Photo credit: Alex Eckhart


“Finding a partner is difficult nowadays,” a friend texted me.

“Why do you think that is?” I replied.

She went on to write that she thinks love finds you when you are not looking. How she just got out of a relationship that she knew wasn’t right.”

“I stayed longer than I should have,” she wrote.

I started thinking about all of the times that I “stayed longer than I should have.” And not just in romantic relationships.

I remember being sick of my job in New York City. I was not happy. I almost quit so many times. “I should have.” Instead, I went out and bought some paintings and plants for my office. I put the paintings on the wall. I put the plants on my desk. Somehow, this made me feel better about my decision to stay. For a while.

Once I was dating someone who invited me to a big event in the new year. It was July. I avoided answering her invitation, because in my mind, I was about to break up with her, a few weeks from now. I was not happy. “I should have,” ended things. But I didn’t, and we went to her event. I stayed with her. For a while.

I started my business almost 8 years ago in San Francisco. It was the perfect place to launch my career as an entrepreneur. For the last year, I was getting an itch to return to New York City. I was clear that I wanted to go, and that I’d spend the fall in New York City. When November rolled around, I was still in San Francisco. I felt that “I should have” left by now. But I had a few really close friends that I did not want to leave behind. We had 7 Friendsgivings together in the month of November. That helped me feel better about staying. For a while.

I once asked someone I loved, in the middle of having a lot of doubts and challenges around our relationship, “How will we know when we should stop pushing to make things easier? How will we know if we should end this?”

“We will just know,” she said.

Just like that. Clear, concise, confident.

It made me feel better.

For my whole life, I have wanted “to know.” I want to know if my decisions are the right ones, if the client will say yes to my proposal, if I made the traveling football team, if she likes me.

And almost all of the time, I do know. We always know. The heart’s knowing is the one thing you can’t deceive.

But beating ourselves up with “I should haves” pulls us away from honoring the knowing.

Because I’ve realized that ``knowing” is not represented by one big decision, and then poooof, it’s done.

Sometimes in order for us to grant our heart’s ultimate future “knowing,” there are things we need to do today. And one day, if we make the decision to quit our job, or end our relationship, or leave our city, we can do so, knowing. Not that we “should have done this” earlier. But we knew what we were doing all of this time.

When we bought more plants and paintings for the office.

When we attended an event with a partner we didn’t think we’d still be dating.

When we shared 7 special meals with friends who won’t see each other for a while.

And all along, in the staying, in the leaving, and in everything in between.

We knew.

And we know.

International Speaker and CEO of a Life in Shorts. Daily Vlogg’in my journey on YouTube @brianrashidglobal. Helping brands of all size tell stories that sell.