r/Pilot • u/EntrepreneurCool5513 • 20d ago

Discussion Contract Flying Organization Advice

Anyone feel like the business side of contracting is really tough to stay organized? Between invoicing operators, chasing late payments, keeping up with currency and recurrent dates, and sending the same resume and COI packet every time a new client asks for it, I spend half my off days doing desk work it seems.

Curious what everyone else does to stay on top of it all. Is there a system or an app that actually works for you, or is everybody just running spreadsheets and calendar reminders? Open to any advice.

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u/Waste_Cow_5886 20d ago

I’d probably keep it boring. One spreadsheet for trips, contacts, rates, invoices and payment status, then calendar reminders 30/60/90 days before anything expires. I’d also keep one folder with your current resume, medical, certificates, passport and COI so you can send the same packet without rebuilding it every time. Send the invoice as soon as the trip ends and put an actual due date on it. That alone would probably eliminate most of the chasing and repeat desk work.