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Mastermind Playbook

Structured peer groups that keep you honest, inspired, and moving.

Mastermind Playbook

What is a mastermind?

Small group (3–8) that meets consistently to share goals, troubleshoot challenges, trade feedback, and hold each other accountable. Not therapy, not networking—peer-driven growth.

Ideal members

  • Similar life/career stages (transitioning vets, early PMs, founders)
  • Consistent attendance
  • Open sharing—wins + losses
  • Action-oriented, low ego
  • Give as much as they take

Tip: diversity of background is great; shared ambition is essential.

Common formats

Format

Description

Weekly check-in

30–60 min to review goals + blockers

Hot seat

One person presents a challenge per session

Monthly deep dive

Longer strategic sessions

Virtual-only

All Zoom; flexible for remote members

Hybrid

Mix of virtual + in-person meetups/retreats

Without vs with a mastermind

Without

With

Drift, isolation

Clarity, accountability

Guessing at next moves

Strategy shaped by peers

No accountability post-transition

Weekly gut-checks

Transactional networking

Real relationships

How to start or join

Start: invite 2–4 trusted people, set cadence, agree on norms, structure (updates → challenges → feedback), track goals in Notion/Google Doc.

Join: tap MBA cohorts, veteran networks, curated programs (Honor Foundation, Veterati), or DM Sitreps for upcoming groups.

Bring vs leave behind

Bring

Leave

Clear 3–6 month goals

Vague “I just want to improve” energy

One big challenge

Small talk updates

Honest progress

BS or bragging

Willingness to ask for help

Ego/lone-wolf mode

What you gain

  • Tactical input on job searches/interviews/ventures
  • Honest feedback outside boss/spouse bubble
  • Warm introductions through trusted peers
  • Emotional support during pivots
  • Confidence via shared momentum

Want in on a vet/MBA mastermind?

Sitreps curates groups by stage (transition, MBA, builder). Drop us a note to join or build your own.

Join a mastermind

Discussion

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