There was a week During diligence when the process stopped feeling like a project and started feeling like a second job with worse benefits.
Same daytime company to run. Extra nighttime company to explain. Sleep became optional in theory and mandatory in biology, which is an awkward conflict.
What the week looked like
Mornings: operating realities, team questions, customers who still needed us to be present.
Midday: diligence packets, clarifications, finance reconciliations, counsel threads.
Evenings: rewriting answers so they were precise, then rewriting them again so they were precise and short.
Nights: the brain replaying a question you answered at 4pm and wondering if the wording created a new question.
That is the second job. It is cognitive load with a data room.
Bandwidth is a leadership problem
If founders absorb every diligence thread personally without redistribution, the company gets quieter in the wrong ways. People wait. Decisions slip. Morale gets weird because everyone can feel the tension without a name for it.
We had to staff the second job explicitly: who owns which folders, who drafts, who reviews, who protects customer-facing focus.
Diligence does not remove the need for management. It increases it.
Sleep is strategy
This sounds soft until you watch a tired answer create three follow-ups.
Start treating sleep like a deal asset. Not perfectly. Better than the macho alternative. A clear eight-hour brain writes shorter emails. Shorter emails close loops.
Team morale under glass
People imagine deal processes as glamorous. From inside, it can feel like being graded constantly while still expected to score goals.
What helped:
- honest updates without fake cheer
- visible progress checklists so the work felt finite
- protecting some normal rituals (standup jokes still allowed)
- celebrating small packet completions, not just big milestones
- naming stress as normal, not as personal failure
Humans can sprint if they can see the track.
What to would do earlier next time
1. Pre-build more of the data room in calm months 2. Appoint a diligence PM sooner 3. Set response windows instead of continuous partial attention 4. Schedule hard cutoffs most nights 5. Keep one trusted person who can say “that answer is spiral, sleep first”
Checklist for a diligence-heavy week
- Owners named for each major request cluster
- Daily 15-minute triage, not all-day ambient panic
- Team told what not to drop in core operations
- Personal sleep floor set
- One recovery block on the weekend protected if possible
The human truth
That week was hard. It was also temporary. Temporary hard things are survivable when you stop pretending they are normal forever.
We got through it because the team cared and the process eventually became a path, not a fog. Still remember the fog though. Memory is useful if it changes how you prep next time.
Closing
When diligence feels like a second job, treat it like one: staff it, scope it, and recover from it.
Do not try to be a hero who never sleeps and never drops a ball. Heroes write sloppy footnotes. Operators build a week they can finish.
After the week, debrief
When the intense week ends, write a short after-action note: what requests hurt, what artifacts were missing, what staffing worked.
That note is how the second job gets cheaper next time. Without it, you will reinvent the same suffering with better snacks.
Closing
Second-job weeks end. Prep and staffing decide whether they end cleanly or end in a pile of tired mistakes. Choose staffing.
Partners and family
Tell the people who live with you that the week will be weird. Not every detail. Just the shape. Surprise absence plus silent stress is harder on a household than a named sprint. Diligence is a team sport beyond the company org chart.
Food and water, seriously
Bottom line
Diligence weeks are not the time for caffeine-only nutrition. Treat basic body maintenance like deal hygiene. It is.
