Money is one of those touchy subjects that most people don’t like talking about, so most of the time we are walking in the dark keeping up with social norms.

In relationships, when people ask about money it’s usually about “who should pay” and there is no one way to go about it. I’ve seen many happy couples who split the bills, and others in which one gender foots most of the bills. There are all good and happy relationships. “Who pays” has nothing to do with a good relationship. The problem arises when there is a misalignment in expectation leading to resentment, and ultimately leading up to a fight.

This article is going to focus on “who pays” on the first dates. My advice there is for the guy to be ready and offer to pay. I’m sure you can split the bill or one gender can manipulate the other to foot the bill, but in the long term, it’s a stupid strategy. During the first date, the objective is to learn about the person in front of you so I treat paying as a test. The keyword here is “offer to pay”. At the end of the meal, I ask “can I pay for this?” and observe how the girl react.

After agreeing for me to pay, one date started telling me “horror stories” of her past dates who expected her to split the bill, pointing out that he was not a “gentlemen”. For me, I am not a big fan of self-entitled people, so I had to let her go. I have another friend who takes this to the next level, he goes on dates and said “order whatever you want… this one is on me”, which is also another way to observe someone.

I’ve also been in situations where my date has asked to split the bill. I usually ask her to pick up the next bill instead. This allows an opportunity to go for a second date. But even if you don’t want a second date, the way to save money is not to split the bill but to do a coffee date instead of fancy dinner. And if you find it hard to pay for 2 cups of coffee, that could be a sign that you are not ready to take care of someone. I suggest focusing on making money for yourself first.

There are also rare occasions where the girl really insists on getting the bill. This is an opportunity to find out more about her values. It is usually about power dynamics and not wanting to feel obligated for the next dates. In which case, let her foot the bill.

During the later stage of dating, one of the classic scenarios is that you really like the girl but she has an expectation for you to keep paying for things. This scenario is the start of resentment and contempt. To deal with it, the first step is to suspend judgement and use curiosity to ask why. Sometimes, the problem can easily be solved with a conversation. Other times, you might learn that her expectation was derived from her upbringing that she wants to be “taken care” of. And if this does not suit you, then my advice is to walk away. It’s really hard to change someone. Treat it as a lesson that “splitting the bill” is an important value to you. Next time, look for it early in the dating process before sunk cost starts.

All that said, this article is not about who should pay. There is no one kind of good relationship. It’s about alignment. So, if you like to pay, then pay. What’s kryptonite for you, might just be diamond to others.

Alright… enough ranting. Time to make some money for my upcoming dates.

Famous management consultant, Peter Drucker might be right about a lot of things but I disagree that “culture eats strategy for breakfast”.

To our definition, culture is not a mission statement on the wall. Culture is not a set of values that we memorize and regurgitate. Those are aspirations. It’s not about the things we say or the things we say we want to do, it’s the things we DO as a company, organisation or group. Culture is “people like us, DO things like this”.

As pointed out in What We Do is Who We Are, there are tactics to cement and move the culture. Shocking rules, company lore and even object lesson, to name a few. As an example, shocking rules are funny rules that make people question about the rules. And through that, remind people about the company values/aspiration.

When Amazon first started, they made their tables from cheap doors brought at Home Depot. By that, every time someone works out of those tables, it reminds them of frugality. This works with Amazon’s strategy, to be the place for people to find the lowest price.

On the other hand, Apple spent 5 billion dollars building its new campus. Who knows, they probably spent $5,000 just on the doorknob alone. Apple strategy is to build the most brilliant, beautiful and desirable products where people pay top dollar. Apple strategy would not work for Amazon. Yet, they are both industry leaders.

Culture, if you know-how, can be a strategy. They are not two things. They are parts of the same breakfast, elevating each other to build an enduring company.

If done well, it’s a generous act. An opportunity to connect, friendship waiting to blossom.

The modern world tricks us that, with enough resources, we can be self-sufficient. As we can see in the current pandemic, we realise no amount of money can buy us into the hospital that has lines out the door. Humanity is more inter-dependent than ever before. And money, the all mighty dollar, is not that mighty after all.

We desperately need each other. We want to be seen.

Invest some time and do your homework. Make a reasonable request, something easy and mutually beneficial. Above all, make it easy for the person to decline. Maybe not now, maybe later. Yes leads to yes which just maybe leads to the relationships you were seeking.

The world is filled with lonely people waiting to make the first move. When are you going to ask for help?

The interview process is flawed and it’s impossible to fix.

