Always Have a Plan B and C Teed Up


This post is by jasoncalacanis from The personal blog of Jason Calacanis.


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I spent 10 years living in Los Angeles, traveling up to the Bay Area every other week, sometimes weekly, to do angel investing.

During that time I learned that SFO is a complete disaster, with Karl the Fog creating all kinds of trouble. Also, I was frequently missing flights with insanely unpredictable traffic patterns in L.A. and the Bay.

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When I made a little cheddar, I started treating myself to the fully refundable Southwest Premier tickets, you know the ones, that let you board first and take the aisle seat in row two. The coveted seat that lets you put your bag under the seat in front of you which in turn lets you bolt past the row one customers who are fumbling for their overhead luggage.

So, I started having my EA book me three flights back 5PM, 6PM and 7PM to avoid the issue of delayed and canceled flights and traffic snafus.

I also started booking two flights out — one landing at San Jose, which is 3x farther from the city but has no delays — in addition to my SFO flight.

So, five flights booked for a two-flight need.

Paranoid? Overkill? Unethical?!

The results speak for themselves: zero missed meetings, no delays and no drama, with the only cost being an extra 30-45 minutes of an EA’s time (to book and refund 3 flights, 2x). If you look at the cost of an EA, say $40 all in, it’s $20-30 to have this kind of parallel planning.

What’s the cost of missing a meeting with a new hire, investor or customer!?

Answer: more than $20!

I bring this up because there is a bigger issue from this lesson, which is, not only should you always have a Plan B, you should have a Plan C as well and, if possible, have them teed up to switch to — in your startup and life.

Inspired by Fred’s post while he was stuck at LAX: “If The Train Is Delayed, Find Another Way Home”

What’s your favorite travel hack? Gray and black hat techniques are welcome but not condoned.