Today I’m sharing my favorite way to make big life decisions.

From:

• Selling my house in the suburbs
• Moving my family abroad
• Choosing between jobs

There’s no “right way” to make these decisions. But I found this model simplifies the decision-making process and reduces anxiety.

No pro and con lists.

No sleepless nights.

By answering a simple question, you can remove complexity from similar life decisions.

The 1 question to help you make life decisions

I knew a tech executive who got a dream offer:

Head of growth at the fastest growing social-audio app. It was the “it” app. Fresh off a $4 billion valuation a year into the business.

And he turned it down.

Other executives told him he was crazy.

His response?

“I’m not optimizing for brand.”

In other words:

Others thought it was a no-brainer because of the “logo.”

What they didn’t understand: he didn’t care about logos.

He was playing a different game.

To make good decisions, you must know the game you are playing.

As Morgan Housel put it:

“Don’t be persuaded by the actions and behaviors of people playing different games than you are. The main thing I can recommend is going out of your way to identify what game you’re playing.”

Before you make big decisions, ask:

“What am I optimizing for?”

I’ll dig into 3 examples where I use this framework:

“What am I optimizing for… in life?”

In 2021, my wife and I bought our first home. Six months in, we realized we weren’t ready for suburban life.

We considered moving to Europe, a “bucket list” item we talked about for years.

There were a lot of unknowns:

• What about the house?
• What about school for the kids?
• Would we be able to work?

Research answered some, but not all our questions.

Then we asked: “Right now, what do we want to optimize for in life?”

We decided to optimize for adventure.

Optimizing for adventure comes with tradeoffs:

• We traded a reasonable mortgage payment for high rent
• 15% haircut in the currency conversion
• Double-taxation

These are not easy tradeoffs, especially if you were raised with an immigrant mindset.

What we realized: a low mortgage rate and reasonable taxes are important. But you don’t build your whole world around it.

At different points in your life, you’ll optimize for different things:

• Relationships
• Hobbies
• Career
• Health

This is normal. It’s healthy.

What you value evolves.

So check in with yourself. Stop and ask:

“What am I optimizing for in life?”

“What am I optimizing for… in my career?”

The question “What am I optimizing for?” can help you navigate your career.

Your goals and stage shape how this optimization.

If you’re:

• Starting out? You might optimize for brand.
• Trying to build a specific skill? Optimize for role.
• Mid-career and targeting a VP product role? Title.

Here are some levers you can optimize for:

• Stage. Joining a company based on its growth trajectory.
• Role/title. You’re pursuing a skill, a role, or a title.
• Brand. A brand-name logo on your LinkedIn can open doors.
• Culture. What does the company value? What do they stand for?
• Core competencies. What you’re good at.

What does it look like when you apply these levers?

A few years ago, I was on the market. I had a hypothesis for my next role:

• Impact. I wanted to impact a large number of users.
• Brand. I wanted some tech brand name recognition.
• Size. I wanted to work and learn from a team of PMs.
• Narrative. I wanted to consolidate my shift career narrative around technology.
• Stage. Late-stage but pre-liquidity event. I wanted medium confidence for that liquidity event but still early enough to capture some upside.

Then I evaluated 38 companies. I talked to a dozen close friends and mentors. I told them exactly what I was looking for.

In turn, they gave me laser-focused advice (and referrals).

For example, one mentor said flat out: “no public companies.” So I removed Disney, Netflix, and Facebook. I focused my search elsewhere.

In the end, I landed a growth PM role at Noom, which satisfied 90% of my criteria.

By asking “what you’re optimizing for”, you’ll target better-fit roles, and roles that best advance your career in the long run.

“What am I optimizing for… right now?”

The question “What am I optimizing for?” helps you prioritize on a weekly, daily, or even hourly basis.

This is a critical skill. Especially for parents.

(The best way to become superhuman at prioritization is to have a child.)

You begin to constantly evaluate:

What is the best use of my time, right now, at this second?

The answer constantly evolves.

What was unimportant 2 hours ago may now be critical. And vice versa.

What does this look like?

Every morning I create a schedule for my day.

This is the source of truth for how I’m spending my time, in 30-minute increments.

By the end of the day, it looks something like this:

Every few items, I pause and ask:

“What am I prioritizing for right now?”

Sometimes it’s working Saturday morning to hit a deadline.

During the workday, it might be 45 minutes to build some Lego with my son.

Will you ever “check off” everything on your schedule? No. And that’s not important.

What is important: you are intentional with how you invest your time.

Down to the hour.

Down to the minute.

Conclusion

One question, three variations to help you make big life decisions.

• “What am I optimizing for… in life?”
• “What am I optimizing for… in my career?”
• “What am I optimizing for… right now?”