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  • Writer's pictureMark Olivito

Working Towards a 2am Friend…..In Business

Updated: Jul 1, 2022

In February of 2014 I wrote a post on the holy grail of relationships: The 2am Friend. Who would you call at 2am if you were in a real bind, stuck on the side of a road 100 miles away from home? Or some other bind where you cringe picking up the phone and only 1 or 2 people come to mind.

Bill Cosby tells the story in 6 minutes as only he can.

“Friend” is a loaded word these days, and with Facebook it has been marginalized in my opinion, but that’s another story for another day.

Friend generally applies to life OUTSIDE of work. Sometimes the lines of work and life outside of work merge and they become one. Many people have very strong philosophies to not socialize with work colleagues, keep lives separate. I personally believe that is very difficult to do, although I do see the logic.

Here’s the thing that’s worth noting with the 2am friend concept: Why would it NOT apply to your critical WORK relationships, become something worth striving towards?

Said differently, if work is a critical area of our lives, as it is for everyone, do you have a handful of genuine 2am friends? The key word is GENUINE.

Sometimes business gets messy when authority structures make relationships a bit more complicated.

A trusted colleague of mine painted a picture of the future with me a while back. She said “you and so and so can work to be 2am friends.” It’s a sentiment that brought a very big smile to my face, as the person is a critical component of our success. And truth be told, it left me a bit uneasy.


I have not managed the relationship where 2am friend status is possible. Productive relationship? Yes! 2am level? Not even close.

Sometimes it takes a simple conversation and a look in the mirror to step up your game.

Every business has a handful of people where IF a 2am relationship was achieved, results, satisfaction and fun would simply soar through the roof. I have been fortunate to have more than a handful in my career.

The reality is that people run through relationships like they are running to the next meeting: Cordial. Efficient. Respectful.

The 2am concept is different. A 2am friend would move heaven and earth to fight for you, even if you have conflict…..which always exists in business.

Like most leadership principles on Hustle or Bust……the first step towards the 2am Friend in business is a look in the mirror on what YOU control. Then take appropriate action to change your future, and the future of those around you.

What if all leaders identified who are those (very few people) they need 2am status with?

Then they look in the mirror and ask if they are doing their part to move in that direction?

Great relationships, like most things in life do not happen by accident.

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