Relationship Regret Audit
Find the close relationship becoming a future regret and invest now
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 94%
Vaynerchuk frames his most meaningful regrets around whether he spent enough time with people he loves. He reviews past deposits, such as years spent with his parents, but also looks for current relationships where the balance is worsening. His example is a lifelong best friend with whom one-to-one friendship time has recently become too scarce. The audit therefore moves from a close-relationship inventory to actual time, a specific brewing regret, and a concrete deposit before loss creates urgency. It does not require equal time for everyone or assume every relationship should be repaired. The output is one deliberate act of presence aligned with the relationship the person would most regret neglecting.
Origin
When Bartlett asks about family and personal trade-offs, Vaynerchuk says regret is grounded in whether he spent enough time with people he loves. He identifies reduced one-to-one time with his best friend Brandon as a brewing regret he wants to address.
Core principles
- 01The most consequential regrets may cluster around people you love
- 02Past time together can reduce regret but does not eliminate current drift
- 03A brewing regret is a prompt for action before a loss
- 04Intent matters less than actual time and attention
How to run it
- 1
Name the inner circle
List the people whose relationship genuinely matters, without using status or obligation as the test.
Pro tip Include old friends as well as immediate family.
Watch out Do not include people whose presence is unsafe merely because the relationship is socially expected.
- 2
Audit actual deposits
Review recent one-to-one time, attention, contact, and important shared moments rather than relying on affection alone.
Pro tip Compare the last few months with the pattern you believe exists.
- 3
Find the brewing regret
Identify the relationship where continued drift would be most painful if circumstances suddenly changed.
Pro tip Complete the sentence: I would regret that we stopped doing this together.
- 4
Define the missing interaction
Specify whether the relationship needs conversation, one-to-one time, a visit, appreciation, or repaired contact.
Pro tip Prefer a concrete interaction over the vague goal of being closer.
Watch out Respect consent and the other person's desired level of contact.
- 5
Make the deposit
Schedule and complete a realistic act of time or attention before work fills the space again.
Pro tip Protect recurring time when the relationship needs a pattern rather than one gesture.
In the wild
Vaynerchuk describes meeting Brandon Warnicky on his first day of high school, building the family wine business with him, and remaining best friends. Approaching 50, he notices that they have not had enough one-to-one friend time and says he wants to work on it.
→ A vague concern becomes a named relationship and a specific missing form of time together.
Common mistakes
Counting affection instead of time
Caring about someone does not by itself correct a pattern of scarce attention or contact.
Waiting for a crisis
The value of a brewing regret is that it can prompt action before death, illness, or permanent distance removes the option.
Is it for you?
Best for
It is best for people whose work or public commitments are crowding out valued family and friendships.
Not ideal for
It is not ideal where contact is unsafe, unwanted, or would violate another person's boundaries.
From the transcript
“real regret is only grounded in a very small circle of the people you love”
“I've got a brewing regret”
“did I spend enough time with the people I love”
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