I've heard an interesting theory lately: as AI handles more of our routine work, good decision-making becomes one of the few skills that still matters. For me this idea feels similar to another trend I read a lot about, the impact of being "high agency" - the ability to make decisions with the information you have, and to take ownership for those decisions.
With personal and creative projects, I’m not always great at this. I get stuck in over-thinking and second-guessing. I can think about executing on an idea for five times as long as it would take to actually just try the thing.
This week, I've been reading about mental models and realised I'm often asking myself the wrong questions. Here are my favourites for getting unstuck and making better decisions.
"Am I climbing the right hill?"
When to use: When you're making progress but something still feels off
In programming there’s the hill-climbing algorithm: Start with an arbitrary solution to a problem, make a change, keep what's better, discard what's worse.
Works great when you know what the top looks like. But the limitation is its myopia: it moves only to immediately better neighbours and stops at the first peak it can’t beat locally.
Mentally, that translates into habits like staying in a comfortable job or routine because each tweak still feels like progress, even if a radically different path would be much better. Sometimes you need a bold diagonal leap, or to zoom out and checkout the other hills. Think sabbaticals and career changes vs climbing the career ladder you’ve always known.
"How Easy Is Hitting Undo on This?"
When to use: Any major decision that feels permanent
Most decisions feel more permanent than they are. Taking a sabbatical feels like career suicide, but you can return to corporate. Starting a newsletter feels like a public commitment, but you can always stop. Even moving cities or changing careers can be more reversible than they seem.
Easy undo (reversible): Trying freelancing for 6 months, starting almost any side project, taking online courses
Hard undo (irreversible): Having kids, getting a face tattoo, burning professional bridges
The easier the undo, the faster you can make a decision.
"What would 80-year-old me regret not trying?"
When to use: When you're torn between safety and taking a risk
When you're 80, will you regret not starting that YouTube channel? Or trying to sell your art? Or going on that once-in-a-lifetime trip? Or spending more time with your family?
I’m not always a fan of “regret as a motivator” but there are times where we need a reminder that we tend to overestimate the pain of failure and underestimate the cost of regret.
"What would this look like if it were easy?"
When to use: When you're overcomplicating a decision or project
We love making things harder because difficulty feels more legitimate.
When I first started this newsletter I thought I had to write super original long form articles at-least once a week. I put off starting a podcast because if it wasn’t a video podcast filmed in a high quality studio and I hadn’t done hours of research on each guest then it wouldn’t be good enough.
What actually worked was giving myself a simple template for every newsletter post and letting the podcast be audio-only and focusing on enjoying the conversations.
Do it easy. Do it fun.
"When was the last time I updated the map?"
When to use: When your plan might not match reality
Your plans are just a model of reality, not reality itself.
I once worked on courier tracking software where we'd show delivery routes on maps. The bugs? Couriers kept "flying through buildings" that didn't exist and taking shortcuts not on our maps. They knew the real territory - alleys, pathways, and routes that our version of reality couldn't capture. We had to update our maps based on what couriers were really doing.
Want to be a career coach? Go talk to a few. Ask what they love/hate, how they got started, what their days look like. Want to write a book? Try writing for 5 minutes daily - see if you like actually doing it vs. just the idea of it.
Get real-life data. Update your map.
"What can I actually control?"
When to use: When you feel overwhelmed by the unknowns
This is the classic “locus of control”. I think this works best on paper. Grab a pen, write down all your worries, then sort them into three buckets:
Control: Things you can directly change (your work quality, how much you practice, what you ship)
Influence: Things you can affect but not control (networking, building relationships, feedback)
Concern: Things that affect you but you can't change (social media algorithm changes, market trends, others' opinions)
Focus 80% of your energy on Control, 20% on Influence, 0% on Concern.
In all cases, the goal isn't perfect decisions, it’s being comfortable moving forwards with the information you have and adjusting as you go.
I’ll leave you with this quote from Obama on decision-making: "It might be a 51-49 decision, or a 60-40 decision, but I can say I heard all the voices involved — gotten all the info, seen all the perspectives — so when I made decision, I was making it as well as anybody could make it."
On the pod
Last week I had a chat with Dr. Rod Berger about living a life worth telling stories about. Rod intentionally lives a "Forrest Gump-like" life - saying yes to opportunities that come his way even when he isn’t sure where it will lead.
It made me rethink how I approach opportunities and decision-making which is perfect timing alongside this week's theme.
Worth your time this week
How to Finally Do the Thing - I really loved this post by
, it completely describes the journey I’ve been on trying to do more of the creative work I’ve always wanted to do. If you read one thing this week, make it this!Mental Models: The Best Way to Make Intelligent Decisions by James Clear - goes much deeper than what I covered here with tons of practical examples.
The Map is not the Territory - This is great further reading on the ‘map vs territory’ concept.
More To That - Lawrence Yao's blog is a wonderful resources of articles all about life and the things that make us who we are.
How not to lose your job to AI — We’re already losing our jobs to AI, so what can we do about it? If you’re as concerned as me about this, you’ll like this article.