How Pramod Raheja Manages 2 Careers (Pilot, Entrepreneur)

by | Sep 14, 2020

Meet Pramod Raheja. He is a remarkable multi-careerist based in the Washington DC area. He is a captain at a large national airline. He is also a tech entrepreneur who is building a company that enables aerial robotics at scale. He connects the dots between his careers and achieves balance so that he’s more fulfilled. I met him over LinkedIn, and I’m excited for you to learn more about his journey.

Pramod’s careers:

  • Captain at major airline (for 26 years)
  • Tech CEO/Entrepreneur (for 24 years)

On his motivations for having multiple careers

“When I first flew an airplane, I was hooked. When I started my first side hustle many years ago, I was hooked! I wanted to do both, I figured out how to balance the two and make it work, and the side hustles became full-time and full-fledged businesses. I love the diversity and mix of skillsets and mindset that intersect with each other.”

Advice on having many careers

“It can be challenging to excel at multiple things, figuring out the ‘balancing act’ is not necessarily easy and you’ll have to experiment with ‘what works for you’…what works for someone else may not work for you so focus on your own personal style, practice self-care so that you can optimize your mindset and energy levels and focus on what you’re working at that time.”

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Overcoming obstacles

“When I was first going through flight school. There was a time when I thought I wasn’t good enough to be a professional pilot. I had struggled that week going through the early stages on my instrument rating, which is a big jump up from the private pilot license that most hobbyists receive. I spent an entire weekend focused on the areas I was having trouble in. On Monday morning, I had turned everything around.

In the business world, when trying to get a lease in a class A building, no landlord would give me a chance because I didn’t have much history to go off of so it took a year for me to open my business….that was tough because I wanted to start ‘yesterday’ but I had to have the patience to overcome the obstacles that were laid out in front of me.”

On how multiple careers are mutually beneficial

“Because of my entrepreneurial career, I have contacts all over the world. When I travel as a pilot, I am able to set up meetings to advance my business objectives.

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From a mindset perspective, many skills translate over. For example as pilots, we do much more than just fly the airplane, actually steering the aircraft is only a very small part of what a pilot really does. There is so much that needs to come together before the flight even departs. We build a new team every time we fly because we fly with different people. So setting up the tone so that it is conducive to good teamwork is essential, which means leadership.”

On managing personal time

“I have to make sure that I calendar everything….but the point is that I have to manage my calendar very tightly in order to be as effective as I can at everything I do. I have a virtual executive assistant that handles my calendar, she has access to all of my calendars including my flying schedule.  Discipline is the key!”

What he wishes to have learned earlier

“I wish I had embraced it. I thought I was weird, I mean who would take on so much on themselves. Why? But eventually I figured out that I was able to have a much larger positive impact on the world, combine my two loves (flying and entrepreneurship) into a lifestyle that worked for me and is very rewarding.”

Overcoming the stigma of having a portfolio career

“I believe that the stigma is around not being able to properly focus. I usually never lead with telling new people that I meet that I’m a pilot. Eventually they learn that fact and are impressed….but even more impressed than when they thought I was just an entrepereneur/CEO.”

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A Day in the Life

On a day I’m not flying:

  • 6 am – wake up & do morning routine
  • 6:30 am – breakfast, begin working (I like focused work and no meetings in the morning)
  • 10 am – 5 pm – off/on meetings
  • 5 pm -6 pm workout
  • 6 pm – dinner
  • 8 pm – work
  • 10:30 pm – bed

On a day I am flying:

  • 5 am – wake up
  • 8 am (ET) – flight from IAD-SFO (or connect)
  • 11 am (PT) – arrive SFO
  • Noon short nap/lunch
  • 1 pm – 4 pm – work/calls
  • 4 pm – 5 pm workout
  • 5:30 pm – 7 pm dinner
  • 7 pm – 8:30 pm – work/wind down/bedtime

Where to find Pramod


Kabir Sehgal is a Multi Grammy & Latin Grammy Award winner, as well as New York Times bestselling author of fifteen books. His latest work is Close the Loop: The Life of an American Dream CEO and His Five Lessons for Success (Hachette, 2020) with his father Raghbir Sehgal which is a Los Angeles Times & San Francisco Chronicle bestseller. Follow him on LinkedInInstagramFacebookTwitterSpotifyYouTube.