entries for all my frequent flyer/hotel/credit card information. I can revoke those at any time, and keep them updated. This is much easier with a company credit card, because the company has the ability to get recourse if something goes wrong (which I don’t suspect will happen, but they have more money than I do).

Then I gave her a rough set of parameters to work with. I prefer to fly Delta. Window seats. No AirB&B if we can help it. Hotel rooms in the $150-$250 range if possible. I’ll take care of my own transportation on-site. We also did a chat where I talked about things I just liked in general, and what it means when I travel for work. (14 hours days a norm)

So, for the Europe trip, I booked my inbound and outbound flights, and then sent Carly that information and the dates of the conferences and meetings in London, Bordeaux, and Marseille. Those were my fixed points. I told her that I wanted to spend some time in Bath (which was magical), and that I preferred the train to flying in Europe. She sent back an itinerary for my approval. For all my London stays, I was in one hotel, which was nice and consistent and I just had to learn one route to and from the Tube. Because I wanted to do walking in Bath, she booked me a hotel in the historic parts that was lovely and gracious and still less expensive than staying in London. In Bordeaux, she found this ridiculously lovely off-season glamping/chateau experience.

King-size bed in a rustic wood and canvas room.

It was in Bordeaux that I was desperately grateful to have her. I had gotten pickpocketed in the half hour I spent in the Paris Metro, so I only had my backup card, which was an American Express. It’s not the card of preference in Europe, if you were wondering. Instead of me trying to argue with taxi drivers about what kind of payment they’d take, she booked me a car and driver. And when the train I was booked on told her that they weren’t going to stop in Marseille due to flooding, she rebooked me onto a flight so I would get there in time.

When I got home and there were all the usual annoyances of travel, like my hotel nights were not properly credited and I needed a refund for the cancelled train ticket, I could hand those off to her instead of trying to deal with it myself.

None of this was impossible for me to do. She’s not a travel agent with access to their mystical systems. She’s a human who gets paid to make things happen for me, another human. And it’s such a blessing to me. Her decision matrix is much smaller than mine. I’ve told her my preferences, she optimizes for them, but she doesn’t end up deep in the weeds of what’s professional and what’s self-indulgence. I don’t want to walk more than half a mile to get to a conference venue, she accounts for that and doesn’t wonder if it’s worth an extra $20/night to save 10 minutes, etc etc.

NOTE: if you are a frequent traveler and no one has given you a company credit card, raise hell. If you WANT to put it all on your personal miles card, that’s fine, but you are traveling for company business, and they are going to pay eventually, so make sure they pay now. This is especially true for people who are young, have low credit limits, or have shitty credit. I can drop 10k on a month of travel bookings, easily. I do not have a personal credit card with a 10k limit, nor do I want one. Companies should not make private wealth a prerequisite to career advancement.

What can you ask for?

LaunchDarkly is paying for this service, because it’s cheaper to pay her rate than to pay my “rate” for me to do this, only less well. Those hours I don’t spend on travel booking I spend on watching conference talks or reading articles or writing blog posts. It’s better value for money.

Because my employer is doing this, I try to keep my requests to work-related things, mostly travel. I would also feel ok asking Carly to file my expenses (if our system wasn’t so stupid-easy), or send confirmations or other things that related to traveling and speaking.

If I were paying her myself, I could also ask her to book medical appointments, send birthday presents, order flowers, get someone in to clean up my lawn. We have apps for a lot of this now, but it still takes time and effort to do, and time and effort is exactly what I don’t have to spare right now.

If you ever watched The West Wing and admired Mrs. Landingham as a highly-competent person who enables Jed Bartlett to be Bartlett, that’s like the highest expression of getting help to delegate executive function to. Few of us can have a secretary, but many of us could possibly spend a day’s wages to save that time and thought for something else.

But what if?

I think the scariest thing for most of us is having our identity stolen. Going through a proper organization is going to buffer against that. I wouldn’t hire someone random off Craigslist to do that, even though they’d probably be fine. I like having someone who is accountable. Also, let’s be real, our identity is scattered across a dozen databases on the dark web already.

