In conversation, assumptions occur.

Where do you like to swim? (Assumed they swim)

When are you going to have kids? (Assumed they want and can have kids)

Have you tried A or B? (Assumed they want your advice)

And every once in a while, when we unintentionally offend someone, and the conversation feels stunted.

What happens next?

One thing we could do is to ignore and talk forward. Another is to try and name it.

“Hey. I noticed something is off here. I want to check. Is there anything that I said or assumed that may have unintentionally upset you?”

I saved so much money, buying, instead of renting a car.

So far, I’ve bought 4 cars, Honda Accord (US$1,300), Ford Econoline (US$1,500), Honda Civic (£900) and Toyota Siena (S$3,000). Renting a car would cost US$1,500 a month.

Mostly, I re-sold the cars for the same price or a profit.

That said, it takes about 2 full days, to research and buy the car. If travel is longer than a month, I always choose to buy.

Here’s how.

1. Go to listing sites, Craigslist (US) or GumTree (UK).
2. Search for Honda and Toyota. Japanese cars can easily run up to 300K+ miles and parts are also easily available.
3. Rank by price, use filters for listing under $5,000.
4. Open up all listening in new tabs.
5. Look out for listing prices, mileage and appearance. Ignore cars that are not working. Get a sense of the market price and what is a good deal.
6. Narrow down to 20 listings. Message or call them. “Hi, I’m interested in your car. Is it still available? Negotiable? I’d love to check it out”.
7. Once they respond, ask “What’s your best price?” Then reply, “I’m looking at different cars. I’ll get back. I’m waiting for other’s response.”
8. Look for a reputable car mechanic on Google Maps. Call ahead to arrange for a full-service check ($50 – $100). Smaller shops can usually check it, on the same day.
9. Narrow it down to 3 cars and arrange to meet. “Can we meet at ADDRESS, the mechanic will do a car check. Is that okay?” If anything smells fishy, walk away.
10. After the check, if anything needs repair, let the seller know and negotiate for a better price.
11. If you feel good, complete the relevant paperwork. For the US, it’s the Bill of Sales.
12. Make sure the photo ID name matches the car ownership document. Take a photo of their ID, face and car ownership papers (Car Titles).
13. Get the cheapest online insurance. Because the car is cheap, it’s faster to pay for your own fixes/repairs, than dealing with insurance claims.
14. Pay up. Drive off now!
15. Change the car ownership to your name at the local vehicle licensing office. If you don’t have a friend in town, use a mail forwarding service.
16. Once you get the new license plate, put it up. You’re all set.

AAA membership ($70) for extra security when the car breaks down on the road.

To adventures and beyond.

Generally a good rule, except when it’s not.

You like vanilla, and she likes chocolate.

You might benefit from 10,000 steps, he might enjoy swimming.

They might want guns, and you don’t believe in it.

You might need advice, he might need a listening ear. Someone to be with the pain.

When in doubt, share your kind intention, and ask if the person wants it.

Assuming, then imposing, might be a good rule.

But generally a bad idea.

Many broken, and great friendships later, I’ve gathered some observations, insights and advice. And I hope you find something useful.

