From: Grant
To: Ax Ali
CC: Those who dare to dream
The Danger of deciding what you’re not good at
Hello Ax,
Quick vent:
To me, there’s nothing more annoying than the overconfident, internally-inconsistent founder.
“If you want it done right, do it yourself.” Ugh. One sentence later: “My job is to empower my team and make myself unnecessary.” Okay. “Pay for bookkeeping/accounting? Don’t be an idiot. Waste of money. I do that myself with AI.” Next sentence: “Yeah I pay Cooley $100K/day. The peace of mind on legal is really worth it.” “Engineers actually slow you down.” “There’s no replacement for a 10x engineer.” “Design is commoditized.” “Design is what we are selling.” You get it. Talk to a founder long enough, and one of these will come up.
If I take a step back and try to be more empathetic, I realize that this is kind of endemic of a bigger thing in today’s tech world: we are all increasingly struggling with questions of relative advantage.
Relative advantage is as simple as: if someone else can do something better than you, they should do it, not you. Of course, there’s time and money factored in and all kinds of other stuff too. The underlying question is, “am I good at this?” Design: am I good at this? GTM: is this my superpower? CX: is this my “zone of genius?”
In the dot-com era, I could see how you could know these things. Maybe you scored particularly well in some subjects and poorly in others–and these subjects kind of mirrored professions. Maybe someone told you you were really good at something. Over time, you make small decisions about your strengths, which end up guiding what you do at work, which guides your career path. Industries changed slower back then, and you could spend your career profitably building on a few self-perceived strength areas.
Critically, you also make decisions on what you are not good at. This guides what you outsource. This limiting felt rational–how could it be efficient to be proficient at everything? But the times have changed, Ax.
Hot take: we can no longer reliably infer what we are bad at or good at. Legal is not like English class. Sales is not golf-schmoozing, nor is it banging on a CRM. The nature of our work has changed so much (yes, with AI), that our self-ascribed identities are no longer predictive. The underlying tasks here are now totally, totally different. Your mental framework for what they are is built on what they used to be. And the belief that they are your relative disadvantage makes them further away from you than ever before. Now you really won’t know what you’re talking about.
So what? So, deciding what you are good at is still fine. Deciding what you are not good at is very dangerous. That small decision drives knowledge areas you willfully avoid. In today’s scary job landscape, that area you fully outsourced, your “relative disadvantage”, could actually be the thing that makes your career a bit safer (downside) or wildly successful (upside).
Concretely, this does not mean that you must be the person who thinks it’s better to do everything yourself.
It does mean that you must try everything before you decide on it–and you can’t try it just once. You need to retry every few quarters–because the underlying tasks are changing so quickly. Because you used Cooley at your last startup does not mean you should use them again (or vice versa! (nothing against Big Law here)).
Example:
I have a strong and cohesive product vision, but…
2023: “I suck at product design” - yes, I sucked at design. I had no fluency in any design software, my ideas were cohesive but unoriginal. I avoided it and let the experts do their thing.
2025: “I suck at design” - yes. AI design tools suck. It’s easier and better for a human to do it, and that human needs to tightly integrate with engineering.
2026: “I suck at design” - no. Now my cohesive product vision is the biggest strength–and the bare execution is provided by AI. Now I can massively accelerate my team’s pace by stepping in and contributing here.
I’m glad I explored this area and allowed myself to develop some skills and domain knowledge. Beyond the business benefits, it ignited a lot of newfound passion for my work.
By contrast–even with AI, I do suck at legal.
One more risk: sometimes we think we are being rational in deciding on our relative advantage, but we’re just as often being avoidant.
Example: I tell myself that among the household chores, cleaning the fridge is something I’m just not as good at as my wife. Da truth: I just hate cleaning the fridge because old food grosses me out. And I think unconscious avoidance is the greatest plague of the founder. But that’s a topic for another day.
What do you think, my friend?