(1) It’s slow. Really slow. Job post, resume looking, first interview, technical interview, team interview, culture interview… and 3 months fly by.

(2) People lie. The candidate says what he thinks will get him hired and conveniently covers up the blemishes. He lies to himself about what he wants and lies to the interviewer to get the job.

When the hiring manager shift to sell mode, he glosses over the bad bits, exaggerating the good ones (“Everyone here is really creative, and there’s no office politics…”)

(3) The important qualities can’t be measured through a conversation. Courage, leadership, empathy, enthusiasm and the ability to learn, to name a few.

(4) People don’t know themselves. If you watch American idol, you would see many people who think they’re incredible singers who are terrible, the people who think they’re terrible singers and they’re incredible, and the people that think they’re great singers and they’re great. That last bucket is really small.

Now, this may not work for you and it certainly does not work for every job. Here’s the way I’ve been the happiest with it.

You can’t work for me until you’ve worked for me. I’ll hire freelancers. I’ll hire people to do project work. I’ll pay extra to hire several people for the same task. I will work with people and then I’ll offer them a job.

That means the vast majority of the workforce is not available to me. The vast majority of the workforce will not come to work with you for two months as a temporary project manager because they have a day job. That’s ok because in exchange they get to have the best job interview in the world— actually working on the job. That’s how you find out if they can do it.

Instead of telling others how they “should” be doing things (which sounds like guilt), what if they “could” do it because it’s a better way? Or because it’s worth it?

I used to think that people have to act in a certain way. I was caught unhappy, most times. So, I accepted people should act the way they want to act.

And if I want others to act in a different way, then it’s my responsibility to help them see. Maybe perhaps we could (not should) do it this way instead. What do you think?

Goodhart’s law states that when a measure becomes a target, it ceases to be a good measure.

When the Soviet Union factories were given targets for how many nails they needed to produce, they make small and useless nails.

When the hospitals in Britain were penalized for wait times longer than four hours. The hospitals asked their ambulances to take the long road to the hospital. Even though the roundabout path hurt patients.

When Uber took on an aggressive win-at-all-cost expansion strategy, HR covered up a sexual harassment case from a high performer. It blew up in their face and the CEO got fired.

There is nothing that focuses the mind like a single target. But when money is the end goal, we easily forget our health and family.

There is a solution. As pointed out by Andy Grove in High-Output Management, it’s important to have a target but it is equally important to track counter metrics for context.

For customer service, it could be the speed of tickets closed and counter that with customer satisfaction.

For engineering, it could the percentage of ticket closed and counter that with the importance/priority of the ticket.

For sales, it could sales revenue and counter that with the renewal revenue or returning customers.

Life is never about one thing or one purpose, at all cost. When it’s the case, it ceases to be a good measure. What’s your target and what’s your counter metrics?

Panic is a hobby. Hobby in the sense that it doesn’t produce a useful outcome. That is something we can choose to do or not do, based on how we tell ourselves a story. 

As I looked back, I identified some tools that have helped me along the way.

Worst-case planning – let me look into the worst future and imagine it. Once I’ve accepted (death), there are very little things that I need to be panicking about. 

Tim Ferriss’s fear setting exercise allows me to shine a light at the boogie-man. And the boogie-man is only scary because it exists in our heads. Turn on the lights, and it’s gone. 

I do the 5-minute journal every day. It is 4 simple questions that help me plan my day, be happier and get it done. 

I ditch the gym commute and practice The Happy Body every day, 20mins a day. It’s like yoga with weights at the comfort of my room. 

60% Revenue – is a planning exercise to see what you’ll do when your salary or revenue is cut by 60%. It might feel ominous to do it. But it prevents stupid decision when the hair is on fire. And in my experience, having a plan B in place is the best way to be prepared. 

Canned Sardines is a great source of protein and can last for a long time. If you can be happy with that, you’ll be a happy camper. 

Similarly, toilet paper is a luxury. The human has survived as a species without toilet paper for a long time, and I’m sure I can do without. This could be a real skill to live without, back to the basic. 

Organise a zoom lunch. If you’re the organiser, you’ll always have a seat at the table. Bring people together, to have lunch, to work, to play a game together. 

Learn how to get an online side-gig. It could be writing, research, coding, designing or video editing. Pick something you are interested in, start a profile and learn a skill that can make some side income online. 

This pandemic is not new to the human race. We’ve been through the Berlin Blockade, Cuban mission crisis, the Vietnam war, HIV, 9-11 and the 2008 real estate crash. There is no avoiding it. It’s coming. We’ve done this before and we’re going to do it again. Together.