As human beings we are often programmed to live life in forward retrospect. While time is moving forward your mind keeps going back. I like to call this a case of the shoulda, coulda, wouldas. Often times this is brought on by menial daily things like ‘I shoulda said something to that mom who looked at my daughter a little crooked- she knows nothing about our life.” Or, “I coulda managed that employee differently.” Or, “If I woulda known she was a raging lunatic, I wouldn’t have invited her into my home for girl’s night.” Most of these things can be handled with an extra glass of wine, a more developed managerial plan, or a pass on the girl’s night in favor of staying in and eating takeout in bed.

But, when tragedy strikes the shoulda, coulda wouldas aren’t as easily solved.

You find yourself at a loss for words or even the ability intellectualize what has happened. Your brain is foggy for days or even weeks as you process emotions you didn’t know you were capable of. The shoulda, coulda, wouldas aren’t as concrete now as they were when it came to the mean moms or problem employee. The tragic shoulda, coulda, wouldas can suffocate you. Leave you feeling helpless and sometimes hopeless.

The recent passing of an icon, Kate Spade, had me in shock for days. Though I never met her, our lives were very much paralleled. We both had fashion businesses we built with our husbands. She started her business a few years before I did and I always looked to her as a beacon of hope. If she could do it, maybe I could too? Even though the first handbag factory I met with in Brooklyn rejected me by saying “I only make Kate Spade handbags” I never felt at odds with her- no not even in the slightest. I had this feeling that we were both just two women who believed in ourselves and wanted to live our dreams everyday.

When the alert came through on my phone about Kate’s suicide it brought me to my knees. I was truly sad, as though I had lost a friend. To be honest, wasn’t Kate everyone’s friend? Even if you didn’t carry her products, there is no doubt the corners of your mouth turn upward when you see her brand. I poured myself into reading all the articles I could about her in an effort to find answers. The shoulda, coulda, wouldas crept into my mind – the illusive questions that we will never know because we are thinking of them in retrospect.

As I read more and more about her, I started to understand our similarities and how creativity, art and design fuels us. But, I also got to thinking about how draining living a creative life can be. You pour your heart into creating something people may or may not like or even worse into things that never come to life. And, in Kate and I’s case we are both under the pressure of running businesses tied to our creativity. The pervasive feeling of having to move on to the next thing to create something bigger and better feels like a hamster wheel of never feeling ‘done’ or ‘brilliant’ enough. It can be lonely and intoxicating all at the same time.

Should we have seen this coming? Could someone have helped? Would the help have made a difference? We will never know.

But what I do know is this. The retrospective shoulda, coulda, wouldas are healthy for a little while, and then they are debilitating. We cannot trap ourselves in the past in hopes of changing it.

We can shoulda, coulda, woulda to learn but not to live.

As my business has changed over the years I have caught myself ‘reminiscing’ in the shoulda, coulda, wouldas more than I should. I have let myself get bogged down with answers I’ll never know about scenarios that will never replay themselves. I’ve learned through a series of both fortunate and unfortunate events that life will keep moving without you. If you allow yourself to stay back with the shoulda, coulda, wouldas the life you eventually go back to has moved on without you. You have to show up everyday. You have to fight the good fight. You have to live with purpose- even when the shoulda, coulda, wouldas invade your psyche.

You SHOULDN’T fall backwards while trying to move forward. Think of what you COULD miss, WOULD you really want that? Because, it’s right here, right now, where we find each other, and with each other we have all we need.

Rest in peace Kate. I hope heaven is as colorful as the legacy you left behind.

XO, Elaine