My 5 year rule for sustainable relationships

If you won’t be in my life 5 years from now, you won’t be in my life now.

I may engage in transactional relationships, of course, but I don’t invest in them. I invest only in sustainable relationships and I would encourage you to as well.

I look at all relationships in my life through the lens of sustainability with the goal of investing the precioius amount of my time into only relationships that are healthy, beneficial and constructive. Anything else, I cancel


These are relationships that are viable, healthy, growing and will improve you just by being in them

  • Co-workers, team members, professionals in your network who are a positive influence, growing and improving. They will inspire you in your journey
  • Mentors who can help you. If you are lucky to have one, hold onto them
  • Family (in most cases). Nobody loves you like family. When you are down and many who you thought were your friends disappear, family will still be there. But sometimes no one can hurt you like family as well
  • New people I meet who demonstrate positive energy, good attitudes and other admirable traits. I always think the next person I meet will be the coolest person I’ve ever met in my life. With remarkable frequency, people don’t disappoint. Sometimes all you have to do is take your ear buds out and introduce yourself
  • Yourself. You must invest in yourself, so you can be there for your other sustainable relationships

Not sustainable

These are destructive relationships, that in the long run will waste your time, make you unhappy and prevent you from growing as a person.

  • Relationships that previously ended in failure whether professional or personal. I’m a big believer in that if a tree falls over, you will never get it to successfully grow again
  • Toxic relationships, of any sort, that negatively affect you. Work on investing in yourself, and you will be more willing and able to cast off these negative relationships in your life
  • People who aren’t willing to grow, learn or improve. These people will actively sabotage your attempts to improve
  • People who will take from you, whether it is your money, enthusiasm, optimization or faith in your fellow (wo)man. No matter how successful you are, if you have these people in your life, like parasites, they will rob you of the fruits of your success
  • People who have demonstrated the propensity to lie, steal, hate and perhaps a few others. Be fortunate that you recognized these traits, as often they are well hidden, but be decisive in how you respond
  • Broken people who can’t listen, learn or benefit from help. Until they can change, they can’t be helped and in trying to help them, you will be dragged down too

Some unsustainable relationships I cancelled

  • I had a great attorney who was also really kind of a friend. He moved to a new firm and immediately overbilled me. He became an ex-attorney
  • A friend who wouldn’t invest in his career and was just flatlining
  • A team member, and friend, who could not manage his personal demons related to anger and hate
  • A sales manager in my company who refused to commit to our business model and was actively undermining it
  • A principal in our company who wouldn’t adopt our values
  • A team member who disparaged my company
  • Various people who have lied to me over the years
  • Anyone who ever disrespected me by attacking me personally or challenging my ethics or character
  • Any company or organization, that I felt would limit my growth and potential
  • A private equity group who disparaged the country that I have built my businesses in
  • Family members who were not supportive or loving. Yes, I cancel family too as much as it pains me
  • People who cancelled me, unfairly, then tried to come back into my life
  • Any team member who quit without notice or otherwise left irresponsibly
  • Anyone who was overtly supportive of any public/political figure who espouses authoritarianism, racism, nationalism, xenophobia etc

People don’t change

People can grow and improve, but they can’t change their personality profile or core values. If the relationship you have with them is currently unsustainable, at a fundamental level, it won’t change. So stop kidding yourself, don’t wait and hit the cancel button

Why cancel?

The problem with unsustainable relationships is twofold.

One, they bring you down. Even if you yourself are trying to grow, these relationships will undermine your ability to do so. Even worse, they carry an opportunity cost by precluding you from forming relationships that could actually improve you (see next)

Second, they crowd out your ability to form new sustainable relationships and invest in existing ones. You only have a certain amount of time, and if that time is wasted in unsustainable relationships, it precludes you from ever improving your relationship profile. You will be stuck with a toxic combination of unsustainable relationships. Instead, cancel your unsustainable relationships and reclaim that time for people in your life, and even people you haven’t met yet, who will make you a happier and better person.

Don’t have any sustainable relationships yet? That is OK, they are out there. Free up some time and go find them. Your unsustainable relationships aren’t ever going to change, improve – so stop waiting for something that will never happen and cancel them, even if you don’t, currently, have anything to replace them with. I’ve always been an advocate that the devil unknown is better than the devil known.


I’ve cancelled some people in my life that I regretted. But they were very few and far between. For me, ultimately, I would rather make a few mistakes than allow my life to be negatively impacted by bad relationships. Most of my cancellations have been validated, over time.

People who cancelled me

I’ve been cancelled (at least implicitly), and in many cases rightfully so.

I think most of them fall into the category of people who I pushed to hard and/or too fast. I worked hard in the last 10 years to get better at managing people and my cancellation rate declined steadily during my career. But I still have regrets related to this, mostly going back to the earlier years in my career.

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