1. Love yourself. The unloveable parts of yourself. The parts that get you in trouble. The part that eat the leftovers that were not yours. The more you can accept those parts of yourself, the more you accept those of others.
2. Learn to be by yourself, with yourself. When you enjoy yourself, you would bring joy with you. And your presence becomes a gift.
3. Share your difficult times, your journey of overcome. Be a fellow traveler, not a critic.
4. Be curious. Find out what is hard for others and why. Ask for permission. Most people don’t need advice, they need company. Facing difficult things is difficult. As Thich Nhat Hanh would say to his friends, “Dear one, I know you are suffering. That is why I am here for you.”
5. Okay, I take that back. Maybe they need advice, but ask first “Would it be helpful if I brainstorm and share some ideas with you, not sure if that would work for you?”
6. Be interesting. Do projects that contribute. Learn things that light you up. List them down and share them.
7. Be honest and hold strong morals. How you do after your mistakes is more important than what it is. Don’t be the person that others need to watch their back around you.
8. Fall in love with people. With humans. In their potential, their goals and their journey. Fall in love, not for the things you can get, but the things you can give. People like people who like them.
9. Learn to listen for what isn’t said. For context, for emotions, for energy. Suicide hotlines or coaching schools are good places to learn.
10. In every interaction, your job is to find out what they care about, what’s getting in the way and how you can help. Connections, ideas, lived experience and presence, are gifts to offer.
11. Two good questions. “What topics are you curious about, in this season?”, “If you are writing an autobiography of yourself, what would you name the current chapter?”
12. Most people are unaware of what they are gifted at, it comes easily, and assume everyone is also good at it. When you spot it, tell them. And what you appreciate about them. Works only if it’s genuine.
13. Vanessa taught me to practice the answer when asked “What do you do?” It pays dividends. The goal is to intrigue, not to tell your life story. Or worse, sell them something they don’t want.
14. Remember their names, their kid’s names, their birthdays, things they care about. Write it down.
15. Budget time to follow up, within a week, preferably. Share links, share your network, share ideas for bettering. Follow-up shows sincerity.
16. After each interaction, ask yourself “How is my engagement level and energy level?” Check if they are your people. And don’t lie to yourself.
17. Double down on your people. Ask them out, go to them and give an easy out. “Love to grab coffee one of these days. But totally understand too, if you are busy. I can come to you.”
18. Gift good gifts. And they don’t need to be expensive. Snacks, toys, books, candles. Something useful, something delicious, something delightful. Lea has a great book coming.
19. Don’t take away the opportunity for someone to help you. Ask for help. “Hey Janice, I got a favor to ask. I’m going through a weird time. If you got time, love your presence with me.” “Hey JR, do you have 30mins? I love to get your analysis on some houses that I’m considering. But no worries if you’re busy. I’ve asked a few people.”
20. Donate to their cause. Buy what they make. Recommend their business to others. Cheer for them, whenever you can.
21. If you see a friend walking into a trap, however uncomfortable, share your observation. Take the risk. If it doesn’t work out, you’ll learn who they are.
22. Don’t assume, ask. When a friend is going through something ask, “How are you feeling about it?” It creates an opportunity to connect and find out what they really need.
23. Lastly, lean into each moment, and every encounter expecting magic or miracles to happen. (Thank you, Adam)

To my friends who treated me with grace, thank you.

Here’s the prequel to this post…

1password transforms the pain of remembering, typing and sharing passwords into a delight.

Arc (free) is a different internet browser experience. Spaces, Split Windows and Command bar are a few things that would sadden me if it’s gone.

Bartender (US$16) organises my menu bar into something useful and beautiful.

As platforms grow, so are places to connect. Beeper (free) consolidates them into one app. WhatsApp, Slack, Facebook, Telegram, Instagram and Linkeldn. Scheduling messages too, it’s about time.

Fantastical is my Calendar app, it has not failed me.

Cardhop (made by Fantastical folks), gives me access to my contacts with a few keystrokes. I save baby names, dog names and cities of the people I love.

CleanShot (US$29) saves full website and text messages, as I scroll.

Dropbox (US$17/m) protects my files and photos. Pricier than iCloud or Google Drive, the security, support and delight is worth every penny.

Dropbox Capture to record and share design feedback and report bugs.

I save inspiring videos with Downie (US$19). There’s something about owning and organising that helps me remember.

DaisyDisk (US$10) finds out what’s taking up my disk space. Works on Dropbox and Google Drive too.

A new way to edit podcast interviews using words, Descript (US$12/m). At least 2x faster, your mileage may vary.

Fathom (free) record and transcribe Zoom conversations. For certain meetings, it frees my attention from note-taking.

Flux (free) changes the screen colour to help with sleep.

A nifty app, Maccy (US$10) keeping my copy history. Saves me from switching back and forth when copying text.

Magnet (US10) organise my application window, with shortcuts. Full, left, right, up, down.

Notion, has replaced Apple Notes, Gdocs, Gsheets, Asana and Evernote. It took 2 years to fully move everything over, I have never looked back. Marie Poulin has a great course.

Rewind (free) record everything on my Mac screen. Peace of mind is worth the extra disk space.

Things (US$50) is my to-do list. I dump ideas, tasks, and articles and free up my mental space for more to come. GTD method.

Apple Photos (free), together with the iPhone and iCloud, feels like magic. Finding old photos of friends 10 years ago, is a real treat.

As my work has become online, I have come to appreciate software. Tools that are made with attention and care.

Updated on Apr 3rd, 2023.