Dating, Lessons Learned, Ramblings

The Lean Dating Manifesto

I was cleaning out my cloud drive the other day when I ran into an article I wrote in Hawaii two years ago, so today I am going to complete my thoughts then and share something a bit different on this blog.

What if we treated relationships like a lean startup?

I’ve been involved in startups for most of my career. Now in a startup you don’t really have a lot of resources, so you have to make it count. There’s a pretty popular school of thought (made popular by the book The Lean Startup) where the idea is to fail fast and early so that you can iterate on your mistakes without wasting too much time, energy, or money. Then the idea hit me: We try so hard to make our businesses successful – why not also apply it to the way we approach dating?

Let’s face it, relationships are really hard. Perhaps you have good luck and have met your chosen one right from the get-go but not me. Every relationship that I was part of has been a humbling learning experience. In the beginning I knew I wanted someone to be with long-term and that was pretty much it. I was pretty adverse to the idea of asking people for advice because I wanted to invent my own way of doing things and prove to myself that it was a viable way thing to do it – maybe not so smart in retrospect but I think I’ve tripped over myself long enough to figure out what generally works for me and what doesn’t.


Who I think this is useful for

If you’re someone that is looking to find a compatible person to be with you for the long-term, I’m writing with you in mind. My metrics of success is to optimize for:

  1. Time and energy spent figuring if the person you’re dating is this person, this includes possibly dating multiple people.
  2. Minimizing the gap between what you think you want vs what you actually want.
  3. Developing a solid foundation for having difficult conversations.

Assumptions

Before I dive into the manifesto, I’d like to lay out some broad assumptions or observations I will be using as talking points:

Be wary of the “Honeymoon Phase”

I’ve had various relationships in the past, some with a long honeymoon phase and some with none at all. On occasion, I hear about people craving this component in their dating life, but I’m personally fine with out it.

Getting too deep into the honeymoon phase could get dangerous. I remember getting really blinded from someone I’ve dated because it started out like fairy tale movie. I didn’t really take the time to internalize and understand who she was and what was important to her. Even small conflicts felt impossible to resolve because my expectations were all over the place.

Trying to save a long-term relationship is a sunk-cost fallacy

I generally think indefintely waiting on your partner to change into something you’re happy with is a bad idea. Merely staying in a relationship you really no longer find joy in because you’ve been in it for so long is also a bad idea.

We usually only re-evaluate our expectations after breaking up

I think generally we stop accelerated rates of learning and personal growth after our mid-twenties. We mostly know what we will feel or behave given certain situations and become accepting and comfortable with who we are. Beyond that, major life events are the only times that we are forced to take a cold hard look at ourselves, it’s only then when we realize our own framework of how we expect the world to look like didn’t quite line up with reality. I’ve often felt “I should’ve done that back then” about my relationships only after I’ve broken up with someone when its really something I could have been working on proactively with the person I was dating.

Humans are generally too optimistic

People are generally optimistic when it comes to a relationship. We always want things to work out (and ideally with minimal effort), so we often fill in the rest of what is still unknown to us with a bit of something I’d like to call optimism. I kind of blame mainstream media for this, but I believe we think about the romantic “what ifs” way too often in the initial phases of dating.

Don’t try to help others that doesn’t want to be helped

This has been one of my greatest weakness: I keep trying to help people who don’t want my help. One of the best lessons I’ve learned (and am still learning) as an adult is when someone is complaining to me about something is to ask: “Do you want me to listen or are you looking for a solution?”. I find that most of the time they just want talk to someone who would listen.

Date enough to know your preferences

What ratio of romance or companionship do you look for in a relationship? Do you like outgoing people or introverts?

Honestly, he best way to figure out if you like something is to try it out. If you are planning to find a lifelong partner, your best bet is to date enough variety of people to figure out if he/she is right for you. Obviously nobody wants to end up being just a data point – but I find that biasing what I look for in my next relationship has helped me hone down what I really want.

There is no such thing as “the one”

There are billions of people in the world, I’d say its pretty close to impossible to find the best person for each of us. But luckily, I think we can come pretty close and the pool of those people is quite big. Being able to answer “how good is good enough?” to me is a huge accomplishment.

What that also means is that there is always someone out there that is “better” for you than the person you are dating and I think we have to be comfortable with that. I once talked to a taxi driver who was married with kids but had another woman in his life that he referred to as his soulmate. It was a novel situation to have heard that as a kid, but now I know things like this happens all the time.


The Lean Dating manifesto

Who doesn’t love mental frameworks? Here it goes!

