Embrace Unreasonableness: Calculated Risks Unlock Fulfilling Careers

Key Quotes

"I've been very lucky in my life to be surrounded by people that are really ambitious and part of that is you know when I was younger I had some friends who were you know 10 years older than me that owned businesses and and they were kind of further down the path than I ever thought I would get and they would just kind of talk about how they did stuff because they didn't know they weren't supposed to."

Jason Lengstorf explains that his ambition was influenced by older business owners who acted without knowing conventional limitations. This suggests that a lack of awareness of "how things are supposed to be done" can be a catalyst for pursuing ambitious goals. Lengstorf implies that this perspective, combined with curiosity, drove him to explore possibilities regardless of perceived feasibility.

"My entire career my entire life has sort of been a series of that like okay well what do I stand to lose if I try this probably not a lot let's see what happens and and it just sort of led to this this uh continuous chain of weird stuff that if you'd look at any of it in isolation sounds completely unreasonable but ultimately it's led to me I'd I honestly could not think of a of something I'd rather be doing than what I'm doing right now."

Lengstorf describes his career as a series of calculated risks, where he assesses minimal potential loss before attempting new ventures. He notes that these actions might appear unreasonable individually but have cumulatively led him to a fulfilling career. This highlights Lengstorf's philosophy of prioritizing exploration and personal satisfaction over conventional expectations.

"The value of college is the network not the skill set... because if you go to MIT you don't really learn anything that you can't learn for free on the internet but what you get is access to a whole bunch of MIT alumni and so it's much easier to get a foot in the door to get an interview to you know because people want to work with people that are like them."

Lengstorf presents a "hottest take" on the value of college, asserting that the primary benefit is the network it provides, rather than the skills acquired. He argues that most skills can be learned independently, but a prestigious alumni network offers significant advantages in career advancement. Lengstorf suggests that connections and shared affiliations are key to gaining opportunities in the professional world.

"The ingestion of information is not learning or thinking it's the synthesis right like taking that information and doing some active work to take those thoughts combine them with your own thoughts and experience and then turn that into action steps or a new spin on an idea or a change to your perspective."

Lengstorf distinguishes between passively consuming information and actively learning. He defines true learning as the synthesis of new information with existing knowledge and experiences to generate actionable steps, novel ideas, or shifts in perspective. Lengstorf emphasizes that this active consolidation process is crucial for meaningful understanding and application.

"I think it's really just a matter of figuring out where your attention should be and not closing yourself off to other information but being willing to passively observe information that's not relevant to you right now with the strict goal of just being surface level aware of it until it's relevant to what you're trying to do so that you don't burn cycles on stuff that you can't act on."

Lengstorf advocates for a strategic approach to information consumption, suggesting a balance between focused attention and passive observation. He advises being aware of emerging trends without immediately acting on them, reserving action until the information becomes directly relevant to current goals. This method, Lengstorf explains, prevents wasted effort on fleeting or inapplicable technologies.

"My philosophy has has ultimately become this this form of i've heard it called sunny nihilism where i i believe that the only true meaning in life is internally assigned and so for me time spent on a thing that is interesting and challenging is not wasted time even if it doesn't work."

Lengstorf describes his personal philosophy as "sunny nihilism," where he believes meaning is self-created. He asserts that time invested in interesting and challenging pursuits is never wasted, regardless of the outcome. This perspective, Lengstorf explains, allows him to pursue ambitious projects without the fear of failure, framing them instead as opportunities for learning and regret elimination.