What if your assistant screws up? Well, so far my assistant’s track record of screwing up is far below my own record. I am the queen of being really bad at booking flights that cross midnight and realizing belatedly I’ll arrive on the wrong day. Inevitably it will happen, but when it does, I’ll have someone to help me figure that shit out.

In conclusion

Yes, it’s totally worth the money to get an assistant if you have a life like mine. I was feeling guilty about being “lazy” when I felt overwhelmed about booking my own travel, until a friend pointed out that for me, it’s an accommodation, and for everyone, it’s an efficiency.

It is a build vs. buy proposition.

I could work hard to make this work in my own system, or I could pay money and save opportunity cost to get a better end product.

On a jet plane…

I’ve been in Europe for the better part of three weeks now, and I’ll be going home Saturday. As you can imagine, I thought long and hard about everything I brought with me. I never want to take more luggage than I can comfortably manage on my own, up and down subway stairs.

This is a long post, so if you’re not interested in travel-nerdery, go ahead and skip it.

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Lady Conference Speaker: 14 Travel Tips

I was talking to a fellow ladyish conference speaker, and I reeled off a list of my travel tips as they pertain to people who are working for small/nimble enough companies that you don’t have to book through The Corporate Site.

An array of bags and the things they contained, including laptop, cords, stickers, portable keyboard, medicine, neck pillow.

Last year’s conference travel assortment. I’ve upgraded my bag since then.

  1. Remember that your time is usually more valuable than the amount you can save by optimizing flights. Before you spend 4 hours trying to save $100 and adding a 3 hour layover to your flight, consider your hourly rate.
  2. Pick an airline you can deal with, stop looking at others. I use Delta because I live in a Delta hub.
  3. Pick 2 hotels chains with a variety of price point options. I use Hilton and Marriott, but Quality or Best Western or anything similar will work.
  4. Be reasonable about your expenses, but not chintzy. This is not human travel, it is business travel. The value of business travel is that you arrive in a place capable of interacting with humans.
  5. Pack what you need for each day in a roll so you don’t have to spend any brain resources when you get there.
  6. Where you are going, they sell most things. You can solve a lot if you have underpants and a bra and a company t-shirt.
  7. You’re probably not going outside as much as you would as a human traveller. You don’t need an umbrella, or sunscreen. Travel the world, visit exotic conference centers.
  8. Bring a hoodie, because of the patriarchal thermostat hegemony.
  9. Upgrading to Comfort+ is pretty cheap for the amount of unfrazzling it earns you.
  10. You will always look sharper than the dudes, by virtue of your awesome haircut, ride on that.
  11. But if you don’t feel confident, mascara+lipstick is pretty much all people actually use to read “professional lady makeup”.
  12. Assemble a small travel kit of meds – most of us on the road a lot have a “sinuses are the devil” section and a “let’s not talk about my digestion” section.
  13. There are a lot of things you can solve by money that you couldn’t easily fix when you were traveling on your own, such as: Too Much Walking, Lost Luggage, Forgot Charger, Missed Flight, etc. Don’t be rude about using company resources to fix personal problems, but ask my boss how many cities he’s bought a Macbook charger in. It’s better to have it than to not be useful.
  14. Your average mid-range hotel and above (Not Super 8, yes Garden Court) has a wide variety of forgotten chargers you can borrow. Also they will bring you for a small fee or free a bunch of useful forgotten or unluggable items, like toothbrushes, razors, and full size humidifiers.

This is not human travel, it is business travel. The value of business travel is that you arrive in a place capable of interacting with humans.

There are a lot of other tips I have, but those seem like the most salient. Just keep in mind that you are worth shipping across the country carefully because you are a precious and hard-to-replace part of the company, and they want you to arrive undamaged, functional, and able to do good work.

Bonus tip: Pick a type of tourist attraction you like to see and look for it in cities you go to, if you have time. I’m fond of botanical gardens.

Spiky green glass sculptures that echo the shapes of desert plants.

Glass and biology at the Phoenix Botanical Gardens

 

My first year, a personal review

I woke up to a cheery email today telling me that a quarter of my stock options had vested. That means I’ve been with LaunchDarkly a whole year! (there are worse anniversary notes to get).

