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  • Writer's pictureKathie Scalf

Failing Upward

I recently had to compile a list of my work-related accomplishments while updating my portfolio and while I was initially dreading the task, once I finished and had the arc of my career laid out in one clean sheet of paper, the dread was replaced with a great deal of pride. Even though it hasn’t always felt like it, over the last 20 years or so I really have been doing something with my life! And all those perceived missteps, missed opportunities and rejections where I had to start over and rebuild from nothing were actually a little something I like to call “failing upward.” Who knew?

There really isn’t any big secret to mastering the art of failing upward. I personally had to learn the hard way by doing everything I wasn’t supposed to do multiple times before I finally figured out that it wasn’t the actual tragedy itself that was ruining my life, it was my reaction to the adversity. I’ve said it a million times, but it bears repeating: in this life, you can either be a victor or a victim, a pitbull or a pansy. You can be someone who whines and cries about the series of unfortunate events we all call “life” and let chaos lead, or you can take action and control your destiny. Once you get sick of wallowing in your own crap excuses and make even the smallest positive changes, it’s like magic how the better opportunities start rolling in.

The year I really turned things around and started to take notice of this cause-and-effect relationship in play was 2015. For most of my 20s I was not someone I’m very proud of, but I don’t think that is unique to me and I no longer hold the guilt I once had about extending the college experience long after I graduated. By that year I was 29, engaged and feeling like I no longer fit in with the bar crowd where I was still working, even though I loved my co-workers and made great money. I had stopped going out and was really focusing on my health at that time, when lo and behold I was offered the opportunity to step up into a salaried managerial position at a new restaurant with hours and atmosphere that much closer aligned to the lifestyle I wanted. So I took that position but it was short lived- I was a horrible fit for the company culture and was axed in a very embarrassing and unexpected fashion in less than a year. I knew I couldn’t be without work; I’d just self-funded a wedding 4 months prior and had begun extensive home renovations. The easy way out would have been to regress into my comfort zone and ask for my old job bartending back. But I knew that would be a step in the opposite direction of where I wanted to take my life. So I saw an opening the next day for an administrative position, interviewed and was offered the job at a ridiculously low rate of pay, with the promise of a $4 hourly raise as soon as I mastered my job expectations. Within 2 weeks I’d earned my raise and within 2 months was given another title which came with more money, and by the time I left I’d doubled that salary. The only reason I left that job was because I was finally given a shot in alcohol sales which is where I’ve always wanted to work but kept getting passed over. In hindsight I truly was far too immature to handle this industry prior to that point; I partied way too hard and lacked the discipline to turn down the temptation of tastings and alcohol-centric events and would’ve been fired or worse.

In true failing upward fashion, after a few years that job came to a screeching halt. I lost myself to a crushing heartbreak and let it interfere with my job performance and was let go- at the time a double whammy and what I thought the final devastating nail in the coffin for me. But instead of giving up, I saw this as my shot to finally make my dream of moving away happen. I had some money in the bank, I had no relationships tying me down and now no job. So with that I began my job search in Nashville and the rest is history.

I could do this all day- if I had let that heartbreak defeat me and went back to old habits and my comfort zone I never would have moved to Nashville, where I lost my job to Covid 9 months later. And if I’d let that defeat me and given up then I never would have studied and passed WSET II then applied for a job at a larger distributor, and I never would have had the experience for my current role as a multi-state market manager for a single supplier.

You have to realize every time you are forced to start over, you’re not at rock bottom rebuilding from scratch; you have the materials for building a foundation and it’s called experience. Take the lessons, both good and bad from these major life moments and don’t let them be in vain. Dust yourself off and keep it moving forward, never backward. What has this perceived failure now made room for? What did you gain from the experience that you can utilize in your next step and what did you do wrong that you don’t need to repeat? And always take the high road no matter what because that truly always comes back and pays off. No matter how angry or upset you might be or how wronged you were by someone, keep your mouth shut unless you’re wishing them well because I absolutely promise if you rise above the current distress with grace and positive action, you WILL thank those people for doing what they did. I wake up every single day of my life and silently thank my ex-husband for leaving me because it set me free to experience a life that is far beyond what I could have ever imagined. If he’d never left, I’d never have met and experienced true love, and then I would never have experienced true heart break and without that I never would have learned how to really learn to love myself. See, I could honestly do this all day.

There is going to come a point where you can only fail upward so many times before eventually you’re going to be looking down, surprised at how far you’ve come like I am after piecing together my portfolio. And at that point I think you can stop calling it “failing upward” and simply acknowledge it as “success.” For some reason it’s difficult for me to give myself a pat on the back or speak openly about my wins, but I think we should all be more comfortable taking pride in the things we do, both good and bad. You earned those outcomes, so own them! There’s nothing conceited about overcoming obstacles in life and coming out victorious.


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