1. Keep a running list of personal values and deal breakers

Take some time to figure out what kinds of minimums you would accept in a meaningful relationship. It’s more effective to do this when you’re not dating someone because our brains tends to make “exceptions” when we are high on love. There are obvious ones, but here 4 value categories that I use to evaluate if I want to be serious with somebody: Sex, Money, Kids, and Religion.

Keep in mind that this is meant to be a living document that should be revisited and updated constantly. Recognizing that something else is now more important over time is a sign of understanding yourself better.

Strong points in a partner can’t make up for other qualities that are severely lacking

Keep in mind that great attributes in someone can’t make up for other core values that you think are misaligned. I believe a partner in a strong relationship should always satisfy all the bars you’ve set for yourself, but I would also consider revising the standard if I’ve dated enough to know it is not realistic.

2. Do “relationship reviews” every 3 months

People often laugh when I tell them I do relationship reviews every quarter with my girlfriend and then they stop laughing when they realize I’m not kidding.

It’s hard for me to get into the brainspace of doing a deep retrospective on my relationship in the moment, why not plan for it so the “we need to talk” talk isn’t going to scare anyone shitless. My first one was in my room, but also have done it over a nice restuarant as we got more comfortable talking about the relatioship to each other. Honestly, the more we do it the better we get at it, and the more enjoyable the process becomes.

How to best prepare for it:

  • Make sure you are in a safe space (physically and mentally).
  • Be an active listener and in the mindset to take feedback. Seek to understand rather than to immediately defend your viewpoint. Remember it’s not so much ‘me’ vs ‘you’, but rather how do we make ‘us’ work. If it helps, take a few minutes to walk around if you start to feel emotional or tempermental.
  • Crying is okay.

Talking points:

  • How were the last 3 months for you?
  • What were the biggest challenges?
  • What were the biggest wins?
  • What were the things that we wanted to get better at last time we had a review? Did it happen? Why didn’t it happen (if it didn’t)?
  • Do you have any feedback for me? (It’s really important to ask for this about yourself rather than waiting for the other person to give it to you)
  • What are next steps for the things that we need to work on? How do we hold each other accountable or help each other achieve them?

3. Give immediate feedback – Address the concern while they are still relevant and work together to resolve the issue

I won’t lie, I ripped this one right out of my manager training from my job. It’s really hard to do well and the gains are not immediate, sometimes even invisible.

When people bottle up negative emotions towards the other for a long time bad things happen: 1. Future disagreements will not be small or focused enough to be resolvable. 2. People’s feelings and expectations towards each other will be increasingly misaligned. I think this is partly what has happened when people say they’ve “grown apart” over the years.

The important point to keep in mind is thinking about the relationship as an active investment where you would have to make effort and compromises for it to work out. One thing to keep in mind is that there is also a hard limit of how much one is willing to compromise or put effort into and that is okay. So long as they are recognized and talked about, thats really the best thing I can expect from two people trying to work it out.

4. Set a deadline for indefinite issues

“Let’s try it out and see how things go.” Sounds familiar? When there are some clear outstanding issues that needs to be resolved, setting deadlines for them is the best way to make sure you aren’t wasting your time. This can be indefinite long-distance relationships, waiting for values alignment in your relationship, and waiting for people to change their habits. (e.g. “Im going to quit smoking to be with you”). The deadline should trigger something actionable.

The main goal of this is to recognize that we are making a promise to our future selves and to remove the emotional feelings that often clouds our judgement in the present. Heck, write a letter to your future self if you have to – how can we expect to treat other people well if we can’t even threat ourselves with respect?

5. Life Goals Tracking

Believe it or not I have a spreadsheet with my partner to keep track of any short term goals that we have. Typically its better to be focused on 1 or 2 goals, but make sure they are actionable and measurable (“Getting better at x” is not a SMART goal).

The key to doing it together is to hold each other accountable. Much like how we care much more for our pets than ourselves, we are typically more objective about making sure the other person achieves their milestones. I also find rewards and punishments to be good motivators in helping each other reach their goal.


That’s it! I hope to be updating this manifesto as I go through more life events, but my hope is that this has sparked some thoughts in some way, even if you disagree with them.

If you have any questions or thoughts I’d love to hear them!

Q & A

This is a lot of process, you’re killing the magic in a relationship!

We are typically pretty good at the unstructured aspects of a relationship, letting things fall into place when it needs to happen. Having the kind of structure and cadence mentioned above is important because sometimes it is really hard to bring up these topics in our day-to-day lives.