Proximity Beats Planning
Replace abstract planning with direct exposure to the work you want
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 6
- Confidence
- 99%
Proximity Beats Planning addresses the tendency to manage uncertainty by constructing increasingly detailed plans from afar. Such plans can feel reassuring while remaining based on assumptions about an unfamiliar reality. The alternative is to move physically, socially, or operationally closer to the desired field before making the largest commitment. Practitioners conduct informational interviews, shadow experts, join relevant communities, undertake side projects, or apprentice under experienced operators. Proximity creates three outputs: evidence about whether the work is genuinely desirable, practical knowledge about how to enter and perform it, and access to people who attract opportunities in that domain. Planning still has a role, but it follows contact with reality rather than substituting for it. The result is a better-informed decision with less imagined uncertainty.
Origin
Extracted from Masters in Business through Cassidy's explanation of moving toward entrepreneurial environments and advising aspiring technologists to shadow, interview, and work alongside practitioners.
Core principles
- 01Direct exposure produces better information than distant speculation.
- 02Proximity tests whether an imagined career matches reality.
- 03Practitioners reveal paths that abstract plans cannot.
- 04Opportunity concentrates around active environments and capable people.
How to run it
- 1
Identify the Rough Direction
Name the field, role, or environment that currently interests you. You do not need a precise endpoint before beginning.
Pro tip Frame the target broadly enough to permit discovery.
Watch out Do not pretend that an attractive job title describes the daily work.
- 2
Locate Real Practitioners
Find people and organizations already operating in the target environment. Use your network, professional communities, or direct outreach.
Pro tip Seek practitioners at several experience levels for a less distorted view.
Watch out Avoid relying exclusively on high-profile success stories.
- 3
Create Direct Exposure
Arrange informational interviews, shadowing, volunteering, a side hustle, or a small project. Get close enough to observe actual constraints and routines.
Pro tip Choose an activity that lets you contribute rather than merely watch.
Watch out Consuming content about a field is not the same as operating within it.
- 4
Test Desire and Fit
Compare the experienced reality with what you imagined. Assess whether you want the process, not merely the status or outcome.
Pro tip Notice which activities create energy and which consistently drain it.
Watch out Do not dismiss one poor environment as proof that the entire field is unsuitable.
- 5
Learn the Entry Path
Study how effective practitioners developed their skills, credibility, and relationships. Convert those observations into the next concrete move.
Pro tip Ask what small experience would make you useful immediately.
Watch out Do not copy another person's path without adapting it to your constraints.
- 6
Escalate Commitment Gradually
Increase your investment only after proximity produces supporting evidence. Move from conversation to project, then from project to a larger career choice if warranted.
Pro tip Set an explicit review point after each level of commitment.
Watch out Proximity should inform action, not become endless sampling.
In the wild
Cassidy describes a financial analyst who thinks they want to become a chef. Instead of immediately entering culinary school, the analyst can spend time around chefs and restaurants, observe the work, and learn from people already doing it.
→ The analyst tests genuine interest and learns the route into the profession before making a major commitment.
A graduate interested in entrepreneurship can conduct informational interviews, shadow an operator, and moonlight on a small venture while retaining a day job.
→ The graduate gains practical evidence and contacts before taking a larger entrepreneurial risk.
Common mistakes
Planning From an Imagined Reality
Adding detail to an assumption-based plan creates emotional comfort without producing better evidence.
Making the Mighty Leap First
Committing to expensive training or quitting immediately can expose you to avoidable downside before testing fit.
Observing Without Participating
Passive proximity offers less insight than doing a small piece of the actual work.
Is it for you?
Best for
It is best for people considering a field they understand only from a distance.
Not ideal for
It is not ideal when access would create unacceptable legal, safety, confidentiality, or financial risks.
From the transcript
“you learn a lot more by being proximate than planning from afar”
“getting close helps you identify the thing you think you want is what you really want.”
“Just get close and start with something small.”
From the episode
Sukhinder Singh Cassidy on Entrepreneurship (Podcast)
Sukhinder Singh Cassidy