And what a year it’s been. I thought about doing a photo essay of all the conferences I went to in the last year, but there have literally been 36 this year, and I had speaking slots at all but 5, and of those 5, I ran open spaces at 3. Too many pictures!

I went to 3 other countries – Australia, Santo Domingo, and Canada. I made platinum status on my airline, missed my kid’s 13th birthday and every single concert, and wore out a TravelPro suitcase. I made a bunch of new friends and acquaintances, and got to know others better, and worked my ass off to learn a new career.

When I started, I had exactly one day in the office to get my new laptop, meet my new co-workers, and have an enthusiastic and influential conversation about stickers. Then it was off to Kansas City Developer Conference, my first official conference as an official Developer Advocate.

Let’s just say I was glad for my thorough interview prep!

You can see that my sticker conversation ended well. This is Velocity New York, I think.

I made it back to Oakland for LISA and the office Halloween party

I celebrated company milestones, even if I wasn’t always in the office for the official parties. I ate this bread pudding in New Orleans at RubyConf. It was delicious.

I sewed a bag for the sticker collection I tote with me to conferences. The inside fabric was an in-office thank-you gift, and the fastener is one I got in the Garment District of New York

Toggle the Space Explorer in a bag of stickers

I met this sleepy lion when I was in Sydney to visit Atlassian. It was my first customer on-site and it was kind of mind-boggling. They had so many great ideas for new features and ways to work with our product.

Lion outside the Atlassian Sydney office

There was a caricaturist at Index San Francisco. I’m pleased that I happened to be wearing this jacket that I made.

Caricature drawing of a white woman with brown, pink-tipped hair and blue eyes

This was a sketchy diagram I took a picture of and sent to our awesome product/graphic person, Melissa. She’s the one who does all our striking stickers and visual look and feel. This ended up as a slide in my Waffle House talk.

Messy handwriting diagram of success/failure continuum.

Here is my glamorous life. I took a nap in the office before a redeye flight home. This is the old office, which we have now outgrown, but the view was amazing. I am wearing technology socks, but I can’t remember right now whose.

A person's socked feet, a view of the clocktower in Oakland

The key to never feeling bad about putting stickers on your work laptop is to first cover said laptop with a clear case. It gives you a little bit of ablative impact resistance, and when you change computers, you can keep the case for your wall!

I’m proud of the work I did, and in the next post, I’ll talk a little bit about what I think is happening.

Slow is smooth, smooth is fast

If you recognize this mantra, you may know it comes from marksmanship training. The idea is that it is better to move slowly and not have any hitches or unexpected bumps, rather than to hurry and have a less predictable outcome.

Another way to phrase this is

You don’t have time to do it right, but you have time to do it twice?

There are lots of obvious applications for this philosophy in technology, but I’ve been dealing with it in a much more tactile realm – handwriting. I’m one of the cusp generation that got taught cursive and typing in school. I obviously type much more quickly than I handwrite – most people do, or we wouldn’t have invented typewriters. My kids got some very minimal cursive education, but mostly so they could read it, not write it. No one is grading their penmanship and most of their assignments are turned in on Google Docs. When I was learning cursive, my teacher told me, and I believed, that it was because it was faster than printing.

In the last month or so, I fell down a hobby rabbithole and took up fountain pens. The DevOpsDays Vancouver people gave out a lovely writing set as a speaker gift – proper fountain pen, ink, high-quality notebook. I found out that what the nerds on the internet have been saying is true – writing with a fountain pen is a significantly different experience than a ballpoint or even a rollerball. Fountain pens finally made the point of cursive writing make sense to me.

It turns out that some methods of communication are tuned to specific tools.

Who knew, right? So I spent all of my grade school cursive time frustrated because cursive didn’t feel any faster to me, and I would get lost in the middle of a letter or a word, and aaaaargh. Which has made it really funny to take up learning not just “how does a fountain pen even work”, but also “Spencerian Penmanship” (which, the purists would like to inform you, is not calligraphy). It turns out that 10 year old me had a few compounding problems:

  1. Not enough time/practice to gain mastery. I’m a notoriously slow learner of physical skills. It took me 3 years to learn to ride a bike. So learning time that was probably enough for my peers was not enough for me.
  2. Attention problems meant that I would literally lose focus in the middle of a word, or forget how to form letters, or try to move faster than my muscles were prepared to go.
  3. I did not find it intrinsically rewarding.

