Relationships & Business Ventures: Learning when to break up

Like so many other people during this bleak snowless Wisconsin winter, I unexpectedly found myself a victim of “breakup season.” And I have to admit, it is amazing how much something can hurt, even when you weren’t sure you wanted it in the first place.
This particularly painful breakup has left me with all sorts of things to think about. If I’m being honest with myself, I knew from the beginning that this relationship was not a great fit, for either one of us BUT, there WAS a chance, and if it had gone good, it could have been REALLY good, so… I went for it.

In all fairness, I grew to have much love for this person. Even if I was not ever ‘in love’ with him, what we did have was real, we both learned a lot, and it was good for the time that it lasted. Unfortunately no matter how badly I wanted it to work, it was out of our hands. We were in completely different stages of our life and as much as we tried to meet halfway; it just wasn’t possible.

In hindsight, it is almost unbelievable that it lasted as long as it did.

So heres the problem: Unfortunately, by the time we both realized how doomed we were, I had invested so much of my time and energy into the relationship that I found myself fighting to hang on to something I did not even want anymore. By this time, it was hard to tell what I was clinging on to, him or my investment in time.

I did not want to be wrong in how I had spent my time and where I had placed my faith, and because of that, I made a mistake and continued to try and recover my investment. What’s interesting to me is that while I was in this relationship, I willingly watched others (who had high potential) come and go. All opportunities I missed because I was preoccupied trying to hang on to a sinking ship.

One of the hardest parts of life is deciding whether to walk away or try harderNow it is over and, I am ashamed to admit that even though I like to think of myself as a confident person, I feel absolutely crushed. My self-esteem took a tremendous hit. I feel completely inadequate, and I am so embarrassed that I could not make it work with that in mind; ashamed I even tried.


Whats worse, I’m afraid to try ever again.

What I have also realized is that my best characteristic is to be able to look any situation throughout the eyes of an entrepreneur. Sometimes as an entrepreneur you become so fixated on the idea of what your business baby could become that you stop seeing it for what it is. When you have a failure of a company in the palm of your hand, it can be incredibly difficult for you to see it and, even more, difficult to let it go. We get so tied up in our fear of failure that sometimes we forget that failure really can be a positive thing.

1) Just because something feels like a good idea, doesn’t make it one. It can seem like the best idea ever, it could even be the best idea ever, but sometimes if the timing is off, or the market is not ready,  there’s nothing you can to do to make it work.

2) Don’t be afraid to cut your losses! Learning is about experiences wins and losses, and frankly, sometimes it is time to give up.

3) Don’t let failure close you off from trying again. Just because one thing did not work the way you planned doesn’t mean you should give up altogether.

The bottom line is that whether it is a relationship or a business venture, a bad fit is a bad fit, no matter how much we rationalize why it should keep going. And learning when to quit is a good thing, as sad as it may be. We learn from our failures, but that can only happen if we learn to realize and accept them first.

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