Now that I’m an adult, and I can afford not only the proper tools (relatively cheap), but tools that I find exciting and fun (less cheap), I feel more rewarded. I am not trying to turn in a homework assignment, I’m just learning a skill, so the time and accuracy penalties don’t apply. Unsurprisingly, I have better handwriting when I slow down. And as hobbies go, this one is really easy to pick up and put down, even more than knitting.

I also have learned years of skills in how to teach myself things, how to self-correct and do mindful improvement. Because I spent so many years as a solo writer, I had to learn to look at my own work, iterate, and improve. That basic skill now serves me for all sorts of things in my life. As a result, I now understand the value of drill and practice. Even if it’s not fun.

Handwriting practice sheet

The first thing to do is draw lines

I used to feel bad about my hobbies – sometimes I’ll get really into something, and get all the equipment to do it, and take Craftsy classes and and and… and then a few months later, I’ll drop it. I would punish myself when the next passion came around. “Remember embroidery? You have all the equipment and you only ever finished 2.5 projects. No, you don’t get to do the fun thing!”. I’ve been easing up on that attitude. I mean, I do try to start with a minimum viable kit for what I want to do, but if I enjoy it, I’ll dive in. Why not? I have an allowance for frivolities, I’m not hurting anyone, and it makes me happy to learn things.

Practicing one letter over and over to refine what I want and learn the motion

All hobbies are fractal, when you start examining them. I’m not sure the same is true of work, or maybe it’s just that deep expertise is less easy to share. So for the top-level hobby fountain pens, the fractal might look like this:

  • Handwriting
    • Penmanship
    • Calligraphy
    • Hand-lettering
  • Ink
    • Purchased
    • Hand-created
    • Mixing
  • Pens/Hardware
    • Prestige collection
    • Hacking/fixing
    • Restoration
    • Design

Each of those could be pursued further and further into tiny corners of specialized interest. That’s amazing. Seriously, thank you, internet. Hobbies are fandoms, and we can all find a place that suits us somewhere. I figured out that I love road cycling, but I hate bike maintenance. I can pay a shop to do that. There are other people who love tinkering, tuning, and upgrading their bikes. I like piecing quilts, but consider hand-quilting tedious. That’s ok, I can be a machine-quilter.

Once I thought of hobbies as fractal, I realized that we could not only drill down into sub-hobbies, we can back out to get a bigger picture of why we want to do hobbies, and it gives us an insight into why we want to do anything.

I like learning things. It gives me a feeling of satisfaction and control in my life. I feel about new ideas like a magpie feels about shiny beads. This basic tendency really accounts for most of my career – I used to joke that technical writing is a lifetime of writing research papers, but it’s not far off. It’s more like journalism, but the reporter is still going to walk away knowing more about the story than ever makes it into the paper.

My hobbies are a way for me to nourish that passion in a way that is good for me, as well as an employer. Sometimes I want a tactile thing to do when I got back to a hotel room in another city, completely worn out from people. Sometimes I need to remind myself that the difference between art and craft, work and hobby, is about how much you get paid, not how valuable it is. Even magpies can only pick up so many shiny beads before they really just want a break and some tinfoil.

What does that have to do with marksmanship? Everything. Because slow is smooth, and sometimes we need to move slowly to appreciate and learn what we need. Because smooth is fast – it pays to think through what we want to say and write before we commit it to ink. Because everything we do to learn a hobby is itself a way to learn the skill of teaching ourself.

Packing, optimizing, and satisficing

I’m off on a two-week trip that happens to be broken by an 18 hour stop at home. (Nodevember, North Bay Python, SpringOne Platform, LaunchDarkly writing sprint). Every couple months, I try to clean out my bags entirely, get rid of the trash that accumulates, make sure that I have room for all the new fidget spinners, that sort of thing. This time I thought I’d share what it is I take along.

In summary, if you are at a conference with me and need Imitrex, Immodium, condoms, period supplies, emergency protein, or stickers, I’m your gal.

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